Pinball Mode (with Keith Cowing) episode artwork

EPISODE · May 29, 2025 · 38 MIN

Pinball Mode (with Keith Cowing)

from Work Face · host Benjamin Jackson

When was the last time your leader admitted they didn't have all the answers? With boards and investors watching every move, most executives feel pressure to project confidence, even when facing unprecedented change. But what if the most valuable thing a leader can offer their team isn't certainty about the future, but transparency about the present, and clarity about what to do next?Keith Cowing, executive coach and product leader, shares his advice for leaders in times of rapid change: from labeling their leadership modes to communicating how decisions are made and openly calling out misaligned incentives.(00:00) Pinball Mode(03:59) The Disney Credit Card(11:39) Dispelling Founder Myths(13:51) The Power of Naming Behaviors(16:12) Leading Through Uncertainty(19:58) Why Transparency Is So Challenging(23:07) Calling Out Misaligned Incentives(27:32) Two Flavors of Honesty(31:43) Leadership Team Mistakes During Uncertainty(34:08) Creating Psychological Safety(35:48) The Value of External FacilitationKeith Cowing is an executive coach to CEOs and product leaders and a visiting lecturer at Cornell's MBA program. Previously, he served as Chief product Officer at Vesta Healthcare, VP of Product at Flatiron Health, and as a product manager at Twitter and LinkedIn.Listen to Keith’s podcast, Executives Unplugged, follow him on LinkedIn, and read his writing on leadership at keithcowing.com.See also:SCARF: a brain-based model for collaborating with and influencing others, by David RockBoost your team’s engagement with this leadership tactic: behavior labeling, by Keith CowingDisagree and Commit--Work Face is produced by Hear Me Out, a culture strategy firm for leaders with the courage to listen. We help them cultivate trust by having real conversations with employees at all levels about what’s working and what’s not.Learn more at hearmeout.co and follow us on Instagram, Bluesky, and LinkedIn.

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Pinball Mode (with Keith Cowing)

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This episode was published on May 29, 2025.

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When was the last time your leader admitted they didn't have all the answers? With boards and investors watching every move, most executives feel pressure to project confidence, even when facing unprecedented change. But what if the most valuable...

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