5 Myths About Design Management

In 2007, I moved into my first design management role. At that time, I didn’t really give the decision much thought. I saw a problem: my friend and colleague, Anna, was working until 9pm frequently and was crying at her desk many of those late nights. I believed there had to be a better, more efficient way to work that would allow Anna to go home at a reasonable hour. We happened to have a recent management departure, so I persuaded my former boss’ boss to give me a chance to fix the problem.

11 years later, I’ve managed to gain a modicum of perspective about managing. Often I hear from designers interested in transitioning into management; usually, there’s a gap between their expectations of the role and the reality. My hope is to bring a bit of clarity about what design management is and isn’t to help aspiring managers make a more informed decision about their career path.

Myth #1: If you become a manager, you won’t get to design anymore.

Truth: Limit your team size or adopt a broader view of Design, and you can keep designing.

“I don’t know if I’ll be happy if I get too far away from designing,” is probably the most common concern I hear from would-be-managers. I’d like to challenge that assumption. The easiest way to keep designing is to limit your team size. It’s realistic to continue designing with 1–2 direct reports; management isn’t a fulltime job at that stage. 3–4 direct reports will be a stretch, but you could probably still design 10–15 hours a week at that point. At 5+ direct reports though, it’ll become nearly impossible to both make the work and manage it. If you care a lot about working on design deliverables like screens, flows, prototypes, etc. then capping your team size is the way to go.

Alternatively, I encourage you to take a broader view of Design and what it means to be a designer. In managing larger design teams, I’m unable to design and deliver screens or flows; however, I get to design teams, culture, and process. My deliverables are happy employees, successful designers, high performing teams, and impact to our product experience and overall business trajectory. So, you’ll never stop designing — it’s just that your design challenges and deliverables will evolve.

Myth #2: Management is something to aspire to.

Truth: Most days management is a shitty job.

When I was younger, I had all of these notions of what it meant to be a manager. It sounded pretty nice. No deadlines. Didn’t have to make anything. You just hang out with people in meetings all day, and you get paid a lot more money for doing less work. Pretty sweet, right?

Nope. Most days management is a shitty, thankless job that no one in their right mind should go into. If you’re doing your job remotely right as a manager, then “shit rolls uphill”. Which is to say, managers exist to make their people and teams successful; therefore, they can add the most value when things aren’t going right — when there’s collaboration issues, low performance, misalignment, etc. Managers should be magnets for hard problems. And given that, as a manager, you’ll spend most of your day hearing about what’s not going right and what others expect you to do about that. Management is essentially an unending series of hard conversations.

Most days, management is a shitty, thankless job that no one in their right mind should go into…only go into management if you can’t help yourself.

That said, it can also be extremely rewarding and fulfilling. Managers get to watch people grow into better versions of themselves and play a small part in that transformation. Managers work on tons of interesting and very important challenges. And the opportunity for impact is outsized — 1 person can only do so much, but 10 can do exponentially more.

Often I tell people, management should be avoided at all cost. Only go into management if you can’t help yourself. If you’re compelled to run into the fire whenever you see a burning problem, like I was by Anna’s situation, then going into management is probably a foregone conclusion for you. But definitely don’t go into management for glory. You’ll be deeply disappointed.

Myth #3: You get to tell people what to do.

Truth: You can try, but you won’t be in management long.

In general, people hate being told what to do. The art of managing people is to use your role to get the best out of them. I’ve found when given time and opportunity the best designers will create surprisingly novel solutions — much, much better solutions than I came up with in the five minutes I spent thinking about their design challenge. My job is make sure those surprising moments happen more frequently per designer and for more designers. I can’t get there by telling people what to do. Trust, empowerment, guidance, insightful questions, patience, and opportunity are the tools of an effective design manager.

Managers ultimately sink or swim based on the caliber and performance of their team. The most surefire way to get to an underperforming team where your best people quit and you get fired is to not trust them and tell them what to do.

Myth #4: You can enforce design quality.

Truth: No design leader can mandate quality. It takes a village and time.

This myth is just patently false. I wish it were true though. Although a design manager can hold a high bar for quality among his or her direct reports, that’s only half the battle. Quality is a team effort — a blend of culture, strong hires, good process, and very dependent on the moment in the company’s evolution.

To break that down further: Even if a designer had designed amazing mocks, the work may be descoped when handing off to engineering. It could get descoped further to hit a looming ship date. The implementation may be off from the mocks. The functionality may be buggy. The designer may have missed a few edge cases he wasn’t aware of. And the design may just fail at being better for users when tested. It’s really, really hard to ship great work, and it requires everyone in Engineering, Product Management, and executive leadership to be bought in.

At best, design management can socialize and advocate for a higher quality bar. It can make a case for why quality matters. But often quality is a reflection of what moment that company is in their maturity. A company like Slack, with 100,000+ employee companies paying millions of dollars and relying on their product to get work done each day, will have a much, much higher quality bar than a 10-person startup trying to find their first customer. Slack’s customers necessitate that the company invests in quality. Whereas the early stage startup lacks that. They may not have even built the right thing to achieve product-market fit, so they certainly shouldn’t spend the time to make it amazing yet. That’d be poor stewardship of their limited time and resources. Often times true quality stems from business necessity, until then Design (and design management) will do it’s best to deliver the best designs it can. The hope is to live long enough, as a company, to get a chance to make the experience as amazing as designers believe it can be.

Myth #5: Design management = managing designers

Truth: That’s only half the job.

The most successful colleagues I’ve worked with tend to have one trait in common: they all act like business owners. When you own the business, you don’t actually care about your own personal success, credit, or glory. As a business owner, in order for you to succeed, the company must succeed. A personal win means nothing if the team takes an L.

Similarly, as a design manager, managing designers well isn’t enough. Ultimately, you need the whole team (inclusive of engineering, product management, marketing, analytics, et al.) to win. Let’s say Design put together the most beautiful mocks and they never got built. Success? Nope. Or Design managed to hit every deadline for the quarter. Big win? Still no.

I write from the context of building software. Given that context, success is extremely cross-functional. No one function, Design or otherwise, will be successful on its own. Therefore, it’s the job of the design manager (and every other type of manager) to create the conditions for team success.

Roughly half of my time goes to my designer. The other half goes to all the things surrounding them: coordinating with other cross-functional teams, collaborating with PM and Engineering management, planning, hiring their teammates, and a bunch of hard conversations when things aren’t going well. Successful design management extends beyond the bounds of the design discipline because every function needs to bring their A-game for the team to win.

So what happened with Anna…

Looking back on 2007, management wasn’t quite what I expected. But within my first month, we’d brought all of our project management online, understood in realtime the demands on the team, started saying “no” to requests we couldn’t staff properly, and Anna was home for dinner every night. That’s the impact managers can have. Ultimately, as a design manager the challenges are substantial: the work is thankless, but it’s often rewarding and the opportunity for impact is massive. Obviously, I don’t know if design management is the right path for you or not, but hopefully, you have a bit more clarity about what to expect.

If you want to chat more about design management, shoot me an email at jj@thumbtack.com. Otherwise, I’ll leave you with a shameless recruiting plug. Thumbtack is hiring for tons of design roles. Join us!