Operational Lessons From My Mom

garbage apologies

In honor of Mother’s Day (that’s when I started to write this, so who knows when I’ll finish it or when you’ll read it), I’ve been thinking about some of the things she taught me, both expressly and by example. In my household, my Mom was most directly responsible for teaching me how to deal with my many screw-ups. (No knock on my Dad, here — he was first responder to a couple of doozies, like getting thrown out of Little League, but my Mom has him beat on raw volume.)

For some background, my Mom got stuck (or chose) to take on this particular aspect of child-rearing for a couple reasons. While both my parents worked full-time, my Mom’s hours resulted in more direct face-time with her kids. Plus, as a teacher, she had a better grasp than my Dad did of the problems that faced my generation, and a larger sample size to compare it to. For instance, it was very difficult to convince my Mom that I had a unique, acute attention deficit disorder when she dealt with 30 other rugrats all day who were sometimes even worse. My Mom’s career also made her particularly… err… “invested” in my behavior at school; if you really did have a bad teacher, circumstance, etc., there was no stronger ally to go into battle with than my Mom. But God help you if you weren’t honest about the situation, or were contributing to the problem yourself. I get chills just thinking about parent-teacher conferences to this day.

Anyways, the point is that my Mom was on the front-line of my countless mistakes, so her reaction, advice, and thoughts on them were probably more important to me than anyone’s, even if I vehemently disagreed with them at the time. And one thing she had absolutely no tolerance for were weak, forced apologies. “Sorry doesn’t do anything,” she’d say. “If you’re sorry, do something to make sure it doesn’t happen again.”

pivots as apologies

I could write a whole piece about the different flavors of cynicism, but for the sake of this particular argument, you just have to know that I’ve never thought of cynicism as a universally negative thing, probably because I was raised by a couple of New England yankees with limited tolerance for bullshit or self-serving rationalization, and we live in a world that seems increasingly full of those two things. I’ve read lots of historical takes about how Massachusetts and the Route 128 belt missed out on becoming Silicon Valley for a bunch of policy/regulatory/infrastructure reasons, but the Valley as we know it simply couldn’t exist in New England because it’s a creative engine of amazing economic potential powered by — let’s face it — a nuclear reactor of horseshit and nonsense. Even real companies out there like Facebook and Google are constantly hand-waving away limits to their business models with massive, ambitious, absurd attempts to enter new spaces and pretending they have any idea what they’re doing. That kind of thing just doesn’t fly in the original thirteen colonies… unless you’re related to someone. We have our own problems with that.

In venture companies, the closest thing to a common childhood apology is the pivot. This is where you stop doing something that isn’t working and try something different with the same pile of money you originally raised by saying, very confidently, that the first thing was totally going to work and make everyone rich. There are two basic ways to couch this kind of pretty obviously bad news.

  • Pivot as learning experience — “Hey investors, I know we were going to build the ultimate snack delivery company, but it turns out that the logistics of delivering snacks are a lot more complicated and expensive than we thought. BUT, in building out our amazing snack library, and serving our customer base, we’ve learned that we could create the same kind of value for our customers at a fraction of the cost by re-inventing the vending machine experience. So that’s what we’re going to do. We got rid of our delivery function and are building out a vending machine team.”
  • Pivot as a rationalization — “Hey investors, just want to let you know that we have COMPLETED OUR MISSION to disrupt the snacking experience, and are moving on to an even bigger challenge; the vending machine space. As the number one snack delivery provider, and best-capitalized vendor in the industry, we’re uniquely equipped to take the next step in achieving our vision of making the right snack available to everyone on the planet at the exact moment they need it.”

One of my biggest problems with VCs, in my limited experience interacting/dealing with/being affected by them is that in general they’re much harder on that first response than I think they should be, and much, much, MUCH more lenient on the second one. The result is that approach #2 is a lot more common than you think, even when it’s obviously ridiculous, and well-capitalized startups end-up being even more vulnerable to delusional thinking than large, established companies when it should really be the other way around.

the “make sure it doesn’t happen again” part

The costs of mistakes and incorrect operational decisions are pretty obvious — it’s the immediate thing you have to deal with when you screw up. But if you’re in any kind of growth phase (as a company or, say, a kid), the opportunity cost of hand-waving away mistakes as either GLORIOUS VICTORIES or random one-off outliers (“no one could have foreseen the breach of the levees”) is usually even greater than the cost of your screw-up.

I’m obviously not proposing ripping up every process the minute it doesn’t work — but just about everything can be iterated on, tweaked, or re-examined as situations, markets, and conditions develop. That’s simply how things get better, and how kids, entrepreneurs, and teams learn and improve, no matter how smart you are coming out of the gate. I think the best organizations operate like this whether they admit it or not, but the way this kind of thing is messaged (and encouraged by boards and management) matters, especially in growth environments.

So with all that said, I think I’ll put my Mom on the board if I ever end up running a company. Good luck trying to spin that disastrous Q3 product rollout to her as a validation of your strategy.

Incentives & Rules

One thing I’ve noticed over the last year or so is that I spend most of my time trying to get people to do things. I’ve been in marketing for a while now, and while I’d like my efforts to be focused on getting people to do things that make sense for them, at the end of the day I work for a business and the business is happy when our market does what I want them to do, and sad when they do not. So there’s that.

The other thing I’m increasingly involved in is management and organization or process building, where I’m trying to get people I work with, or manage (or maybe I work with someone who manages them) to do things. This sounds super manipulative, but it’s really not — I’m very upfront with everyone I work with about what I’m trying to get them to do, partially because I’m a terrible liar, and partially because every once in a while people will just do what you ask them to because you asked them to.

Most of the time, however, they don’t, because this is work, and what I’m asking people to do at work is usually annoying, counter-intuitive, or effort intensive for them — otherwise I wouldn’t have to ask for it. So here I am, with a thing I want people to do that isn’t interesting or valuable enough for them to do automatically, and two basic ways to solve it.


The first thing I can do is adjust people’s incentives. Messing with incentives is very in-fashion these days, possibly because it’s the information age and it’s easier to test things, or possibly because everyone I met in college had or wished they could have an economics degree, and all of those people are in their thirties now and writing books and getting into management. I suppose there could be a third reason, but I’m pretty sure it’s one of those two.

Traditionally, I’ve been very pro-problem solving via incentives, because like many (older) millennials, I am irritatingly conflict-averse and also slightly lazy, at least to the extent that I hate repetitive tasks with no obvious ending point. Unfortunately, my love of incentives has spent the last few years crashing into the brutal reality of actual implementation, and I’ve had trouble with a few things.

  • Money is a great way to create or adjust incentives, but people become irrational economic actors in a much larger number of scenarios than I ever imagined they would. Basically, people get really excited about the idea of controlling how much money they get out of doing something, until they end up having to actually do it, at which point they often choose to find a equilibrium between effort (or emotional satisfaction or whatever) and return that does not align with the outcome I’m trying to incentivize. I’m not saying this is unsolvable, just that it’s a lot harder to execute in practice than you might think.
  • Measuring behavior and outcomes accurately and with proper context is usually much, much harder than it first appears. Nothing is more frustrating than building out a logically air-tight incentive program, and then being told that you need to rebuild it without a key piece of information on which your program relies. Sometimes (many times), you can’t, or the resulting half-measure isn’t compelling enough to generate the behavior you want.

In short, I still love incentives and they are theoretically superior to any other way I’ve come up with to get people to do what I want, especially at any kind of scale. However, trying to solve everything with incentives in an actual business with resource limitations and plenty of other important things to do is often a great way to spend a lot of time in front of a white-board without, in the end, actually changing anything.

Of course, there’s another way…


Yes, that’s right — it’s the old “because I said so” school of management/parenting/Little League coaching, which was a staple of my younger days. In fact, I think one of the reasons young-ish professionals are so enamored with incentives-as-management is that they’re simply excited about the prospect of any incentive other than “not getting in trouble”. However, the simplicity of implementing compliance gets more and more appealing as you deal with the complexity of building and executing elaborate, often contradictory incentive schemes for different groups of people, and before long, it’s easy to find yourself fantasizing about simply crushing every obstacle in your way with the merciless hammer of autocracy.

To quote my favorite management consulting resource, Green Day’s 1994 album “Dookie” :

“Do you ever want to lead a long trail of destruction and mow down any bullshit that confronts you?”

If your answer is “yes, yes I do”, you’re going to love compliance, at least in theory. Unfortunately, the fact that implementing compliance is “simple” has zero connection to it being “workable”, or “effective”, and even in my limited deployment of this strategy, I’ve run into a couple problems.

  • Compliance isn’t actually all that different than incentivizing — you’re often just sort of threatening negative incentives, or maybe just inferring them if you prefer not communicating clearly. So in a lot of scenarios, compliance is just as complicated, because you have to build negative incentive schemes that are just as complicated, but much less exciting or motivating. For instance, if I just tell you to do something, what happens if you don’t? Is that clear? Is it established? Is it… anything? The idea of not being yelled at, or not disappointing someone, can be extremely compelling or not compelling at all based on lots of factors — it’s just that with most compliance plans we don’t think about any of it until later, so it seems simple enough.
  • Leaders, managers, and even governments all constantly overestimate their ability to enforce compliance. Keeping people from smoking pot by putting them in jail or harassing them (i.e., compliance) has never worked, and still doesn’t work, but there’s still a vast army of politicians, police administrators, and others who are so disgusted by the idea of soft, subtle positive incentives for good behavior (people who smoke a reasonable amount will perform better at work and generally be happier than people who are constantly stoned, etc.) that they’ll just keep banging the drum forever. When I worked at Efficiency Exchange, we spent a lot of time engineering the right set of positive incentives for manufacturers in developing economies to behave the way their customers wanted them to, and people were constantly baffled by the idea. They all just wanted to make requirements and throw them over the wall, assuming they had sufficient economic weight to enforce their will when they absolutely do not.

oh no, not a mix…

So no, neither of these are one-size-fits all solutions in the real world. I can’t imagine you’re surprised. I battle with this every day, and here’s what I’ve learned so far.

  • Start by removing positive, perverse incentives for actively undesirable behavior. There are probably more of these than you realize, especially if you have data problems. (hint: you totally do)
  • Save compliance for things where people have recently suffered from their own refusal to comply. Nobody wants to carefully fill out a report every Friday, but good people will do it if they remember terrible things happening due to a lack of good reporting. Same thing with project management behavior, etc.
  • Don’t resort to compliance just because you don’t feel like figuring out the incentives, or because you are annoyed by the fact that people who work for you aren’t just happy to have a job. It’s understandable, but I’ve never seen it work in the private sector.
  • Don’t create incentives you aren’t equipped to measure accurately — your flawless whiteboard theory is worth less than nothing if you can’t build an effective bureaucracy to execute it. And don’t be arrogant or dismissive about the way that stuff is calculated. If you can’t trace back a couple edge cases and audit the results yourself, you’re playing with fire.
  • Create a very simple, rock-solid incentive that is bigger than anything else, and more important than anything else, and then experiment on the margins with more granular, less important stuff. If your experiments are stupid, the bigger thing that works will prevent people from doing anything too damaging until you can fix the smaller stuff or kill it.

I certainly haven’t done all of this stuff yet, or done it well enough to get the outcomes I want, but I can at least say that this kind of thinking has helped me make a number of stupid things significantly less stupid. And I’ll take that any day.

Management & Me

A lot of crazy things happened to me in 2016, but the biggest two had to have been the birth of my first kid back in February, and a pretty dramatic change in my job where the number of people I was responsible for went from one to ten. That’s a 1000% increase!

Unsurprisingly, this changed a lot about what I needed to get done on a day to day basis, and forced me to deal with a lot of things I’ve never had to be especially good at. Still, since I started my management adventure back in June (after returning from paternity leave), I’m pretty happy with the results. Some of those results are simply the business performance of myself and the people who work for me, and some of them are how my group has dealt with various mistakes in judgment I made along the way.

Anyways, in the spirit of paying it forward, here are some very broad things I learned over the last six months or so that I think are worth noting. My situation is it’s own special little snowflake (aren’t they all?), so of course, you’re mileage may vary — but I think there are some universal truths buried in here as well.

1. get there the right way

Not everyone has this luxury, but for me it was extremely helpful to have already spent a lot of time working with the people on my team as regular old non-boss Nate, and to have done so as someone fairly senior. At some point in my career, I’ve done little aspects of everything our team does, so even before I got promoted, people tended to ask me for help and advice with things. That meant putting me in charge didn’t seem particularly risky for my colleagues — they could all be reasonably confident that I wasn’t likely to go on some massive power trip, and we all had established routines for working together and kicking around ideas. If anything, it was probably nice that my job required me to make time for this stuff, instead of it being a “favor”.

Given my personality, this is probably the only way I was ever going to be put in charge of a large team, so it’s not like I made some brilliant strategic move here. But I’ve worked with plenty of young ladder-climbers and seen promotions and management work out very differently for them. Pay your dues — not because “the man” says you should (screw that guy), but because it’s often really good for you and your relationship with your team.

2. communicate properly, and be yourself

I’ll admit it — I take an embarrassing amount of pride in being my own person, and not worrying about things that I don’t think are important. But that doesn’t mean, on the eve of running a multi-person team for the first time in my life, that I didn’t worry about stupid stuff like whether I needed to buy new clothes or stop cracking so many jokes at work.

In the end, I realized that was probably never going to work — as I mentioned, all of these people knew me, and authenticity was probably the best thing I had going for me (and the last thing I’d want to burn) as I tried to figure out how to manage properly. Of course, that doesn’t mean I don’t handle myself a little differently. There are things I need to keep from people sometimes, which sucks, and being the official arbiter of a disagreement between two people who work for you is a very different animal than being a friend who is able to give everyone candid advice. That took some getting used to, but I’m getting better at it.

Still, a large portion of my interactions with people are exactly the same. I didn’t suddenly become worthy of reverence just because I click the little button that approves people’s vacation requests, so there’s really no reason to talk to me differently, and frankly, I don’t think anyone does. I’m more than okay with that.

3. acknowledge reality

One of the ways I’ve been able to minimize the changes people have had to make in how they interact with me is to proactively make some changes in the way I interact with them. These are small things, and I learned a lot of them from my Dad, who went through similar organizational changes in his career. The basic principle is to acknowledge the fact that no matter how weird it seems, you really are someone’s boss, and they really do probably have the same fundamental “boss concerns” that everyone has when they interact with you. You probably do things that frustrate them, or things that they really want to make fun of you for but don’t feel totally comfortable talking about when you’re around.

Again, some of this is just my personality, but I definitely try to give the people on my team plenty of venues to blow off steam and probably make fun of me “behind my back” (which sounds way worse than it is). While we all make jokes at my expense to my face — it’s pretty easy — it’s a good idea to make yourself scarce now and then so people can take it to another level for a while. And hey, maybe people don’t do that, because I’m just so great. But I really shouldn’t be the arbiter of that, so I’m not.

It doesn’t hurt that my idea of a relaxing lunch is to sit alone and stare into the alley, either.

4. isolate problems and issues

Some problems are fixable. Some aren’t. But one thing that’s impossible — at least in the pretty dynamic business environments I tend to run in — is solving everything at once. There are just too many converging factors, too many data problems, and too many intertwined theories to figure everything out at once. In my case, my boss was responsible for creating an effective, scalable demand generation operation for our business, which is a pretty enormous, complicated goal. I saw my job as mostly trying to make sure we could provide her with clear, verifiable information about these efforts so she could make better decisions. It doesn’t sound that hard, but we were pretty in the dark when it came to a lot of information, and a lot of the information we did have was anecdotal or hard to pull regularly, so we had almost entirely apples to elephants comparisons that didn’t help us decide anything.

With nothing to lose, I basically set out to break down everything we needed to know, and honestly assess whether we really knew it or not, and if not (FYI, it was always “not”), what was missing that prevented us from knowing it. We simply chipped away at problem by problem, and since we have a bunch of smart, hard-working people on the team, my main job was to keep people from getting distracted by the larger problem, and focused on delivering concrete answers for the sub-problems. Once we nailed a couple of those, the larger answers became more and more obvious to everyone, and since we had the sub-problems permanently solved by process and logic improvements, we kept getting smarter and smarter. Anything that was too big to solve, we punted on, which was okay because we had a zillion problems to address.

What I wouldn’t recommend is simply demanding a vague form of excellence and performance in every task, and assuming that’s going to add up to a better functioning department or team. I mean, it might, but there’s no guarantee, and in my experience people (including me) hate being managed that way. Something is probably wrong at any given moment — so figure out what it is, focus on making it better, and let the rest of the stuff cruise until it becomes your biggest issue.

5. eat your disgusting dog food

Here’s something that I think is important for all managers, but particularly for new people coming out of functional positions — don’t ask people to do anything you’re not willing to do yourself, at least the first time. For me, the best example of this was reporting, which is really important in any kind of systematic demand generation, but is a huge pain in the ass when you don’t have mature, automated reporting. There’s a lot of manual collection, filling out spreadsheets, and discovering halfway through that your report structure is inherently broken or useless.

I knew it was crazy to ask a bunch of extremely competent but relatively inexperienced people to go through this nightmare themselves, hand me what I asked for, and then tell them why it wasn’t good enough and that it had to be done again. That’s literally the definition of an annoying boss, and the opposite of someone who is in the trenches with you trying to actively solve problems.

That’s why I built and filled out prototype versions of all our reports — each time I requested a change, I’d do it myself, so I knew exactly what was annoying about it, and what was reasonable to expect from the process. Frankly, the people who work for me are a lot better at this kind of thing than I am, so in my case I’d build a report, share it with our team, apologize profusely, and then our marketing managers would just fill it out and say “it’s not that bad” and maybe make a few suggestions we’d usually implement right away (and I would appreciate, having some experience doing the work myself).

This doesn’t mean you have to do this work forever, of course — one of the hard things for me has been acknowledging that, and letting people on our team take these things over (and improve them!) without me even necessarily looking at them every week. But working directly on the early versions of things is really helpful to make sure you aren’t just wasting people’s time and putting people through frustrating exercises you have zero empathy for.

6. acknowledge expertise

I got into this a little bit in the last section, but again, just because you’re responsible for people doesn’t mean you know more than they do, and just because you know more than they do doesn’t mean you’re better at everything than everyone who reports to you. Figure this out immediately, and start leaning on people to do things they’re good at.

I have no idea if I’ve done this sufficiently on my team, but I sure as hell realize the importance of it. I’d have had a complete nervous breakdown if it weren’t for the talent on my team, so you can be sure I’m always looking for the best way to take advantage of it, and foster its growth as much as possible.

7. set proper red lines

In even a mid-sized organization, one of the big things you provide as a manager is clarity on what people’s responsibilities are to work with and do things for other teams. This is certainly something I think our team was looking for when I was promoted — someone to very quickly draw some lines about what they needed to prioritize outside of their day to day work, and who could make those decisions.

In general, I think the goal here is to have some very basic red lines, and then a lot of flexibility for situations until they approach said lines. So for instance, when someone on another team wants a person who works for me to do a bunch of work for a client, my default response is to try to facilitate, and move things around on our end so that you’re not just asking your team do generate time out of thin air. But I’d also let the person know that this is one time thing, and not a permanent responsibility — if we need to do this for other clients, the person requesting this work needs to talk to me so we can systematically free up time going forward.

8. don’t panic

Again, related to the previous point, so much of the drama and daily conflict that goes on in the workplace is totally unnecessary. Maybe this is a startup thing, but everywhere I go, people are constantly distracted by various mini-turf wars or acts of perceived disrespect. The number one request I’ve heard in my adventures in startup land (this crosses several companies) is “role clarity”, which apparently refers to an unbreakable covenant that empowers certain employees to total control over various parts of the business.

This is obviously insane, because businesses aren’t about top-down, dictatorial control of channels and functions — they’re about problem solving, which often involves multiple channels and multiple stakeholders. If everyone has their channel under control, but problems don’t get solved, you won’t survive. That means instead of knowing exactly what they own, and who can and cannot parachute in with requests, people are forced to deal with the dreaded SITUATIONAL AMBIGUITY, and then they panic.

“What does this proposed solution say about my job? My performance? My skills? The way I’m viewed by my peers, and my bosses? My future at the company?”

Defusing this kind of panic requires a lot of explanations, a lot of empathy, and frankly, a lot of work. Sometimes the answer is just for people to grow up, but sometimes it’s really not — and either way, the last thing you want to do is add to the panic party.

For me, I’m always trying to keep the ship steered towards progress, towards solutions we know are better than the status quo, and towards general principles of good work and sounds strategy. If you do nothing else as a manager but reinforce this kind of thing among as many people as possible, in and outside of your team, you’re probably a net positive.

9. be useful!

I’ve referenced the importance of being someone who’s ready and willing to work alongside the people they’re responsible for, but really that’s just a subset of the belief that as somebody’s boss, the best thing you can do is whatever it takes to get them to do their best work. I think an unfortunate truth is that we gravitate towards things like “holding them accountable” because it requires the least amount of empathy and self-examination on our part — if we look hard enough, it’s actually pretty easy to see that a lot of people are in extraordinarily difficult positions, or can’t do their best work because of an obstacle they don’t have control over.

But you might. That might be because you have experience, or the ability to communicate clearly with another team, or relationships with people at work that can make solving a problem easier or less frustrating. Maybe you can approve a small expense, or dig up an example of old work you’ve done that can make things seem a little more manageable. Or maybe you just need to roll up your sleeves, divide that horrible Excel spreadsheet in half, and tag-team some particularly nasty, unavoidable administrative work.

Whatever it is, find that thing you can do to help, and do it, whether it feels like good “management” or not. More often than not, I’ve found that’s actually exactly what it is.

Why I Remember Accuracy & Precision

I don’t actually remember when we learned this, but for some reason one of the random school things I distinctly remember learning was the difference between accuracy and precision. Now, as it turns out, I don’t remember it 100% correctly (yes, I see the irony there given the subject), but I looked it up again and for the most part the difference stuck with me pretty well over the years.

Here are the basics — essentially, accuracy is the distance of a measurement from a reference sample (a.k.a., the objective truth), and precision is the variability of the measurements you take. So let’s say you throw three darts, and you’re within an inch of the target, but in three different places. Then, you throw three more, and hit the exact same spot three times in a row, six inches from the target. Your first “sample” of darts would be more accurate, and less precise, than the second sample.

That’s pretty much the gist of it. Now, the more philosophical takeaway from this kind of thing is that it’s possible to conflate hyper-specific knowledge of a situation with an accurate assessment of that same situation — and I think this is an increasingly dangerous problem in the information age.

Anecdotal Precision in Current Events

One of the obvious places I’ve noticed this issue is in the ridiculous, never-ending intellectual tire fire that we call the 2016 U.S. presidential election, and around politics in general lately. When I was growing up, and first started paying attention to political arguments, they mostly revolved around people’s different preferred best practices for problem solving, as opposed to especially damning quantitative facts. This wasn’t always great — for instance, certain candidates could get away with measurably irresponsible or dishonest policies because people felt like that person was inherently responsible and honest — but it also left a lot of room for discussion. When you’re having an ideological argument about the logic behind something like gun control, or free trade, there’s really no card that anyone can just pull out and say “you are empirically wrong”. You’re forced to argue about why you think certain things happen, and that can very instructive if you’re open to it.

Like anything else, accurate (there’s that word again) data is an incredibly helpful (and important) tool for grounding these discussions in reality, and the collection and understanding of data has exploded since my first election in 2000. Unfortunately, a lot of people have taken that the wrong way, and started looking for data that justified their largely unexamined, qualitative views — and of course, that’s easier to find than ever through perfectly legitimate online research, or lazier, vulnerable-to-confirmation-bias channels like Facebook.

What I find jarring is how comfortable people are falling back on data, but how bad they often are at validating any of it. I got the “there’s way more violent crime in the U.K. than in the U.S. because the police are unarmed” argument thrown at me the other day, and I was actually kind of frozen by it. “Really?” I thought. It seemed weird for a couple reasons that my brain immediately flagged :

  • It had never come up in any of the discussions I’ve had with gun rights advocates (and I live in VA, so those discussions are pretty common) before.
  • It didn’t make a ton of logical sense — were police being overpowered by armed criminals? Was the idea of being shot at some kind of deterrent for people who probably didn’t expect to be caught anyways?
  • If this was the case, why wouldn’t the U.K. react? Giving patrol cops guns (or taking them away) isn’t an insanely radical policy anyways, and you’d think it’d be something you’d experiment if you had an emperical policing problem.
  • It seemed weirdly specific, even though in some way that gave it an odd feeling of credibility.

But of course, this is me, so even though all these red flags went up, I was curious about what could have been a huge personal blind spot. So, as I often do, I started looking for information on the issue, and I immediately found two things that explained the conversation.

I can't believe people get their news this way.

  1. a low-resolution JPEG meme (pictured here) stating this same “fact” with a pithy rejoinder at the end about how gun control doesn’t work
  2. a long, boring Politifact examination of the argument which convincingly argued that the data indicated no such trend, but that the argument was effectively comparing apples and oranges and would require better information to conclusively make

So basically… this statement is bullshit, and once I thought about it a bit more, that actually seemed pretty obvious. And yet, I didn’t dismiss it the way I dismiss vague conspiracy theories. Why? I think it’s because of that last thing — the claim was so specific, and I feel like human beings (myself included) have a tendency to assume specific arguments are inherently more sound than broad ones.

And sure enough, when I think back over my interactions with different people, and I assess all the different sources of truth I’ve dealt with in the past — from outright liars to the well-intentioned but incompetent — this is really does feel like a pattern. It really does feel like I’m constantly (and increasingly) innundated with hyper-specific, objectively wrong arguments.

Data Illiteracy

I’ve read lots of things about the problem of financial literacy in a world where making good, often complex financial decisions is a bigger and bigger part of getting and/or staying out of poverty. I think data literacy is the professional corollary to this challenge. Sure, real data people are fine — actual data scientists, certified accountants, professional economists, etc., because they’ve always needed to be data-literate. But almost everyone else has seen data injected into their various professions and areas of expertise seemingly overnight, and while we understand many of the things all this data is supposed to represent, we’re often fundamentally unprepared to assess the data itself. Where did it come from? How are different labels and thresholds defined, and what happens to your data if you change them? What is a sufficient sample size for various measurements? What’s the difference between causation and correlation? Do you see things like daily tracking polls and Salesforce reports as objective facts, or is your initial response to ask about their methodology?

To those real data people I mentioned (i.e., not me), these are obvious, basic questions. To regular people in business functions, they may not seem important at all. I’m fortunate enough to have grown up as the son of an engineer who literally designed test & measurement equipment, so while I’m personally unqualified to do any kind of academically rigorous data analysis, concepts like accuracy and precision have an emotional weight to me that I don’t think a lot of people necessarily share. That, combined with just enough education to get by (thanks, Social Science Statistics 101!) has given me a decent toolset for challenging the kind of flawed data conclusions I encounter every day. Even when those conclusions are incredibly specific.

Tips for Non-Experts

Just like we don’t all need to become developers to benefit from a broad, conceptual understanding of how software works, we don’t all need to become data scientists to get better results from our increasingly data-infused careers. We just need data literacy, which to me is mostly the ability to understand what we know, and what we don’t. In my experience, that has a lot more to do with the ability to ask intelligent, often humbling questions and our own insecurities than anything else, which is probably why it’s such a challenge for so many of us. There are just too many people walking around, armed with “data”, who lack either the humility, experience, or skills to resist using it to clumsily justify incorrect assumptions.

For me, I’ve spent the last couple of years trying to figure out how I can get the most out of everything from business to product usage data, and I’ve had the most success doing the following :

  • Simplifying what I’m trying to track, and what I’m trying to conclude.
  • Using the extra time and effort I save from that to focus on consistency of collection and larger sample sizes.
  • Sharing what I find with people outside my functional area, and encouraging them to ask about my methods and logic.
  • Iterating on my methods based on holes those people find, including cutting my losses on things I’ve been tracking that aren’t useful.
  • Being generally skeptical of big trends you discover, and eager to poke holes in the logic behind them.

In other words, don’t start looking at data when you need to prove to someone else that you’re right about something really specific. Start looking when you can afford to prove yourself wrong about nearly anything — and use your findings to improve your process. Then, when you really do need to make a data-driven decision, you’ll hopefully have more relevant data, consistent collection methods, and some amount of fluency in thinking about it. That doesn’t necessarily mean you’ll make the right conclusion (remember, you still probably don’t really know what you’re doing), but it’s a lot less likely you’ll make the wrong one.

Hustling, Grinding, and Building

Here’s a tweet I saw the other day that made me — as the kids say — “LOL”.

Touche. This is a really, really annoying part of today’s cult-of-entrepreneurship. You can blame it on internet culture, or venture capitalists, or the way the media covers and informs the public about these things, but either way the end result is often a incredibly clumsy grouping of unrelated challenges into a single, stupid bucket. You don’t have to be an especially cynical person to roll your eyes at the idea of how “tech companies”, “startups”, “SaaS businesses”, or any number of vaguely defined groups of things are supposed to behave, because like any other vaguely defined group of things, correlation is easy to find and causation is extremely difficult to pin down.

What everyone from famous people like Elon Musk and Peter Thiel, to a million different poorly credentialed Forbes contributors, have managed to do is convince themselves and any number of hangers-on that the solution to every problem is intelligence, or their own self-identified hard work. If you buy that logic, their success is not only immediate validation of how intelligent and hard working they are (because problems can only be solved by intelligence and hard work, and they solved a problem), but validation that they can solve any problem they put their mind to (because, again, problems are solved by intelligence and hard work, and in this system, they have proven themselves to possess one, or more likely both, of these things).

In many ways, we have a tendency to do this with strategy as well as leadership, which is slightly less annoying but arguably more dangerous. I get this a lot when people want to tell me how to do marketing work, and get frustrated with its alleged complexity — here’s how company X did it, company X is successful and respected, why aren’t we doing what company X does?

If you are a frequent reader or someone who works with me, you can probably guess my extremely predictable response. What is company X selling? Who are they selling it to? What kind of resources do they have? How much risk are they willing to take on? Can we connect the success of this thing company X does with company X’s success? And finally, are there any major differences between these answers for company X, and for us? Because if there are, company X may not be what we want to emulate. Nobody really likes this answer, but for the most part I think it helps people to generally start to understand the complexity of the issue if they haven’t already.

Now, at a slightly more abstract level, I do think you can group business challenges (or any sort of productivity one, to be honest) into categories that can help you start to think about the best way to address them. These are more philosophies than they are tactics, but that’s ok — you have to start somewhere.


I define hustling as the frantic pursuit of any positive opportunity you can identify. Hustling is really important when you’re first starting out with an idea, because that’s when it’s the most unproven, and when it’s most likely that what you’re doing is worthless and requires you to radically change. It’s also important (although often times more depressing and less exciting) if you’re running out of money.

Some businesses are always about hustling, at least in theory — my guess is that commodity traders and venture capitalists are almost always in a hustling mode, running from thing to thing trying to maximize the chance that they’re in on the ground floor for the next great opportunity. People who are great at hustling are often thought of as “entrepreneurial”, even though building anything other than a ponzi scheme often requires that hustling eventually evolves into something else. But there is something really magical about professionals who can drop into hustle-mode when the time is right — those people are usually one (or more) steps ahead, and they can be a lot of fun to be around.


Grinding is the repetitive, iteratively improved act of day-to-day execution. If you start grinding before you’ve sufficiently hustled, your best case scenario is that you get really good at executing a less-than-optimal business. That’s not a necessarily a terrible thing, but it’s an obstacle to reaching your full potential, and the worst case scenario is that you get really good at doing something worthless. The later scenario is not uncommon, and that’s why “grinding” through your job sounds like a bad thing.

Still, grinding is important — essential, even — to building anything other than a hilarious frat-house startup, and contrary to what you might think, a ton of learning occurs during grinding. In fact, while you learn large, existential things while hustling, most of those things are useless in the long term, because you end up hustling on to something else. Things you figure out while grinding, on the other hand, get baked into your core business operations and help you indefinitely. Grinding is often thankless, but essential, and personally, I think most mid-stage startups fail or end up missing their opportunity not only because they failed to grind, but because they assumed grinding would be pretty straightforward and wouldn’t require a lot of focus.


Sometimes you hustle around and find the right opportunity, but there’s no way for you to successfully grind it into a real business. This is usually because you either don’t have an essential part of the necessary grinding process, or because it doesn’t exist yet. Either way, this means it’s time to build, whether that means creating a product, improving a technology, or changing the way your organization works and solves problems. Building is very rarely a direct revenue-generator, so it’s hard to get companies to agree to do it, and even harder to get them to agree to make it a priority over hustling and/or grinding (“you can build as long as we are hitting our numbers” is one I’ve heard a lot). The truth is that regardless of your cash or goal situation, the time may come when you simply can’t go any further until you build something, and that means you have to find the time and resources to do it, or else you die.

What these modes have in common, and what makes them different

If I were a betting man, my money would be on the average CEO responding to this breakdown by explaining that “the interesting thing about our business is that we really need to do all three”. This is, of course, a total leadership cliche and is not interesting at all.

Still, to some degree it’s often true, especially if your organization is big enough to have multiple major challenges. But that doesn’t let management at any level off the hook when it comes to setting the tone for the company as a whole, or for setting that tone on a team by team (or employee by employee) basis and not sending mixed messages about how each person should be approaching their job. Maybe inside sales is grinding as they improve their process for handling inbound leads, and business development is hustling as they go after new verticals or try to find someone to buy a new product. Maybe the back-end team is hustling as they try to figure out a cost-effective way to store all this data they weren’t expecting to be responsible for, while the QA team is building new tests. Maybe Bob is grinding through highly standardized marketing campaigns and looking to optimize results, while Barbara is trying to build an account-based marketing system and get it up and running.

The point is, these are really different workplace attitudes that have their time and place depending on what you’re trying to do. If you’re looking at a certain part of the business (or sometimes even the organization as a whole), and people in leadership have fundamental disagreements over whether you are hustling, grinding, or building, you have what I would consider a fairly important alignment problem.

One other thing that’s really interesting about these three very different mentalities is that none of them have a monopoly on any of the things we value at work, like creativity, or hard work, or discipline. These things are useful in all stages, but do have to be applied appropriately. One person’s idealized vision of hard work is really a form of hustling, and it’s possible they’ll see a highly efficient form of grinding or building as lacking in effort or urgency. Until fairly recently, I personally lacked sufficient appreciation for the subtle creativity that’s involved in effective grinding, or the discipline that comes with an exceptional hustling mentality.

More than anything, I find this type of classification useful to get a sense of why people think they’re doing what they’re doing. If you’re baffled by someone’s priorities, or feel like smart people are doing seemingly dumb, pointless things, it doesn’t take much more than a quick conversation to figure out what kind of mentality everyone is operating in, and where the source of the disconnect is.

Plus, you get to say “grinding” at work a lot, which is fun.

Why is it So Hard for Workplace Tech to Make a Difference?

The cyborg generation that never was

When I was in high school, the world was all abuzz about the fact that many people my age had “grown up with technology”, which really meant “grown up with personal computers and, for a while, dial-up internet”. The idea was that while our parents’ generation struggled to deal with trash can metaphors and concepts like double-clicking, to us bleeding-edge early millennials, digital technology would be second nature, and thus we’d all be really good at it. At the time, this made a lot of sense to me, and I eagerly awaited a world in which technological incompetence was effectively obsolete.

Well, more than fifteen years later, you know what I’ve noticed? Most people my age are actually pretty terrible with technology — even the kind we grew up with. Oh sure, we’re used to it. We use PC-like phones every day, constantly interact with different web applications at work, and voraciously consume things via various forms of the internet. But in a lot of ways, the technology really just caught up with us, by becoming simple, consumable, and socially ubiquitous enough that deep understanding simply isn’t required. Most people don’t understand why Netflix isn’t loading (or more importantly, why it’s not not loading), why their phone gets hot, or why some JPEGs look crappier than others. The products they use have just gotten better and better at making that knowledge unnecessary.

Is this how things get better?

I’ve thought about this a lot recently in the space I’ve worked in for a while now, which is information tools. In fact, for the last seven years or so, all I’ve really worked on is building, designing, and helping to sell tools designed to allow people to work with different kinds of relatively complex data. But in every place I do this, I run into the same problem — the vast majority of people (even paying customers) fail to use even fairly intuitive tools effectively to actually do anything. Many of them want to, and they often understand what the potential benefits would be if they were to figure it out. They simply get stuck as soon as they have to make a critical decision about how to use what we’ve handed them. And the fact is, most business productivity tools require you to make these kinds of choices, and most people are really bad at it.

Ezra Klein had a really interesting piece in Vox about a problem that I think is related to this — how technology has struggled to really change the way people work except on the margins, especially compared to how it’s changed the way people relax at home. If you’re waiting for a technology tool to make a paradigm-shifting difference in the way anyone other than highly technical specialists work, you’re going to be waiting for a while. That’s because (as has always been the case) most people simply aren’t that good at using most kinds of tools. For people who are, the right tool is amazing — but that number is often so small, you rarely see major social changes come from better tools alone.

(Notable exception : social tools, which don’t require high quality decision making to be used, or have a major impact in our lives. Actually, the fact that social tools are changing society even though most of us make poor decisions in how to use them is probably why we have such a mixed reaction to the post-social network world. But I digress.)

What about consumer behavior?

For the average person, I don’t think consumer interactions with technology are that much different from workplace interactions with it. The big difference is that:

  1. consumer technologies are designed to provide you with an end result — your favorite TV show, a constant, ample supply of laundry detergent, a ride to the airport, etc.
  2. professional technologies are designed to empower you to do something — share information, analyze data, make decisions, etc.

As I’ve indicated, my kind-of-cynical new theory is that radical improvements doesn’t come from empowered people; they come from technology eliminating the need for people to do something at all, so they can do other stuff instead.

So you don’t end up with better, smarter people. You just end up with the same people spending more of their time doing things they’re good at, or enjoy, and less time doing things they are terrible at.

For instance, hailing a cab is a pretty bad way to get a ride somewhere. If Uber was designed to enhance my ability to make cab-hailing decisions, it might be useful, but I don’t think it radically changes anything. Instead, it’s a big deal because anyone with the intelligence of a child can pull out a $50 piece of electronics, clumsily paw at a few pictures on a screen, and boom — they get a ride anywhere they want. That’s not improved, empowered cab-hailing; it’s the removal of cab-hailing from the list of things that people do.

Consumer internet technologies get this, and more importantly, consumers get it, because they are usually aware of their own laziness and incompetence, and are eager to mitigate it. Business technologies may or may not get this same principle, but businesses themselves — or at least the decision makers inside businesses — definitely don’t get it, probably because it goes against their self-interest. Consumers desperately want to remove as much effort and challenge from their life as possible; it’s in their interest, and it’s at no one’s expense for them to do so. Professionals want to do this too, but only to a degree, because most of them feel like if they were to completely eliminate one of their tasks, or a decision-making point, they’d be reducing their value to their organization. If I’m in charge of some critical accounting task at my company, and I find, test, purchase, and integrate a flawless accounting robot that does my task for me, I don’t get to stay on the payroll and go golfing. At many companies, I don’t even get promoted — I’m probably out of a job, especially if what I’m best at is doing the robot’s task.

Most professionals are not entrepreneurs (yet)

This artificial, self-interested inefficiency is a problem pretty much every organization larger than a couple of people has to deal with, and it’s such a normal, internalized part of professional culture that I don’t even think we really notice it anymore. We just say “big companies are different”, or “the enterprise has certain needs”, when 90% of what we really mean is that maximum efficiency runs counter to the best interests of the people who work at these companies, and anything you want those people to buy has to take that into consideration.

Of course, there’s one group of people whose interests are solely aligned with the efficiency of the company. Owners! When I showed my owner-operator friend how AdWords could handle many of the manual adjustments he was making automatically, he didn’t grumble, or get into a big argument about the value of human intelligence and intuition. You know what he said?

“This is great! I hate doing this, and now I don’t have to do it anymore!”

In most cases, you’re not going to hear that from middle managers, especially if they have vague, business-related titles, and even more especially if they have mortgages to pay. That’s a human problem that is going to continue to slow the pace of technological improvement in the workplace, especially since business technology vendors are smart enough to know it. That’s why so many of them tailor their offerings around it giving you lots of data, but not necessarily altering any of your work routines. Lots of dashboards, lots of analytics, lots of empowerment — and very little “we’ve simply removed this from the list of things you need to do”. No matter what inefficient, dumbass thing you want to do at work, there’s a piece of enterprise software that will help you do it with charts.

Now, there are also plenty of valid tactical reasons that get in the way of major technological change inside companies, too — security issues, regulatory hurdles, and the simple fact that it’s a lot riskier to screw with a revenue or customer-related business process than it is to screw with the way you watch Game of Thrones or order a pizza. But the human, psychological element really is enormous. Everywhere I go, I’m shocked by how hard it is for extremely intelligent people to feel comfortable with the idea of truly removing work from their daily routine.

(As an aside, in my experience it’s actually a bit easier to get the truly incompetent to buy into more aggressive technological change, because they’re less likely to make the connection between their irrelevance and their job security. They just think they have a job because they are awesome people. And that association with incompetence — the idea that you would only hand over your work to technology or process if you are stupid, or unacceptably, shamefully bad at doing it yourself — is yet another stigma technological improvement has to overcome in the workplace.)

Baby steps

There’s no easy answer to undoing untold years of professional insecurity inside our workplace culture. I wouldn’t even know where to begin inside of a large company, but in the startups I’ve worked at over the last couple of years, I’ve had some luck with leading by example and trying to demonstrate that you can be a great asset to a company and still be really bad at certain things. In fact, you can be bad at almost everything, but if you’re really good at finding cost-effective ways to eliminate the impact of those things on your company, you can actually be incredibly effective. (I probably won’t be putting that in my LinkedIn profile anytime soon.)

Of course, that’s not easy, or especially common. Instead, the situation I see most often is a very talented, knowledgeable professional who by their very two-handed, bipedal nature, cannot scale the same way an awesome system can. And while they often “get” the system, they remain hung up on things the system can’t do (usually edge cases and certain hyper-specific ways of reacting), while glossing over the much more damaging fact that compared to a system, they’re really freaking slow and mistake prone. That concern comes from a good place, but in a lot of operations work it’s ultimately limited. We’re not brewing artisanal coffee, here.

Anyways, I always try to be the opposite of that, and I express no shame at all. When channeled properly, a little laziness can be a powerful accelerant to productivity, because it keeps you from accepting the necessity of grunt work and pushes you to find better ways to get it done. But I’ve written about that before.

Confidence : Organic vs. Constructed

One of the truisms I’ve run into in life is that “confidence is king”. This is one of my least favorite truisms, because I’m a naturally skeptical person who very intentionally applies that skepticism to his own ideas.

But that personal inconvenience doesn’t change the fact that everywhere I go, confident people are winning arguments, making decisions, and driving the institutions I care about — whether that’s off to fame and glory or an obvious, avoidable cliff. People worry about whether leadership is “confident” all the time, but so far in my professional experience, I’ve never worked for a management team that didn’t clearly exude confidence. Despite this, not every venture I’ve been a part of has been successful, which goes to show that at least some of those confident people I’ve worked with and for were… well, they were wrong, and probably wrong about one or more pretty important things.

The obvious question, then, is “does misplaced confidence hurt”. Twelve years into my professional life, I’m ready to say “yes, it does”, although that’s not true in every circumstance I’ve dealt with. Here are some things I’ve found require confidence whether it’s warranted or not :

  • raising venture capital
  • selling expensive things
  • getting hired somewhere cool
  • copywriting
  • certain kinds of leadership
  • shooting three pointers
  • singing in a punk band

I’ve had various degrees of trouble with all of these things, and for the most part, I’ve only succeeded at them when events on the ground changed, and I felt better that my confidence was warranted. It’s no coincidence that my career opportunities have gotten demonstrably cooler and more exciting as I’ve gotten older and more experienced — it’s only now, after going through my different experiences that I feel legitimately confident in the judgements and opinions that jobs like mine require. I needed a lot of reps and to face a lot of different, unexpected scenarios in a lot of different capacities to get to the point where I can tell someone I work with that their career track isn’t a dead end, or that a process change is worth the embarassment of acknowledging it and the headaches of implementing it. I needed to shoot a whole lot of three pointers at the park before I came to the honest-to-God conclusion that it made sense for me to shoot them in games whenever I got open, and that getting open for such a shot was the best way for me to help my team.

organic confidence

In other words, I built confidence in these things by spending that rarest of currencies — time. I literally put years into organically resolving these doubts by going through experiences, making mistakes, assessing why they happened, and filing away my conclusions. As someone who isn’t inherently confident about much of anything, having this kind of experience-driven confidence is incredibly powerful. While it accumulates slowly and painfully, there comes a tipping point with all of these things (or at least there did for me) that’s simultaneously exhilarating and freeing, when you realize that you really do know what you’re doing, and can just take control of various situations where that’s the case. When you present an idea to a group of smart people, and your first thought isn’t “oh crap, these smart people are going to find the holes in my idea and I have to defend them”, but is instead “this is great, these smart people are going to ask awesome questions and I’m probably going to be able to come up with good answers because I understand this topic as well as anyone”, there’s nothing quite like it.

Organic confidence is a pretty rare commodity, because it requires a combination of at least some aptitude, and a fair amount of experience — and experience takes time. It’s hard to be organically confident about more than a couple things, which is why the list above of the confidences I’ve built up is actually pretty complete. I’m not very confident in the kitchen, arguing on the spot, dancing, navigating, doing anything other than very rough math, or taking binding action in any number of other common scenarios. Not that I’m done trying to get better — I’ve improved my kitchen confidence since our daughter was born and I’ve taken over breakfast and basic dinner duties — but these things all take reps and there have only been so many hours and legitimately educational experiences in my life so far. That’s not a personal failing, it’s just the result of a bunch of reasonable choices.

constructed confidence

If you’re impatient, or even in a hurry for a valid reason, there’s a shortcut towards effectively exuding confidence. You can construct it, through a combination of guessing, imitating, and discipline. Sometimes constructed confidence is almost as good as the real thing. I’ve seen people gain confidence in public speaking that’s taken them from being very poor public speakers, to average or above average ones simply through coaching and discipline, even if they are still pretty bad on stage, and don’t really know what they’re talking about. Sure, they’re still bad, but they’re a lot better than they would be if they didn’t exude confidence. Before I developed organic confidence in my ability to drive, my Dad taught me to drive with more confidence than I naturally felt, and while it didn’t make me a good driver, it at least made me functional enough to gain some experience and become one organically over time. To return to basketball, you can be a better offensive teammate and make the defense work a little harder simply by looking like you know what you’re doing.

So confident! So wrong.

So confident! So wrong.

I think many of the people who achieve really amazing things in this world rely on a mix of constructed and organic confidence when they deal with other people, and that they’re successful because they find the ideal mix of the two. They only make critical, risky decisions when they’re organically confident that they know what they’re talking about, and they use constructed confidence when cirumstances paint them into a corner they’re forced to address before they’re really ready. We have a tendency to look at Steve Jobs as a genius, or a total sociopath, but I think he was just really good at balancing these two forms of confidence, to the point where it was often hard to tell which kind he was even relying on for any given argument or decision. Other people aren’t so hard to read — if Jeff Bezos walking onto a big stage and assuredly describing the world-changing nature of a ridiculous Amazon phone that buys things you point at isn’t a textbook case of constructed confidence, I don’t know what is.

constructed confidence is everywhere, and it’s become corrosive

I suppose a grosser analogy is to think of constructed confidence as the filler in the meat of organic confidence. Yes, you can stretch a limited resource in a useful way with judicious usage of filler, but the filler itself is pretty useless, and if you rely on it too much, you’re not really eating meat anymore. And that’s where we are with way, way too many people. If you know the usual axes I like to grind, you won’t be surprised that I think this has a lot to do with two things.

The first one is the pressure cooker we raise kids in today, and the pointless, surface level measurements we use to validate them. We probably should have seen this coming — the more your ranking relative to other people matters (college, internships, jobs, etc.), the more younger people are expected to gain competence (and by extension, exude confidence) in things with unrealistically low levels of experience. For all but a select few geniuses, it’s literally impossible to develop that kind of organic confidence so quickly and so completely, so it shouldn’t come as any surprise that college students and young professionals take the obvious, necessary shortcut of constructing it instead. Heck, we often coach them to do this. Then, since they’re already supposed to be experts at whatever they’ve sold themselves as, they’re under even MORE pressure to appear even MORE competent and MORE confident each and every day. That doesn’t leave a lot of time for learning anything, and it puts a lot of talented people in positions to fail very, very badly.

The second reason constructed confidence is so common is the almost child-like level of impatience we have with the progress of doing anything, including the fairly important act of making money through old-fashioned, non-financial-shenanigan value creation. At the simplest level, a business or a company makes money because it’s good at doing something — landscaping, building software, tutoring, manufacturing tiny metal objects, whatever. The fact that you have the great idea to manufacture tiny metal objects is nice (you probably had to read the market correctly and assess why it would be a good thing to do), but it doesn’t really matter if you suck at manufacturing tiny metal objects.

Unfortunately, doing almost anything well is complicated, and usually takes a combination of practice and mistake-making. That’s true if you’re a cop, or a cook, or a professor, or a chemical engineer, or just some mid-level business guy like me. If you don’t put the time in (and it’s a lot of time, and no, what you did in college probably doesn’t really count towards it because college is a giant laboratory monitored by professional evaluators), it takes an extraordinarily long, self-immolating process to get good at something, determine why you’re good at it, and eventually develop the organic confidence that comes from surviving the whole ordeal.

“Pressure makes diamonds.” Except, no, it doesn’t. Pressure and time make diamonds.

There’s plenty of pressure out there — but not a whole lot of time. So yes, “successful” people increasingly fake it, often because they’re encouraged to fake it, or directly coached to fake it. That leads to unforced errors, nervous breakdowns, and a never ending “confidence-war” among ambitious, insecure professionals that continually raises the stakes and values perception and alpha-dog posturing over skills and sound decision making.

yet another shortcut

Ultimately, the problem with constructed confidence is that it’s a quick fix for the wrong problem; a sugar rush of self-importance that anyone can generate but no one can sustain in a real-world environment without it eventually blowing up in their face, and the face of anyone relying on them. Maybe, if all you want to do is glorified consulting or public speaking, you might be able to float from one encounter to the next, confidently declaring things and moving on before your lack of battle-tested knowledge becomes apparent. But if you want to work with other people, or build something significant? The best outcome for using constructed confidence there is that you get through a situation you’re not prepared for and back to a core competency as quickly as possible — and then you figure out how to avoid that situation again in the future. It’s horrifying to me when a friend or colleague gets through some encounter they have no real qualifications for with nothing but bluster and bravado, and comes out the other side somehow more confident about their abilities, as if they’ve gone through some kind of crucible by successfully feigning expertise. Going to a bunch of meetups and hanging out with engineers doesn’t make you a developer. In my case, fumbling through Learn Python The Hard Way and never actually building anything other than a bunch of if-then-loop powered fart jokes than run in the console doesn’t do it either.

I am not confident in my carpentry/engineering skills. But that didn't stop me from building this pointless box and getting the tiniest bit less incompetent.

I am not confident in my carpentry/engineering skills. But that didn’t stop me from building this pointless box and getting the tiniest bit less incompetent.

But hey, it’s okay to be bad at some things, and it’s more than okay to recognize that and control your exposure to said things. You can even try them out in safe environments where outcomes don’t matter, like I do with programming. Go to open mic nights and bang on your guitar, or tell jokes, or present a pitch deck to other nerds. Get into an argument about finance with someone more qualified than you at a party, and see if anything you say actually holds up under scrutiny. If it doesn’t, ask questions and try to find out where you’re wrong. You might even get better at these things, and — over time — build up real confidence in your abilities that you can break out in real situations with real stakes.

But don’t use important situations to test out your “expert” poker face, even if you see other people doing it, and being rewarded for it. Sure, your peers may get promoted ahead of you for a while, or get media mentions, or become “thought leaders” in fields you know more about. Those people never do anything that really matters, though — because they don’t actually know how to do anything. And in the end, knowing how to do whatever it is you do really well is the most valuable, stable thing you can buy with that all-too-rare currency of your own time.

Parents with Great Jobs

“This is my daughter.”

I keep saying that as often as I can because it doesn’t seem possible. But since Sunday morning, it’s been undeniably true — this little freaking person lives in my house and loves me and my wife more than anyone in the entire world.

There’s a playbook for having a kid when you’re someone like me; a.k.a., a college educated white guy professional in his early-mid thirties. Not everyone follows it, but a lot of people do — having a child changes the way you see everything, puts your high powered career into perspective, and makes you add “Dad” to your Twitter profile. If you have a daughter, you ocassionally blog about Gamergate and say “I have a daughter” and people tell you how brave you are.

Maybe, like a lot of things, that playbook is just public-facing nonsense and nobody’s being honest. Or maybe people really do act so predictably in response to something that most people go through at similar points in their life. I have no idea, and honestly, I’m not particularly interested in finding out. What I do know is that so far, being a parent has been small, incredible moments surrounded by a mix of boredom, guilt, and a strong motivation to care about things you’ve never been able to before. Again… it’s been two days. I’m going to let it breathe for a while.

Parenting and My Job

My situation is unique for a lot of reasons, but the most interesting one is that my employer has a wildly progressive parental leave policy that allows me to stay at home with my new baby for an extended period of time. This is simultaneously a very small amount of time in the life of a growing person, and an enormous amount of time in the life of a busy, rapidly growing company (which is what we are). That puts me in the weird position of feeling like I am both entitled to every minute of singing and rocking and napping with my little girl, and impossibly negligent when it comes to doing something I am really, truly passionate about — building a great company and revolutionizing an industry.

If you know me, and my endearing, often cynical brand of gallows humor, you’re probably waiting for the punchline here. But there isn’t one. I really feel this way about what I’m doing, and as a result, for the first time in my life I think I really understand the challenge some people face in making family their top priority. That reality hit me in the face when I came down the stairs on Saturday morning to work on some dumb slides for work (okay, they aren’t dumb, they’re actually really cool, and I’m saying that without a trace of irony). I only had about a week until my wife’s due date, but my colleagues and I had a pretty good plan for wrapping up a few things and getting both my team and the teams we work closely with on a great path for the next few months.

“Hey!” my wife said, as I scrounged around the living room looking for my laptop. “Wanna have a baby today?”

Wait, what?

So of course, everything blew up in high-speed slow motion. I worked on my dumb slides (again, not really dumb) in between contractions, typing the same sentence over and over again before realizing I wasn’t getting anywhere, and watching The Goonies until labor starting getting serious. We had our kid at home (which was an amazing process, I could write a whole post about our midwife team), so we pretty quickly transitioned from “casual Saturday” to “AHHHHHHH!!!!” before I really knew what hit me. And while I have a million very typical “new Dad” thoughts on the whole thing, the weirdest thing is probably how much I thought about work. Not about some form I had to fill out or anything, but about my actual purpose there, and how real the cost of my departure was going to be to the things I was trying to do, and to at least some degree, the things that people I work with are trying to do.

The fact that this cost exists is not a bad thing. Who wants a job where their departure doesn’t matter? What does that say about what you do all day? But if you care about what you do and the people you do it with, that doesn’t make acknowledging the cost any easier, and the fact that you love your new little kid (someone you barely know, but immediately know really well, which is very weird) doesn’t make that cost go away. It just makes you think “this enormous cost is worth it”, which is the kind of thing I associate with buying a new roof, or maxing out the RAM in my laptop, not using my amazing parental benefits.

an honest acknowledgement of a real cost

When I first found out about the benefits at FiscalNote, my first thought was “how can they do this?” After really diving in there for the last six months, and taking just three days of those benefits, I now totally understand it. Having a family has an enormous personal and professional cost, for an enormous personal gain, and a very nebulous professional one. It’s not some magic, everyone-wins scenario where my company benefits from me being gone for months at a critical time in its growth. It’s just the acknowledgment of the truth — a lot of people you’re going to want to have at your company are going to want to have families, and having them take a measly couple of days off for the birth of a child like they’re taking a vacation to the Jersey Shore instead of bringing a brand new human into the world doesn’t reduce the cost of the endeavor. It just hides it, or offloads it onto your employees marriages, creativity, mental health, or some other finite personal resource that, once depleted, has a high risk of destroying them as a professional and a team member. Sure, you can expect Mom and Dad to be back at their desks and passionately arguing for their choice of action at the next product development meeting, but you can’t expect the emotional and intellectual cost of doing so to evaporate simply because you’ve determined that you don’t want to pay it. Employees are people. People want families. Families take a lot out of people. The math is pretty straightforward.

So yes, I desperately want to be here for my daughter, and I absolutely, 100% want to go into the office tomorrow. What can I say? It’s on me to reconcile those things. It’s on my company to give me the opportunity to do so, and in my case (unlike with most jobs) that’s exactly what they’ve done. I’ll never forget that I had this opportunity, not because I think it’s a gift or a bribe that shouldn’t exist, but because it takes a lot of faith in your people and your business to acknowledge real costs of life and allow your team to pay them.

I’m paying them now, and trust me, it’s expensive. Expensive, and hilarious, and enlightening, and wonderful.  

(… and by the way, there’s something extra validating about a company that supports things like this also enabling its newest Dad to get off to a great start with his daughter. Warrants mentioning.)

The Proper Work Metaphor

junior varsity disclaimer

Since I’m about to extol the benefits of sports (or at least some of the thinking behind them), I should probably clear up a few things. While I’ve always loved sports, I am not an especially good athlete, and never have been. I was an abjectly terrible baseball player who quit Little League once it started becoming clear that how well you played baseball had very little to do with how much you loved baseball (so about 11 or 12). From there I floated around, playing pickup basketball and football with normal kids, until at 16, I managed to carve out a spot at the end of the bench on my high school basketball team.

That’s it. By any measure, I’ve always been better at school than sports (which isn’t saying much, but still), so it’s not like I’m some jaded meathead pining for the days when I could solve my problems by shoving someone into a locker. I was much closer to being the one getting shoved.

But the fact is that I’ve learned a whole lot from sports, particularly as an adult without any of the social or identity pressures that come from playing on a team as a kid. And as I get older, the number of problems I’m able to solve by thinking like an athlete seems to grow, while the number of problems I’m able to solve by thinking like a student — even a good one — keeps shrinking.

Here I am, solving problems with my awesome band of basketball misfits. 

what’s wrong with the student mentality

I’m of a certain generation of people who grew up in an interesting time. I’ll spare you the navel-gazing “old millennial” think-piece, but the long and short of it is that a lot of the “alarming trends” that affect people coming out of college these days started to gestate back when I was that age. For instance, when I was in high school, things weren’t nearly as competitive and Hunger-Games-y as they appear to be now. I was a pretty lazy high school student who generally stayed out of trouble and got by largely by drawing my teachers attention to things I was already good at, and simply gritting my way through terrible grades in things like Physics and Calculus (I was inexplicably in the smart-kid versions of both of those). I wasn’t cutting class or smoking cigarettes in the parking lot or anything, but I basically did everything at the last minute and tried to avoid doing work whenever possible. I also assumed I’d get into a decent college — if I couldn’t afford whatever would let me in, I had good enough grades and test scores to go to the University of Rhode Island for basically nothing, which seemed like a really good idea to 17-year old me.

Anyways, this is all besides the point, other than that while I was skating through high school reading ahead in American History while literally losing my Chemistry book, something else was happening. People were panicking about their own futures. Not just kids who desperately needed scholarship money, or who needed to stay close to home to help a sick relative or something. Regular old upper-middle-class kids, freaking out about whether we had enough AP classes, or how many valedictorians we’d allow if fifteen different students ended up with perfect GPAs. By my junior year or so, I was actually encountering situations where individual students — mainstream, popular ones — were more motivated by their own academic performance than they were the social well-being of the group. They wanted the class to be hard, and they wanted people to know it was hard. They cared about (and worried about) our high school’s academic reputation, which seemed absolutely ludicrous to me; I was much more animated about, say, whether we’d get to go outside for Physics lab. Obviously, this kind of thing rolled right on into college and got significantly darker, as I watched people cheat on exams, commit blatant acts of plagiarism, and increasingly look out for number one as they prepared for whatever prestigious environment was next on their life agenda.

Looking back, I guess that behavior makes sense, given the way this works. None of these social institutions were permanent — that simply didn’t occur to me as an immature goofball of a kid who grew up in a small town and went to school with the same people for my entire childhood. I valued the “community” I was familiar with, (could we get the teacher to skip this book if we stalled them long enough?) while my more mature classmates knew our social ties would be meaningless at the next level, and thus were prepared to cast them aside for their own benefit if necessary.

My understanding is that this kind of thing is no longer the exception, and is more of the rule. College is more competitive, internships are currency, and entry-level candidates are expected to have resumes you can critically evaluate, which seems absurd to me. But hey, I don’t make the rules, and if that’s the way it is, it’s hard to blame kids for hoarding their professional chips. Sometimes that takes the form of the morally dubious things I witnessed in college, but more often it’s simply a mindset that develops that doesn’t prioritize group success at the expense of things that end up on your personal list of achievements.

So keeping that in mind, follow the professional development track from infancy to entry-level employee.

  1. compete to get into preschool
  2. compete to get into gifted programs/travel teams/camps
  3. compete to build a college resume
  4. compete to build an undergraduate resume
  5. compete for internships
  6. maybe keep doing this for graduate school if you like debt
  7. compete to get hired

All these steps have two things in common — one, they’re all about you; specifically preparing you for something more important. Two, they’re all disposable environments that only exist to determine your next environment. That’s fine (if a little cynical) for places that exist to serve your needs, like school, or your expensive university. But it’s less fine if the place you’re using to build yourself up is simultaneously trying to use you to build itself up, which is — hello! — what actual for-profit institutions do.

And so you run into the problem with the academic model. It’s entirely about the individual, and presumes that the environment is disposable.

why the team sports mentality is better

Now, don’t get me wrong. Helicopter parenting and insane soccer coaches and all that have done their best to turn sports into the same worthless college-prep exercise that school is for many kids. But in general, teams are a much more difficult environment to be truly selfish in, and often map to the challenges of everyday professional business a lot better than school does. While some professions (pure research, and certain transactional activities like sales or trading) map perfectly to individual performance, most do not. In many cases, smart, inexperienced workers are asked to go from a world in which their own performance and skill determines success, to a world in which their only hope is to improve the performance of someone else by any means necessary. While this is baffling and weird to a lot of great students, it’s painfully obvious to anyone who’s ever needed someone to grab a rebound, or hold off the approaching defensive end for another two seconds while the tight end goes down the seam.

In other words, one of the most important lessons in life is that you can’t do everything yourself, and that truly great accomplishments in life can often only be done by enlisting and facilitating the help of someone who is better at something than you are. If you’re an artist, or a dictator, or genius, it’s possible to live a very large portion of your life without figuring this out. If you’re a point guard, you probably learned this before you hit puberty.

constructive failure

There’s another great lesson from team sports that I’ve found extremely useful at work, and that’s the concept of constructive failure. I’ve been on a lot of terrible teams, and part of a lot of broken plays where someone essential either forgets to do their job, or is incapable of doing it. What then? When you’re working alone, the most efficient solution is simply to stop executing incorrectly, and if all you ever do is work alone, pretty soon that’s going to become your preferred method of problem solving. That’s why Type-A managers who aren’t creative problem solvers often see poor performance on their team and think “this person is a poor performer”, or “how can I change this person”, instead of thinking about ways to restructure the environment or the system to make that person a part of something that works. That’s not to say certain people don’t need to change, or can’t be unacceptably bad at something critically important. It’s just that many individual-oriented managers tend to default to that assessment, which doesn’t leave you with a ton of options. 

When you’re on a team with a broken component, it’s amazing how creative you can get when it comes to solving problems. My beloved Boston Celtics dominated basketball and won a title in 2008 with two guys who couldn’t shoot by giving them creative roles that maximized what they were good at, and actively facilitated shots for the other three. The guys who couldn’t shoot didn’t see themselves as ineffective basketball players — they saw themselves as essential parts of a larger process that required them to excel at their specialties in the context of a team offense. The longer I play on adult rec teams, the more my thinking has shifted from “what am I good at” to “what can I do to make this team better”, not out of some virtuous elder wisdom, but because winning is fun and causing winning by being smart and observant and building up other people is even more fun. When we didn’t have any guards, I started bringing the ball up. When we didn’t have any size, I started throwing my weight around in the paint. Even professional sports reinforce this kind of subsuming of ego with great examples every day. Watch Stephen Curry hit shots from the locker room tunnel, and still make the right pass out of a double team every single time. Watch the San Antonio Spurs do literally anything.

It’s easy to watch this and think “oh, all these guys are high performers”, but they’re all wildly different players who are all actually terrible at variety of important basketball-things. But the system they’ve built stresses what they’re good at, minimizes what they’re bad at, and as a result generates incredible, impossible looking results. It’s wonderful, and the Spurs continue to re-invent themselves every year as necessary. The idea that their coach, Gregg Popovich, may be the greatest coach of all time is not crazy. 

this is learned behavior, and you have to get good at it

Unselfishness is a lot more complicated than simply not being a jerk, or caring more about the outcome of something larger than yourself. It’s understanding, and coming to terms with the power of putting aside your own abilities, and sometimes your own judgment, and making the leveraging of that power as natural as breathing or waving to a co-worker in the parking lot. It’s about seeking out skill and potential you realize you may be able to unlock, and seizing that opportunity with the same or greater excitement than you would the opportunity to excel yourself. It’s not necessarily about “deferring” — it’s about getting excited to make a block that frees the runner, or more aptly, to make the pass that leads to the pass that leads to a better shot. When you love doing that, and go to sleep smiling after your games because of it, you know you’re in a good place as a teammate.

Very few people operate this way right out of the gate. I sure as hell didn’t, and I’m not even particularly good at anything — I’m just yet another irrational lunatic who gets nervous sitting on a plane because I’m not actually controlling the plane. But you can start learning how to think this way at any point just by trying. If you’re lucky enough to work in an environment with a lot of talent waiting to be channeled (like I have been at many spots in my career), it’s almost impossible to not notice the results. 

Let’s Talk About $$$

I’ve been meaning to write about how people in my kind of work get paid for a while, but it’s a tricky thing to talk about in any kind of publicly consumable form. That’s because people — even myself, regrettably — can get incredibly sensitive about how they and their co-workers are compensated. So let’s get a few things out of the way, for the sake of everyone’s emotional health.

1) I really like my current job, and I think I get paid a fair amount, based on my admittedly limited knowledge of the job market. I also like the way my company has handled talking to me about my pay, benefits, and everything else. So this isn’t any kind of reaction to my daily events — I’ve been meaning to write about this for literally years, but it’s a thorny topic and I’ve always wanted to get it right.

2) The only job I ever actually left over money was my first — in 2005, I got a job offer as a technical writer, which was a huge improvement from the peanuts I was making out of school as an support/email monkey. When I told them I had another offer, my department head at the time took me out for a sandwich and asked me if it was an offer they could match. I told him what it was, and he said “good luck, it was nice working with you.” Other than that, I’ve been fortunate enough to be able to pick my jobs based largely on opportunity over money (partially because my wife also works, and we haven’t had any mouths to feed).

Anyways, now that we’ve got that out in the open, let’s get started.

Three approaches to $$$

It's actually kind of amazing anyone was willing to pay 22-year old me $12.20 an hour in 2004, to be honest. It’s actually kind of amazing anyone was willing to pay 22-year old me $12.20 an hour in 2004, to be honest.

In my experience, there are three kinds of emotional/logical impacts salaries and money can have on people. Here they are, in order of complexity and general weirdness.

$$$ as a need

I don’t know if you’re aware of this, but you do need some amount of money to survive. Technically, you can probably survive without any money at all, but it’s very complicated — in general, there’s a certain income level most people need to be at in order to live normal, healthy lives, especially if they want to avoid constantly borrowing against their future. I haven’t had to make decisions based on this perception of money very often, but I’ve definitely been there.

When we lived in Cleveland, I had friends who thought I had a lot of money just because I didn’t take out payday loans or buy things on installment plans (instead, I bought almost nothing). But to me, barely being able to pay your rent without borrowing money from someone else qualifies as an appropriate time to start thinking about income as a need. When that happened to us, we left Cleveland for greener pastures (an option not everyone has) soon after.

$$$ as a resource

Most “regular” people (ahem) who are doing pretty well in the 21st century economy — i.e., usually college educated or at least highly skilled, in some kind of growth industry — don’t have to make money decisions based solely on survival. Instead, money is more of a tool or a resource that allows them to do things they want to do. Buy a house, have a family, take a trip, get a dog, watch movies on a big TV, play the piano, whatever. Everyone knows at least one person who’s taken a job they hate in order to get enough resources to do something outside of work they love, but in my experience most people regret it unless it’s extremely temporary.

I got the biggest raise I’ve ever gotten in my life in 2011, when I got another offer and considered leaving Bamboo. I didn’t need the money in order to pay my rent or anything, but it did allow my wife to work on her fledgling business without us reverting to Cleveland-style “don’t spend any money” mode, which was a huge improvement to the quality of our daily life.

$$$ as a scoreboard (eww…)

Now, where things get really weird and complicated is when people start thinking about money as something other than compensation — an indicator of how much people value (or should value) their opinion or judgment, how much authority they have to direct other people’s work, or how much responsibility they should bear for any problems the organization is having. This is why salary disclosure is such a minefield (it’s not necessarily bad, just complicated) for all but the most radically-transparent organizations — and why handling compensation on a strictly employee-by-employee basis can result in so many problems down the road.

I’ve never turned down more money from an employer (unless I was leaving altogether, which I guess counts), but I’ve also been very judicious in how tightly I tried to turn the screws in the few instances where I had a lot of leverage and was trying to get a raise for whatever reason. Part of this is just the way I’m wired, and some of it has to do with the fact that my work is often very deliverable based, so I usually have a really good sense of whether people value what I’m doing. When I’m outperforming my salary, I can usually tell. That’s probably not true for people wedged into some kind of byzantine, managerial structure where you’re not sure exactly what anyone does. I have plenty of friends in the latter situation, and a lot of them make more money than I do — but they’re also more frequently worried about whether they’re properly credited for success, or if they’re missing out on a potential opportunity for a raise. Since their value is hard to measure or even witness directly, it’s often determined by the dreaded “optics”, or how valuable they look. The sad truth of the allegedly efficient private sector is that many people make a lot of money simply because they’ve made a lot of money before, which creates an unhealthy incentive to “get there” as quickly as possible, by whatever means necessary. This usually doesn’t end well, and even with well-intentioned people frequently leads to insecure people with vague authority running around trying to be tangentially involved in lots of things so they look and feel productive.

Side note — one of the fun parts about being any kind of technical person is that you can often break this informal structure (the kind of thing various people I’ve worked with have referred to as “the game” or something similarly creepy and rich-person-sounding), and it drives people who depend on it absolutely crazy. I think that’s why so many executives and investor people are obsessed with figuring out a way to control how much software developers get paid — you can lecture those guys all you want about the value of different business units, or quote some book about organizational structure to them that dictates why they should do what you say, but at the end of the day, the person who knows how to build stuff have all the cards. Do you want this database to work or not? If you’re so smart, and I’m so dumb, why don’t you do it? Professional suits can pull this with work like pointless reports, boring PowerPoint decks, or other things everyone/no one is actually good at. But they can’t fake technical skills, and that doesn’t change no matter how much anyone gets paid.

My approach

I don’t think anybody — at least anybody I know — is completely above any of these motivations; we’re just all on different parts of the spectrum for each. Once I got settled in D.C. in my mid-20s and got a little momentum going, I went several years without thinking about my salary as meeting some kind of survival-themed need until we started doing the math about having a kid. Just like that, it was 2006 again, and I was biting my nails thinking about whether I could afford to go to Subway when I already went last week. I didn’t leave Contactually for a bigger salary, but the simple fact is that the (admittedly complex) insurance math that resulted had a non-trivial impact on my decision to join FiscalNote.

As for the “salary as a signaling device” thing… well, left to my own devices, I’ve never been especially curious about how much people get paid. What I need is pretty much exclusively between me, my boss, my wife, the mortgage processing guy, and maybe the guy behind the counter at Guitar Center when things are going well. But the fact is, a real-world office environment never really leaves someone like me to my own devices. The company has bad quarters, or someone underperforms, or somebody gets a big raise and then starts walking around like they’re Lumburgh from Office Space, and people start asking questions. Eventually, some number starts floating around — whether it’s accurate or not — and it’s hard for people with hopes, dreams, or actual financial responsibilities to keep from wondering if they’re being stupid for leaving money on the table. That’s the feeling you really want to make sure your employees don’t get.

I’m not sure exactly how you prevent it, but a lot of the best practices I hear out there are good places to start. Don’t hire people for the smallest amount you can get them at — pay a market rate as soon as possible. Try give people consistent small raises, instead of putting out fires by dumping big promotions on people who you’re suddenly worried about losing. Be careful just throwing around big titles to make less experienced employees happy in the short-term (especially when you can’t pay them enough), or you can end up with a company full of people who think they’re in charge of each other. Create real, time & achievement-based paths to advancement for people (think quantitatively and qualitatively), and make sticking to them an actual, operational priority. Remember that employment is a two-way street, and that employees who are also responsible, adult citizens are obligated to look out for themselves in ways that won’t always align with what your company needs right now — and don’t take it personally.

There’s also a generational component to compensation and promotion that I’m not sure even a lot of people my age (early/mid 30s) are able to fully comprehend. Remember, outside of government, careers are often constant works-in-progress. The days of digging a nice little cave in Accounts Payable and living in a big house in the suburbs are over — now, if you’re not moving, you’re dead. And while people pay lip service to this realization (often while clinging to one of these old school careers and complaining about young people), today’s 20-somethings are living it. Most of the professionally skilled ones are highly educated, and more-importantly, come from a world where some kind of performance — and acknowledgement of that performance — is the currency of their lives. In general, the young white-collar professionals I’ve worked with see their first job as a direct extension of their super-competitive college experience, where things are broken up into semester-length goals, and most importantly, there’s a clear path to advancement where not advancing is failure. That’s how school works, remember? I never really thought about things this way — I enjoyed high school, but never thought it was very good way to evaluate people, and I outright despised everything about the culture at my faux-elite private university. For me, joining the working world was exciting because I got to escape constant, often-arbitrary quantitative evaluation (getting a numeric grade for a written paper always made me crazy) and return to the more nuanced world of everyday professionalism. That’s not how a lot of kids are wired now, but it shouldn’t surprise anybody — we wired them that way so they’d get into these schools and these achievement/reward cultures in the first place.

Don’t blame people for being rational

Like a lot of things, I think the most useful quality in dealing with compensation is real, honest-to-God empathy — it’s the only way to figure out which of these various perspectives on money is currently driving a given employee, and respond to them with something that makes sense. If someone is freaked out that their career is stagnating, it’s important to be able to tell the difference between someone who’s dealing with a necessary ego correction, and someone who is legitimately scared they aren’t going to be able to survive the increasingly real pressures of the 21st century without making a career change. It’s easy to tell a 25 year old that “everything is going to be fine” when you’re the one who has the most control over that possibility. Do you know how much your employees pay for rent? Do you know what their student loan situation is like? If their parents are counting on them for support? You don’t necessarily need NUMBERS for these things (that seems a little too prying for my taste, and is probably an HR violation of some kind, anyways), but if you don’t know the relative impact of them on someone’s life, it’s easy to misinterpret why someone wants to get paid.

Besides, remember the last time you got a raise that changed the way you felt about your career? I sure do. Don’t forget how important that feeling is to people to who haven’t experienced it in a while. Or ever.