Coaching for Leaders, Episode 770

How to Make Change Irresistible, with Phil Gilbert

Host: Dave Stachowiak
Guest: Phil Gilbert, former IBM General Manager of Design, author of Irresistible Change

Date: February 16, 2026

Episode Overview

This episode explores why traditional, mandated change initiatives often fail—and how leaders can make change so attractive that people eagerly choose to adopt it. Phil Gilbert, renowned for leading IBM’s design-driven transformation, shares practical insights and hard-won lessons from his experience scaling change across massive, entrenched organizations. The discussion dives into treating change as a product, the power of agency and sustainability, the importance of branding your change initiative, and strategies for truly lasting organizational adoption.

Key Discussion Points & Insights

1. Phil Gilbert’s Introduction to IBM: An Outsider’s Perspective

• Phil describes himself as a “startup guy” whose previous company was acquired by IBM, with the intention to stay only a year to help with integration (02:13).
• Initial reaction to IBM: felt shocked by an uncreative, “hollowed-out” culture focused on financial engineering, not human outcomes.
• Early desire to leave due to "the antithesis of a human centered organization that wanted to deliver new and great outcomes for its users." (03:03)

2. Change as a Product, Not a Mandate

• Phil’s key epiphany: “Change should be regarded as a high value add product that deserves the same levels of resource support and operational rigor as any of your top performing products.” (06:30)

• Product analogy: Like startups, change initiatives face the challenge of getting people to notice, adopt, and champion something new in the face of inertia.

• Mandate vs. Offer: No one is “mandated” to adopt a new product; you must make it genuinely desirable and solve real problems for users.

  “If the teams and the employees don't embrace my changes, it's on me to figure out why… I forbid anybody on my leadership team to use the words ‘they just don't get it.’” —Phil Gilbert [10:15]

3. Sustained Cultural Adoption vs. Quick Wins

• Critical distinction: Many leaders focus on “immediate competency,” but the real target is “sustained cultural adoption.” (10:45)

• Phil warns against measuring success by superficial “quick wins” (e.g., innovation teams achieving results in isolation), as these rarely translate to broader, long-lasting impact.

• Success is about “proving scalability and sustainability” by targeting mainstream, high-impact teams, not just innovation outposts.

  “People typically get wrong that we're going to go make a team's outcome better and we're going to tell the world about that. That's only a subset of what has to happen to prove that the approach is going to sustainably change the organization.” —Phil Gilbert [12:08]

4. Rigorous Team Selection and the “One-Way Door”

• Gilbert’s approach: select high-profile, mainstream teams for change pilots and commit fully (not part-time roles; no “feet in both worlds”).

• Teams entering the branded Hallmark program operated solely in the new way from that point forward (15:28).

• The approach minimized the temptation to revert and maximized the visible impact and credibility of the change.

  “Once you were into our program and we named it, we branded it, it was called the Hallmark program. Once you came into the Hallmark program, you were in the Hallmark program. And from that point forward, that team only worked in the new world forever and ever.” —Phil Gilbert [15:52]

5. Agency, Not Compliance

• Mandates breed only surface compliance (“compliance theater”); offering change and giving people agency fosters true, durable adoption (18:38).

• The Hallmark onboarding included an explicit offer: “If at the end of this week your project hasn’t advanced 10x… you should exit the program and you'll never hear from us again. Go back to your old ways of working.” (19:28)

• No one ever chose to leave, underscoring the effectiveness of giving teams choice and ownership.

  “The sustainability of whatever somebody willingly adopts is a thousand x the sustainability of something that they're merely complying with.” —Phil Gilbert [19:49]

6. The Cupcake, Birthday Cake, and Wedding Cake Analogy

• Start with small, delightful, complete “cupcakes” (solutions that fully solve a single problem), not half-baked slices of a grand vision (“wedding cake”).

• “Every single one of those cupcakes is going to solve a hundred percent of some part of somebody’s problem.” (22:23)

• Focus on delivering fully lovable, valuable increments rather than trying (and failing) to deliver the perfect end-state from the start.

  “It has to completely overwhelm them with love and delight. Which a cupcake can do.” —Phil Gilbert [25:00]

7. Branding the Change Program

• Brands matter: people respond to brands, not just products. Choosing a neutral, distinctive brand (“Hallmark”) vs. loaded terms (“AI”, “design thinking”) sets a clear, shared meaning and avoids baggage.

• Branding enables you to define program values, scope, and vision—rather than being trapped by the assumptions of legacy terms (27:27).

• At IBM, the three Hallmark values:

  1. User as North Star
  2. Continuous iteration ("restlessly reinvent")
  3. New, diverse, empowered teams

  “As we thought about this as a brand, then all of a sudden it not only freed us up into being able to change things way beyond what appeared to be our initial scope, it also allowed us to insert the values underneath the changes that were actually more important than the tactics of the change itself.” —Phil Gilbert [29:30]

8. Middle Management: From ‘Frozen Middle’ to Accelerators

• Phil’s biggest change in thinking: the assumption that middle managers are always blockers (“the frozen middle”) is flawed (32:17).

• Reflects that his own team’s bias and structuring of the program inadvertently excluded or misunderstood the real drivers and concerns of middle managers until late in the process.

• Once engaged properly, middle managers became key accelerators for change.

  “My big learning in the process was the role of middle management is one of the most critical accelerators of change, if you get it right.” —Phil Gilbert [32:54]

Memorable Quotes

• On Responsibility for Change:
  “If they didn't get it, that wasn't their fault. It was our fault. And we had to figure out why.” —Phil Gilbert [10:15]
• On the Power of Agency:
  “Agency makes all the difference in sustaining the change over time… The sustainability of whatever someone willingly adopts is a thousand x the sustainability of something they're merely complying with.” —Phil Gilbert [19:49]
• On Brand and Values:
  “People buy brands, they don't necessarily buy products... The brand enables you to insert the values underneath the changes that were actually more important than the tactics.” —Phil Gilbert [27:27]
• On Middle Management:
  “The role of middle management is one of the most critical accelerators of change, if you get it right.” —Phil Gilbert [32:54]

Highlighted Timestamps

• 02:13 — Phil’s first impressions of IBM and desire to leave
• 06:30 — Treating change as a product
• 10:15 — Accountability when teams resist change
• 12:08 — The importance of sustainable, not just immediate, change
• 15:28 — Methodical team selection and “one-way door” approach
• 18:38 — Offering agency vs. enforcing compliance
• 22:23 — Cupcake-birthday cake-wedding cake analogy for launching change
• 27:27 — Branding the Hallmark program, IBM’s values
• 32:17 — Changing perspectives on middle management’s role

Tone & Style

• Pragmatic and Empathetic: Both Dave and Phil speak candidly about organizational challenges, emphasize real-world practicality, and continually circle back to empathy for users and teams.
• Invitational, Not Prescriptive: Much talk about “offers” vs. “mandates,” and agency for those experiencing change.
• Reflective: Phil shares what he learned the hard way, especially about assumptions around middle management.

Bottom Line Takeaways

• Treat change as you would a product: make it valuable, appealing, and worthy of adoption—not just a compliance box.
• Don’t settle for visible “wins”; focus on mainstream, sustainable adoption.
• Give people agency and ownership: offer, don’t mandate.
• Make your change initiative a branded experience, with clearly defined values.
• Start with “cupcakes”—small but complete, delightful wins.
• Middle managers aren’t the “frozen middle” by default; unlock their power as accelerators of change.