Executive design leadership coaching

I’ve been leading design teams and advising executive design leaders for more than 20 years—as a consultant, agency founder, and in-house leader. I’ve seen organizations of all kinds from the inside out, from huge multinational companies all the way down to small community organizations. Today, I apply all of that experience to one-on-one coaching with design executives, helping them develop the skills to lead with greater purpose, intention, and creativity.

Less noise, more signal.
Less reaction, more intention.

Executive design leaders have no shortage of vision or knowledge to draw on. But they often struggle with changing their own practices and mindsets to enable them to bring their visions to life. Working with a coach can help you shift your patterns, clarify your intentions, and set a course to go after them.

Congratulations, you’re in charge—now what?

Every design leader faces a new level of challenge when they become the head of design. To the business, you’re the face of design as a function, and its fate in the organization is now bound to your own. Within the design team, you’re now managing other managers, with their own needs for power and autonomy. And both are looking at you as if to ask: Whose side are you on?

Finding your own authentic leadership style

Many become executive design leaders without ever having had good mentors or models for effective leadership—but lots of negative examples they’d like to avoid. Conflicting advice from management gurus who don’t understand the particular needs of design leaders can only confuse things more. Getting clear on how to lead means getting clear on your own strengths, and optimizing for them.

Building solid partnerships and healthy teams

Managing your relationships is essential for any design leader’s success, and for executives it can be critical. Your team’s effectiveness relies on your ability to develop trust and goodwill across the organization, not just within your team. But your designers need your help as well, to develop the team cohesion and resilience necessary to take on the unknown and unexpected together.

Leadership is just another
design problem.
Let’s solve it together.

Too many design leaders feel they have to leave their creative selves behind when they reach the executive suite. Working together in a series of private one-on-one sessions over a 6-month coaching program, we’ll tap into the creative spirit that enables your growth and success, and take the steps needed to make them real.

Satisfied clients. Real results.

People love both the process of working with me and the changes it can create in their lives. Here are just a few quotes from my clients:

Experiencing Jesse’s sustained focus and listening in our regular 1-on-1 sessions was life-changing. Receiving his perspective on my day-to-day life as a design professional was just a bonus. I’ll continue learning from our time together for decades to come.

The impact of Jesse’s coaching has had real results – I’m being recognized at work, and suddenly finding myself influencing a cultural shift at my organization in just a few short months.

I’m bringing a greater sense of purpose, direction, and boldness into the work I do, something I look forward to carrying with me throughout my career.

Jesse is an incredibly supportive and thoughtful coach who leads with empathy and heart. I left our sessions feeling both seen and heard. He helped me identify key blockers to achieving my goals and adjust my mindset and strategies to tackle them.

As a coach, Jesse was supportive, but challenged me in a way that inspired me to go beyond my comfort zone, and he provided actionable feedback that built up my confidence and trust within myself.

Book your free Exploration Session

In this free one-hour session for potential clients, we’ll explore your situation and your goals together to discover how coaching can help you achieve them. (All sessions conducted over Zoom.)


Jesse James Garrett has been one of the most prominent voices in digital product design for more than 20 years. His career highlights include co-founding the groundbreaking UX consultancy, Adaptive Path; writing the foundational book The Elements of User Experience, whose iconic five-plane model has become a staple of the field; and defining Ajax, the dynamic interaction model that transformed web technology and design in the Web 2.0 era. His work has been published in more than a dozen languages and he is a frequent keynote speaker on making designers and organizations more human-centered in their work.

Finding Our Way

Finding Our Way is the new design leadership podcast from Jesse James Garrett and Peter Merholz, co-founders of Adaptive Path.