How I assess a new design team

Stepping into a new design leadership role can be both exciting and nerve-racking. You've inherited a team—maybe one that's thriving, maybe one that's struggling—but either way, your job is to understand the current state of the team and chart a path forward. It's easy to jump straight into fixing things based on your past experiences. But before making any big changes, you need a clear picture of the business and the team, how things got to be the way things are, and the expectations of your role.

Here's how I would systematically assess a design team so you can lead with clarity and confidence and smash your goals.

Understand the Business and Team Goals

Before you evaluate the team, it's crucial to understand what they're working towards. Teams don’t exist without having specific business goals. What are the company's short and long-term objectives? How does the design function contribute to those goals? If design isn't seen as a strategic player, why not? If design isn't a competitive advantage, why not? Understanding this will help you make informed decisions and effectively lead your team.

Spend time with product, engineering, and business stakeholders to get the big picture. Dig in to understand how design is measured, if at all. If it isn't, start defining what success should look like. A design team without a clear purpose will struggle to have an impact—your first job is ensuring alignment on why the team exists.

Define Expectations—of You & Your Team

A common mistake new leaders make is assuming they already know what's expected of them. Maybe you were hired to scale the team, build a design culture, or drive measurable improvements in product experience. However, expectations vary widely between companies and even between leaders within the same company.

Ask the hard questions:

• What does success in this role look like after six months? A year?

• Are there specific metrics?

• What did my predecessor do well? Where did they struggle?

• What gaps or weaknesses does leadership believe exist in the design team today?

• What questions do I need to answer?

At the same time, clarify what's expected of your team. Are they seen as execution partners, strategic thinkers, or somewhere in between? Understanding this will help you assess whether the team's current skill sets match the expectations placed on them.

Talk to Key Leaders & Stakeholders

You don't want to build a team in a silo. Strong design teams operate at the intersection of product, engineering, marketing, and business strategy—so their success is directly tied to how well they’re involved and collaborate with others.

Set up 1:1s with leaders across the organization. The goal isn't just to hear what they want from design but to understand where friction exists:

• Do they feel like design is a trusted partner or an afterthought?

• What's working well in the current collaboration model? What isn't?

• How do they see design's role evolving in the company?

Patterns will emerge quickly. If multiple leaders express frustration with slow design cycles or misalignment with product strategy, those are signals to pay attention to.

Map Skills for Team’s Success

Once you have clarity on business needs and stakeholder expectations, it's time to evaluate your team's capabilities. A great design team isn't just a collection of talented individuals—it's a balanced system of complementary skills.

Start by listing out the critical skills your team needs to be successful. These might include:

• Product Thinking: Do designers deeply understand user needs and business impact?

• Visual & Interaction Design: Is the craft strong across all touchpoints?

• UX Research & Data Literacy: Are insights driving decisions, or is design operating on assumptions?

• Collaboration & Influence: Can the team work effectively across functions?

• Execution & Delivery: Are designs making it into production efficiently? Or at all?

Review Past Work

A team's past work tells you a lot about their strengths, weaknesses, and where they've been focusing their energy. Look at:

• Recent product launches and their impact

• Design artifacts like UX flows, prototypes, and research reports

• How design decisions were made and documented

Pay attention to patterns. If the team produces beautiful UI but lacks user insights, research might be an area to strengthen. If work is strategic but slow to ship, process and collaboration could need attention.

Get to Know the Team—Individually & Collectively

Beyond the work itself, you need to understand the people behind it. Set up 1:1s with every designer, researcher, content strategist, etc. The goal is to learn what motivates them, where they thrive, and what's been frustrating them. This open communication will build ongoing trust and help build a positive team culture. If you build the relationship now, it'll help the team accept and understand any future changes.

Some good questions to ask:

• What do you love most about your work here?

• What's the biggest challenge you face day to day?

• Where do you want to grow in the next year?

• What's one thing you'd change about how this team works?

You'll start seeing gaps—some might feel stuck in execution mode; others might be hungry for leadership opportunities. This insight will help you shape a team culture where people can do their best work.

Map Skills and Passions to Team's Needs

After your 1:1s, take your skills map and start mapping individuals onto it. Who's already strong in key areas? Who has potential but needs mentorship? Where do you have glaring gaps?

This is where passion comes into play. Just because someone is skilled in an area doesn't mean that person wants to focus on it long-term. Ideally, people's strengths and interests align with what the team needs—but when they don't, you'll need a plan to either develop new skills internally or hire for them.

Identify Gaps & Build a Plan

Now that you've got the whole picture, it's time to act. Are there missing skill sets that require hiring? Are certain processes slowing the team down? Are there cultural or structural issues holding people back?

Your next steps might include:

• Hiring to fill skill gaps

• Mentoring team members to step into new roles

• Changing collaboration models to work better with product and engineering

• Introducing better design systems, workflows, or research practices

But don’t forget your stakeholders. Check-in with them to ensure your observation and plans make sense. Sometimes the path forward is bumpy, and they need to be sold on the journey as well as the final destination.

Final Thoughts

Assessing a design team isn't about judging individual performance—it's about understanding the system as a whole. Your job as a leader is to set the team up for success by aligning their skills, motivations, and workflows with the needs of the business.

It's tempting to make big changes right away. Instead, take the time to listen, observe, and map out a thoughtful approach. Once you have a clear picture, you can make informed decisions that strengthen the team rather than disrupt it.

So before you start changing things, start learning. The best way to lead a design team is to understand it first.

Read, Adapt, but Don’t Copy: Avoiding the Pitfalls of Blind Implementation

Don’t blindly implement what you read in a book

Books, frameworks, and case studies are valuable—they distill years of experience into actionable insights. But context is everything—what worked for one company, team, or industry may completely fail in yours.

🚨 The pitfalls of blindly applying a book’s advice:

Ignoring your unique challenges – A startup can’t implement the same processes as a 10,000-person company. A UX team in fintech faces different constraints than one in gaming.

Forcing a framework that doesn’t fit – Not every team thrives with Agile. Not every company should “Move Fast and Break Things.” Context dictates success.

Overlooking culture and team dynamics – Leadership strategies that work in one environment may backfire in another. A process that fosters collaboration in one team might create bottlenecks in yours.

Wasting time and resources – Implementing a system just because it worked for someone else can lead to overcomplicated workflows, disengaged teams, and solutions that don’t solve your problems.

✅ How to assess if a book’s advice will work for your team:

Is it a one-way or two-way door decision? A irreversible or costly-to-reverse extensive can be thought of as a one-way door. These decisions require deeper scrutiny—restructuring a team or shifting core strategy isn’t easy to undo. Two-way doors (reversible decisions) are safer to experiment with—if a new design critique format or sprint cycle doesn’t work, you can revert.

Does it align with your team’s size, stage, and constraints? A process that works for a company of 10 designers might break when scaled to 100. Instead, look for snippets that can plug into existing processes or ways of working.

Have you pressure-tested it against your company culture? Does the advice assume decision-making power you don’t actually have? Or, will it build a culture that doesn’t align to your business values?

Can you run a small, low-risk experiment? Before overhauling a workflow, try a pilot version with a small team. Gather feedback, iterate, and only then consider scaling. When things do go well, shine the spotlight on that team as a bright-spot in the company. This will help with change management over time.

☠️ But what if you’ve already implemented something, and it didn’t work?

Reversing a bad decision isn’t easy, especially if it’s hurt morale or trust. But there are a few different approaches on how to walk back a bad decision and potentially help minimize the damage without losing your team’s confidence:

1️⃣ Own the mistake—transparently. Acknowledge that the change didn’t have the intended impact. Your team will respect honesty more than defensiveness.

2️⃣ Share the “why” behind the reversal. Explain what you learned. Was it a misalignment with team needs? An unforeseen bottleneck? A cultural mismatch?

3️⃣ Involve your team in the next steps. Instead of dictating the fix, ask for input. What would they keep? What should change? This shifts ownership back to the team and builds a more collaborative, iterative culture.

4️⃣ Rebuild trust through action. Demonstrate that you’re listening. If you say you’ll iterate, follow through. If you promise fewer top-down changes, commit to it and make it so.

5️⃣ Make “experimentation” part of your culture. If your team sees decisions as learning opportunities rather than rigid mandates, they’ll be more open to future changes.

The takeaway:

The best leaders and designers don’t just follow advice; they adapt it for their context.

Read widely. Learn deeply. But always test before you implement—and be willing to course-correct when needed.

What’s a book or framework you’ve had to walk back after realizing it didn’t fit your team?

Escape the Swoop-and-Poop Cycle: How to Manage Up Like a Pro

Is Your Boss a Swoop-and-Pooper? Here’s How to Fix It.

Does your boss fly in, dive deep into an area outside their expertise, challenge your direction, push ill-formed ideas, then disappear—only to repeat the cycle later? Do they constantly ask for updates or bombard you with new ideas when you’re already swamped?

Yeah, we’ve all had these bosses. `It’s frustrating and exhausting. So, how do you deal with it? Pack your bags and pull the ripcord? Maybe—if the entire job (culture, environment, team, the problem you're solving) is toxic. But if the job is otherwise good, quitting over a meddlesome boss may not be the best move.

The Hard Truth: It’s Probably You, Not Them

Two things are likely true:

Your boss is invested in the outcome of your work. It’s tied to their strategy and, ultimately, their success.

Your boss answers to someone—their own boss, the board, shareholders, or other stakeholders.

This means they need to be confident in your ability to deliver on key outcomes and that they can adequately represent the value to their stakeholders. If they’re constantly buzzing in your ear, it signals a lack of confidence in your execution.

Put simply: your boss doesn’t trust you—at least not entirely. That doesn’t mean you’re unqualified, but it does mean there’s a gap in trust, understanding, or communication.

So what do you do?

How to Stop the Swoop-and-Poop

Your goal is to proactively close the trust gap. Here’s how:

1. Identify What’s Missing

What aspect is unclear to your boss? Is it the vision (how your work aligns with company goals)? The execution (confidence that work is progressing well)? The strategy (whether the plan is sound)? Understanding this will help you communicate effectively.

2. Provide a High-Level Plan

If your boss struggles with the big picture, create a high-level plan with clear milestones. Walk them through it and establish a shared understanding. Then, keep it updated as you make progress. This ensures they know where you’re going, how you’re going to get there, and reassures them that you’re on track.

3. Offer Proactive Updates

If they’re micromanaging the execution, it’s because they feel out of the loop. Solve this by regularly sharing structured updates. If your boss is asking for updates, you’re already behind.

• Maintain a running document with weekly or biweekly summaries.

• Include bullet points, key decisions, blockers, and progress highlights.

• Provide links to artifacts (docs, mockups, dashboards) to minimize back-and-forth.

4. Manage Expectations

Set clear expectations for when and how you’ll communicate. If they know they’ll get a detailed update every Friday, they’ll be less likely to swoop in mid-week with random check-ins.

5. Engage Them on Their Terms

Some bosses are high-level thinkers, others love details. Pay attention to how they process information and tailor your updates accordingly. Do they prefer concise summaries? Visual dashboards? Data-heavy reports? Give them what they need in the way they prefer.

6. Make Them Look Good

Remember, your boss has their own pressures. The better you equip them to report up confidently, the less they’ll meddle. Give them the talking points they need to communicate your progress effectively.

The Payoff: Trust and Autonomy

Once your boss sees that you’re proactively managing your work, keeping them informed, and delivering results, they’ll begin to trust you more. Over time, their need to swoop in will decrease, and you’ll gain more autonomy.

If you’ve tried all this and they’re still interfering? Well, then it may be time to consider other options. But in most cases, better communication and proactive transparency can turn a swoop-and-pooper into a supportive, hands-off leader.

Design team should mirror your user base

You design your product for your users, but are you designing your design team to mirror your user base?

We obsess over user personas, edge cases, and accessibility—ensuring our products meet the needs of diverse audiences. But when we look at the people shaping these experiences, do we see the same diversity reflected?

That means thoughtfully building a team of different cultures, different educational backgrounds, and even different ways to breaking into design. This will help your team solve problems different, ask questions differently, and connect deeper to your users.

A design team that mirrors its users isn’t just a checkbox for representation—it’s a competitive advantage. It means:

✅ Deeper empathy—lived experiences inform better design decisions.

✅ Fewer blind spots—diverse perspectives catch issues before they become problems.

✅ Stronger innovation—different backgrounds lead to richer, more creative solutions.

If we want truly inclusive products, we need to start with inclusive design teams. That means rethinking hiring, fostering belonging, and ensuring every voice is heard.

How are you shaping your design team to better reflect your users? Let’s share strategies!

Keep having those 1-on-1s

Airbnb's Brian Chesky got rid of his standing 1-on-1 meetings. He says they're fundamentally flawed, and "you become like their therapist." I get that. But if you're a design leader thinking about canceling all those 1-on-1s and reveling in all that free calendar time, take a breath.

Chesky speaks from the perspective of a CEO who has very senior leaders as direct reports. If you're like most design leaders, you have middle managers or individual contributors reporting to you. And if that's the case, here's my case for keeping those 1-on-1s.

Your team still need you

They're still growing in their career, learning to manage up and down. That means they need more hands-on time with you and other leaders to ensure they're growing in ways that benefit the employee, the team, and the company. You invest in them, and the ROI takes shape in the team and product quality.

Build relationships for a better team

Regular 1-on-1 meetings help build closer relationships with your direct reports, which leads to better conversations, stronger results, and longer employee tenure. As the saying goes (but isn't always true)—people leave bad managers, not bad jobs. Staying connected to your team also helps you spot signs of burnout or other issues before they become serious problems.

Stay connected to the work

Regular 1-on-1s also help you stay better connected to the work. Suppose you condition your team to wait for you to check in before surfacing updates or problems. In that case, you might not get looped into projects until a problem gets bigger than it should.

Mentorship to grow them into better leaders

As a design leader, part of the 'product' you're building is the team. That means you're investing time and knowledge into your team so they can grow into those executives who one day report to the CEO. Part of the mentorship is enabling and teaching them interpersonal problem-solving skills so they don't use the CEO as a therapist.

While it's tempting to pump the brakes on your 1-on-1s, remember that if your team isn't learning good habits from you, they might be learning bad habits from others.