Design Leadership 101: Lessons Learned from My First Year as a Manager


I recently started managing designers. It felt weird at first, like starting from scratch in some ways. Or like being tested for an exam you never studied for (we’ve all had that dream, am I right??). To date, I have been evaluated as a designer by the quality of my work and my ability to collaborate effectively with others. I felt like I had clear expectations on what makes a good design. I also knew when I produced good work.

Managing is a completely different skill set (duh, you say) - one with parameters that felt much more vague at the beginning. As someone who likes to measure the impact of my work, how did I know if I was doing a good job? How would I define success? How did others define success for me?

I have a lot yet to learn, but I thought this was a good opportunity to reflect on the past nine months and document a few processes that have been working well so far as a manager.

Schedule conversations with other managers at your company (or not at your company) that you admire

You are not alone. There are other people who have gone through this process before, and have probably had similar feelings about it. This is a good time to check in with your support system and strengthen relationships! When I first became a manager, I felt a sort of “okay, now what??” moment. I fell back on what designers do best: user research. I began to treat the transition as an excuse to connect with people at my organization and beyond and hear from them about their own transition and priorities.

I made a list of cross-functional people at my organization that I admired and thought I would benefit from speaking with. I scheduled calls and asked the following questions:

  • What was the transition from individual contributor to manager like for you?
  • What is something that you know now that you wish you had known at the time?
  • How are your priorities different now? What are your current priorities?
  • What is a current problem space you are trying to figure out?
  • How do you see us interacting?
  • Are there ways you’d like to see the design team engaging with [X initiative or team] that we are currently not?
  • How have you worked effectively with designers in the past?

I realized I was operating at a different level now. Instead of being embedded on a single product team, I was across teams and working with different cross-functional partners. My day-to-day priorities had changed and my thinking and schedule prioritization needed to change along with it.

Establish Clear Expectations and Communication Styles

The first thing I wanted to do with my team was have a sort of “level-setting” conversation. I held an initial conversation with each of my team members that focused on communication and feedback. I wanted to establish expectations for us both from the start of our new relationship, especially around preferred working styles. Even though we had been working together as colleagues (friends, goobers, buds, you name it) up until this point, our relationship had changed and we needed to get to know each other in a new way. It was a nice excuse to check in and get back to basics.

I asked the following questions in these conversations:

  • How do you like to provide feedback?
  • How do you like to receive feedback?
  • What is energizing you work-wise at the moment?
  • What is draining you work-wise at the moment?
  • If you could change one thing about your job, what would it be?
  • What are your professional goals while working at [Company]?
  • Is there something you’d like to work more on that you haven’t been able to do?
  • Think about your best Manager to date. What made them great?

One question that I didn’t ask that I wish I did: Tell me about the relationship you had with your previous manager. Were there any in-progress conversations that I should know about? Are there any initiatives or goals underway that we should continue to work towards?

Establish a Framework Around Giving and Receiving Feedback

Oh feedback. So easy to talk about, so hard to do consistently well. I credit my years spent at a creative agency for teaching me to be more receptive to feedback — nothing makes a designer more resilient than saying “thank you for this feedback” to a client who hated your designs, then crying in the bathroom at their office am I right????

In all seriousness, feedback is important to consistently share. It also goes both ways — it is as important for my team’s development as it is for my growth as a designer, leader, and manager. Below are a few tactics I use when providing feedback.

Provide Specific and Consistent Design Feedback

When it comes to design work, I try to regularly provide constructive feedback on my team’s work without micro-managing. Note: this is hard to do and also depends on the 1. relationship you have with your teammate and 2. type of feedback they prefer to receive and when they prefer to receive it. I try to document and be specific about what I liked about the designs and what needs improvement. I learned from my manager (shoutout Scott) to ask clarifying questions about work before providing feedback, instead of immediately jumping into critique mode. I try to first understand what the designer was trying to communicate in the designs before providing thoughts of my own.

Here are a few clarifying questions I’ll ask when providing feedback to my team:

  • What kind of feedback are you looking for?
  • Where are you in the process?
  • Note: Timing is important! This also helps me decide what to say and when.
  • When would you like it by?
  • Are there are open questions that are stumping you?
  • How would you like it documented (e.g. bulleted in Slack, Figma comments, mockup ideas, etc)?

Employ the Player-Coach Mentality

The player-coach mentality refers to a mindset where the designer not only creates the design but also takes on a teaching or coaching role to help others understand and implement it. I’m sure this comes from sports, but I don’t watch sports so I wouldn’t know. Well, if Ted Lasso counts as watching sports, then I’ve learned a lot about player-coach mentality. This can involve providing guidance, feedback, and support to team members or stakeholders involved in the design process.

I’m sure the phrase player-coach mentality comes from sports, but I don’t watch sports. But if Ted Lasso counts as watching sports, then I’ve learned a lot about player-coach mentality. Player coaches [design stuff] but also [teach stuff] which can involve providing guidance, feedback, and support to team members or stakeholders involved in the design process.

I try to pay attention to when to lean in and when to get out of the way. I’ll give my boss more kudos on this front (shoutout Scott). He is a great example of a player-coach. He probably watches sports too, than son-of-a-gun. Oftentimes, he will show us a new trick in Figma that we didn’t know ourselves. He doesn’t overstep and micro-manage our day-to-day work, yet is also able to call attention to an element of a design that should be rethought. He also makes himself available to collaborate with team members and participates in our team design challenges.

Conduct “Keep Doing, Do More Of” Feedback Sessions Once a Month

I believe this approach started with our VP of Product (shoutout Lucy) and has caught on like gangbusters at Storyblocks. Once a month, I started doing “Keep Doing / Do More Of” sessions with my team, where we each bullet two to three items under each category for the other and talk through them during a 1:1. I love these sessions for a few reasons:

  • They foster a culture of giving and receiving feedback. Not only is feedback encouraged, but it is also expected. It also gives me a chance to show my team that I value their insights and can take feedback well (a skill that took years to develop and honestly I’m still working on it). It feels scary to give feedback to your manager — and I have a responsibility to listen attentively and take the feedback I am given seriously, putting it into action.
  • It leads to more feedback outside of these sessions. Creating space for bi-directional feedback just makes us more comfortable giving feedback. It shows my team that I too am a work in progress and want to get better. I can also practice accepting feedback
  • It allows for things to be said that don’t fit neatly into other 1:1’s or one-off calls. Sometimes I think, “I don’t really have anything to add, maybe we shouldn’t do this exercise today.” But you know what? Dedicated even a few minutes to writing down feedback gives me a ton of ideas. Creating the space for this exercise makes you pause and reflect, something that this fast-paced gal is not always great at doing 🙃.

Foster a Collaborative and Trustworthy Environment

Designers work best in a collaborative environment. As a design leader, I try to foster this culture of learning and sharing by creating opportunities for designers to learn from one another, share their ideas, and provide feedback to one another. This can help generate new and innovative ideas, leading to better work. A few tactics I’ve used include:

  • Pair two designers with complementary skillsets together on a longer initiative, such as making gains in our Design System work
  • Share recognition widely with the team - one of your designers succeeding means you’re succeeding. We have a section of our weekly design team sync specifically dedicated for shoutouts. I love a good shoutout. Acknowledge your designers’ hard work and celebrate their successes. This can be a simple thank you or a public recognition of their achievements. A win for your teammate is a win for you. And make sure shoutouts happen every week. It’s okay it they’re heard multiple times, and with different groups of people.
  • Create something together during monthly design challenges that help us reflect, learn, and/or share. We were doing these informally as a team - sharing tutorials that we liked, websites that inspired us, etc. We now take turns leading exercises that help us all practice our skills and grow as designers.
  • Create the expectation that work should be shared with the team every week. We have a running board where designers sign up to share a design and include how long they need to present, links to any designs, and whether they’d like work to be reviewed with the entire team, a small group, or async.
  • Trust your designers. In any working relationship, trust is a foundational element that sets the stage for success. It's important to trust the expertise of your designer and resist the urge to micromanage every aspect of the project. By giving your teammate the autonomy to make creative decisions and solve problems on their own, you are empowering them to do their best work and contribute to the success of the project. It's also important to keep in mind that trust is a two-way street, and building a strong foundation of trust requires open communication, transparency, and a willingness to listen to each other's perspectives.
  • Think proactively - be on the lookout for opportunities for your team. This can include identifying areas for growth, advocating for them to get involved in projects that interest them, or just being available as a sounding board when they need it.

A few final reminders

  • Be kind to yourself. I have a tendency to overthink, overanalyze, and be overcritical. I remind myself almost daily that this work does not happen overnight and that my experiences over the years with add up to complete my whole picture of people manager. AND I’ll never stop learning new tricks along the way!
  • We’re all human. Our jobs are only one part of what we do and who we are. Get to know your team on a personal level. The little life details add up to the big picture.

Written by

Rebecca Basnight