Work Face

Benjamin Jackson
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A podcast where people finally tell the truth about work. Workplace culture expert Ben Jackson hosts refreshingly honest conversations with people from all walks of life about what actually happens on the job.

Episodes

  1. Pinball Mode (with Keith Cowing)

    MAY 29

    Pinball Mode (with Keith Cowing)

    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 -- 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.

    39 min
  2. The Art of Diplomatic Dissent (with Catt Small)

    APR 22

    The Art of Diplomatic Dissent (with Catt Small)

    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 -- 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.

    36 min
  3. Just Grateful to Be Here (with Bijan Stephen)

    MAR 20

    Just Grateful to Be Here (with Bijan Stephen)

    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 -- 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.

    35 min
  4. Your Manager Is Winging It (with Melissa and Johnathan Nightingale)

    MAR 4

    Your Manager Is Winging It (with Melissa and Johnathan Nightingale)

    Have you ever wondered what’s really happening when a manager makes you feel small? Maybe they were multitasking in a meeting, or late to a career defining conversation. What happens when people are given power without the tools to wield it responsibly? And what might our organizations look like if we invested in management competence before employees reach their breaking point? Melissa and Johnathan Nightingale, founders of Raw Signal Group, share their experiences working for “incompetent” bosses, and explain why most managers don’t learn the basics of the job until they have no other choice. (00:00) The Scrap of Paper (03:25) Crying in the Bathroom Every Day  (08:30) The Manager Manager Manager (14:26) The Tools Every Manager Needs (20:18) The Problem with Most Feedback (27:34) “Nobody Wants to Work Anymore” (33:12) Management Tools vs. Leadership Bumper Stickers (38:31) Taking Control of Your Own Career (42:42) Building Skills and Finding Better Workplaces Johnathan and Melissa are the founders of Raw Signal Group, world experts on management and leadership, and bestselling authors of the book “How F*cked Up Is Your Management?” Follow Johnathan and Melissa on Bluesky, find their work at rawsignal.ca, and subscribe to their newsletter at worldsbestnewsletter.com. See also: Out of Office by Charlie Warzel and Anne Helen Petersen How F*cked Up Is Your Management? by Johnathan and Melissa Nightingale Situation-Behavior-Impact Feedback Model -- 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.

    47 min
  5. Friends Don’t Fire Friends (with Dustin Liu)

    FEB 19

    Friends Don’t Fire Friends (with Dustin Liu)

    Have you ever had a manager who acted like a friend instead of your boss? They confide in you, trust you with important work, and treat you like a peer.  How do you say no when you’re completely overwhelmed and can’t find the courage to disappoint them? Dustin Liu, senior associate director at NYU Stern’s Initiative on Purpose and Flourishing, knows exactly how this feels. After years of advising leaders at Stanford and NYU and interviewing employees about their experiences at Hear Me Out, he explains why the best managers often set the clearest boundaries. (00:00) Setting Boundaries with Your Boss (03:13) Investigating Workplace Culture (09:14) When Your Boss Becomes Your Friend (14:44) The Meaning of Workplace Flourishing (20:26) Company Values vs. Reality (24:38) The Return to Office Dilemma (27:52) Leading Through Disruption (32:23) Reimagining Multi-Generational Work Dustin Liu is the senior associate director at NYU Stern’s Initiative on Purpose and Flourishing. Previously, he was the associate director at Stanford’s Life Design Lab. For the last three years, he’s also been a moderator at Hear Me Out, where he interviews employees about their workplace experiences. Connect with Dustin on LinkedIn and learn more about his work at the NYU Stern Initiative on Purpose and Flourishing’s website. -- 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.

    30 min
  6. Do What You Love, and Treat It Like a Job (with Rob McRae)

    FEB 11

    Do What You Love, and Treat It Like a Job (with Rob McRae)

    Have you ever stayed in a job you hated because you thought that's just what adults do? Maybe you even convinced yourself it was character building, that being miserable at work was some kind of badge of honor. What if the real sign of maturity isn't suffering through a job you hate, but respecting yourself enough to set healthy boundaries while doing what you love? Rob McRae, a digital producer, writer, and social media manager, shares his experience transitioning to media after burning out at a Big Four consulting firm, and explains why it’s never too late to discover new skills. (00:00) What Adults Do (01:46) First Job After Law School (04:02) Living for the Weekends (06:12) Confiding in Coworkers (11:05) Mental Health and Performance (15:25) Finding Your Voice Online (19:32) The Taco Bell Tweet (21:51) Breaking Into Media (24:42) Being Who You Are (27:25) Using Your Imagination (29:47) Loving Your Job Without Losing Yourself (30:59) Advice for Managers (32:34) Final Thoughts Rob McRae is a producer at Meadowlark Media, who previously worked as a digital producer and staff writer for Desus & Mero, following the show from Vice Media to Showtime.  At the age of 30, Rob completely reset his career, moving from a Big Four consulting firm into working in social media at Vice.  Follow Rob on Twitter/X or Bluesky and find his work at latebutstill.com. See also: Make Your Own Job, by Eric Baker Designing Your Life, by Dave Evans and Bill Burnet Work Won’t Love You Back, by Sarah Jaffe The Internet is Talking | 2016 Taco Bell Quesalupa Commercial with George Takei Pablo Torre Finds Out on YouTube -- 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.

    34 min

  7. FEB 4

    Work Face, a New Podcast from Hear Me Out (Trailer)

    I’m Ben Jackson, the founder of workplace culture strategy firm, Hear Me Out.  For years, I’ve been listening to people tell the truth about work, the kinds of stories that usually stay hidden behind NDAs. Through these conversations, I’ve discovered something important: whether you’re dealing with office politics or trying to protect your mental health, the challenges you’re facing aren’t unique to you. That’s why I created Work Face. Every week, you’ll hear stories from people who’ve faced similar challenges. Stories that will help you navigate the tension between being yourself and doing your job, protect your well being without derailing your career, and find the confidence to speak up when it matters most. Together, we’re asking the questions about work that everyone has, but no one brings up.  We hope these conversations will help you put words to what feels wrong in your own workplace and give you the confidence to inspire change. -- 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.

    2 min
  8. Wellness Is Caring For Each Other (with Ashwin Rodrigues)

    FEB 3

    Wellness Is Caring For Each Other (with Ashwin Rodrigues)

    When was the last time your company announced a new wellness initiative?  Maybe it was a meditation app subscription, or a fitness challenge, or another program promising to optimize your performance. Now ask yourself: When was the last time someone at work just asked how you were feeling? Ashwin Rodrigues, a freelance writer whose work has been featured in Defector, GQ, The New York Times, Vice, and Wired, shares his journey from burned-out tech worker to wellness culture critic, exploring how corporate wellness programs focus on perks over genuine human connection. (00:00) The Egg Problem (03:07) Young and Insecure in Big Tech (10:59) An Unhealthy Sense of Urgency (14:29) Finding an Escape Route (24:12) Tech's Obsession with Optimization (28:02) When Wellness Programs Miss the Point (35:15) Building Care Into Company DNA (40:18) Protecting Your Own Mental Health Ashwin Rodrigues is a freelance journalist whose work explores the intersections of technology, wellness, and culture. His recent piece in The New York Times, “I Refuse to Cede My Love of Fitness to the Far Right,” examines how wellness culture has become both a coping mechanism and a source of anxiety for tech workers.  Follow him at ashwinrodrigues.com or on Bluesky. See also: I Refuse to Cede My Love of Fitness to the Far Right by Ashwin Rodrigues -- 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.

    37 min
  9. Forum Drama in the Work Slack (with Allegra Rosenberg)

    FEB 3

    Forum Drama in the Work Slack (with Allegra Rosenberg)

    These days, the platforms we use at work look a lot like social media. But on most teams, these digital workspaces are run almost entirely without moderation. Allegra Rosenberg, a writer, fandom expert, and cultural critic, shares her experience as a major label talent scout and explains why allowing off-topic channels in Slack might be a bigger risk than you'd expect. (00:00) Everything is Everywhere Online (02:32) Insecurity in the Music Industry (14:20) Slack Channels as Digital Infrastructure (17:27) Breaking into New York Media (24:44) The Dark Side of Employee Engagement (25:11) Why "No Structure" Isn't Freedom (28:52) Dealing with Workplace Disillusionment (29:00) Finding Better Ways to Connect Allegra Rosenberg is a freelance writer whose work has appeared in The Atlantic, National Geographic, and The New York Times. Her forthcoming book on the history of fandom culture will be published by W.W. Norton. She’s also the founder of Terror Camp, a polar exploration conference.  Follow Allegra on Bluesky and find her work at allegrarosenberg.com. See also: The Smart Cow Problem on Wikipedia Depths of Wikipedia on Bluesky The Tyranny of Structurelessness by Jo Freeman -- 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.

    31 min
  10. Luckpilling the Meritocracy (with Dr. Aaron Rabinowitz)

    FEB 1

    Luckpilling the Meritocracy (with Dr. Aaron Rabinowitz)

    What if most of what we believe about success and failure at work is just a story we made up? What if the core ideas driving modern workplace culture might be making us less effective, less innovative, and a whole lot more anxious? Dr. Aaron Rabinowitz, Ethics Director at the Creator Accountability Network, shares his experience in off-Broadway theater and discusses his dissertation research on “luckpilling,” a radical new way of thinking about success, failure, and who deserves help (spoiler: it’s everyone). (00:00) Who Deserves Help? (01:44) Theater Work and Insecurity (06:03) Workplace Power Dynamics (13:40) Restorative Justice at Work (20:26) The Just World Illusion (25:20) Performance and Psychological Safety (32:54) Leadership and Organizational Change (34:42) Navigating Disillusionment (37:39) Leisure and Human Worth Dr. Aaron Rabinowitz is the Ethics Director at the Creator Accountability Network and host of the podcasts Embrace the Void and Philosophers in Space. His research focuses on how beliefs about merit and deservingness shape culture and behavior in educational settings.  Follow Aaron on Bluesky. See also: Luckpilled: A New Pedagogy of Luck Introduction on Embrace the Void Behave by Robert Sapolsky The Meritocracy Trap by Daniel Markovits -- 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.

    39 min

Trailer

About

A podcast where people finally tell the truth about work. Workplace culture expert Ben Jackson hosts refreshingly honest conversations with people from all walks of life about what actually happens on the job.

Information

  • Creator
    Benjamin Jackson
  • Years Active
    2K
  • Episodes
    10
  • Rating
    Explicit
  • Copyright
    © 2025 Hear Me Out
  • Show Website
    Work Face