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What does it mean to be an exceptional design leader? Transitioning to design leadership can be challenging for individual contributors. The skills that got you there often don’t translate into your new role. Insights from design leaders who have been in those shoes can help you gain confidence and tactical skills.

In this book, you’ll learn how to grow as a leader and build a first-class design team.

Contents

Becoming a design leader

You'll never be 100% prepared

Building the team

Chemistry is key

Managing a design team

Serve and protect

Operationalizing design

Build the process

Forging alliances

Design is a team sport

Shaping design vision

The story of why

Chapter—01

Becoming a design leader

You'll never be 100% prepared

Andy Law spotted an opportunity. As a designer at Netflix, he saw firsthand the need for someone to step up and bridge the gap between mobile design and the company’s engineering management. Things would be more efficient with some design leadership. Andy raised his hand and found himself in a new leadership position.

Though he had a clear understanding of the product and his craft, the mechanics of leading a team was new territory with an intimidating learning curve. He approached leadership as he would any design challenge—with research.

He interviewed managers both at Netflix and tech companies in the Valley to better understand what it means to be a design leader. Andy also carefully observed leaders and spotted the gaps in the organization where leadership was needed.

"I think one of the most difficult things to do is leading without a title…It's almost like trial by fire…I'm still learning every day."

Andy Law — NETFLIX

Most designers, when presented with a leadership opportunity, leap into the role enthusiastically, unaware of the challenges ahead. Not Andy Law; he wanted to be sure he knew what he was getting himself into.

Figure 1. Andy Law had to plow through a stack of books to get his bearings as a design leader.

He spoke with people who’d once been managers but returned to individual contributor (IC) roles, asking what about management didn’t work for them, and what should he look out for. He learned that in most cases people struggled with the new duties required of them. Their talents as an individual designer didn’t translate into management.

Andy pored over leadership books like Michael Porter’s Competitive Strategy and Dale Carnegie’s classic How to Win Friends and Influence People to fill gaps in his knowledge. At first skeptical that some of these books from decades past would still be relevant, he found that the principles—largely based on human interactions—were still quite relevant.

Andy knew his new role would occasionally feel uncomfortable. Despite doing his homework, he would at times feel unprepared, and he would certainly make mistakes. But all great design leaders start their careers with doubts and misgivings. Andy once told his boss:

“I’m never going to be 100% prepared to be a design leader, but I’ll always be 100% committed.”

This philosophy guided him through the transition as he found his footing. As a manager, Andy learned how to deal with all types of personalities, how to motivate people, and how to develop rapport to be effective.

Andy Law’s preparation for his new role as a design leader is exemplary, but for the rest of us, a little guidance can make the transition smoother. This guide will help you get your bearings. We’ll show you the essential skills you’ll need to cultivate, and we’ll provide you with practical methodologies to be more effective in your role.

Here’s how to become a design leader.

"The qualities of leadership are simple…They have to do with being able to listen well."

John Maeda — Automattic

What it means to be a design leader

The transition to a leadership role is hard for many designers because their love of craft runs deep—leading design means less designing. As a leader, you’ll spend most of your time managing the team. That doesn’t mean you’re no longer a designer; it just means someone else will be implementing the design. Your new position is an opportunity to provide vision and guidance.

You’re no longer just playing an instrument. Now, you’re conducting the orchestra.

As a designer, you’re accustomed to thinking carefully about the customer experience, a skill that will also come in handy as you lead your team. You’ll be designing an environment and structure that brings out your employees’ best work to serve both the company and its users.

"A lot of the anxiety about moving into leadership is that the typical introverted, thoughtful traits associated with designers are not a natural fit at the executive level. Therefore, designers wanting to increase their scale and influence have to be fully aware of the emotional challenges that are likely to result."

Bob Baxley — FORMERLY APPLE, PINTEREST, YAHOO

There are emotional challenges that come with a transition into a leadership role. As a leader among leaders, you’ll be working more often with people who don’t necessarily think like a designer, which is not bad—it’s just different. You’ll need to express ideas differently. To your design team, you might say, “This one feels like the right direction.” But to an executive, “This meets our business goals” will make more sense.

You’ll be adapting to new cultures and speaking new languages, but soon foreign territory will become familiar and you’ll find ways to be effective in most any situation.

"Driving the concept of creativity and design in large organizations comes with a long-term commitment, which will not be a sprint but more a marathon."

Eric Quint — 3M

PRO TIP — What Got You Here Won’t Get You There

You’ll need to cultivate an entirely new set of skills to be an effective design leader. While Marshall Goldsmith’s book What Got You Here Won’t Get You There isn’t about design, it is about making big career transitions, and will give you the guidance you need as you make the leap from an individual contributor to a leader in your organization.

What you’ll learn

Design leaders do more than spend their days giving thumbs up or down in design critiques. In this handbook we’ll help you get your bearings on these essential skills:

Build your team: Find people with the right balance of technical and soft skills for your team. You need to be searching for talent even when you don’t need it! Find the right organizational structure to make your team productive.
Manage: Evaluate each team member’s performance, coach them so they can grow, and minimize conflicts.
Operationalize: Keep your team moving efficiently by standardizing the design feedback process, managing projects, and coordinating with other teams.
Forge alliances: Build connections with other team leaders and executives to make sure your team gets what it needs.
Provide vision: Though you’re no longer pushing pixels, you still need to play a central role in crafting a vision for your product and brand.

As a design leader, you’ll have a lot on your plate! Let’s take a look at each of your responsibilities in detail, starting with how you’ll build your team.

Defining team values

Your team is unlike any other team in your company—though your team is part of the broader company culture, you have your own sub-culture too. The act of design is uniquely emotional, as it requires exploration of new and uncharted territory. Because design is a qualitative endeavor—operating on feel, not numbers—it introduces a level of vulnerability that is atypical of product management or engineering. It is a unique discipline with its own set of values.

And those values are important. They will shape your culture, hiring decisions, team member evaluations, productivity, and ultimately the happiness of each person on your team. As a design leader, you should work with your team to define the core values that will shape your culture and establish a motivational foundation for the work you do. When there’s buy-in from everybody, teams operate more cohesively.

This process will help you identify your team’s values:

Seed the conversation. Before getting the team together, gather values from other design teams and jot down a few notes about the values you’d like to see your team consider. This sample team values doc will give you and your team a starting point for your discussion and help you understand how values affect your work.
Gather your team and share your thoughts with them. Have each team member write down 5 values on sticky notes privately, then post them on the wall for discussion.
Let each team member explain the values they identified.
Group common values on the wall to narrow your options and identify trends.
After discussion, give each team member 5 small dot stickers to cast their votes for the values they feel best represent the team.
Further discussion may be required to trim the list to the essentials. Once you have a final list, create a shared document with a detailed description of each value.

Figure 1. When your team’s values are visible they remain on everyone’s mind.

Consider making your team values visible. A series of beautiful posters can help them sink into your team’s culture more effectively.

Pay close attention to these values over time. Do they remain an accurate representation of who you are as a team, or are they merely aspirational? If the latter, realign the values to better reflect the team.

"Hand out priorities, not tasks, and let your people be creative about their own execution."

Kavin Stewart – REDDIT

Hiring

"Self awareness is a big one…know where you are, knkow where you are weak and where you are trying to build."

Ian Spalter — INSTAGRAM

Whether you’re at a startup that’s doing well or a more established enterprise, your team is probably growing (as Y-combinator founder Paul Graham writes, startup = growth). To keep pace with your current and future growth, you’ll need to ensure hiring is ingrained in your workflow.

Hiring the right people is actually your most important job. The people you hire will form the foundation of your team, and may in turn hire others as growth continues. They’re also your greatest legacy. Some will outlast your tenure and carry on the work you started. Think carefully and invest your time accordingly.

If you’ve ever freelanced or run an agency, you know how critical it is to keep your project pipeline full. The same goes for hiring; if you wait until you have an open position to begin searching for talent, you’ve waited too long!

Doug Dietz, GE Healthcare

Listen Online: Flipping soft vs. hard skills

Think carefully about the needs of your team and the company as you consider candidates. You may be tempted to evaluate candidates based on their technical skills, and you may write them off if they’re missing one skill you think critical, even if they fit other requirements perfectly. The primary reasons for letting an employee go rarely relate to a lack of technical prowess; rather it’s a shortcoming in soft skills. Missing technical skills can be remedied with coaching, but shortcomings in soft skills are much more difficult to correct.

"The 1:1 interview is your chance to assess soft skills: self-awareness, social awareness, self-management, and relationship management. These are all ingredients for emotional intelligence, which are critical for design success."

Irene Au — KHOSLA VENTURES

Assessing soft skills can be difficult, especially in the constrained environment of an interview—the interviewee is likely anxious and trying to impress you. You want to set your interviewee up for success, so get to know the person before discussing technical stuff. Find out what they’re passionate about and how they see the world. It can sound like casual chatter, but it provides the clues needed to evaluate soft skills. Here’s what to look for when interviewing candidates:

Broad perspectives

Diverse backgrounds and interests introduce different perspectives to the team. You don’t want to hire a bunch of employees who are just like you; this is why it’s best to avoid hiring for “culture fit.” Instead, to really foster innovation, look for people who bring new dimensions to your company, and strive to build teams with a variety of voices and outlooks.

"If you want diversity of thought, you have to bring in people around you who have diverse experiences."

Victoria L. Brescoll — YALE SCHOOL OF MANAGEMENT

Adaptation and grit

Listen hard to your candidate’s life and work experiences. Stories of overcoming adversity, not fitting in, or moving to a new country, for instance, provide clues about how someone deals with challenges. Adaptation skills demonstrate that the candidate has the aptitude to overcome a tough problem, team change, or new project.

MacArthur Fellow and psychologist Angela Lee Duckworth calls this quality “grit.” Grit is more than just perseverance; Duckworth ties grit to a focus on long-term goals and a commitment to following through on them. Candidates who’ve overcome adversity over a long period of time because they can see the payoff are gritty, and usually make great hires.

A collaborative mindset

Few skills are as important to a team as collaboration, but it can be hard to gauge during an interview how well a candidate will work with others. However, there are ways to pick up signals, like by asking the candidate about the dynamics of other teams they’ve worked on, and discovering how they like to collaborate. Look for red flags, like if the interviewee blames failures on other team members.

It might make sense to create a small, tightly scoped project to help you evaluate candidates. Here are 2 project ideas:

New product ideation exercise

Assemble your team and the candidate in a room with a whiteboard for a 1- to 2-hour ideation session. Identify a product idea to explore as a group—one that you and your team have no prior knowledge of so you’re on equal footing with the candidate. Work through a simplified Design Sprint process to explore design solutions to the presented problem. Sketch individually, present ideas, and discuss. Work through revisions of the ideas together and observe how the candidate works with your team.

Reimagining existing product exercise

Invite the candidate to conduct a detailed evaluation of an existing product (it needn’t be yours), identifying flaws in the user experience. From those observations, have the candidate design an alternate solution and present it to the team for discussion.

When the design is presented, listen carefully to how the candidate responds to critical feedback from the team. Are they defensive or open-minded? Do they talk more than they listen? Do they seek credit? You’ll learn a lot in that short exchange.

Doug Dietz, GE Healthcare

Listen Online: Hiring for collaboration

Social aptitude and energy

Beyond structured collaborative activities, social time with a candidate provides everyone a chance to get to know each other—invite candidates to lunch as part of the interview process.

Spending time together benefits both you and the candidate. You can determine if the candidate is still excited about the job opportunity. Do they gel with your team? Can they hold a conversation, or is there awkward silence? Discomfort in the interview process will be amplified if the candidate joins the team, so pay close attention. For the candidate, social time provides a preview of the working relationship.

Look for red flags and green lights, and be sure to listen to your gut. Gut feelings can tell us a lot if we’re willing to listen.

Liz Danzico, NPR/SVA

Listen Online: Assessing working

Humility

Humble people make great teammates, as they’re willing to listen to and learn from others. They don’t crave credit, so they’re natural collaborators, and they treat others fairly and with kindness.

A candidate’s humility, or lack thereof, comes through in a longer interview process. When they checked in, how did they treat the people at the front desk? Did they ask a lot of questions of the people they met? Did they take the time to learn about the company, you, and your team before the interview? It’s hard to ask about humility directly in interview questions, but tune into the language your candidate uses and you might get an accurate reading. Listen for an abundance of self-congratulatory statements and a lack of shared credit.

Though humility is an attractive virtue in a candidate, be sure it’s balanced with confidence; confident designers act upon their judgements but are humble enough to know they could be wrong.

PRO TIP — Genius designers

It can be alluring to hire a genius designer with an ego to match, but be sure to consider the costs to the team. A strong-willed designer can intimidate others—intentionally or unintentionally—and make people feel like there’s no place for their contribution. Thoughtful leaders will choose people who unite, not divide. There are, however, rare cases where a genius can be a great hire. When given the independence to experiment, a relatively isolated genius can produce innovative results.

Easy to hire, hard to fire

It can be tempting, as a project grows and existing team members are overburdened, to try to save the day by hiring the first halfway decent candidate that walks through the door. But it’s critical to take the time to make an informed decision—hiring too fast fills your company with people you don’t want to work with, who will derail your progress, and who will demoralize your best performers. Fast hiring often leads to slow, painful firings.

PRO TIP — Design/UX recruiting resources

Khosla Ventures has assembled a great series of resources that will help you recruit, review, and interview candidates for your design team.

Remember, as a design leader there is nothing more important than hiring. Put in the time, get to know each candidate well, and choose people who bring new perspectives to your team.

"The assignment I give teams to start with…is to write and agree on a thank you letter."

Jared Spool — UIE

In the High Resolution podcast, Bobby Ghoshal and Jared Erondu learn a technique for writing a useful job description from Jared Spool of UIE.

The designer hiring process

This hiring schedule will help you get a good read on design candidates and help you see how they’d fit into your team:

Phone screen (30 minutes): You or someone in HR will have a casual conversation to see if the candidate has any immediate red flags and gauge their personality.
Phone screen (1 hour): You and someone else on your team will speak with the candidate by phone to learn about their work history, interests, and views on design. Leave time for the candidate to ask questions, which will inform both you and the candidate!
On-site visit (4 to 6 hours): You’ll invite the candidate to your office to present their work and field questions about their process. Include your team and representatives from other departments, and leave time for more casual conversations.
Decision time: Get each team member’s feedback individually, not as a group—people can talk themselves out of red flags. If the candidate didn’t make the cut, give honest and constructive feedback to make this is a learning opportunity.

PRO TIP — How Facebook hires designers

Julie Zhuo, VP of Product Design at Facebook, shares a behind the scenes look at how Facebook hires designers. Bestselling author and Wharton professor Adam Grant has developed a series of questions to help you hire Trailblazers, Nonconformists, and Originals.

Firing

Sometimes, even if you follow a great hiring process, things just don’t work out. Before the situation becomes unworkable, take the time to coach your employee, and communicate feedback clearly and often. If things aren’t headed in the right direction, the employee should know and have a chance to improve. A firing should never be a surprise.

"There’s never a great time to fire someone, but delaying the execution only makes it worse. Every interaction between when the final decision has been made and until it’s carried out is a painful charade."

David Heinemeier Hansson — BASECAMP

Firing is painful for all involved. It can cause you sleepless nights, and inspire doubt in your abilities as a manager. But the sooner you fire a bad employee, the quicker you and your team can right the ship than if you put off the painful task.

You may also inherit a team with mediocre players. Unfortunately, mediocrity begets more mediocrity—it’s hard to attract top talent to the “B” team. Make improvements to the team quickly or you will find yourself stuck with a second-rate team.

A toxic team member can pollute the whole team and give other teams pause before collaborating on a project. If you have a bad apple, experiment with a temporary reassignment to see how the team dynamic shifts. A dramatic, positive change in your team with the problem team member absent will be a clear cue that stronger measures are needed.

It can feel brutal to fire somebody, but in virtually every case you’re doing them a favor since it frees them up to find another opportunity that is a better fit for them.

Bob Baxley — FORMERLY APPLE, PINTEREST, YAHOO

If you do get to the point where the employee needs to be let go, be respectful, and help them find a new opportunity. This transition will help them reflect on their career and could be the change they need to rekindle their passion for their work.

PRO TIP — You should have fired them sooner

Cindy Alvarez, Director of UX at Yammer, shares a helpful list of 5 types of people she should have fired sooner.

Team structure

You’ve done the hard work of hiring the right people for the right roles, and now you need to organize your team so they can be most effective. What organizational model should you follow?

"Everything we make has constraints, and unless we know what they are, we cant design for them."

John Maeda — AUTOMATTIC

There are many possible team structures, each with benefits and challenges. None are perfect; instead of searching for a single solution, consider what’s right for your company right now and craft what’s right for you.

PRO TIP — Optimize for today

The team structure you choose today won’t fit your organization in the future; no doubt you’ll have to change course at some point as the team and company evolve. Optimize for today, but be prepared to change.

Let’s take a look at 3 different models and explore what they have to offer.

Centralized

A centralized team structure keeps all designers in the same team in a shared space. Some refer to this as the “agency model” as other teams come to the centralized design team for their services—much like the way a client would approach an agency.

Centralized design teams can work in a shared studio space where work can be posted and discussed regularly, which can help designers grow in their craft more quickly.

Pros

Designers get frequent feedback from peers, helping them grow and stay engaged with their work
When a centralized design team monitors all UIs on a single team, it’s easier to create a unified user experience across many products on multiple platforms
Instead of focusing on incremental improvements, a centralized team can take a broader view and create a grand vision for a product.
A design culture is cultivated when all designers are together regularly

Cons

Designers leave important collaborators like engineers out of the ideation process in this structure, which can create political conflict
Designers are disconnected from technical requirements when they’re isolated from engineers
Designers must work harder to bring people into their process

Andi Law, Netflix

Listen Online: Building a high-performing design team

Embedded

In an embedded model, designers are positioned in cross-functional teams with engineers and product managers working on a specific product or feature. Cross-functional teams are a hallmark of the Agile process. This model is often referred to as EPD—Engineering, Product, and Design.

Alex Schleifer, VP of Design at Airbnb, likens EPD to a 3-legged stool: if the team was lacking a design role from the onset, or if the role was added after the engineering and product management team had already matured and grown, then the design leg ends up being shorter and the stool topples over.

At Airnnb, each EPD function “is involved and aligned from a product’s inception to its launch.” At least one member from each of the 3 teams is involved with working groups for new features, or in product marketing, or user feedback sessions. In Alex’s observations, companies that successfully grow these functions in parallel as the organization scales do 2 things: they hire and unleash a design lead from the start, and they grow the headcount of the design team in step with engineering and product hiring.

Designers have the opportunity to learn from and build close relationships with colleagues from other domains in a cross-functional team, and can gain a better understanding of the technical and business requirements of a product. But designers are often outnumbered by engineers and can feel pressure to conform to engineering values.

Mike Davidson, former VP of Design at Twitter, says that “designers in product teams are vulnerable to ‘path of least resistance’ behavior—engineers will ask the designer to make things simpler so implementation is easier. You’re accountable to a different set of values when you’re working with other designers.”

PRO TIP — Stranded on an island

Never leave a designer solo on a cross-functional team. Eventually they’ll feel lost and their growth will stagnate. Either place a minimum of 2 designers on each team or follow Slack’s example and pair designers from different teams.

"Having that kind of collaboration be really low friction…brings the quality of everything up."

Diógenes Brito — SLACK

Pros

Working closely, designers and engineers develop a strong understanding of their colleagues’ craft
The rapport established within cross-functional teams fosters empathy and respect that make collaboration easier (and more fun)
Communication is much faster. Designers are immediately made aware of the technical challenges their decisions create, and engineers learn when function diminishes form.
Diverse perspectives each step of the way lead to better product solutions
Shared ownership dampens political fighting and builds trust

Cons

Designers can feel isolated and find that their growth has stagnated
Maintaining a consistent user experience across multiple products and platforms becomes difficult
Cross-functional teams tend to work iteratively in sprints, which lend themselves well to iterative improvements, but not big leaps in innovation

Andi Law, Netflix

Listen Online: Ratio of specialists to generalists

There are many ways to organize a cross-functional team. You can organize around:

Platform: Spotify has different teams for their desktop, Android, and iOS apps
Feature: Facebook has teams that work on News Feed, Messenger, and Profile
Customer experience: Airbnb has separate teams for the host and guest experiences of their service

Hybrid

You can, of course, blend models as well to create a hybrid design organization. You can position designers in a temporary cross-functional team to work on a focused project with a clear deadline, as is common at MailChimp. When they’re done, they return to the centralized design team.

You can distribute your designers in cross-functional teams, but pull them back together for design reviews, stand-ups, and fireside chats as Twitter does.

When a company has reached sufficient scale, a centralized team can manage a code design system that serves designers distributed in various cross-functional teams. This is Spotify’s approach—they bring designers together in a design guild for design reviews, but with a focus on adhering to design systems.

Sometimes a change in your seating chart is all you need. Lendingtree has positioned their centralized design team among engineers and product managers to promote collaboration, but each designer still reports back to a design leader.

"These days you see some companies investing even more heavily in design…"

Irene Au — KHOSLA VENTURES

Team structures evolve over time, especially as a company scales, and there’s no single path to building great design teams as a company grows. However, we can apply the problem solving skills and iterative approach that we use to build great products to also build great teams.

Point your team in the right direction

It can be tempting, now that you have a team that can execute quickly, to dive in and start building. But as Laura Martini, product designer at Google, writes in her article So Your Boss Doesn’t Believe in Design Research, it’s critical that your team is headed to the right finish line, and user research can help you get there. However, it’s not always easy to convince stakeholders that this is a pivotal step in the design process.

Laura Martini, Google

Listen Online: Moving fast & finishing smart

When your team is under the gun to produce results quickly, baking research into the design process can seem like a daunting challenge. Just mention of the word “research” seems to imply that it will be expensive and time consuming—something more suited to a particle physics lab than a product design team.

But research doesn’t have to be difficult or take a lot of time. Erika Hall, partner at Mule Design, outlines a wealth of techniques for low-effort user research in her book Just Enough Research. And if you’re too constrained on time and resources to read the book, you can use her great technique—a Minimum Viable Ethnography—to get invaluable insights for less than $300 over 3 days.

Using an approach like this, you can often sneak research in under the radar. When you share the wins with stakeholders, you can show that a little research helped you get big results. This may give you more latitude to include research in your design process for future projects.

"Do fewer things, better."

Irene Au — KHOSLA VENTURES

Key takeaways

Define your team’s values to help your team make great hires and keep your culture healthy
Hiring is your most important job—invest your time accordingly
When vetting candidates, focus on soft skills. Technical skills can be coached, but soft skills are hard to change.
It’s easy to hire, hard to fire. Devote enough time to the hiring process so you and your team get to know the candidate.
Provide honest and timely feedback (the kind that’s not easy to hear) to help change negative behaviors
Firing is your last resort. Offer ample coaching and clear warnings before you consider termination.
Consider establishing cross-functional teams to improve collaboration and communication between design and development. The EPD structure—Engineering, Product, and Design—is becoming common in design-driven companies.
Conduct regular design reviews or even a design guild to help designers embedded in product teams to remain connected to their peers

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.

The 1-on-1 is the only place where I get to connect with a person to help them and the company succeed. It’s where I get to find out what’s going on in the company without sticking my nose in and micromanaging.

Rich Armstrong — FORMER COO OF TRELLO

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.

While it’s not the manager’s job to set the agenda or do the talking, the manager should try to draw the key issues out of the employee. The more introverted the employee the more important this becomes.

Ben Horowitz — ANDREESSEN HOROWITZ

PRO TIP — 15five

You can keep your 1-on-1s on track and make them more productive using 15five.com. Each week, 15five.com emails team members a short survey that helps them reflect on their work. It takes them 15 minutes to complete, and you 5 minutes to review. Their responses will spark discussion in each 1-on-1 meeting.

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!

PRO TIP — On managing a UX team effectively

Joseph Dickerson, UX Pursuit Lead for Americas at Microsoft, echoes and expands on the design leadership guidance offered here in his Quora post entitled What Do I Need to do to Manage a UX Team Effectively.

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.

Management is not a promotion, but a separate track.

Alex Schleifer — AIRBNB

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.

PRO TIP — Hunters and farmers

The MailChimp UX team was shorthanded as it wrapped up a key project, and to help us meet a deadline I brought in another designer to help. The product workflow had been sorted out—we just needed some details polished. After reviewing the work in progress, the new designer immediately started redesigning everything. These were interesting ideas, but none of the work was in the project scope. In the end, the designer pushed the team further off course, making it even harder to hit the tight deadline.

I had sent a hunter to do a farmer’s work.

Late 1 year, with some extra time on our hands, I asked 1 of my designers to begin exploring ideas for a major redesign of MailChimp. She created dozens of concepts, but I could see it wasn’t going well. Her stress was palpable. She continually sought guidance, but we had little to offer—we were venturing into new territory. After 2 months of exploration, she could take it no more—operating without constraints proved too stressful.

I had sent a farmer to do a hunter’s work.

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:

Farmers

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

Hunters

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

PROTIP — Bob Dylan and Leonard Cohen

You’ll hear echoes of farmers and hunters in Malcolm Gladwell’s podcast Revisionist History, in which he compares the creative processes of Dylan and Cohen, and Picasso and Cezanne. Turns out farmers and hunters exist in every creative medium.

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.

Setting the stage for feedback

By changing your space to create the right environment, you can set the stage for feedback and collaboration in your team. For distributed and remote teams, this is doubly important—establishing dedicated times and places for sharing works in progress keeps everyone connected.

In person

The walls of your design studio are a sacred space. This is where your team’s ideas can be shared, debated, retooled, and celebrated. Make it clear to your team that the studio walls are not a gallery—this is work space!

If you don’t already have one, invest in a large format printer and get the whole team connected. Print design work daily and post to your studio walls for scheduled design reviews and casual conversations.

If your walls aren’t ideal for posting work, you can buy 8-foot by 4-foot sheets of foam core and lean them against your walls. Get some nice Washi tape to post your designs in style (and easily peel off later). Leave markers and sticky notes nearby so your team and anyone in the company can easily jot down a bit of feedback and post it.

"Our work is plastered and posted all over the walls of the studio — not finished things, but notes, photos, and artifacts of what we’re working on. Over time, we see projects unfolding as they’re posted, and we can give each other feedback along the way. By sticking your work up on a wall, you invite an ongoing dialogue about making your project better. It makes your work tangible, shareable and visual, which gives it a much better chance of receiving feedback and critique."

George Aye — GREATER GOOD STUDIO

The design team at Greater Good Studio has gone so far as to create project bays, a modular space to post work for critical discussion. Each new project they begin gets its own bay—a physical manifestation of their progress.

Figure 1: A project bay at Greater Good Studio.

The fidelity of the work you post can influence the feedback you get. Pixel-perfect comps may lead others to believe the work is finished, which will inhibit feedback. Work that’s a little lower fidelity or with notes scribbled on it will make it clear to all that you’re still working through ideas.

"Building a safe place for your team to be creative and do their best work might be the most useful thing a leader can do for culture in design focused organizations."

Richard Banfield — AUTHOR OF DESIGN LEADERSHIP

PRO TIP — Don’t forget the screen

Be sure to work through design ideas on the screen too. Interaction design, animation, and responsive design aren’t easily communicated on the printed page. Print brings more people into the conversation (which is important!) but ultimately you’ll need to solve for screen display.

Remote

Remote teams can also set the stage for feedback using tools like Slack, Trello, Google Hangouts, and of course, InVision. The entire design team at InVision is distributed and uses their own product to conduct design reviews. LiveShare, a design collaboration feature in InVision, lets the team present their work and get real-time feedback. Early ideas are explored with Boards, later becoming Prototypes that are again shared with the team for feedback.

With so many affordable tools at hand, remote teams can easily build feedback into their design process too.

With the stage set for feedback in your team, you’re ready to establish the format for each type of feedback your team will need.

Operationalizing the feedback process

Designing out in the open is just the first step. Your team will also need to get feedback on their designs, sync with teammates to make sure progress is being made, and learn from mistakes so they can improve. This is a tall order, and calls for different types of feedback processes.

Let’s take a look at a few ways to get your team the right feedback at the right time.

“We have design critiques for every team…”

Katie Dill — AIRBNB

Design reviews

When they should happen: All the time! They’ll keep your team moving forward

Who should be there: The designer plus no more than 7 people

How it helps: Designers get the feedback they need to refine their work

Design reviews are critiques that let designers get detailed feedback that’s framed by the project goals. Design reviews can happen at a number of different points in a project. It’s often helpful to do one early on so the designer can get fresh perspectives before investing too much time in an idea that may be misguided. The midway point and toward the end of a project are also natural times to get additional inputs.

Never use a design review as a big reveal of project. If you wait until you have everything polished, you’ll be too invested to accept the feedback you’re given.

Design reviews are a great opportunity to bring in experts from other teams to make the work better. Colleagues from support, engineering, product management, QA, legal, marketing, or even an executive may have a new perspective to help you see the problem differently. But try not to overload the guest list in these reviews—too many people and you’ll have a hard time guiding the conversation.

PRO TIP — Design reviews at GV

The Google Ventures team has written a nice guide to conducting design reviews.

Design standups

When they should happen: Daily for large or distributed teams, less often for small teams

Who should be there: Everyone on the design team

How it helps: Your team gets the chance to sync up on projects

Design standups are short, daily check-ins that help your team stay abreast of the work that’s being done. As the name suggests, everyone remains standing in these meetings so no one can get comfortable enough to launch into a soliloquy.

In a standup, each team member answers 3 questions:

What did you do yesterday?
What will you do today?
Are there any impediments, or blockers, in your way?

While most teams choose to conduct standups in the morning, you may want to consider doing them after lunch—the morning is when our minds are clearest and ready to focus on creative work. For remote teams, pick a time that accommodates multiple time zones.

Don’t let standups turn into impromptu design critiques. If someone needs immediate design feedback, ask that they hold the request until after the meeting—a standup should be short and focused on project progress.

Retrospectives

When they should happen: After a project is launched or a sprint is completed

Who should be there: Everyone who worked on the project

How it helps: Your team will internalize lessons from each project

Every project is a learning opportunity, but if you don’t pause to take stock, valuable lessons will slip away. When you’ve launched a project or completed a sprint, it’s a great time to reflect on what went well, what was confusing, and what didn’t go so well.

Matt Spiel, Director of Design at Treehouse, conducts retrospective meetings regularly. He sends a pre-retrospective survey to the team before the meeting to capture each person’s perspective individually. This helps to eliminate the bandwagon effect, which happens when the views of the group conform to those of a few vocal people.

"Retrospectives are a valuable tool to use because they help teams identify strengths and weaknesses. They help provide the designers at Treehouse an opportunity to give feedback on our processes in order to grow and improve."

Matt Spiel — TREEHOUSE

Matt asks his team to rate their performance both as a group and as individuals on a scale from 1 to 5, where 5 is the highest. Ratings tend to cluster in a similar spot, but occasionally there are outliers. Team members who’ve given starkly different ratings are asked to share their views in the meeting to promote transparency and honesty.

Discussion in Treehouse’s retrospective meetings is centered around 3 questions common to most Agile retrospectives:

What worked well for us?
What didn’t work well for us?
What can we do to improve our process?

These questions are sometimes referred to as Start, Stop, Keep—what should we start doing, stop doing, and keep doing?

Honest conversation about each of these questions becomes easier with the cultivation of trust and plenty of practice running retrospective meetings.

Postmortems

When they should happen: After a project has gone poorly

Who should be there: Everyone who worked on the project and an impartial facilitator

How it helps: Your team will learn from their mistakes and find a way forward

Not all projects go well. Some go horribly wrong, requiring all teams involved in the project to come together to consider and learn from the mistakes they made.

Though projects rarely go awry at Etsy, they’ve established a strong process to guide them through those that do. Their process follows many of the recommendations set forth in the Agile methodology.

Here’s how to run a postmortem:

Before the meeting: Send an email asking the team to identify key points in the project timeline. This will be used to construct a master timeline of events, which will be discussed in the meeting. By focusing on events, you’ll avoid negative finger pointing, which can derail the process.
Moderator: Choose a moderator who wasn’t on the project and can be impartial. This person should be guiding the conversation from the whiteboard, taking notes for all to see.
Ground rules: The moderator should first point out that this is not a blame session, but an opportunity to learn. It’s a conversation about the shortcomings of the team’s process, not the people involved.
Facts: People recall events differently. The moderator can help the team agree upon what actually happened so lessons can be extracted. Establishing a timeline of events can help pinpoint where things went wrong.
Lessons and actions: As key lessons are identified, they should be written on the whiteboard for all to see. The actions required to mitigate the problems stemming from the failed project also need to be identified, assigned an owner, and provided a clear deadline.
After the meeting: The lessons learned from the postmortem should be emailed to the entire team, along with the action items that are to be completed.

Postmortems can seem rough, but they’re far superior to repeating the same mistakes. They’re a powerful opportunity for your team to learn and improve your processes.

Once your team’s operations are sound, you need to start thinking beyond your borders. How will you interact with other teams in the company? This challenge is less about operations, and more about just getting to know people.

Key takeaways

Build a culture of feedback help your team grow
Get your team in the habit of posting their work for all to see. Feedback comes more naturally when you create the right environment.
If your team is remote, set the stage for feedback using tools like Slack, Trello, Google Hangouts, and InVision
Conduct regular design reviews to give designers detailed feedback framed by the project goals
Conduct design standups regularly to help your team stay abreast of the work that’s being done
At the end of each project, hold a retrospective meeting to collect the lessons learned and continuously improve your team processes
When projects go poorly, run a postmortem meeting to learn from your mistakes without finger pointing

Educating your company about design

“The secret is to make people aware that they too can do great design.”

Andrea Mallard — OMADA HEALTH

Even if your team is already visible within the company, it can be challenging to find ways to focus the company culture on design without hiring more design resources. One method is to find alternate means of educating non-design colleagues about how designers solve problems.

At Netflix, Andy Law approaches this in several different ways. Once a quarter, Netflix holds a “UX Progressive,” where engineers and others can visit a designer’s desk to get a demo of current work in progress. Andy has also used screenings of InVision’s DESIGN DISRUPTORS film as a way to educate colleagues about design: “There are a lot of people interested in how designers approach and solve a problem, and DESIGN DISRUPTORS does a really good job of synthesizing what that is.”

Another approach is to host one-on-one sessions with colleagues who are interested in learning more about design, or who seek design help with a project. When Irene Au was at Google, the design team held weekly “office hours” where colleagues could come with questions and get feedback on their projects.

No matter the approach, educating colleagues about design and empowering them to use elements of the design process offer opportunities to increase the visibility and influence of design within your company.

Key takeaways

Set design review days on your team’s calendar and invite specific people to participate
Your org chart is not a list of names; it’s a group of potential allies. Get to know them.
Post your work in an accessible space. Present your work at company coffee hours. Talk about your work and answer questions in a company Slack channel.
Solicit feedback every step of the way. This isn’t design by committee, but good ideas—and constructive criticism—can come from anywhere.
Find opportunities to educate your company about design (UX progressives, film screenings, office hours).

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.

Conclusion

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.

Discover. Learn. Elevate.

In this book, you’ll learn how to grow as a leader and build a first-class design team.

"I think one of the most difficult things to do is leading without a title…It's almost like trial by fire…I'm still learning every day."

"The qualities of leadership are simple…They have to do with being able to listen well."

What it means to be a design leader

"Driving the concept of creativity and design in large organizations comes with a long-term commitment, which will not be a sprint but more a marathon."

What you’ll learn

Further reading

Defining team values

"Hand out priorities, not tasks, and let your people be creative about their own execution."

Hiring

"Self awareness is a big one…know where you are, knkow where you are weak and where you are trying to build."

"The 1:1 interview is your chance to assess soft skills: self-awareness, social awareness, self-management, and relationship management. These are all ingredients for emotional intelligence, which are critical for design success."

Broad perspectives

"If you want diversity of thought, you have to bring in people around you who have diverse experiences."

Adaptation and grit

A collaborative mindset

New product ideation exercise

Reimagining existing product exercise

Social aptitude and energy

Humility

Easy to hire, hard to fire

"The assignment I give teams to start with…is to write and agree on a thank you letter."

The designer hiring process

Firing

"There’s never a great time to fire someone, but delaying the execution only makes it worse. Every interaction between when the final decision has been made and until it’s carried out is a painful charade."

It can feel brutal to fire somebody, but in virtually every case you’re doing them a favor since it frees them up to find another opportunity that is a better fit for them.

Team structure

"Everything we make has constraints, and unless we know what they are, we cant design for them."

Centralized

Embedded

"Having that kind of collaboration be really low friction…brings the quality of everything up."

Hybrid

"These days you see some companies investing even more heavily in design…"

Point your team in the right direction

"Do fewer things, better."

Key takeaways

Further reading

“It’s important to establish that in design leadership, there are two paths…”

I used to think that if you cared for other people you need to study sociology or something like it. … I concluded if you want to help other people, be a manager. If done well, management is among the most noble of professions.

1-on-1 meetings

The 1-on-1 is the only place where I get to connect with a person to help them and the company succeed. It’s where I get to find out what’s going on in the company without sticking my nose in and micromanaging.

While it’s not the manager’s job to set the agenda or do the talking, the manager should try to draw the key issues out of the employee. The more introverted the employee the more important this becomes.

Say thank you and celebrate

Introducing new management layers

Management is not a promotion, but a separate track.

Right person, right project

Farmers

Hunters

Resolving conflicts

Key takeaways

Further reading

You know you have a healthy design culture when people are giving each other feedback.

Setting the stage for feedback

In person

"Building a safe place for your team to be creative and do their best work might be the most useful thing a leader can do for culture in design focused organizations."

Remote

Operationalizing the feedback process

“We have design critiques for every team…”

Design reviews

Design standups

Retrospectives

"Retrospectives are a valuable tool to use because they help teams identify strengths and weaknesses. They help provide the designers at Treehouse an opportunity to give feedback on our processes in order to grow and improve."

Postmortems

Key takeaways

Further reading

“I think there is a lot you can do to build rapport with your engineers…”

"Your legs are your most effective design tool. Get out and connect with people."

We see our greatest successes when we involve the right people along the way.

“Sometimes we feel like we can change behavior simply by talking…it works much better and much faster when you just get to doing the work.”

"I often invited influential people in the company to my team’s design reviews so our work remained visible. My team was a little nervous about showing their early work to company leaders, but I knew it was important to do."

“How do you put design…in front of the company, so that everybody cares about it as much as the design team does?”

Educating your company about design

“The secret is to make people aware that they too can do great design.”

Key takeaways

Further reading

“What are we here to do? … What is the best alignment between what we have to offer, and what people need?”

I think what’s most important is you have to have a North Star or vision set. If people don’t have that, the mess builds up.

Talking about the why

"What I’m starting to gain a greater appreciation for is that the best results are achieved not by talking about the how, but by talking about the why."