How Great Leaders Use Questions to Build Trust, Uncover Risk, and Improve Decisions

After two back-to-back weeks of board meetings, I found myself reflecting on the train ride from New York back to Philadelphia. A few observations came to mind.

People want to be engaged.
When board members ask thoughtful questions, it energizes the room. It signals that the work matters and that leadership is paying attention.

Recognition matters.
Not empty praise, but authentic acknowledgment of meaningful results. Genuine recognition reinforces the behaviors and outcomes organizations want to repeat.

Boards bring perspective.
Because board members aren’t running the business day to day, they can often see patterns, risks, and opportunities through a different lens. Their greatest value isn’t having all the answers, it’s offering perspectives management may not yet have considered.

Tone matters as much as the question.
People don’t just want to be heard; they want to feel respected. Curiosity creates dialogue. Condescension shuts it down. Some of the best conversation starters I’ve heard are:

• “Help me understand…”
• “I may be missing something…”
• “Walk me through your thinking…”
• “What are we seeing…”
• “What would make us change our minds…?”
• “Where do you have the lowest confidence?”
• “How is the team doing?”

Those simple phrases demonstrate both emotional intelligence and humility.

Be willing to share your failures.
Board members aren’t omniscient despite what some may think. We all learn through successes and mistakes. I’ve always found it more valuable when a board member shares where something didn’t work, what they learned, and how that experience shaped better decisions. That’s wisdom, and wisdom is one of the board’s greatest responsibilities.

It’s not enough to report on today’s weather. Great board members help management think through what might be coming next, why it may happen, and how to prepare for it.

Trust is built between meetings.
The board members I’ve valued most throughout my career are those who invest in establishing relationships outside the quarterly meeting cadence. They get to know the team. They ask questions. They stay engaged.

That trust becomes invaluable when the business inevitably hits turbulence.

No company wins forever. Even exceptional businesses eventually face market shifts, competitive pressure, or unexpected disruption. The strength of the board-management relationship is often tested most during those moments, not during the good quarters.

One final thought for management teams:

Know your business’s motion.
Know how the key drivers interact. When one variable changes, what typically happens next? That’s different from having all the answers. It’s understanding the dynamics of your business well enough to explain its expected behavior while remaining open to new information.

I call that controlled confidence…speaking with conviction while remaining intellectually curious. Confidence comes from experience. Experience grows through continuous learning.

And finally…

Be yourself.

It’s remarkable how often people change their personalities in boardrooms and executive meetings. Authentic confidence builds credibility. Manufactured confidence usually creates doubt.

People don’t expect perfection. They expect honesty, preparation, accountability, and a willingness to learn.

Those qualities earn trust with your team, your board, and ultimately, your customers.