I recently shared the following memo with one of my coaching clients who was working to create an environment where people felt comfortable speaking candidly. It’s a challenge I see in many organizations, so I thought I’d share it here in case you find a few ideas that are helpful.
I’ve been thinking about our conversation and wanted to put together a few thoughts while they were still fresh.
Over the years, I’ve worked with quite a few leadership teams that struggled to get people to speak honestly about important issues. Every organization is different, but I’ve found that the underlying challenge is highly consistent. People rarely stay silent because they don’t care. More often, they conclude that speaking up creates more personal risk than remaining quiet.
That’s why I’ve come to look at this primarily as a leadership challenge rather than a communication challenge.
Communication is simply where the problem becomes visible. Leaders must create enough trust that people are willing to have what I call courageous communication. I’m talking about the willingness to bring up concerns early, offer a different perspective, or raise an issue.
Those conversations become more difficult as the distance between two people grows. A frontline employee speaking candidly with a supervisor is one thing. Raising a concern with a senior executive or the CEO is something else entirely. Whether it’s fair or not, people understand that senior leaders have a great deal of influence over their work and future with the organization. Before they decide to speak up, many people perform a quick mental calculation: What is likely to happen to me if I say this?
Leaders and employees often view the situation very differently.
Most leaders sincerely believe they want people to speak openly and would welcome honest feedback. Employees reach their own conclusions by watching what actually happens inside the organization. They notice how leaders respond when someone raises a difficult topic, admits an error, or delivers bad news. They remember whether that person was taken seriously, dismissed without discussion, thanked for speaking up, or left feeling embarrassed. Those experiences become far more influential than anything written in a values statement or trumpeted by a senior executive during an all-hands meeting.
Employees don’t limit those observations to their direct manager. If another senior leader dismisses a concern or reacts defensively when someone speaks honestly, people throughout the organization notice. Before long, they develop a shared understanding of what behaviors are actually safe, regardless of what any individual leader intends.Â
One of the simplest ways to encourage more open communication is by slowing down your initial response when someone brings you bad news or challenges one of your ideas.
It’s natural to want to explain your thinking or justify a decision. Resist that impulse. Listen carefully before responding. Ask a few thoughtful questions. Let the other person finish before you begin evaluating what they’ve said. Even if you don’t like what you’re hearing, acknowledge the courage it took to raise the issue. Say something like, “I’m not happy we have this problem, but I’m really glad you brought it to my attention. This is exactly the kind of conversation we need to have.”
I’d also be very explicit about your expectations.
Don’t assume people know you want them to raise concerns or question decisions respectfully. Many people have spent years in organizations where those behaviors were discouraged. Give them permission. Tell them that bringing forward a problem early is part of their responsibility. Then reinforce that expectation every time someone has the courage to do it. Make it safe to speak up and celebrate candor.
Finally, when someone brings you an important issue, let them know what happened.
Explain your thinking. If you decided to move in a different direction, help them understand why. Even when people don’t get the outcome they hoped for, they appreciate knowing they were heard. Nothing discourages future communication faster than feeling that honest feedback was ignored.
Ultimately, courageous communication develops over time through hundreds of small interactions that gradually reduce fear and increase trust.
When people consistently see curiosity instead of defensiveness and understanding instead of judgment, they become much more comfortable raising difficult issues before they become serious problems.
Organizations don’t become high performing because everyone agrees. They achieve better results because people trust one another enough to speak honestly, challenge ideas respectfully, and solve problems while they’re still manageable. Creating that kind of environment is one of the most important obligations of leadership, and it begins with the example the leader sets every day.
Organizations are expecting more from the people they bring in to speak.
A strong keynote still matters. But leaders are also looking for practical tools, planning support, useful takeaways, and someone who understands the pressure behind the event.
John Spence was named the 2026 Thinkers360 Thought Leader of the Year. He does not just walk on stage, deliver a keynote, and leave. He works with you as a trusted partner from the first planning conversation through the final follow-up.
