Leaders Are Often the Last to Know

Recently, a client—I’ll call her Jessica—shared frustrations about her boss’s behavior. What struck me most wasn’t just the behavior itself—it was that everyone on the team seemed to share the same concerns, yet no one was giving the boss direct feedback.

It reminded me of a story Leslie Perlow and Stephanie Williams shared in Harvard Business Review about a team leader at a Fortune 100 company: “Every week, Jeff spent hours writing elaborate project updates for his boss, Matt—time he felt was completely wasted. But even though Jeff complained endlessly to his peers, he never said a word to Matt. Meanwhile, Matt was equally frustrated, seeing the Tuesday morning meetings as ‘Painfully Meaningless Meetings.’ Yet neither of them brought it up. The cycle continued, frustration grew, and the project kept falling behind.”

At a basic level, these are examples of teams with low levels of psychological safety. People fear that speaking up will backfire, so they stay silent. In the case of Jessica’s team, the boss had asked for feedback previously but had reacted poorly when the team shared criticism. Even though the leader believes she’s created an open team culture, the team knows honest feedback is risky.

Similarly, I once worked with a nonprofit CEO who was confident everything in his organization was great because no one complained (to him). What he didn’t realize was that the absence of complaints was probably the clearest sign that something was wrong! In reality, the team had a culture of toxic positivity, but the boss was the last to realize that.

The macro lesson is that leaders shouldn’t assume people on the team experience the team culture the same way they do. This is especially true for psychological safety because how safe we feel depends on our position on the team. Even in the most psychologically safe courtroom, the judge will feel safer than the defendant, and no part of the judge’s leadership intention will override the underlying power dynamic.

Secondly, the best measurement of safety is what people do, not what they say. Amy Edmondson’s original research showed that medical teams with the highest levels of psychological safety also had the most errors. It’s not that they had more errors than others—it’s that people on those high-safety teams felt comfortable enough to speak up and report the errors. Knowing exactly what’s wrong is a signal of things going right.

Or, as another client said to me last week after describing her team’s negative reactions to decisions she’d made, “I’m proud that people feel confident enough to say crazy things to me and still keep their paychecks.”

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