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9 expert tips for moving into design leadership

The best part about having strong relationships with design leaders in the tech space is that we can create opportunities and space for those leaders to share their insights, missteps, wins, and career paths with designers interested in moving into design leadership. Senior leaders Zach Gotlieb of Uber, Ryan Scott Tandy of Instacart, and MacBeth Watson of Strava answered questions and shared advice at our Design Matters Series: Design Leadership event on September 24th. Hear below their best advice to take your design career to the next level:

Photo provided by Werqwise, our venue for this event.

Earn respect by providing coverage

Did you ever have to pivot from an IC to managing peers on your team, and if so how did you navigate that transition?

“I always thought of management as just clearing the roadblocks for people. It’s about where you can put yourself so that you can make sure that the work actually gets done and give your team as much coverage as possible. When you do that for the team, it builds a lot of respect and trust really early on, and that is one of the biggest keys to being a great manager, or a great leader,” says Gottlieb.

Be vulnerable

What do you think are the skill sets needed to become a design manager? 

“For me, having kids made me incredibly empathetic. I was able to start putting myself in someone else’s shoes, and when you do that, you start working other muscles that I think are really foundational to being a great manager. Being as open as possible, making yourself vulnerable, and admitting you don’t always have all the answers is really important,” says Gottlieb.

“As designers, we need to be able to give and take feedback, but we also have to know how to navigate challenging conversations. Having empathy and caring for the people you work with is an important management skill to have,” says Watson.

Be flexible

We know talent in Silicon Valley is scarce, and that there are always more opportunities than people. For people that don't have that experience on paper, have you ever hired someone despite their lack of experience?

“I’ve definitely trusted my instincts before. If a candidate is super coachable or had similar experiences, such as coaching a sports team, or something where they had to be thoughtful of others, that’s usually an indication they’d make a good manager. I had success with that at both XBox and Pinterest,” says Watson.

“Hiring managers will want to see other experiences you’ve had and look at how you’ve worked through challenges in the past,” says Gottlieb.

“Domain expertise is important too. If someone has experience in search, e-commerce, b2b tools, and are experts in that area, they can probably be coached on how to lead and manage the people side,” says Tandy.

Teamwork makes the dream work

How do you build a design culture where everyone works and functions as a team?

“A lot of it comes down to rallying people around the purpose and your users; Make sure that the team is actively using the product that they’re building and participated with people using it in a really personal way,” says Tandy. “Having really strong principles that the team aligns on and helped craft, also gives people some skin in the game,” he adds.

“At Uber, we made sure that everyone “went and drove”, because there’s no way to build an app for people unless you’ve experienced from a user’s perspective,” says Gotllieb. “If you’re trying to build a culture you need to think about how designers are going to integrate with the rest of the teams. Design is not an insular thing; It has integration across the rest of the company,” he adds.

“I recently went from 4 designers to 9 at Strava. The main thing I did was bring the team along in the hiring process. Each person we added could add their own skills, background, and personality. We took the time to understand what helps each of them do their best work, what drives them, and what they get excited about. Also, we make sure that all designers are excited to collaborate,” says Watson.

Photo provided by Werqwise, our venue for this event.

Deliver feedback with tact

How do you navigate giving and delivering feedback from your direct reports?

“I always solicit feedback, and I see feedback as a gift. None of us is going to get better at what we do unless we get that feedback,” says Gottlieb.

“I like to start with really small things. If you start with prompts like: ‘How did you think that meeting went?’, then, you open that conversation and dialogue, which makes bigger conversations like performance reviews easier. Ask designer how they’d like feedback, and make sure that it’s an authentic conversation and that they know you’re there to support them,” says Watson.

“I like to create space for people to let go and vent (almost therapy style) at the end of the week. That safe space is important for designers and managers to let their guard down and talk about what’s important to them,” says Tandy.

Should you stay or should you go

What are your thoughts on internal mobility? Do you think it’s easier to move up to management internally, or would you encourage people to look outside their own companies for opportunities?

“If you have a supportive environment that you’re working in, then it’s much easier to take baby steps into that role and set up a mentor relationship on the team. Then, when there is an open role for a manager, you’ll be a shoe-in,” suggests Watson.

No internal options

Is there anything you’d recommend a designer do when an internal promotion isn’t possible?

“Some candidates I’ve hired showed their leadership skills in other ways. The work you put in your design portfolio, even if it isn’t your direct work shows that you’re in the right space to go into management. If you helped find a solution or helped get a project to its end state, then show that in your portfolio,” says Watson.

Advice to your past self

If you could have given one piece of advice to your past self, what would it be?

“The biggest thing for me as ive moved into leadership is being authentically me. It’s easy when you’re starting out to try and emulate others’ techniques whom you respect, but be very self aware. In the end, you’ll do much better if you're just yourself,” says Watson.

We’re all in this together

After you become a manager, how do your relationships change among the managers in non-design disciplines?

“There is an opportunity for design to balance out the different things that engineering and product are bringing to the table. Design leaders really have to show their counterparts where the true value of design is—-and make sure you’re pushing back where necessary,” says Tandy.

“You have to understand what the other teams’ needs are, so that you can communicate it back to your design team. If you know that the Head of Engineering is really driven by numbers, then you can use that as a conversation and a way to build trust,” says Watson.

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