Olly Headey

September 13, 2022

It's not your job anymore

One of the realities of being a startup founder is having your fingers in all the pies. On the one hand you get to do a job you love, the way you want, day in day out. On the other hand you get the honour of taking on that heap of far less interesting things that need doing. This could be company finances, customer support, sales, marketing, or even washing the office tea towels (you know, right?).

Whatever job needs doing, you just gotta do it. For better or for worse.

Some of these jobs are a royal PITA. In my experience most founders despise having to do the hiring – writing job posts, publishing them somewhere, figuring out an applicant tracking system (or, worse, trying to roll your own). Same with customer support, or writing blog posts. Whatever it is, it can feel like a chore and a distraction. This is actually a really good response because it means you go and hire someone to do the job for you (except, for a while at least, washing the tea towels). The relief is undeniable.

This is a great result for those jobs you find irritating. The easy-to-let-go-of ones. When your fingers are in all the pies, if they don't taste good, a bit on the Fray Bentos side perhaps, then you can't wait to wash your hands.

The problem comes when the pies are tasty. Delicious, homemade apple pies like writing marketing copy for the website. Mouth-watering key lime pies like coding a quick feature. These pies taste really good so you want to keep coming back for more. Having your fingers in these finger-licking pastried delights is hard to give up, but if you want to scale your business, at some point you're going to have to go cold turkey. 

It's not your job any more.

When a company scales, people move from being generalist to specialist. You love your early employee generalists because they've had to do everything, and they've gotten pretty good at it. But you can't replicate them. Try as you might, people you hire this way will never stack up in your eyes. Instead, you need to get your generalists to focus on their core skills and responsibilities, to make them more specialist. You then need to hire specialists to do the other stuff because – and this is difficult to let go of – the specialists will do a better job of their thing in the long run. By hiring specialists you'll fill all the cracks in your walls properly, rather than just skimming over them. Your generalists might not like it but, hey, guess what?

It's not their job anymore. 

One of the biggest decisions I made as co-founder/CTO was hiring a VP Engineering. It was a big decision because I did this in the correct way, which is to make that person a peer rather than an understudy (that never works). I reported to the CEO, so did they. I was handing over some major responsibilities, and I needed to let them run with it. They were the professional in this area, I wasn't. 

It wasn't my job anymore.

So I let it go. And the business got better, way better. I learned a lot, and it made me better.

If you're a founder, embrace this move to specialisation. You (or the other generalists) can never know everything, or be the best at everything. It might look like that for a while after these new specialists come onboard, but don't be too hasty to judge. Gaining context at a new company takes way longer than you think. Focus on setting the cultural tone, maybe set some boundaries, while bearing in mind boundaries will inhibit creativity. Maintain an oversight but give it time. Ask questions and offer feedback, but don't step in because you think you could do it better, or more quickly. Nudge when things need nudging, but do it rarely.  

Focus on giving people context, and give them time to thrive. Get your fingers out of those pies. Let the specialists specialise. 

About Olly Headey

Journal of Olly Headey. Co-founder of FreeAgent. 37signals alumni. Photographer.
More at headey.net.