Transitioning to Design Management is Hard, Risky and Requires a Lot of Luck

I know a lot of people who have followed the first path. They joined an early stage start-up as its first designer, and four years later are running a team of 40 people as Vice President.

It’s easy to see how this happens. As Designer number one, you’re responsible for hiring designers number two, three and four. For the first 18 months or so you’ve moved from being a regular designer to a lead designer. You understand the design system, and know why certain decisions were made, and everybody comes to you for advice.

When it’s time to hire your fifth, sixth and seventh designer, you’re the one who ends up writing the job spec, doing the interviews, and onboarding the new hires to the team. Once folks start, they report to you, and when they want a pay increase, it’s you they come to first. You probably don’t have the title of manager yet, but you’re effectively doing the job of one.

A lot of career advancement comes that way. You accidentally find yourself doing a particular job, and the title, salary and job description follows 6 months later. Eventually you’re doing so much people management that you move out of production, hire a couple of leads who eventually become managers themselves, and now you're a Head, Director or VP of Design.

This is a wonderful career trajectory and looks amazing on a CV. However it’s a super hard career trajectory to plan, as a lot of it revolves around joining the right company at the right time. This doesn’t diminish the hard work and effort you put in. It’s just a hard route for others to follow with any certainty.

The next approach is more common inside larger, more stable teams. As a designer you’ll see some sort of opportunity, improvement or trend that you’d like to explore. These tend to be internal focussed opportunities like the creation of a Design System, or the formation of a Design Ops team.

Using your natural sales and leadership abilities, you’ll secure some time and budget. If you’re lucky, the project will be a success, and you’ll end up being put in charge of this new initiative. The powers that be will see this drive, and other leadership roles will soon follow.

This is a great way to prove yourself as a leader, but it comes at some risk. Convincing your company to do something new is always a challenge, and if you fail you’ll lose the trust of your superiors and your status in the organisation. As such, this can be especially hard to do for people from more diverse backgrounds, who don’t feel as secure in their role or their ability to leave and walk into another job with ease.

Unfortunately these opportunities are few and far between, so there’s an element of being in the right place at the right time. There’s also a big element of office politics going on here.

As leaders, it’s our job to find these stretch assignments for our teams, but there’s a good deal of evidence that these sorts of assignments aren’t evenly distributed. That promotion worthy stretch assignments get given to white men more than women—who are often given maintenance assignments—or people of colour. As such it’s important for design leaders to make sure that these opportunities are distributed evenly and judged fairly.

The third most common route into management is through promotion. You’re a great Designer or Design Lead, who continuously goes above and beyond the call of duty. Your design work is stellar and your peers consistently approach you for advice. You know how to navigate projects through your organizations successfully, and your stakeholders appreciate your diligence and hard work. The only problem is, there are no leadership roles available.

While most people assume that they’ll eventually be promoted into a leadership role, this happens a lot less frequently than you’d think. Unless the company you’re working at is growing quickly, you’re effectively waiting for your boss to leave; and while individual contributors seem to move roles fairly frequently, managers stay much longer. As such, the only option is to jump ship.

If you’re lucky, you’ll land your first leadership role at a company with a long history of Design Leadership, a group of peers to learn from, and a governance structure in place. However that often isn’t the case for new managers. Instead they’ll often find themselves being hired by companies with little background in design, as a Player Coach.

On the surface, the Player Coach role sounds ideal. You get to learn new management skills, while continuing to do the design work you know and love. The problem is that management very quickly becomes a full time job, especially when you discover that you don’t have basic things like standard job descriptions, team charters, or progression frameworks in place. You spend so much time working on these fundamentals that your design work and people management skills begin to slip. Very quickly you find yourself stuck in the new manager death spiral, and start wondering whether you did the right thing. Maybe life would be easier if you went back to being an IC.

I’ve seen this cycle repeat itself more times that I care to say. Fortunately this feeling will pass. You’re not a bad manager. You just found yourself in an impossible situation, so it’s time to move on. The best thing you can do is use this experience to land a design management role at a much larger company with an experienced design leader, a supportive group of peers, and all the necessary governance and infrastructure in place.

As you can see, none of these routes into Design Management are especially easy, and a lot of them require being in the right place at the right time. However It’s important to be aware of these common tropes, so you can take advantage of them when they present themselves, or know when to step away when they don’t.