Four Recent Episodes on Why People Stay Silent — and What It Costs

If you've read much of my work, you know I keep circling the same question: why do smart, capable people hold back what they know? Sometimes they stay quiet because they tried speaking up once and got burned. Sometimes a softer force wears them down — a few “we tried that already” responses and the ideas stop coming. Sometimes the silence is the leader's fault, and sometimes it's the leader's job to fix it.

Four recent episodes of My Favorite Mistake hit this theme from different angles, and reading them together is more useful than any one alone. I've ordered them to build an argument — from the wound, to the quiet drift, to the leadership failure that causes both, to the CEO who builds the culture that prevents it.

Kate Lowry: when speaking up backfires

Kate Lowry — CEO coach, venture capitalist, and author of Unbreakable: How to Thrive Under Fear-Based Leaders — reported misconduct early in her career and watched it backfire on her, not the wrongdoer. She got marked down for not being a “team player” and carried that on her record for years. That's exactly the kind of experience that teaches a person to stay quiet next time.

What I appreciate about Kate's story is that she doesn't stop at the wound. She gets into how fear-based leadership manufactures silence — including the covert, “West Coast nice” version that's far harder to spot than the boss who yells and throws things.

“If you keep your direct reports in a fear state, their amygdala is activated. They can't access the parts of their brains that do strategy.”

The lesson isn't that Kate should have stayed quiet. It's that the system around her punished candor, and that's a leadership failure, not an individual one.

Why Speaking Up Backfired Early in Her Career & Fear-Based Leaders–with Kate Lowry

Jesse Jackson: how new leaders go quiet

Jesse Jackson, a contact center leader, describes a pattern many of us have lived: you're new, you have a good idea, and a veteran shuts it down with “we tried that, it didn't work.” So you stop offering ideas. Jesse's favorite mistake was going gun-shy — letting that pushback train him into silence.

I like pairing this with Kate's because it shows the other side of the same coin. Kate's silence came from punishment; Jesse's came from a softer, more common force — the quiet erosion of confidence when experienced people wave you off. Both end in the same place: good ideas that never get said out loud.

“You're going to make mistakes anyway. The bigger one is being too gun-shy to try in the first place.”

Jesse also lands on something every leader should internalize: just because you don't take someone's advice doesn't mean you didn't listen to them. That distinction is what keeps people offering ideas instead of going quiet.

Why New Leaders Hold Back Good Ideas – with Jesse Jackson

Deborah Coviello: silencing people without meaning to

Deborah Coviello, known as The Drop-In CEO, tells a story that should make every manager wince. Early in her career she spoke up in a meeting, and afterward her boss pulled her aside and said only, “You shouldn't have said that.” No coaching. No “here's how you might have framed it.” Just a door quietly closing.

That's how good people get trained into silence — not through dramatic punishment, but through vague disapproval that gives them nothing to act on except the lesson to keep quiet.

“When we say things that are different and contrary, there's no coaching to help people position things. So we lose people's passion — because they're told to shut up without coaching.”

For Lean leaders, this is the practical heart of psychological safety. “You shouldn't have said that” causes future silence. “Here's what I'd want from you next time” develops people and leads to more speaking up. Same disagreement, opposite outcome.

Stop Chasing Results, Start Pursuing Peace of Mind – with Deborah Coviello

Mike Grossman: the CEO who makes bad news safe

Mike Grossman, a six-time Silicon Valley CEO and author of Failure Is an Option, comes at this from the leader's chair. His whole approach to running companies rests on making it safe to surface problems early — because, as he puts it, you can't fix what nobody will admit is broken.

What makes Mike's version credible is that he's specific about the behaviors. React calmly. Don't hunt for a scapegoat. Stay transparent about finances, losses, and the deals you didn't win. Rhetoric is easy; people get burned when “my door is always open” isn't backed by how the leader actually responds.

“No one's going to get shot for sharing bad news. If anything, they're going to be complimented for making it visible.”

That's the answer to the first three stories. Kate was punished, Jesse was worn down, Deborah was dismissed. Mike describes the culture where none of that happens — where speaking up is the path of least resistance instead of the risky one.

Why Acting as Your Own Lawyer Almost Killed the Deal — with Mike Grossman

The thread that connects them

Four guests, four very different contexts, one pattern: people had something worth saying and a reason not to say it. Sometimes the reason was punishment. Sometimes it was eroded confidence. Sometimes it was a boss who shut them down without meaning to. The cost was always real — ideas unspoken, problems buried, good people heading for the door.

That's the work in front of us as leaders — not exhorting people to “be braver,” but building systems and cultures where speaking up is the easy choice. Mike Grossman shows it can be done. The other three show what it costs when it isn't.

Have a listen, and let me know which of these stories lands hardest for you.