11 Things I Learned My First Year as a Design Manager

Posted like forever ago
Sixteen-ish min read about Leadership

This is a mirror of a post I made back in 2018 on Medium.

Back in 2016 my manager sat me down and asked me those eight little words that every designer can’t wait to hear: “How would you feel about becoming a manager?”

I had always loved that Etsy has a strong career path for individual contributors, allowing you to not have to become a manager in order to advance your career. However, I realized this would be an amazing opportunity for me to learn and grow in ways I hadn’t had the chance to before, and hopefully help others do the same.

I had no idea how much I’d get to learn in that time. Certain moments of life feel so packed with learning and growth that they feel compressed—like dog years. Though it felt a little crazy at times, I’ve been underservingly lucky to learn from smart and talented mentors at Etsy about how to be a better manager of people, and really, of myself as well.

About a year ago I saw an opportunity I felt compelled to pursue: A chance to help lead our Design Systems as an individual contributor. The decision felt right, but left me with no regrets for my time spent as a manager.

During this moment of transition, I thought it’d be helpful for myself, and hopefully for others, to hear some things I learned by going from designer to design manager.

1. Never stop experimenting

At first management can feel completely alien to the craft of design. The way that you think about projects, planning, and execution has to change slightly and you have to constantly learn new things.

Even though my manager gave me a lot of great tips and I had a lot of amazing support from my peers, it felt like there were thousands of different styles of management and schools of thought I could adhere to. It felt daunting at first, but you have to start somewhere and see where it takes you.

A great way to start, as with any design challenge, is to do some research:

  • Talk to your new reports. Ask them what they liked and disliked about previous managers. Ask how their ideal relationship with their manager is. Ask how they like to recieve feedback. Tell them how you like to recieve feedback. Ask what makes them grumpy. Ask what their favorite desert is (trust me, this comes in handy).

  • Read books and articles. People management isn’t a new concept. Learn how people have been dealing with this for the past hundred years. ( I posted a few links in the footnotes).

  • Talk to other managers across the company. Grab coffees and don’t be afraid to ask hard questions. Learn tips and shortcuts on how to navigate the organization your in and form good relationships with your peers.

  • Talk to managers at other companies. Again, most people problems aren’t unique to your company. Learn what other companies have struggled with and how they’ve solved those problems.

Continue to do these things and make adjustments. Experiment with your processes, your schedule, and your mindset.

Don’t be afraid to try new things, but also be smart and be prepared. We talk a lot about (and even celebrate) failing in regard to products, but we rarely talk about failure of management and the accountability that comes with it.

Understand the full consequences of these potential failures. You might cause emotional harm, stunt someone’s career, or even break the law if you don’t fully understand and respect your responsibilities as a manager.

Beyond understanding the consequences and being prepared, realize that you’re definitely going to fail at a lot of little things.

You’re going to message something poorly. You’re going to jump the gun on something. You’re going to let someone down. You’re going to make decision in the moment that probably could have been better.

Recognize this and prepare for it. Learn how to soak up the most data from your mistakes. Be honest with your reports and your colleagues. Document your learnings, ask others for feedback on how to improve, and move forward with courage in your new learnings instead of fear. Keep experimenting.

2. Help your reports succeed by allowing them to fail gracefully

As a recent individual contributor myself, it was difficult for me to step away and let my reports make mistakes that I knew how to avoid. In the first couple of months I found myself thinking, “I can just fix this and not have to waste the time.” This created created a two-fold problem:

  • My reports and their stakeholders began to depend on me for doing individual contributor work.

  • My reports often wouldn’t get to the “aha!” moment they needed in order to learn, grow, and progress.

It’s always going to feel easier to step in, look like a pro, and “save the day” with your experience. Fight this temptation! That’s not why you’re a manager.

Instead of taking care of problems yourself, the best thing you can do is find ways to help set up constraints and give guiding feedback throughout the process so that your designers can learn how to arrive at key decisions quickly.

There are many ways to do this well, but it all depends who you’re working with. Are they silent thinkers? Do they need group ideation? Do they need ample sketch time with a pen and paper? Do they work best in code or digital formats?

Find what ways work best for your people’s learning style and help them amplify and hone those styles with known, repeatable methods. Show and teach them resources and tricks that work best for them. Note that those things won’t always be the same things that work best for you.

3. Change how your measure output

I found it excruciating at first to cope with a sudden lack of creative output in design-artifact form. I was creating and reading documents, attending meetings, and having long conversations. Very few of these things felt tangible, and I would constantly leave work feeling like I hadn’t done a hard day's work.

It dawned on me that the reason I was feeling this was was because I was used to seeing actual end products come from my work every day.

I needed to change the way I thought about “work.”

With my manager’s help (thank you, Jason), I started setting up better personal key performance indicators and goals to measure my success on a weekly and monthly basis.

I tried to measure my success by my reports’ work and satisfaction, not just my own. I talked to my reports’ stakeholders and made sure they were getting what they needed from design. This way of thinking radically changed how I perceived my work week.

4. Be the “CEO” of your own area of control

When I first became a manager, Cap Watkins, gifted me with a fantastic book titled *High Output Management*. Among the many nuggets of wisdom in that book, one thing that stood out to me was a piece about thinking of management as being the “CEO” of your own little organization.

When you’re at a large organization, it can be daunting to try and fix everything that is wrong. By limiting your scope on your area of focus, you become bolder, try more things, and usually accomplish something more quickly.

This isn’t to say that you shouldn’t collaborate with other managers across the org and become some sort of rogue lone wolf, but rather what can you do to affect your team directly. Then how can you share the learnings with the rest of the org to make everyone’s process better?

5. Define roles and expectations

If you’re not sure what your role is, likely other people won’t know either. Setting clear guidance for what people can expect from you and what you expect from them is the first thing you should try to do as a manager.

Hopefully your company already has a good base for what your roles and responsibilities are as a manager, but I’ve found it helps to go above that and give extra definition that is tailored to you and the team you’re working with.

This should include what your accountabilities and responsibilities are, how you prefer to receive feedback, and most importantly what you’re not responsible for.

Don’t try to get everything perfect the first time, because you very likely won’t, but make sure other managers, team stakeholders, and your reports have a starting place to understand how they’ll interact with you.

Share and get feedback with your reports, colleagues, and stakeholders. Then help your reports do the same. Again, this can be on top of any competency matrix or current role documentation your company has.

If you’re looking for a good starting place, check out Buzzfeed’s latest iteration of their product design roles.

6. Make your calendar work for you

There’s an average of 40 hours in a single American work week.

It sounds like a lot. However, when you start to add in all of the recurring meetings, fires that spring up, and making sure you actually eat lunch that isn’t from the hotdog stand outside your office, this time slips through the hour glass faster than you’d imagine.

Despite all the terrible advice constantly going around that you should simply work more, I would challenge you to simply work more intentionally.

While 40 hours isn’t a ton, it’s definitely plenty if you plan properly.

  • Learn what meetings are valuable. Figure out what meetings you add the most value in and get the most value out of. Help your reports do the same.

  • Cancel valueless meetings. If the output of the meeting is not worth the input by all parties involved, cancel it. Even if that meeting has existed for years (actually especially if that meeting has existed for years).

  • Restructure meetings that are crucial but operating poorly. Find ways to get the most out of less time—90% of meetings can be accomplished in 30 minutes or less if you have a good agenda and set upfront expectations and expected outcomes.

  • Group time based on context. I grouped all of my recurring 1:1s to happen on a single day and made that the day where I focused on my reports’ growth. Being focused on one thing at a time allowed me to give more of my energy to it and helped me say “no” to distractions.

  • Eliminate or reduce ad-hoc meetings. A meeting that comes up out of nowhere usually isn’t structured and will take away focus time. Obviously there are exceptions, but try to look at the ad-hoc meeting requests that come up and see if you can establish recurring meeting times that those ad-hoc meeting needs could fit in. If you don’t have anything to talk about, you can always cancel the recurring meeting and have more free time.

Whatever it is, be smart about how you spend your time and become the master of it. If you don’t master your time, it will certainly master you.

7. You are the last stop

At the end of the day your job is to help something actually get made.

Hopefully at your company, there are either principles or tenants to help ensure that those things are of a satisfactory quality. At Etsy, we recently refined our design principles to help us have more clarity towards creating experiences that are successful and high quality.

Unfortunately, due to time, staffing, or other constraints, those principles don’t always get met 100%. That’s where you come in as a manager. It’s up to you to make sure the project or team you’re managing crosses the finish line in first place.

This is obviously one of the more stressful parts about being a manager, but unless you own this and lean into it preemptively, that stress will overcome you in the worst moments and you’ll end up overworked and burnt out.

Set up checks and balances. Don’t be afraid to give constructive feedback. Look at what’s coming down the pike and make sure your reports are prepared. Have an open door to listen to concerns and problems and address them as soon as possible.

8. Listen at least 5x more than you speak

When I first became a manager I found myself wanting to “prove” that I was worthy of being a manager. I wanted my reports and colleagues to know that I knew what I was doing and that everything would be taken care of.

Because of that I often spoke too much and didn’t listen near enough. After chatting with some of the amazing other design managers (shout out to Kary) I realized that I needed to chill the hell out. As a way to help with this I started a rule to try and listen 5x as often as I spoke.

Instead of waiting for my chance to speak, I would dig into what someone was trying to say and make sure that person was heard and they were able to fully speak their mind. Not only does this make for a much better interpersonal experience, it also usually creates an opportunity for fuller, richer ideas.

9. Don’t just support, sponsor

It’s a hard thing to remember, but none of us would get anywhere in this world if it wasn’t for someone investing in us.

Whenever I became a manager this reality became light as day.

There will be so many opportunities teach and support others once you become a manager. This is one of my favorite aspects about managing and what made me open to the idea in the first place.

While teaching and supporting your reports is fantastic and rewarding, it should be seen as a baseline “duh” requirement for being a manager.

I’ve been very lucky to have great managers that went above this to show the difference between support and sponsorship.

Support is giving someone the tools to grow, but sponsorship is going out of your way to find opportunities for that person to grow, flourish, and become the best version of themselves.

This could be fighting for budget for learning and development, encouraging them to take time off, or looking for opportunities them to be challenged and for their talents to shine best. My manager giving me an opportunity to become a manager myself is a great example of this in action.

This is most most most important when you’re managing someone who is underrepresented in your workplace. You have the responsibility to ensure that this person is given the same opportunities and voice and is provided the support and amplification they need when they take those opportunities.

It doesn’t just stop there—you have to keep at it. The most important thing about sponsorship is following through.

Support is telling. Sponsorship is doing.

Sometimes, if you do it right, your reports may not even realize certain things happened because of your intervention and you might feel bummed that you’re not getting the recognition you “deserve.”

This might seem like a bummer, but being a manager is not about shining a light on yourself, it’s about shining a light on your reports and your team.

(Note that this also doesn’t give you carte blanche to act like a martyr.)

10. Keep everyone looking North

We live in a world fraught with distractions at every turn. Corporate life is not excluded from this. It’s incredibly easy to get lost in the weeds and forget why you’re working on a project or what you’re working towards.

It’s your duty as a manager, and especially as a design manager, to help establish a vision and keep people pointed towards it.

This could be a vision for the company, team, product, project, or sprint. Help people realize where they want to go and help them get there. It’s a simple concept, but can be hard to execute.

Every team operates differently and needs different motivators. This is why it’s important to get buy-in on the vision early on. Have the team help create the vision. Maybe it’s a prototype, a statement, or a list of needs your product is solving for. Find out what works for you and your team.

I’ve found that visual representations help a lot to convey vision. It’s much harder to disagree with visuals than words.

A small rule that I’ve found works for me is “whoever draws first, wins.”

This isn’t meant to say that you should always be trying to “win”, but if you’re needing to get a point across and make sure people understand what you’re trying to say, have a visual to go with it.

You’re a designer after all.

11. Make your job “obsolete”

People will often tell you to “find ways to make yourself invaluable” at a company. This is partially very bad advice.

While it’s great to ensure the company you work for knows your worth and value, it’s even more important that the company be successful even if you’re not around. I’ve found this is doubly true in management.

If you team is so dependant on you that they can’t operate without you, then it’s probably indicative of an inefficient team. Granted there are exceptions to this, and it doesn’t mean that you’ll put out bad work. Sometimes dependant teams actually put out some really great work.

What it does mean is that you and your team are more likely to get burnt out and taking time off will become the more stressful than it is relaxing.

To solve for this, try to set up systems that work for you instead of because of you. Help your team set up and document processes and guidelines for how product development should operate. Make sure everyone is on board with the process, and continue to hone it.

Set clear goals and tenants to help guide your team to make decisions. Set up checklists and structures that ensure product quality. Start removing yourself slowly from certain check-ins, meetings, or decisions and see how things operate without you.

If you get to that point then you start asking yourself, “Well, what do I do now?” That’s where the magic starts and you can start focusing on bigger pictures, problems, and visions.

However, this doesn’t mean you should check out and just let things ride. Make sure you’re still engaged in the now. Find a balance and make sure your reports have everything they need to do their best work.

All of these things have a common connector. They’re all things that designers do already—experimenting, learning, communicating.

Even as a manager, you’re still a designer. Instead of designing flows and experiences, design situations in which people express the best version of themselves and their craft.

I have so much more to learn, and this is but a fraction of what I’ve learned so far, but If you want to learn more about management, here’s some good places to start:

Shout out to Kary Campbell and Cap Watkins for giving this a read through and providing some great suggestions.

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