Jesse James Garrett

Executive design leadership coach, author, and speaker

Do you work with people who get it?

As much as I love helping my clients dream into the new and go after ever more ambitious goals, the truth is that leaders often call on me because something’s broken down. Lately, that breakdown seems to be more acute than ever, and it’s hitting leaders hard: Losing sleep. Losing focus. Losing motivation. They’re facing harsh near-term realities—like narrowing mandates and mandatory staff cuts—while fighting off fears that can feel downright existential.

Peter and I attempted to identify what’s broken down in our latest one-on-one conversation on our design leadership podcast Finding Our Way. From what I’ve seen in my coaching practice, what it comes down to is too many people who just don’t get it.

They don’t get what you have to offer. They don’t get what you’re there to do. They don’t get why you’ve been invited to the meeting. They don’t get why you’re asking that question. They don’t get what design even is.

They just. Don’t. Get it.

Another way to describe this breakdown is as a lack of alignment on value propositions. You will continue to talk past your leadership as long as you remain disconnected on the value you’re there to provide.

Design leaders often see this alignment breakdown as a disagreement about philosophy or orthodoxy but it comes down to something simpler: expectations and perceptions. Every stakeholder has ideas about what design does for an organization, shaped by their past experiences both good and bad. If you don’t know what those expectations are, however, you might find yourself constantly shooting in the dark to try to meet them—or caught in a bind between two sets of expectations that are impossible to reconcile—without even knowing it.

It’s no wonder that working with leaders on articulating their value propositions has become a major recurring theme in my coaching practice. You might not even realize how far off you are from your leadership on the value you’re there to provide if you haven’t named it for yourself. The leader’s challenge is discovering if they really can “get it”, and aligning those expectations to your strengths as a leader and as a team.


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with Jesse James Garrett

Working with a coach can help you make sense of difficult challenges, strengthen your emotional footing, and drive the clarity needed to take action. I offer a free 60-minute coaching session for leaders interested in trying my services. Book your free session with me today!