Design Leadership Handbook

Managing a design team

Serve and protect

by Aarron Walter and Eli Woolery

In the High Resolution podcast, Bobby Ghoshal and Jared Erondu discuss the two paths of design leaders with Kate Aronowitz of Wealthfront. View the full episode on Youtube.

The primary job of a manager is to manage the careers of others. Though management may not be your passion, it will be an important part of your work. As a design leader you’ll help people do great work and develop fulfilling careers, which can have a profound influence on your organization.

Great managers are not bosses, they’re servant leaders who wield their power to help others. Your service will be an example to your entire team, and will encourage behaviors that will make your team strong. Your actions are a far more effective coaching tool than words alone!

Rich Armstrong, the former COO of Trello, succinctly describes the responsibilities of a manager who serves his or her team and helps each person grow:

  1. Discover where their professional goals intersect with those of the organization.
  2. Remove impediments to their achievement of those goals.
  3. Hold them accountable to move forward on those goals.
  4. Show them how far they’ve come from time to time.

The way to deliver on each of these responsibilities is to schedule 1-on-1 meetings with each team member.

1-on-1 meetings

1-on-1 meetings are a great way for managers and their direct reports to connect individually on pressing issues, develop a strong relationship, and ensure that employees feel like they’re working toward their goals. These are not status update meetings; they’re an opportunity to give regular feedback and foster growth.

Feedback flows both ways. Smart managers ask team members for insight into how they could serve the team better. These honest conversations can help everyone improve.

1-on-1s are also an important time to get to know each team member personally and build rapport. The complexities of life often follow us into work and can affect our performance. Making time for personal conversations can give you insight into a team member’s emotional state.

Ask these sorts of questions in your 1-on-1s:

  • Short term goals: How do you feel the project is going so far? Are there any projects you want to work on in the near future?
  • Long term goals: What do you want to be doing in 5 years? What are your big dreams in life?
  • About the company: What is the company not doing today that we should do to better compete in the market? What’s 1 thing we’d be crazy not to do in the next quarter to improve our product?
  • Self improvement: Do you feel challenged at work? Are you learning new things? What area of the company would you like to learn more about?
  • Manager improvement: What could I do as a manager to make your work easier? Would you like more or less direction from me on your work? How can I help you with your goals?

There are so many important topics to cover. Jason Evanish has published 101 questions for 1-on-1s, an invaluable source that will help you spark meaningful conversations with your team members.

Say thank you and celebrate

With all of your responsibilities as a design leader, you’re going to be busy—very busy. As you focus on pushing projects forward and running your team, don’t forget that people need to be recognized for their contributions. Make a habit of saying “thank you” to each team member for their work. Everyone needs to hear it individually and as a team.

After wrapping up a big project, take time to celebrate with your team. They need to feel a sense of accomplishment and recharge their batteries. If you move on to the next project without recognizing the team’s accomplishment, you risk them feeling empty and uninspired to climb the next mountain with you.

Etiquette tip: Criticism during a celebration will just demoralize your team. Save your feedback about the project until after the celebration!

Introducing new management layers

As your team grows, you’ll need to introduce additional layers of management to keep the team and their projects on track. You’ll know it’s time when you no longer have enough hours for all of your 1-on-1 meetings.

When you reach that point, you’ll be anxious to get extra help to relieve some stress, but fight the urge to take quick action. Putting the wrong person in a position of authority will only make your work harder.

When you’ve identified a prospective manager, assign them just 1 employee to manage and observe how they handle the shift in work. If they neglect their new management responsibilities in favor of design work, you know you’ve got the wrong person for the job.

If the team member performs well, add additional direct reports and remove design tasks from their to-do list. Continue to monitor and coach them regularly to help them get their bearings.

Twitter has a unique approach to how they transition individual contributors into management. In other organizations, career growth is often closely connected to a company’s org chart—to make more money you have to become a manager, which incentivizes the wrong people into positions of power. In contrast, Twitter sees the transition into management as a lateral move, and there is no pay raise associated with it. Raises are performance-based, which incentivizes the right behavior—designers who want to further pursue their craft will develop their career without sacrificing their passions.

Right person, right project

There are 2 very different types of designers: hunters and farmers. Each is essential to a design team, but—as Aarron Walter discovered while leading the UX team at MailChimp—when matched with the wrong project, chaos ensues.

Put your designers in a position to succeed by playing to their strengths, and look for traits in each of your designers to identify farmers and hunters:


  • Love constraints, and feel lost without them
  • Enjoy slogging through existing products to find a more refined design solution
  • Thrive on product iteration and refinement


  • Excited by freedom to wander—too many constraints deplete their energy
  • Comfortable with uncertainty and unfamiliar territory
  • Thrive on new products and redesigns

Resolving conflicts

Conflict is uncomfortable, but it’s inescapable as a design leader. When conflict arises in your team, confront it early to maintain the health of your team.

Each 1-on-1 meeting is an opportunity to listen for the stirrings of conflicts. Don’t wait until  deadlines are missed or the team seems ineffective. If a designer reports conflict between other team members, talk with everyone individually before taking action. Matters can be blown out of proportion when information is second hand, and you can make things worse if you act before you’re fully informed.

When you’ve identified a conflict, get all parties in the same room to have an honest conversation. Let everyone have the opportunity to be heard, and don’t conclude the meeting until you’ve collectively identified a pathway to resolution.

Key takeaways

  • Conduct regular 1-on-1 meetings to establish rapport and foster career growth with each team member
  • Take time to thank your team members and colleagues regularly. People need recognition to feel their work is valued.
  • When your team has reached a big milestone, celebrate. It’ll make your team closer and communicate your respect for their contributions.
  • Before moving someone into a management position, let them test the waters by managing 1 person. If they perform well, add additional direct reports.
  • Avoid pay increases when transitioning someone into management. It incentivizes the wrong people to seek positions of power.
  • Put your designers in a position to succeed by playing to their strengths. Pairing the right designer to the right project is key to keeping your team productive.
  • When conflict arises, do your research before you act. Trust, but verify the claims made by your team members.
  • To resolve conflict, get all parties in the same room to have an honest conversation. Let everyone have the opportunity to be heard.
Design Leadership Handbook

Shaping design vision

The story of why

by Aarron Walter and Eli Woolery

What is it about reading a good story that makes it seem so effortless? In The Storytelling Animal: How Stories Make Us Human, Jonathan Gottschall writes:

“…authors trick us into doing most of the imaginative work. Reading is often seen as a passive act: we lie back and let writers pipe joy into our brains. But this is wrong. When we experience a story, our minds are churning, working hard.”

We evolved as storytelling creatures, and the power of story has never left us. As companies scale and teams sprint through product iterations, it’s easy to lose sight of how your product should fit into the lives of your customers. The best way to keep everyone pointed in the right direction is with a clear, compelling story—a story that will unite and guide teams toward success.

Related: Secrets of design leadership—from Stanley Wood of Spotify

Product roadmaps guide team milestones, but they only show us what to build and when. They don’t show us why we’re building a product. Stories, however, are great at explaining why. In Start with Why, author Simon Sinek proclaims that, “People don’t buy what you do; they buy why you do it. And what you do simply proves what you believe.” Similarly, the best product teams don’t merely follow a process; they march toward a shared destination—a vision of the future presented as a story that answers, “Why are we building this?”

Talking about the why

Design leaders need to craft the vision for a product and communicate how it fits into the lives of others. There are many mediums for conveying this story; some design teams create large boards that show design style or tell the story of how their product will fit into the lives of their customers. Others create short videos to illustrate to all how the product will fit into the customer’s lifestyle.

While preparing for a major app redesign, the UX team Aarron Walter led at MailChimp produced a vision video to guide the company on what was to be a 4-month project.

The research team had noticed after a number of customer visits that people were doing work differently. Persistent internet connections on phones and tablets let people work anywhere and all the time, ducking in and out of small tasks. This created a sense of found time that was quickly being filled up with more to-dos.

As people became overwhelmed with their work, they needed to hand things off to others. Seeing these behavioral patterns, the UX team realized they needed to rethink how MailChimp handled collaboration across many devices.

The project required the collaboration of many teams. They wrote a short script and worked with their in-house videographer to produce a brief vision video in about 10 days.

Faced with a major redesign of their platform, MailChimp created this vision video to guide all teams.

The production was inexpensive and relatively fast, but the outcome was of high enough fidelity to guide designers, developers, marketers, and other stakeholders around the company as they worked to realize the vision set forth.

Sketches and storyboards are another great medium for conveying stories. Airbnb worked with Pixar illustrators to create storyboards that showed how their products would fit into the lives of their customers. Their storyboard gave everyone a vision of the product experience they wanted while still giving each team the freedom to solve the problems as they saw fit.


The storytelling mechanism you choose is less important than the story you tell. The act of creating a product story before you begin the design process not only helps you mobilize your teams, it also forces you to clarify your intentions for your product. You’ll step out of the maker’s mindset and consider how your product will fit into the lives of others.

Vision—whether presented through a video, storyboard, or some other means—gives purpose and clarity to our work. Without it teams often lose sight of their mission.


When you come to a fork in the road, take it

As design leaders, we are often thinking and communicating in terms of how design ties into company strategy, and we become less focused on craft. This is just a normal part of how a role evolves as responsibilities grow. As a company scales, CTOs don’t often do much coding, and CMOs rarely have time to write a blog post or draft an email campaign.

But as designers, we are in a somewhat unique position where our craft can inform our thinking. Don Norman, Director of the Design Lab at University of California, San Diego, writes about the tension between craft and design thinking in his essay The Future of Design: When You Come to a Fork in the Road, Take It:

The fork in the road does not have to be a choice between two options: this is an opportunity to pursue both. Design as a craft has a long history of providing great value to humankind. Design thinking is as yet unproven, but it has the potential to provide a different kind of value to the world. Both are essential, so let us take the fork in both directions.

In Don’s view, we don’t necessarily have to give up the craft of design to become leaders, or to convey the vision for a product. In fact, this vision could be stronger if we “learn and think by drawing and doing.” So sharpen your pencils, dust off your sketchbook, and start telling better stories to guide your team to success.

Key takeaways

  • Craft the vision for your product and communicate how it fits into the lives of others. This will serve as the North Star guiding all teams.
  • Use story to communicate a design vision. Video, storyboards, and comics are all great mediums to show colleagues the future you’re creating for your customers.



Our hope is that, after combing through this guide and the readings we’ve recommended, you feel better equipped to lead your team. You now know how to build and manage a team, you have a plan to operationalize design, you recognize that you’ll need to forge alliances to be effective, and you know how to shape a cohesive design vision so everyone in your organization has a North Star to guide their work.

Though your learning curve as a design leader is steep, the rewards are great. You’re in a position to influence the trajectory of your team and your entire organization—that’s exciting.

Design leaders like you will reshape teams, companies, and ultimately our industry. Your wisdom will grow with practice, and as it does we hope you’ll share what you’ve learned with others. Leaders teach, and in doing so the depths of their wisdom deepens.

Thank you for being a leader! We’re rooting for you.

About the Authors

Aarron Walter
VP Design Education, InVision

As the VP of Design Education at InVision, Aarron Walter draws upon 15 years of experience running product teams and teaching design to help companies enact design best practices. Aarron founded the UX practice at MailChimp and helped grow the product from a few thousand users to more than 10 million. His design guidance has helped the White House, the US Department of State, and dozens of major corporations, startups and venture capitalist firms.

He is the author of the best selling book Designing for Emotion from A Book Apart. You’ll find @aarron on Twitter sharing thoughts on design. Learn more at

Eli Woolery
Director of Design Education, InVision

Eli is the Director of Design Education at InVision. His design career spans both physical and digital products, and he has worked with companies ranging from startups (his own and others) to Fortune 500 companies.

In addition to his background in product and industrial design, he has been a professional photographer and filmmaker. He teaches the senior capstone class Implementation to undergraduate Product Designers at Stanford University. You can find Eli on Twitter and Medium.

  • Currently listening to: audio book version of Zen in the Art of Writing by Ray Bradbury
  • Currently giving me inspiration: MasterClass series from folks like Neil Gaiman and Aaron Sorkin
  • Cultural thing I’m loving: Nerding out on the last season of Game of Thrones