Most people in organizations are doing the best they can, and most senior leaders genuinely want to hear what’s really going on. Even so, under pressure, any of us can shut a conversation down without meaning to.

I was at a client’s offsite that was tackling the issue of dropping engagement. Designed as a listening and brainstorming session, it was an opportunity to gather people’s perspectives on what was working, what wasn’t, and what needed to change. In one breakout session, someone asked whether the engagement issues might be connected to the organization’s strategic planning process. The senior leader dismissed the question as “off topic” in his effort to keep things on track.

What had been positioned as a collaborative dialogue quickly turned into a one-way lecture. Hands that had been raised to add ideas and questions were lowered. The change in participation was immediate. In a moment of pressure, the leader created the exact opposite of the outcome the organization had hoped to achieve. 

You may have experienced a similar shift in a meeting. Perhaps you were leading it, and your effort to keep things on track ended up discouraging people from contributing. Perhaps you were the one ready to offer a perspective, and then thought better of it after seeing how the leader responded to someone else. Either way, a discussion can close down just when it needs to open up.

When people become less willing to contribute, you lose access to information you need to lead. You depend on people throughout your organization to tell you where priorities conflict, what is proving difficult to implement, and which risks need attention. If those concerns go unspoken, decisions can look sound while resting on an incomplete picture.

The concern is familiar to executives. In Radical Candor’s 2026 workplace survey, 45.8% of executives surveyed identified a lack of honest feedback across the company as their top concern.

Wanting clear, complete information and feedback is a starting point. How you respond when it arrives helps determine whether people will offer it again.

What People Bring Into the Room

People bring baggage into every conversation: memories of whose ideas were taken up, which concerns were brushed aside, and what happened the last time someone disagreed. Those experiences shape what they are prepared to share and how openly.

Leaders bring baggage too. A difficult board meeting, an unresolved disagreement or pressure to demonstrate progress can affect how you interpret what someone says. A question intended to help you understand a problem may sound like a challenge to a decision you are already struggling to implement.

You cannot clear away everything people bring into a conversation. Recognizing your own baggage gives you a better chance of responding to the concern in front of you. Your response also becomes part of what people bring to the next discussion.

Here are three places to start.

1. Your State Impacts What People Are Willing to Say

Teams read a leader’s state before they weigh their words. Visible impatience, partial attention or a quick change of subject can tell people how much room there is for what they actually have to say.

When you are worried about a result, it is natural to look for reassurance that things are moving forward. You might respond to a difficult progress report by emphasizing the positives or moving straight to solutions. The person reporting may leave with the impression that you want confidence more than a full account of the difficulties.

A four-year study by INSEAD researchers illustrates how anxiety can affect those responses. Executives invited recommendations for improving the organization, then became defensive when the findings pointed to their own ways of working. Their experience offers a useful reminder: asking for honest information and being ready to hear it are separate challenges.

In my book, Lead Conversations That Count: How Busy Managers Run Great Meetings, the first step of the model is Calibrate. Before a conversation begins, pause to notice the baggage you are bringing into the room and intentionally set it aside for now. This internal checkpoint helps you recognize when you are reacting out of pressure rather than responding from purpose, so you can be as present, curious and open as possible.

Part of calibrating is recognizing what you feel compelled to resolve. Are you looking for information, or hoping people will confirm that the plan is working? Have you already decided what counts as relevant? Those expectations can shape your listening before anyone has spoken.

You can also recalibrate during the conversation. If you notice yourself preparing a rebuttal before someone has finished, pause and ask them to explain the concern more fully. You may still disagree, yet you will have a better basis for deciding. I couldn’t agree more with the wise words of Bill O’Brien: “The success of an intervention depends on the interior condition of the intervener.”

Ask yourself: What am I feeling pressure to resolve, and how might that affect what I am willing to hear?

2. Explore the Connections Before Ruling Them Out

No senior leader can see the whole picture alone. People in different roles encounter different parts of the same system. What looks like a planning issue to one person may show up as workload pressure for another and declining engagement for someone else.

Making sense of those experiences together helps people connect the dots. A concern that appears isolated may reveal a pattern across departments, priorities or working relationships. The discussion can change everyone’s understanding of the problem, including yours.

Before setting a question aside, ask what prompted it. “What are you seeing that connects this to the issue we’re discussing?” gives the person a chance to explain their reasoning and others an opportunity to build on it.

Protecting focus still matters. Some questions need a separate discussion. When that happens, explain why and agree on where the concern will be addressed. An issue put aside without a clear next step can easily disappear.

The judgement lies in telling a distraction apart from a connection you haven’t seen yet.

Ask yourself: Have I understood why this person sees the issue as relevant before deciding it belongs elsewhere?

3. Reopen the Conversation and Follow Through

You may recognize only afterwards that your response discouraged someone from telling you more. You can return to the conversation.

Start with the specific response you want to address. For example: “When you raised the implementation concern yesterday, I said everyone was stretched. I didn’t ask what was becoming unmanageable. I’d like to understand that.” 

If the exchange happened in front of the team, consider acknowledging it with the team too. Others witnessed the response and may have drawn conclusions about what they should raise.

Then take up the concern itself. Find out what needs attention, explain what you will do, and follow through. If the decision remains the same, explain your reasoning and how you have considered the information offered.

An acknowledgement can reopen a conversation. What happens afterwards gives people evidence about whether speaking up is worthwhile.

Ask yourself: Which concern have I left unexplored, and what would it take to give it proper consideration now?

You cannot make every conversation comfortable or act on every concern. You can make it easier for people to tell you something that complicates your plans.

The next time someone raises an awkward question, your response will influence both the decision in front of you and what people are willing to tell you next.

P.S. If you would value a confidential thinking partner as you work through these leadership questions, you can learn about my executive coaching here.