The Intentional Design Leadership Circle — Autumn 2026
A 6-week salon for Director-plus design and user experience leaders
It feels like everything, everywhere, all at once. Move faster, with fewer resources. Everything is urgent. And no real strategy at play, only metrics.
— an exhausted VP of DesignDesign leadership was always demanding and lonely, and now leaders are absorbing pressure from every direction at once: executives mandate AI use without clear outcomes, teams who are frightened about their work and their futures, and a discipline whose value proposition is unclear and up for grabs.
Most design leaders are too deep in the work to see it clearly. Intentionality is what separates those who endure from those who transform.
Most design leaders are too deep in the work to see it clearly. Intentionality is what separates those who endure from those who transform.
To address this, Jesse James Garrett and Peter Merholz facilitate the Intentional Design Leadership Circle, a weekly gathering for design leaders who are ready to move beyond surface-level frameworks and wrestle with the real challenges of leading with purpose during turbulent times.
Screengrab of a Miro board from the first Circle, showing topics leaders wanted to discuss
The Circle is not a course. There's no curriculum, no slides to sit through, no certificate. We follow what you bring to it — a reorg you're navigating, a mandate you've been handed, the team you're trying to hold together.
Over six sessions, we'll work through the full arc of intentional design leadership:
- developing a clear-eyed understanding of your organizational context
- articulating a sharp leadership agenda
- building trust and relational power
- making design's value explicit
- managing change (or even transformation!)
- maintaining resilience and equanimity throughout
Drawing upon Peter's extensive work with design organizations and Jesse's deep leadership coaching practice, each session provides a space where peers can speak candidly about what's working, what isn't, and what feels impossible, and support one another with wisdom, tools, or just sympathy.
Over six sessions, we'll work through the full arc of intentional design leadership:
- developing a clear-eyed understanding of your organizational context
- articulating a sharp leadership agenda
- building trust and relational power
- making design's value explicit
- managing change (or even transformation!)
- maintaining resilience and equanimity throughout
Drawing upon Peter's extensive work with design organizations and Jesse's deep leadership coaching practice, each session provides a space where peers can speak candidly about what's working, what isn't, and what feels impossible, and support one another with wisdom, tools, or just sympathy.
Upon the Circle's conclusion, you won't just leave with ideas — you'll leave with concrete strategies for reshaping how design is understood, valued, and practiced in your organization, and connections with fellow travelers who can help one another on their respective journeys.
SESSION STRUCTURE
The Circle is limited to 20 participants operating under the Chatham House Rule to ensure active engagement for all.
For each 90-minute session, Peter and Jesse provide lightweight agenda-setting and then active facilitation. We use a combination of Zoom and Miro to encourage collaboration. Because he cannot help himself, Peter will likely pull up material from slide decks or articles to augment our discussions. We offer a means of communications (e.g., Slack, Discord) to maintain the conversation between sessions.
SESSION STRUCTURE
The Circle is limited to 20 participants operating under the Chatham House Rule to ensure active engagement for all.
For each 90-minute session, Peter and Jesse provide lightweight agenda-setting and then active facilitation. We use a combination of Zoom and Miro to encourage collaboration. Because he cannot help himself, Peter will likely pull up material from slide decks or articles to augment our discussions. We offer a means of communications (e.g., Slack, Discord) to maintain the conversation between sessions.
20 seats total
pricing
Early Bird Price
(buy before September 25)
$799–Corporate rate
(your company pays)
$649–Personal rate
(you're paying yourself)
Full Price
$999–Corporate rate
$799–Personal rate
(buy before September 25)
$799–Corporate rate
(your company pays)
$649–Personal rate
(you're paying yourself)
Full Price
$999–Corporate rate
$799–Personal rate
Location
The Circle takes place on Zoom and uses Miro
Date & Time
Dates
7 October 2026
14 October 2026
21 October 2026
28 October 2026
4 November 2026
10 November 2026 (note this is a Tuesday)
Time
All sessions are 90 minutes starting at:
8:00am Pacific /
11:00am Eastern /
4:00pm UK /
17.00 CET
(On 28 October, 3:00pm UK and 16.00 CET)
7 October 2026
14 October 2026
21 October 2026
28 October 2026
4 November 2026
10 November 2026 (note this is a Tuesday)
Time
All sessions are 90 minutes starting at:
8:00am Pacific /
11:00am Eastern /
4:00pm UK /
17.00 CET
(On 28 October, 3:00pm UK and 16.00 CET)
QUESTIONS?
20 seats · Starts 7 October
Six weeks. Twenty leaders. One ongoing conversation.
Register NowEarly Bird pricing through September 25
Testimonials from past participants
The Intentional Design Leadership Circle combined thoughtful leadership theory with candid dialogue among experienced peers. It gave me the rare feeling of being genuinely seen and understood, while also realizing that many of the challenges I face are shared by design leaders across organizations.
Sandra M. P.
Govt of Alberta
The Circle provided the opportunity to learn about and discuss topics that are most pertinent to senior leaders. We were asked to think more broadly about our organizations, their business context, and how our design orgs can be more successful given the world in which we operate. Thanks for time well-spent!
Sally C.
Sr Director of Product Design
Agenda By Week
7 OCtober 2026
You Are Here
Before we can talk about how you want to lead, we need to know where you're standing. In advance of this session you'll complete an assessment of your organizational context and your own sense of the moment. We then open by looking at the patterns across the group — who's under what kind of pressure, who's optimistic, who's holding on — and use that as the ground for getting to know one another. You'll leave with a clearer read on your own situation and a sense of who else in the room is facing something similar.
14 OCtober 2026
Understanding Organizational Context
The first step in effective leadership is to achieve clarity about the context in which you're operating.
We'll discuss strategies for understanding the mechanics of your business, stakeholders and their motivations, what people expect from your team, and how to articulate a clear definition and purpose for UX and Design.
We'll discuss strategies for understanding the mechanics of your business, stakeholders and their motivations, what people expect from your team, and how to articulate a clear definition and purpose for UX and Design.
21 October 2026
Articulating an Agenda and Point of View
Effective design leaders don't just respond to their organizations — they shape them. In this session we'll discuss how to define the change you're seeking, build a clear leadership agenda around it, and develop the point of view that will anchor everything you do.
28 October 2026
Building Relationships and Trust
Leadership at the organizational level runs on relational power, not positional authority. Together, we'll examine the dynamics of trust — how it's built, lost, and leveraged — and explore strategies for cultivating cross-functional relationships and external alliances.
4 November 2026
Making Design's Value Explicit
Design's contribution is often real but illegible to the rest of the business. This session takes on the problem directly: how to speak about your work in terms your executives already use, what kinds of evidence actually move people, and how to make the case for design's value without reducing it to production speed.
10 November 2026
Creating Change and Seeing It Through
Good intentions don't transform organizations — deliberate action does. We'll cover how to find the right opportunities, cultivate partners, build proof points, and address the need for persistence: the political realities of design leadership and the resilience required to navigate setbacks. We'll close by drawing together what's emerged across the six weeks and what each of us is carrying forward.
