If you’re lucky enough to work at a cool Silicon Valley tech company, there’s a clear process for choosing either path. You can decide to be an individual contributor (IC) or a manager, and — in theory at least — the choice you make won’t have an effect on your earning potential or career prospects. For everybody else, management typically means a higher salary, a higher status and more upwards mobility. However, it also means doing a job you have no previous experience in, and will probably suck at for the next few years. So rather than a crossroads, it can often feel like a precipice.

As a designer transitioning into management, it feels like the sensible thing to do is to find a middle path; a role where you can still be doing day-to-day design, while looking after a handful of designers. This is often described as being a player-coach; somebody who leads their team from the pitch rather than the sidelines. So you look around for roles and end up joining an exciting-sounding company as their first design leader. Happy days. Or so you think. Jump forwards 6 months and you’re wondering if you’ve made some terrible mistake. Maybe design leadership isn’t for you, and life would be better if you admit defeat and go back to being an individual contributor?

This is an all too predictable story I see repeating time and time again, so what went wrong?

This is an all too predictable story I see repeating time and time again, so what went wrong?

I see three major challenges — and one big benefit — of becoming a player coach, so let’s start with the benefit. These player-coach jobs are easier to land for people transitioning into management because they generally don’t require prior management experience. The world is full of companies looking to build out their design teams, but lack the understanding to know what skills are needed. So rather than paying for an experienced manager, they try and get two people for the price of one. This results in them hiring somebody to be both a designer and a design leader, presuming they can do the management bit in the gaps between shipping.

Sadly this is rarely the case and leads us to our first challenge. It turns out that it’s super hard to hold down two jobs, especially if you’re good at one and have no experience at the other. So you either over-index on the design work, and end up being a negligent leader, or you focus on the leadership stuff and quickly become a blocker for your design work. As you’re in meetings all day, you decide to take some of your “real work” home, rationalising that everything will be OK as soon as you get over the current hump.

However, rather than getting better, things are about to take a turn for the worse. You’ve been tasked with growing your team, and there’s headcount to fill. However, as the companies first design leader, none of the infrastructure is in place. There are no pre-existing job descriptions, guides for running successful job interviews, or processes for on-boarding new designers. Similarly, there’s no process for running 1:1s or performance reviews, and don’t get me started on the lack of a progression framework. If you’d come from a previous management role, you’d probably have some of these things already, but as this is your first position, you need to create everything from scratch. So you do a tonne of reading, scour online forums, and start building your processes from scratch, often in your own time. Very quickly you find yourself with a third, hidden job; that of design operations manager.

This is where our third and final challenge comes in; a general lack of organisational support and understanding for your role. As a new design leader, you don’t know what you don’t know. In ideal circumstances, you’d have support from more senior and experienced design leaders, but because you’re the only one of your kind in the organisation, you have nobody to turn to. Furthermore, your probation period is starting to run out and the bosses are wondering why you’re not performing at a higher level. Design work is backing up, the team aren’t feeling supported, and you still haven’t filled those open roles. This is the point where imposter syndrome take holds, and you wonder if you’ve bitten off more than you can chew, and would be better off going back to being an individual contributor.

I’m here to tell you that this is a perfectly natural experience, and you’re not alone. It happens to a lot of first-time leaders who follow a player-coach model. In my experience, it is possible to navigate through this situation successfully, but you’re going to need a lot of spare time, resilience, and a strong support network — preferably with the addition of an experienced coach.

Far from being the easy option, this route is more commonly a baptism of fire. You’ll put everything you have into the role, and will learn a lot along the way. However, it’s a hard slog and many people run aground after 18 months. So it’s quite common for a companies first design leader to move on to a more dedicated — and arguably more sustainable — management role before too long. Ironically the person who comes after you will have a much easier time, as you’ll have cleared the pathway, laid down a trail, and set them up for success.

Fortunately, your second leadership job will almost certainly be better than your first. You’ll have experienced the challenges of starting something from scratch, you’ll understand the need to double down on doing one thing well, and you’ll appreciate the value of working with somebody who has been leading design teams for a while, and can support you in your own career journey.

Of course you can skip this painful learning process entirely, and attempt to land your first leadership role in a company with an established design practice, run by an experienced design leader. But that’s often easier said than done, and sometimes we have to make our own mistakes in order to properly learn from them.

This post was originally published on Medium