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.