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Private Executive Dinner – New York City

Private Executive Dinner Series | New York City

Holding the Tension:

How Teams Build Judgment When Speed and Discipline Pull in Opposite Directions

A second dinner conversation with Joel Podolny and Karie Willyerd, continuing where our July 14 gathering left off.

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JOEL PODOLNY

CEO of Honor Education, Founding Dean of Apple University, and former Dean of the Yale School of Management

KARIE WILLYERD

Head of Strategic Engagements at GP Strategies, Advisor and former CLO

Event Details

  • Thursday,
    October 8, 2026
  • Bucatini: 2 East 45th Street, New York, NY 10017
  • Cocktails:
    5:30 PM
  • Dinner:
    6:30 PM
  • End Time:
    9 PM

Reserve Your Seat.

We’d love you to join us.

Picking up where we left off

On July 14, a small group of Chief Learning Officers, Chief People Officers, and senior talent leaders gathered in New York for a candid conversation about culture, judgment, and leadership at scale. We began with culture. We kept returning to judgment.
 
As AI becomes broadly available, technology itself is unlikely to be the lasting differentiator. The harder challenge is helping people exercise sound judgment: knowing which questions to ask, which recommendations to trust, which to challenge, and how to make decisions that stay aligned with an organization’s strategy and purpose.
 
The group’s favorite moment came when the conversation turned to strategic tensions. Every organization at the table is navigating a frontier between preserving what has made it successful and adapting to what the future demands. That tension isn’t something to eliminate. It’s something leaders have to keep helping people navigate with clarity and judgment.
 
October 8 picks up exactly there. If judgment is the differentiator and the tension is permanent, how do leaders actually develop, activate, and reinforce that judgment in themselves and their people, especially as AI puts new pressure on both sides of the tension: speed to adapt, discipline to preserve?

The discussion arc:

Joel and Karie will lead the room through a working arc rather than a fixed agenda, built to unfold over the course of the evening.
  • Holding onto judgment as we lean into AI
  • Unpacking what judgment actually is
  • How AI erodes the logical side of judgment
  • How AI erodes the intuitive side of judgment
  • Woven throughout: your organization's own judgment
  • Closing: judgment can't be held one person at a time

Collaboration is a combat sport

Questions we’ll bring to the table

Where has your organization gotten this tension wrong, leaned too hard into preservation or too hard into adaptation, and what did you learn from correcting it?

What actually builds judgment in a leader or a team? Is it teachable, or only earned through reps?

As AI compresses decision cycles, does the frontier tension get sharper, or does it dissolve?

An intimate room, again by design

As with July, this will be a peer-to-peer discussion rather than a presentation. We’re keeping the group small, roughly 15-20 senior leaders who are actively shaping how their organizations build judgment and culture at scale. Some of you were at the first dinner. Some of you had to send regrets and asked to be included next time. Some of you are joining the conversation for the first time. All of you belong in this room.

Reserve your seat
Space is limited to keep the conversation genuinely peer-to-peer.
Please RSVP as soon as you’re able.

  • Thursday, October 8, 2026
  • Bucatini: 2 East 45th Street, New York, NY 10017
  • Cocktails: 5:30 PM
  • Dinner: 6:30 PM
  • End Time: 9 PM
Reserve Your Seat