Session Recap: Transitioning to Design Leadership with Andy Polaine

The Leadership Dip: A Common Challenge

Andy introduced the concept of the "design leadership dip," that moment when new leaders start questioning everything. You go from making things to enabling others to make things—a shift that can be disorienting. Designers are used to having tangible output, but leadership is about people, relationships, and influencing stakeholders.

This transition can feel like an identity crisis: you're no longer deep in craft, but you’re also not yet fully confident as a leader. On top of that, the way you communicate changes—your team speaks design, but stakeholders don’t necessarily care about the design details. That adjustment can be tough, and the lack of formal leadership training in most design careers makes it even harder.

Leadership Can Feel Lonely

A surprising (and under-discussed) part of leadership is how lonely it can be. As you move up, your peers are no longer designers. You’re now working with execs, product leaders, or finance teams who don’t always get what you do. And your relationships with your former peers shift—you’re now the person who has to make the tough calls, which can make social dynamics more complicated.

Andy’s advice? Find your people. Connect with other design leaders, whether that’s through coaching, mentorship, or leadership communities. Having a support system is crucial.

Confidence Comes from Experience, Not Perfection

A lot of new leaders seek certainty—give me a framework, show me the “right” way to do things. But Andy pointed out that confidence doesn’t come from always knowing the answers. It comes from getting comfortable with uncertainty. Leadership is about making decisions without a guaranteed right answer—and that’s okay.

If you’ve been promoted into a leadership role, someone already believes you can do it. Instead of waiting for external validation, trust that experience has given you the tools to navigate challenges as they come.

Are Companies Setting Design Leaders Up for Success?

Organizations love talking about innovation, but they also fear change. Design leaders are often brought in to shake things up, but then hit resistance when they try to do exactly that. Companies want quick wins, but real change takes time.

Andy compared this to someone saying they want to look like Chris Hemsworth but refusing to change their diet or exercise. If companies want the benefits of design leadership, they need to create the right conditions—clear role definitions, leadership support, and space for design to operate at a strategic level.

That said, designers also need to meet companies where they are. Instead of pushing change aggressively, it’s often more effective to work within the existing system and build influence gradually.

Navigating the Shift from Peer to Leader

One audience question hit on a tricky transition: how do you shift from being “one of the team” to being the manager? Andy’s take—yes, the relationship changes. Even if you try to keep things informal, your team knows you now have power over promotions, reviews, and difficult decisions.

That doesn’t mean you can’t be friendly, but there needs to be an awareness of new boundaries. Leadership sometimes means carrying information you can’t share, and making tough calls that impact people you care about. Recognizing this shift—and managing it with empathy—is key.

Self-Reflection: The Foundation of Leadership Growth

Good leadership starts with self-awareness. If you don’t understand your own triggers, biases, and fears, it’s easy to project them onto your team. Emotional intelligence, self-regulation, and the ability to reflect on your actions are all crucial.

To grow as a leader:

• Block out time for self-reflection—it’s too easy to get lost in the daily chaos.

• Seek honest feedback from peers and reports.

• Find a mentor or coach who can help you see your blind spots.

• Work on storytelling and communication—your ability to influence depends on it.

How to Influence Without Formal Authority

One of the biggest questions was about increasing influence in one-on-one settings instead of relying on big presentations. Andy’s advice? Ask more questions.

Instead of pushing your opinion, guide the conversation by asking things like:

• "What was your intent behind this decision?"

• "What outcomes are we aiming for?"

• "What evidence do we have to support this approach?"

This shifts the discussion from a battle of opinions to a collaborative problem-solving exercise. It’s also a great way to challenge jargon and vague corporate speak. When someone throws out a buzzword-heavy statement, respond with: “I’ve heard that term used in different ways—what do you mean by it?” It forces clarity and alignment.

Final Thoughts: Owning Your Leadership Style

At the end of the day, the best leaders are those who lean into who they really are. The more you try to fit some imagined mold of what a leader should be, the more you’ll struggle.

Andy pointed out that great leaders—whether in business or Hollywood—have a strong sense of self. They’re comfortable in their own skin, and that confidence is what makes them compelling. So rather than aiming for a perfect leadership persona, focus on becoming a more self-assured version of yourself.

Want to Learn More?

Follow Andy Polaine on LinkedIn and YouTube for more insights into design leadership. And if you’re looking to develop your leadership skills in a hands-on way, join our upcoming Leadership Ateliers event in Lisbon, Barcelona and Berlin.

Big thanks to everyone who attended, and stay tuned for next month’s guest, Julia Whitney, who will continue the conversation on leadership in design!