The Hardest Part of Working at a Growth Startup

The hardest part of working at a growth startup is having to re-interview for your job every year Growth startups require both personal and business scaling.

The hardest part of working at a growth startup is having to re-interview for your job every year.

The challenge of scaling

You’re heading a key function at your 25-person startup. Maybe you’re head of engineering; maybe you run marketing. Hell, maybe you’re the CEO. You kick ass and your startup grows fast – and with that growth, the needs of the company evolve. Things in the new world are now going okay, but perhaps not optimally. Eventually, the CEO and board of directors get in a room to discuss what to do.

I can tell you what will happen in this room. The board will discuss your performance, and compare it to the performance of other, hypothetical executives – just as if you were interviewing for your own job. In your favor: you are a known quantity, presumably viewed as talented, and perhaps even a close friend. Against you: you haven’t done this before, and we need results now.

In many cases this conversation will lead to you being demoted or asked to leave. In extra cruel circumstances, you can literally get fired for having done a great job. This is normal, semi-expected, and sucks. And this happens to everyone – even founding CEOs are not immune.

The hardest part of this situation? These hard truths often go unspoken. Sometimes it’s just too awkward to tell someone who’s been there through thick and thin that they’re expected to be a stand-in for a future big league exec. And if you have a first-time management team, they might not even realize what’s going on – they may also be in the process of not scaling fast enough, either. At least when you’re interviewing, you’re explicitly given the chance to shine; such opportunities may not be spoon-fed to you during hectic growth.

How to scale yourself

To avoid this situation you need to become a self-scaling machine. Read voraciously, and find opportunities to put new skills into practice – during growth mode there’s always too much to do, so take advantage and gain actual battlefield experience. You should constantly have an image in your mind of where you expect your team to be in 6 months and steer towards that future world. Learning to see around corners allows you to scale independently, and independence is a key leadership trait since startups are constantly on fire. Finding mentors who are at least 2-3 years ahead of you in terms of their own careers is another great way to build these instincts.

And most importantly, ask questions. Ask your manager how they expect your job will be different in 6 months (if you’re the CEO, this advice will be slightly different – a trusted advisor and/or executive coach can help). Ask them what they see as your current trajectory in the role. In my experience people are way too shy about asking direct questions in general, especially to their managers – it is literally your manager’s job to provide high-quality answers to your career questions. If you nail this, it’s a fast track towards increasing responsibility and growth.

This isn’t a bad thing!

From the other perspective, well-run growth startups give you the regular opportunity to interview for roles that are a level higher (or two!). This is a proven way to accelerate your career. If you scale with a growing organization, you can pack decades of experience into years.