How Questions Create Trust in Leadership
Questions Part-2
By Rick Aman onSubtitle: Trust isn't built on having the answers, it's built on asking the right questions.
“People don’t care how much you know until they know how much you care.” —Theodore Roosevelt
Recently while facilitating a governing board retreat, it occurred to me to pause the agenda and ask a simple question: “What does success look like for us in three years?” The room went quiet. Then, one by one, board members began to offer thoughtful reflections. The conversation shifted from checking boxes to envisioning impact. That single question opened the door to alignment, clarity, and trust. It didn’t offer an answer. It invited one. That moment reminded me that leadership doesn’t start with certainty. It begins with curiosity.
Why Questions Matter More Than Answers
Traditionally, we’ve been taught to equate leadership with having the answers. Leaders are expected to have vision, confidence, and command. Leaders feel they need to project certainty and provide direction, often from a place of authority. In that model, questions could be seen as a sign of weakness, something to be avoided rather than embrace. But leadership today requires something different. In an environment shaped by rapid change, competing priorities, and immense complexity, answers are often incomplete or outdated the moment they’re spoken. What team members are looking for now isn’t just clarity of direction, they’re looking for precision of intention. They want sincerity, not certainty. It is likely you are in a room with seasoned leaders, they are not novice in their backgrounds and experiences. These team members want to know that their perspective matters and at least heard. They want their experiences to be considered, and that their leaders are willing to pause long enough to truly listen.
This is Where Questions Come In
A well-placed question tells your team, “I don’t just value your input, I need it.” It levels the playing field. It removes hierarchy from the equation, even momentarily, and says, “This is a space where your voice matters.” And when leaders model that kind of humility and curiosity, it changes the relational dynamic. It signals respect. It builds trust.
Research supports this shift. A 2017 study published in Harvard Business Review, It doesn’t hurt to ask: Question-asking increases liking found that individuals who ask more questions especially follow-up questions are consistently rated as more likable, trustworthy, and competent. The reason? People perceive question-askers as more interested, more attentive, and more collaborative. These qualities are essential in effective leadership.
In my executive coaching, I often remind leaders, your job isn’t to be the smartest person in the room; it’s to create a room where smart, honest, and forward-looking conversation can happen. Leaders who listen well, ask carefully, and create space for dialogue often become the people others will follow, not because of what they know, but because of how they lead.
The irony is this, the more willing you are to ask, the more confidence people will have in your leadership. Not because you pretend to have every answer, but because you’re wise enough to ask the right question at the right time. That’s not a weakness, that’s strength. Strategic strength. And it’s one of the most powerful shifts a leader can make.
Questions as Signals of Psychological Safety
Judith Glaser, in her work Conversational Intelligence: How great leaders build trust and get extraordinary results (2016), described how teams build trust not through statements, but through conversations. She called it co-creating, where leaders don’t just share what they know, but invite others to shape the direction with them. Strategic questions, she wrote, signal psychological safety. They lower defenses and open the door to more meaningful engagement.
I once worked with a board chair who routinely asked fellow board members, “What are we missing?” or “Where could this go wrong?” Not as a challenge, but as an invitation. It changed the tone in the room. Instead of reporting what was already decided, the team began to explore ideas with greater honesty. People brought forward concerns earlier, felt empowered to flag risks, and collaborated more freely. That wasn’t accidental, it was cultural. And it started with questions that made it safe to speak.
Five Trust-Building Questions Every Leader Might Use
Consider some form of these five questions to see if they reshape team dynamics and build relational equity in leadership settings:
“What’s one thing we’re not talking about that we should be?” This invites people to surface the quiet or uncomfortable truths that often linger beneath the surface.
“What concerns are people afraid to bring up here?” A bold question. It shows humility and gives permission for honesty.
“What would this look like if we prioritized the student (or client) experience?” Re-centers decisions on mission and values and signals that outcomes matter more than optics.
“How does this decision impact those we serve?” This question shifts the focus from internal operations to empathy and real-world impact. It reminds us that every decision carries potential unintended consequences, so we must thoughtfully consider how our actions affect the people we exist to serve.
“What’s something we’ve outgrown but haven’t let go of?” A powerful reframing question that invites evolution over nostalgia.
These aren’t small talk, they are strategy. Asked sincerely, they can surface what’s true, shift what’s stuck, and foster real connection between leaders and teams.
Culture Is Shaped by What We Ask
If you want to understand a team or board’s culture, listen to the questions they ask most often.
Do they ask:
“Who approved this?” or “Who will this serve?”
“What’s the risk?” or “What’s the opportunity?”
“What did we miss last quarter?” or “What will our students need next year?”
The default questions reveal the culture. And if we want to shift the culture, we need to shift the questions. Warren Berger, in A More Beautiful Question (2014) reminds us that innovative organizations are those that routinely challenge assumptions by asking better questions. That’s as true in higher education and nonprofits as it is in business. When we build a culture where questions are welcome, curious, courageous, and consistent—we create space for people to contribute, align, and grow.
Summary
Trust doesn’t come from job titles or org charts. It comes from listening. And listening starts with a good question. This week, I encourage you to ask one trust-building question in your next meeting or conversation. Pause your agenda, create a little space, and see what happens when you lead with curiosity. You may be surprised how much trust and insight is waiting on the other side of the right question.
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At Aman and Associates, we believe trust and clarity begin with the questions we ask. We work alongside boards, CEOs, and executive teams to guide inquiry-based strategy where thoughtful dialogue drives alignment and action. If you’re ready to lead with purpose, sharpen your focus, and build a culture rooted in curiosity and trust, we’ll help you ask the questions that matter most.
Rick Aman, PhD - Aman and Associates
http://www.rickaman.com/articles
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