How leaders can make it safe for people to share hard truths

Executive overview

Over 85% of employees have stayed silent about an important concern with their boss. Most leaders believe they're approachable — yet the people around them still don't speak up. The gap isn't intent; it's the absence of deliberate signals that make honesty feel safe.

Jeff Wetzler's Ask approach identifies five practices for closing that gap. This episode covers the foundational one: creating the conditions for truth before asking for it.

The core insight: asking questions isn't enough — you have to make it safe first, and safety is the leader's responsibility, not the follower's.

Why people stay silent

• 85%+ of managers across industries admit to staying silent with their boss about an important concern at least once.
• Nearly three-quarters said their colleagues were also aware of the issue — and also stayed quiet.
• 60–80% of Americans admit withholding health information from their own doctor, mostly out of fear of judgment.
• People will guess at your agenda if you don't explain it — and they'll guess more suspiciously than the reality.
• Silence isn't a character flaw in the follower; it's a signal that safety hasn't been created.

Meeting people where they are

• Go to their turf, not yours — the other person's comfort, not your own, determines what they'll share.
• Bill George (Medtronic) refused to invite people to his corner-office desk; Irene Rosenfeld rode along on sales calls.
• Time matters as much as place: the moment that suits you may be the worst moment for them.
• Mode matters too: phone, text, or a two-day delay to think before responding can all increase openness.
• When unsure, ask directly: "What would be the most comfortable way or time for us to talk?"
• Text is often dismissed as too casual for hard conversations — but if it's the medium someone prefers, the second-principle (comfort for them) should trump the first (face-to-face norm).

Opening up to create safety

• Explain why you're asking before you ask — unexplained questions trigger suspicion.
• "Why do you do it that way?" reads as accusatory; adding "You might be onto something" changes the entire dynamic.
• Admitting your own ignorance ("I don't know what it's like to be in your shoes") is disarming, not weak.
• Journalist Amanda Ripley opens interviews by naming her own blind spots and geographic assumptions — and finds it radically increases candor.
• Sharing a tentative point of view ("I'm leaning this direction, but I haven't decided") elicits richer input than holding cards close.
• The rule of thumb: share your view if you're genuinely open to changing it; stay quieter if you've already decided.

Setting a mutual agenda

• Before launching into your own agenda, pause and ask what's on the other person's mind.
• A simple "Is there anything else you'd like to cover?" shifts the conversation from your agenda to a shared one — even when they don't add anything.
• Mutual agenda-setting gives the other person agency and creates a spirit of co-creation.
• It lowers the barrier for the harder thing to surface: if someone has been waiting for permission to raise a difficult topic, this is often the moment they'll take it.
• Example: pausing to ask an investor before a structured check-in revealed a strategic dilemma that was more important than all three prepared agenda items.

Radiating resilience

• People constantly wonder: will they react badly if I tell them the truth? Resilience signals short-circuit that fear.
• Investor Jamie McKee opened every new investment relationship by saying she expected plans to deviate — and would be suspicious if they didn't.
• By framing deviation as the norm and the expected, she made the hard update the easy one to give.
• Language that names the emotion can unlock honesty: "If I were in your shoes, I might feel frustrated or even resentful — I'd understand completely if that's where you are."
• The signal isn't just words — it's demonstrated by not reacting badly when truth is finally shared.
• Leaders who think they're approachable often skip the explicit signal. Making the implicit explicit is what closes the gap.

Changing your mind as a practice

• Wetzler describes getting into an Uber driven by someone he immediately judged negatively based on a bumper sticker and hat.
• Choosing to apply the Ask approach instead of avoiding conversation, he found far more common ground than expected.
• The shift: the flag became a prompt for curiosity rather than a reason to disengage.
• Leadership development — like this approach — is a practice, not a destination.