Debates vs. Discussions

While I wouldn’t say I “avoid” writing about politics on this site, it’s definitely true that I try to focus on other things. This is mostly because there’s already so much good political writing from so many interesting perspectives, and there’s not a ton of value I can add. It’s also because I care a lot about civics and political thinking, and went to school for it, so just spouting off without putting in sufficient time to read and analyze the things I’m reacting to seems unproductive.

Still, for a lot of different reasons (splits in popular culture, fewer mass-experiences, etc.) , our political culture seems increasingly influential at a time where it also seems like an increasingly bad influence. People have been pointing this out for literally years — see Jon Stewart’s famous Crossfire appearance more than a decade ago — but it seems like The Game Show Host President has really pushed things over the edge (or at least pushed these trends into the mainstream), and many of our worst political tendencies are finding their way into our daily interactions.

There are a lot of these tendencies I could cover here, but I’m going to focus on one in particular that has major potential impact on organizations outside of politics and policy — the conflating of debates and discussions.


Debates can be a lot of fun, because they’re a combination of two things Americans love — ideas, and winning. I’m not going to use real debate terminology here (because I don’t know what it is), but for the purposes of what I’m talking about, let’s define a debate thusly :

  • in a debate, each position is represented by an advocate
  • each advocate attempts to convincingly prove that they are absolutely correct, and that their opponent is absolutely incorrect, at least when it comes any conflicts with their own position
  • there is some third party (judges, an audience, voters, whatever) that is going to ultimately pick a winner and a loser (or losers)

When I was a little kid, a lot of adults I looked up to told me that I would enjoy formal debates, probably because I was constantly arguing with them in ways that were only somewhat compelling but extremely entertaining. I even participated in a debate once (just once) in high school and thought it was kind of cool. However, debates actually have extremely limited utility in real life, because many of the key properties of debates I listed above don’t exist in realistic scenarios.

For instance, in real life :

  • the best answer is often represented by no side at all, often because it hasn’t occurred to anyone yet
  • almost every position has flaws, and a lot of bad ideas have interesting elements in them that can be used to solve flaws in better overall positions
  • there is often no third party to validate a position, or the third party is unqualified to do so

There’s a perfectly valid place for pure debates. It’s when you’re down to a few fixed courses of action (often some kind of specific tactic), and a bunch of people have to agree on which one to commit to. Once everyone understands the options and agrees on what they actually are, it can be very constructive to have an advocate for each (it’s even better if they actually believe in the stance), and hash it out for the rest of the group. When my high school punk rock band started taking songwriting (somewhat) seriously, we had lots of useful debates on things. Did this song need a third chorus, or was it too repetitive? Good, honest debates don’t necessarily drive consensus, but at least they get people to a point where they agree on what they don’t agree on, and everyone gets to hear the best story for each option. This is much better than having to do something you don’t like, and don’t even properly understand.


A much more common form of arguing/advocating in the discussion, which is much less emotionally satisfying for competitive people, because you can’t really “win” no matter how clever or well-prepared you are. Discussions occur (again, I’m making all these definitions up, so bear with me) when a bunch of people have to figure out what the right thing to do is, but don’t have a finite list of options they are trying to choose between. People have opinions and biases for sure, but they are often ideological, or directional, and very few if any of them have gone all the way down the rabbit hole to determine an operational plan with costs, benefits, and impacts on everyone. The group is having a discussion to figure out how to solve a problem, and that problem is emphatically NOT “which of these several options should we take”. If you think it is, you’re preparing for a debate, and you’re going to have trouble contributing positively to a discussion.

In punk band terms, our discussions weren’t about making final decisions like our debates; (often choosing between two unpleasant options) they were about figuring out what our next options could actually be. When those discussions felt like debates, it was usually because one of us thought they knew what someone else was getting at, and didn’t like it. These were… not our most productive discussions.

In politics, there seem to be fewer and fewer visible discussions, and even the few we have are framed as “negotiations”, which in practice appears to be largely a debate between various red lines parties really, really don’t want to cross — but might, in the right scenario. Again, that’s not really a discussion.

too many debates, not enough discussions

As mentioned earlier, debates are an emotionally satisfying form of collaboration for people brought up on winning and demonstrable excellence. Unfortunately, they’re only truly useful in a small number of situations, so most of the debates I’m either forced to witness or — God forbid — take part in are pointless. The advocates are primarily there to win approval of a certain position, not explore options or the validity of their own position, so various tactics that improve the odds of winning while making the overall environment more confusing and less productive tend to creep into the room. Some common ones I roll my eyes at :

  • apples versus oranges — defining the definitions used in the discussion based on the debate you want to have, and then forcing every option into that framework (even if it makes no sense) because you’re ready to argue on that turf
  • not relevant — setting boundaries for the discussion that extend to fit around your position, but not necessarily other positions, so you can dismiss flaws to your position (or positives to another) as irrelevant to the current discussion
  • projection — telling other people what they think, so you can turn an actual person’s position into (at best) a proper debate partner, or (at worst) a straw man you’re excited to beat up with your preferred position
  • axe grinding / redirection — undercutting a useful path an open-ended discussion takes as it becomes apparent your pre-established position is not a viable solution to the newly identified challenge (“… BUT HER EMAILS!!!”)

Again, these unhelpful actions are not necessarily a result of someone having a bad idea or weak position; it’s a result of them insisting on having a certain position when the group simply isn’t ready for one yet. The fact that Ted Cruz loves formal debating (and is, from what I understand, extremely good at it) and the fact that everyone in the Senate from both parties actively resents him and wishes he would go away is probably not a total coincidence; he brings an insistence on debates to things that should be discussions, and it’s entirely possible that someone like Cruz is great with debates (which are rare in actual legislating) and terrible at discussions (which are a key component of legislating).

fight to protect the properties of a good discussion

Professionally, people have often mistaken my refusal to take a debate position on some workplace question as a lack of interest in the subject. This is usually wrong; most of the things I truly don’t care about don’t get brought to my desk, and when one of them is, my lack of interest is usually really obvious. For everything else, what I’m really trying to do is protect the integrity of a real, live discussion designed to fix the problem. If I immediately become an advocate for a particular solution, it’s possible — probable, even — that I will do so before I have sufficient understanding of the issue and its impact on everyone else at work. After all, we have entire teams dedicated to very different challenges than mine (engineering, product, sales, support, finance, etc.). How could that not be true?

When there’s a problem that affects everyone, and I’m tasked with solving it, I’m a strong believer that setting up the frame for a proper discussion with everyone is the most useful thing I can do. Often, in doing so, it’s useful to build a theoretical stance that would make sense in the framework I’m suggesting, and when that’s the case, I’ll do it. But — and this is really, really important — you can’t lose sight of the fact that your stance is secondary to that discussion framework. You absolutely have to be ready to throw your stance in the garbage if your open discussion reveals that your stance is not inherently dumb, but simply the wrong type of stance for the actual problem you’ve uncovered. This is something that I’ve had to work really hard to get better at over the last ten years or so, but it’s led to most of the best professional decisions I’ve helped organizations come to.

As Long As I’ve Got My Suit and Tie, I’m Going to Leave It Out On The Floor Tonight

I’ve never been very good at dressing up. My roots are in technical tinkering and the creative arts, with a healthy dose of New England punk rock (and think New Hampshire, not New York), so maintaining appearances was never interesting or natural to me. As a kid, I agonized over even basic, semi-formal requirements for things like school dances, performances, or graduations — never mind things like weddings.

This remained fine as I grew up, primarily because I went into tech instead of my other potential destination, journalism (or, God forbid, law). I interned as a clueless D.C. journalist in the fall of 2002 and enjoyed a lot of what I got to do, but still found myself jealous of the CSPAN cameramen who got to play with cooler equipment and dress like AV guys while I poked at the itchy collar on my shirt and my uncomfortable shoes. So when I started my career at a mid-stage Boston tech startup in 2004 and discovered that they cared a lot more about how fast I could format press releases and assuage customer concerns over the phone than whether I could tie a tie, I knew I had a path.

From then on, nothing brought me any closer to formalwear. Support, technical writing, product management, and eventually product marketing required me to be increasingly strategic, but not sartorially impressive, especially since I worked for bosses who understood my value and trusted my ideas and execution skills, but usually handled dealing with customers and company brass themselves.

As a result of all this, when I found myself running FiscalNote’s marketing team this fall, I suddenly found myself in the unexpected position of representing our company and our function at an executive level — even if somewhat by default. While in the past I had never felt any real internal pressure to figure out how to fit in with the suit and tie crowd, this seemed different. My company had given me a chance to step up into a role even I wouldn’t have thought myself capable of just a few years ago; why shouldn’t I at least try to meet those expectations on every possible front? Customer events, board meetings, etc. — these were important things I was being given an opportunity to attend, influence, and make as successful as possible.

Basically, while I still loved the idea of not wearing a suit (or anything other than Boston sports-franchise related t-shirt, to be honest), actively refusing to didn’t resonate with me the way it used to. That kind of line in the sand just didn’t feel like a part of my identity anymore, and I felt worse about the idea of letting my colleagues down (even just a little) than I did about wearing silly clothes.

Man, did that ever make me feel old.

this suit is black not

So I bought a suit. It wasn’t fancy, but it wasn’t cheap, either — the nice people at the nice store in the nice mall I usually don’t go to tailored it and told me it looked great and had me try on different jackets and stuff. My wife was very helpful, and didn’t laugh at me too much.

I went home, put on my suit, and went to work. Here’s what I learned about the dressed-up version of myself.

  • Clothes aren’t magic. Instead of feeling like a badass captain of industry, I felt self-conscious and stupid most of the day. Worst of all, I felt inauthentic, which I think is an even bigger hang-up for me than it is for most people.
  • I thought about my clothes a lot, which is not a great frame of mind to be in when you need to get work done. There are just a lot of things you can do wrong with formal clothes that people who wear them all the time naturally avoid, and I probably did them all several times.
  • Eating, drinking, sitting, leaning against things, bathroom breaks — pretty much everything is risky behavior when you’re walking around in what are basically pajamas made out of money, and that didn’t make me any more comfortable with my environment.
  • If you’re the kind of person who doesn’t wear formal clothing, and you’re suddenly thrust into an environment where everyone there is dressed up, there’s really no way to succeed when your goal is to fit in and not be a distraction. If you don’t dress up, you’ll make a scene. If you do, people will notice, and you’ll make a scene. (“Whoaaaa, look at this guy!!!”) Hopefully this gets better with time.
  • I’m pretty sure that my problem with most real-time interactions is my preference for honesty and candor. I’m certainly not rude, or inappropriate — I just have trouble naturally interacting with other folks with the right professional safeties on, so rather than say something stupid, I prefer not to say much at all. I don’t hate small talk so much as I’m actively bad at it. I’m not disinterested in you as a person, I’m disinterested in the stupid, safe topic we’re inexplicably discussing, but since many people are uncomfortable having honest conversations with people they’ve just met (myself included), that’s what we’re going to talk about.

In short, my trouble with suits doesn’t really have anything to do with work, or business — I’m actually pretty good at that stuff. The trouble I have is with many of our oldest, most irrational social traditions, and that’s been a problem that’s dogged me since I was a little kid. I literally just don’t understand ties, just like I literally don’t understand how to feign more interest in another person’s story than I actually have, or how to impress a girl in front of a keg in a frat house where I can barely hear what anyone is saying.

(That last one hasn’t been important in about 15 years, so at least I’m making progress.)

“That’s just how things work” has always been the exasperated response from my well-intentioned, more socially flexible friends and colleagues, and I’ve always grudgingly accepted it and never insisted or expected that anyone else think the way I do. The funny thing, though, is that when I am actually praised for my thinking, it’s almost always for clearly and accurately modeling a complex situation into something real and approachable. And yet many people are often surprised by the fact that this same person would struggle to integrate irrational, distracting bullshit into their natural behavior.

Suits and ties don’t make any more sense than skinny jeans, or those crazy things that make you have giant earlobes, or the safety pins on leather jackets kids at our shows used to wear. And while I understand that our society uses them to convey a complex series of social indicators (suits indicate business acumen and wisdom, or at least the possibility of wisdom, now hoodies sort of mean tech, etc., etc.), I’d be lying if I didn’t admit that I still think it’d be a lot more efficient if everyone was just honest with each other and evaluated what we all said and did on the merits.

The fact that I’m old and realistic enough at 35 to realize people aren’t going to do this doesn’t make it any less true, or any less the way my brain works. But I’d like to think being able to work around that is just another thing I’ve been able to improve about myself.

My Saw Man Argument (WOMP, WOMP)

One of the best parts of working at a relatively early stage — or at least growth stage — company is that there’s a general bias towards doing things quickly. This is great, because I’ve found that working with other people on just about anything tends to slow things down for a variety of reasons. More people means more opinions, more views to consolidate, and more fears about failure (both personal and organizational). In mature companies, this basically eliminates the ability to quickly try interesting things unless you set up some kind of specific environment to do so, which is why people like me tend to go crazy at mature companies, or just give up and read the internet too much. Fortunately for my career — and unfortunately for the message boards I used to spend time on in the mid-2000s — I haven’t worked at a mature company in about ten years. Instead, I’ve been working for businesses in the highly motivated “grow or die” stage, where standing still is the only thing you can really do wrong.

Of course, anyone can do lots of random things quickly — that doesn’t take skill, sound decision making, prioritization, or anything other than energy, really. And while doing that in an early stage environment gives you a lot of very satisfying dopamine hits, you also run the risk of generating — and living inside of — the illusion of progress. Yeah, you’re doing lots of stuff, but what’s really different than before? (Sorry, can’t take the time to answer that — have to do more stuff!!!) Marketing departments are often the worst at this kind of thing because they’re where a lot of companies turn for miracles, like unexpected press coverage, or some crazy stunt that suddenly changes undesirable business fundamentals. That dynamic is partially the fault of Marketing people who don’t like to be held accountable preferring to skip around from one crazy project to another, and partially the fault of everyone else for expecting white-elephant type events to overcome less exciting operational or strategic problems.

move fast and accomplish things

While I am abjectly terrible at construction and home improvement tasks, I do remember my Dad teaching me how to use a saw. When he first put a piece of wood into the vice in the basement and handed me his, I attacked the wood exactly as you’d expect a crazy seven-year old with borderline ADHD to. I wildly thrashed about, moving the saw as fast and as violently as possible in an attempt to cut it in half.

This is not a good way to cut wood. So my Dad taught me to slow down — just a little — and make decisive, high quality strokes with the saw. Keep it straight. Make sure the blade is really getting into the wood. Take five or six quality swings in a row to get a rhythm before you start trying to go any faster. Do that, and before long you’re positively flying through lumber at what seems like an unimaginable rate, you’re getting a better cut, and you’re not working nearly as hard.

At work, there’s a healthy cadence to the right kind of moving fast. It’s not chaos — I know the feeling of too many things going on at once, and that usually doesn’t work out very well. It’s also not a passive, stagnant feeling, where you’re waiting for a solution to unsolvable problems to fall out of the sky. Instead, the best environments have that perfect sawing rhythm, and when you’re really going, great progress seems almost inevitable. New process here, iteration here, letting something breathe over here, etc., etc., and so forth. Teams can feel when they are operating this way, and it feels good, as if even complex, existential challenges (while still difficult) are ultimately just waiting to hit the blade and be ground away.

effective speed is what really matters

Thinking this way requires a lot of things, but more than anything, it requires discipline. I’m not talking about the mastering-martial-arts kind of discipline, or even the learning-a-language kind. Just the kind you need to simultaneously realize what today’s limitations are while still understanding the extreme end of what’s possible, and then go out and achieve it. The idea that you can just get as psyched up as humanly possible, and then blast through your challenges like you’re running a Tough Mudder or something is, while in some ways laudable, usually mistaken. If you’re really trying to get somewhere quickly inside of a group, your effective speed — how fast you can actually get that group to make a lasting impact towards your goal — is a lot more important than how furiously you do various sub-activities, even if they seem like positives at an individual level.

You’re (probably) not going to solve the most important challenges with one great idea and ten bad ones all executed as quickly as possible, or a flurry of well-intentioned, disconnected exertion. You’re (probably) going to solve them by making well-executed, focused efforts, and yes… making those efforts a little quicker than everybody else. Because yeah, sometimes you just have to saw a little faster than the other guys.

Depth & Breadth

the most annoying people on LinkedIn

For me, LinkedIn has turned into a sort of career-focused version of WebMD. I almost never start poking around in there for an emotionally healthy reason — I’m either frustrated by something at work and looking to wallow in self-pity for a minute or two, or reading about whatever happened to that incompetent product manager I used to work with. And, as with WebMD, all I really get out of the experience are pangs of insecurity and a fair amount of eye-rolling horseshit.

Now, I have a decent amount of patience for the amount of terrible, uninteresting nonsense on LinkedIn. It’s an inherently self-serving environment, combining the narcissism of any social network with the naked greed and ambition that comes with private business and career advancement. My Dad, who has one foot in retirement after a long, interesting career, has the best LinkedIn profile ever (I’m pretty sure he only had it to look at people he was supposed to interview eventually). It has no accomplishments, no skills, lists one company he’s worked at, and has the same picture he’s used for everything that I’m pretty sure is from my junior year of high school. And it’s not like the twenty year old pictures some people have on LinkedIn, either. It’s not some idealized version of himself — it’s just the standard picture he’s used forever because my Dad places zero weight on your opinion of his appearance, or really anything else about him. Like, actually zero.

The polar opposite of my father — and the source of unquestionably the worst material on LinkedIn — is the insufferable “growth hacking” people, who are usually either digital marketing consultants (sorry, “CEOs” of their one person companies), or people who claim to have worked for like, eleven different startups in seven years. “NINE TIME STARTUP ENTREPRENEUR!!!” Uhh… congratulations?

You can spot these people by their long, self-congratulatory posts about how hard they worked, and how everything is possible through said hard work. (“AirBnB turned me down for a job out of school, but guess what? NOW I’M AWESOME!!!”) They are always white guys in their twenties, except for a couple of white guys in their forties, who are gods to the people in their twenties, and are advisors to no fewer than twenty-five different startups.


Obviously my resume is a little different, with fewer lasers and pyrotechnics. I’ve had real jobs producing some sort of fairly concrete business value since I got out of school thirteen years ago, in 2004. Other than one extremely difficult year in Cleveland, I’ve had steady, pretty intense employment at growth-focused companies the entire time, and I’ve learned at what I can only conclude is an above-average rate for a couple reasons :

  • the growth-focused thing; outside of Cleveland, I haven’t worked for a company on cruise control
  • the companies I’ve worked at have been pretty small, or early enough in their trajectory that you really need to pull your weight and often punch above it
  • most companies have had a strong technology component, and were in a new or rapidly changing industry
  • I’m a little bit of a generalist so I’ve gotten to have lots of different kinds of roles (support, product, marketing, leadership)

I’m very grateful for how all of this has played out, because I know for a fact that I work my hardest and do my best work in environments that really need me (this also explains my extremely inconsistent academic history). I’ve felt very strongly needed everywhere I’ve been since I moved to D.C. in 2008, and that’s not a feeling everybody gets to have.

But here’s the interesting thing; even though I’m really confident I’ve had an extremely productive, challenging, and enlightening first thirteen years of my career, I feel like I’m increasingly running into people who — on paper, at least — have done so much more. I’ll read a resume from a candidate with fifteen jobs, three major promotions, some kind of graduate degree, and one or more entrepreneurial experiences, and then realize they are three or four years younger than me. And the only thing I can think is… how did you do this? Are the annoying LinkedIn people right? Have I simply discovered a sub-class of superhuman professionals? Am I going to have to go back to working in the kitchen of that steakhouse from college again? (Just kidding, they’d never hire me back.)


This kind of thing used to freak me out a fair amount, until I started actually calling these people, interviewing (and sometimes hiring) them, and working alongside them. What I pretty quickly realized is that more often than not, these kinds of people take very little of substance from their experiences, maybe because they are so focused on title, perception, and the next step on their path. Once you experience this, the whole facade starts to crumble, and the realization is pretty jarring. If this is what this person wants to be doing more than anything right now, and they are just sort of so-so engaged, what does that say about their prior experiences?

This has been (and remains) my number one concern about going back to school for any kind of graduate business education. No, I don’t want to spend the money, and no, I don’t want to spend the time away from my kids, my wife, music, the gym, writing, and other things that have long track records of making me happier and smarter and better. But I really would consider sacrificing parts of those things if I wasn’t so worried that the whole experience is a great networking exercise bolted onto a bunch of faux-intellectual nonsense. Given that I have plenty to do, and great venues to do it in already, I’m worried that going to school is actually a less efficient way to learn than what I’m doing now.

I say that because, if you’re really in the gears of how a business grows and operates… holy smokes is there a lot to think about, design, execute, and learn from. That’s certainly true at FiscalNote, but it was true at Contactually, and EEx, and Bamboo as well, and even back when I was writing documentation and filing bugs, I always had access to the core questions and challenges of the business, and could feel the connection between them and my work.

I remember when our investors pushed most of the good people out at Bamboo (there was some personal stuff there). Almost overnight, it became obvious that we weren’t a “business” anymore; we were a bunch of people tasked with jockeying for the favor of our investor group as various people sought to extract cash out of what was left of the company. Some people saw that as an opportunity — “if I handle this right, I can be a vice-president!” — but I immediately knew I had to go even as it was made very clear to me that I was needed for this exercise. But what the hell is the point of working in business if you aren’t motivated by growing and improving a business? I had just turned thirty, so I left and spent the next couple of years frantically, maniacally building a functional company with my wife, which seemed a lot less crazy than whatever was going on Bamboo.

Five years later, I’m a little more sympathetic to the mortgage-havers and whatnot who didn’t have the luxury of my self-righteous professional/moral high ground. But many of those folks were further along in their lives and careers than I am even now, and had more to lose than I can fully comprehend yet. But the point remains that ladder-climbing and cache-gathering isn’t a cost-free exercise, whether you’re in school or at work, and that fact doesn’t always translate well to something like LinkedIn. Basically, resumes and the like are still great conversation starters and rudimentary framing devices, but at this point I now know there’s more depth beneath those titles and accomplishments than I may have fully realized in the past. Or in some cases, there isn’t, and that’s even crazier.

Insecurity 101

I was going to start this off with a really bold, all-encompassing statement like “the root of all problems is insecurity”, but then I thought about it for a minute, and realized that’s nonsense. Some of the worst problems I’ve ever dealt with professionally have come from people who were utterly and hopelessly secure about what they were doing, and in fact, those problems were in all likelihood largely a result of that confidence. Big surprise — most of these people were incompetent.

So anyways, like everything else, professional insecurity isn’t compatible with a snappy, Seth Godin-esque bumper sticker of a blog post. But it is a pretty big problem, and I’ll go so far as to say that most of the big problems I’ve had to deal with that involved talented, competent people resulted largely from insecurity about something or other. That being the case, it seems like something worth digging into a bit.

what do I mean by insecurity?

Not unlike Fight Club, the rules of workplace insecurity are short, and kind of meta. Most importantly, the first rule of workplace insecurity is that it’s almost impossible to exhibit workplace insecurity if you’re worried about your workplace insecurities. I know, what a relief.

What I mean by that is that everyone is insecure about something. That’s just life. Professional insecurity only becomes an issue when you lose track of it, and start thinking it’s something else, like a conspiracy to disrespect you, or a plague of implausibly exclusive incompetence that somehow affects everyone but you and a few people who allow you to complain to them. If you’re working on your insecurities — if you’re thinking about them, and being critical of yourself but pragmatic about how you can improve… well, it’s very unlikely those insecurities are causing anybody problems, even if they keep you up at night.

The truly dangerous insecurities are different, and they’re largely hidden. They often do sneaky things like project themselves onto others (so you can justify them), or create distractions that keep you from addressing them. Those are the ones I’m talking about here.

why are talented people insecure?

I’ve worked with a lot of talented people, and some of those people had insecurity problems that hurt their careers and/or their teams. Most of those people worked through those issues — in a few cases, I’d like to think I helped at least a little — and hopefully the rest will someday. With all of them, though, there were a couple of insecurity-causing scenarios that kept popping up.

(NOTE : There was almost always only one of these per person, although parts of one can overlap onto another.)

  • They took a disingenuous or unfair shortcut in their career, and deep down, they know they did.
  • Their life is based on achieving excellence relative to others, and as you get older and join higher performing groups, standing out from your peers gets harder.
  • Their personal identity isn’t really any different from their professional identity, so when they aren’t an awesome professional they feel like they aren’t an awesome person, and that scares the hell out of them.
  • They don’t want to do some portion of the work that’s necessary to truly excel (or they don’t think they have the ability to), but they aren’t comfortable admitting it.
  • They are objectively bad at something they think they (or people in their role) should be good at, and even if it doesn’t really matter, it makes them crazy.
  • Their job has required them to bullshit a lot (try raising capital, selling something that isn’t really done yet, or spending too much time arguing in favor of your subjective opinion, it’s hard), but they’re an inherently honest person and they feel, in some way, kind of guilty (whether they should or not).

I’m sure there are more than that, but even this list is a pretty broad swath of experiences that all contribute to the same kind of toxic behavior and thinking. In my experience, that behavior includes :

  • lack of empathy, and the feeling that empathy is often excuse making for others
  • a tendency to see weaknesses in a functional area as a result of someone else’s inherent, personal flaws
  • seeing the (often negative) outcomes you expect as inevitable, and any evidence to the contrary as someone’s attempt to deceive
  • frequent false positives that validate bad things about other people, or ideas, that the same person would normally detect as obvious confirmation bias
  • shutting down conversations or necessary arguments as “unproductive”, “pointless”, or “something we’ve already resolved”
  • exaggerated self importance (as if everyone cares as much about the person’s perceived weakness as they do)
  • projection of your perceived failings onto other people
  • the inability to concede portions of an argument and the tendency to conflate multiple, separate issues into a single, all-encompassing thesis people either “get” or “don’t get”

All of this sucks, and it’s frustrating whether you’re dealing with a friend, a boss, or someone you work with and are trying to build up. But… it’s not the end of the world, by a long shot.

the homer simpson boxing approach

For me, the only thing that’s ever allowed me to help someone deal with toxic insecurity is trust. Unfortunately, trust takes a long time to build — unless you’re a perfect match for someone socially, you aren’t going to build real trust overnight by going to a happy hour or on a weekend retreat. No, instead, you’ll work with them on something that triggers their darkest insecurity, and they’ll lash out at you in one of the many ways listed above.

At that point, I like to break out what I think of as the Homer Simpson approach, which is based on the awesome episode of the The Simpsons where Homer becomes an amateur boxer after his doctor determines he has an inexplicable condition that allows him to take repeated blows to the head without incident. Homer is a poor athlete and a terrible boxer, so his trainer (the always wonderful Moe the Bartender) convinces him to simply stand there while his opponents continually punch him in the face. Eventually, they’d become exhausted from all the punching, and Homer would then gently push them over.

It’s a great episode.

The point is, the reason many people act defensive towards someone else is because they are scared of how that person will react to something. Most of the time co-workers have aggressively approached me with complaints about a colleague, it’s a pre-emptive strike over an issue that multiple people (including the person complaining) are partially responsible for. Most of the time people react poorly to constructive feedback (sometimes by criticizing something unrelated I’ve worked on), they’re really just nervous that their work sucks, even if it doesn’t. But these aren’t firmly held beliefs, or even particularly well-thought out ones — they’re irrational, emotional fears, and they don’t last unless they get reinforced.

Hence, the Homer Simpson approach. When someone is exhibiting severe symptoms of insecurity in their interactions to me, I just… let them do it. I let them complain (although I gently remind them of oversimplifications or exaggerations in their complaints). I let them yell at me. I let them call me hypocritical, out of touch, blind, irrelevant, stupid, ignorant, and everything else in the book and simply focus on not doing anything to confirm or reinforce those assessments.

Eventually, unless someone is truly damaged (this does happen), they simply run out of defensiveness-fueled-rage, even if it takes multiple conversations. At that point, more often than not, you can get them to simply tell them what they’re really worried about. And once they do that, you can actually work on it.

postscript : the gandalf corollary

The Homer Simpson Boxing Approach is awesome, but it’s not a flawless answer — there are times where an insecure colleague will respond to your patience not with exhaustion and eventual trust, but by doubling down on the intensity of their attacks, or by incorrectly detecting weakness and turning those increasingly aggressive attacks on you.

When this happens, I’ll admit that I’ve been forced to apply the Gandalf from The Lord of the Rings Approach, demonstrated here by Gandalf himself.

This is one of my favorite scenes in any movie, period, mostly because it reminds me of the way my Dad used to deal with my notoriously explosive, self-righteous temper. He successfully applied the Homer Simpson Approach to my sister and I for years, constantly forcing us to exhaust our insecurities and defenses until we finally just gave up and leveled with him. But in certain moments, like Bilbo, we’d forget who we were talking to. Dad would talk to us as equals by choice — until we started thinking, maybe, just maybe, he was out to get us too! The subtle, clear change in voice he’d use when I was a kid to draw a line (“Now wait a minute…”, or “Hey!”) was never sharp, or defensive like us. It was just strong, almost like an audible reminder of the difference between making an argument based in fear and an argument based in wisdom. I’m pretty sure both me and my sister did that exact same cowering/running in for a hug thing that Bilbo does, except we were probably seven years old at the time, and Bilbo was like, a hundred and twenty or something. But still.

There are a million wrong ways to break out The Gandalf, so I’m incredibly careful with it. I’m sure lots of people (maybe me, sometimes) think they are doing it, but are really just acting on the same types of defensiveness and insecurity they think they’re disarming. But done properly, it’s often the defining moment in a professional relationship.

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.