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 Facilitation

Keith 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 Rock
Boost your team’s engagement with this leadership tactic: behavior labeling, by Keith Cowing
Disagree and Commit

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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.

Speaking up at work is hard enough as it is, but when you feel like the odd one out, advocating for yourself becomes even harder. How do you tell your boss when they're making you uncomfortable or doing something that undermines your performance? The secret is simpler than you think.

Catt Small is a staff product designer, game maker and developer. She's worked with companies including Asana, Etsy, and SoundCloud. She also makes video games, draws art, and is the Executive Director for the Game Devs of Color Expo.

(00:00) A Culture of Excess
(04:05) Proving Yourself in Unfamiliar Territory
(06:32) Navigating Cultural Differences at Work
(13:14) “This Job is Going to Kill Me”
(20:16) From Defensive to Effective Communication
(24:03) Speaking Up Without Burning Bridges
(28:44) Creating Inclusive Team Cultures
(31:35) Finding Your Voice in Toxic Environments

Follow Catt on Bluesky, read her writing at cattsmall.com, and check out her course, “Staff Designer: Influence & Lead as an Individual Contributor” on Maven.

See also:

Radical Candor by Kim Scott
The 15 Commitments of Conscious Leadership by Diana Chapman, Kaley Klemp, and Jim Dethmer
Game Devs of Color Expo Sept. 16-19, 2025

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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.

What does it take to succeed in a creative field like journalism? Who gets the biggest interviews, the coolest assignments, the fast track to a huge audience? The answer has a lot less to do with how hard you work than with how you're seen by the people calling the shots.

Bijan Stephen, journalist and writer at Compulsion Games, shares his journey from magazine assistant to TV host and video game writer—and explains how some people end up being pegged as “talent” while others don’t.

(00:00) The Industry Talent Hierarchy
(04:12) The Old-School Magazine
(07:11) Workplace Hierarchy and Performance
(09:27) Navigating Media Culture
(12:16) The Vice “Pirate Ship” Experience
(14:21) Unspoken Talent Systems in Media
(19:03) Transitioning From Media to Game Development
(21:57) What Game Writing Actually Involves
(26:35) Finding Support in the Games Industry
(29:56) Instability as a Feature of Modern Work
(30:57) Advice for Early-Career Journalists

Bijan Steven is a writer at Compulsion Games and a music critic at The Nation. His work has appeared in the New Yorker, the New York Times, Esquire, Wired and many other places.

Follow Bijan on Bluesky and Instagram, read his writing for The Nation, and check out his games on Itch.

See also:

Media's unspoken "talent" hierarchy by Jenny G. Zhang
South of Midnight Gameplay Trailer (coming April 8)
Night in the Woods Launch Trailer
Oxenfree Launch Trailer
Afterparty Launch Trailer
Deadlock Gameplay Trailer

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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.