Things I learned in my first 73 days in a startup

As you’ve probably already guessed, this was going to be ‘things I learned in my first 100 days’, but then I started writing and realised I had enough to post already. You can probably look forward to the sequel in another 27 days entitled ‘all the things I was wrong about in that 73 day post’ ;)

Anyway, as astute observers of my Linkedin will no doubt realise, I made a rather major career move just over 3 months ago, from the epitome of a large corporation to a 100 person startup by the name of Tetrate. Since changing jobs seems all the rage at the moment, I wanted to make some notes on what my big takeaways have been in my first 100, sorry, 73 days for people jumping into any kind of leadership role at a startup.

Your network really is everything, so build it quickly

If you thought who you knew was important at your last gig, well, you were right, but it counts for even more in a small-mid sized company. This is because the org chart (if there even is one) is at least 50% a work of fiction. Not only is it probably out of date (since there are few, if any, strong processes, including HR ones), but everyone is doing at least two things, probably more like 4-5, and you’ll never figure out what those things are without spending a bunch of time talking to them. All of them, if you can. Yes, spending 30 mins getting to know as many people as you can in the company is going to suck a bunch of time out of your first few months, but it more than pays for itself in the connections you make, and the dots you join along the way. My advice is to go out of your way to meet people who aren’t in your functional area, it’s a thing that’s easy to overlook but for me happened to be where the most valuable things were learned.

You really had better be a ‘self-starter’

Everyone puts this on their resume, it might as well be in the default templates that Word et al give you, but if you’re going to make the jump then it damn well had better be true. If you’re fortunate like I was then you’ll get all the support you could ask for, but in the end no one has time to be telling you what to do beyond a vague sense of ‘this needs doing’, so you’d best be able to live up to all those claims of being able to work without direction.

I’d add on to this that it seems that you also have to be something of the courageous type and be quickly comfortable with sharing thoughts, opinions and work with a group of people you still don’t know, in an area which you’re unfamiliar, trusting in the hope that you do actually know what you’re doing and that the uncertainty you feel really is imposter syndrome, there’s really no room for wallflowers.

On top of this, it’s quite likely that your startup has a flat management structure too, perhaps eschewing words like manager for ‘coach’, which can make it extra hard to know who to even ask for direction if you need it. The real rub, however, is that you also need to be able to make sure that you’re working on the right thing, which brings me to my next point.

Get used to asking awkward questions about vision & alignment

I’m sorry if I slipped into Managementese there for a moment, but bear with me as it’s important. It seems to be a thing that communication breaks down in a startup roughly every time it doubles in size, as the ways of communicating that worked in a team one size fall to pieces as more and more people get involved. The odds are, therefore, that there’ll be (at the least) some rough edges at whatever company you end up at, and as the new person you’ll need to be the awkward so-and-so who pipes up and points them out.

Which brings me back to my Managementese, as it can be very difficult to know which thing (of which there are so many that you could burn yourself out) to focus on. This is where being crystal clear on the company vision, and the short to medium term strategy that it’s been distilled in to comes in, as without understanding both you’ll never know if you’re working on the right thing. The bonus here though is that, aside from the warm glow of ‘doing the right thing’, you’re actually helping out everyone in getting these things communicated in a way that fits the current size of the company. Odds are that you’re not the only one casting around a little trying to work out what to focus on, so well done you for bringing it up

Oh yeah, the burnout thing

It didn’t take me long to really see first hand where the stereotype of the burnout-startup-type comes from, and don’t for a moment think you’re somehow not susceptible to it if you’re the driven ‘want my work to count’ type that is probably drawn to this kind of company in the first place. You see, that’s the big draw and the major difference between a big company and a small one. At IBM, yes my work counted for something but in the big picture sense it didn’t move the needle. At a startup that’s no longer true, the work I do potentially has a significant impact on the bottom line since so much can affect our ability to sell to clients, and every sale counts. When you combine this with the point I made earlier around there being way too much work to choose from, well, you have a recipe for bad things happening.

This is made ‘worse’ by the way that we’re all working from home at the moment (and at remote-first companies like Tetrate, forever), in that even if you’re not working every hour that God sends, the lack of physical boundary between work and home can result in work consuming a lot of your thoughts when you’re not anywhere near your laptop. Fortunately the internet is full of home-working tips and they’ll doubtless serve you well, the key for me was having a clear start and end time, at which point I put my work laptop somewhere that I can’t see it so that I avoid the temptation for just a quick look at Slack…

Oversharing is caring

My final thing (for now) is that it I’ve learned that I need to veer on the side of oversharing what I’m doing than under-sharing and assuming that people have a rough idea and are fine to let me get on with it. I think it comes back to the root of everyone having so much to do, you need to make sure that you’re getting mindshare of the other leaders in the company by routinely reminding them of your existence and the work you’re doing. Don’t skimp on the details, and spend some time paying attention to which communication methods seem to be most effective in your company. I was surprised to find that email was much more effective than Slack in terms of garnering responses, but maybe for you Slack’ll work or a call might be necessary

What did I miss?

I’m curious if anyone has anything to add to this list that might save me making terrible career mistakes (or just contribute to my personal growth, whichever), so feel free to leave a comment or drop me an email at paul@paulmerrison.io. Feedback about spelling/grammar also welcome ;)