The Art of Active Listening: Using Questions to Build Trust

The Thoughtful Leader is a leadership series exploring the importance of thinking deeply, asking the right questions, and embracing diverse perspectives. Leadership is a journey, and a thoughtful approach means considering all angles, challenging assumptions, and making informed decisions to inspire growth, trust, and innovation.

As the speed of business accelerates and KPIs often loom large, the art of listening is frequently overlooked. Yet, for a leader looking to inspire trust and collaboration, nothing is more powerful than a great question followed by active, genuine listening. Building strong relationships and fostering an environment of trust doesn’t happen through commands or even through well-timed advice—it happens when leaders listen deeply, with the intent to understand and connect. Active listening may sound like an oxymoron, but it is one of the most important skills a leader can have in their toolkit.?

What is Active Listening??

Active listening is an art, a skill, and a discipline. Frankly, it takes practice and focus to do effectively. It requires you to focus solely on what the other person is saying and ignore what your brain is doing at the same time, which is processing all the elements surrounding the conversation. When you listen to your brain (and not the other person), your mind ‘wanders’, and you become distracted and inattentive. It goes beyond simply hearing what someone says; it’s about understanding their perspective, emotions, and needs. When you actively listen, you’re sending a message that what the other person is saying truly matters.

Why does active listening matter?

? It builds connection. People feel valued when they know they’re being heard.

? It deepens understanding. Listening actively helps you understand not just the words but the emotions and intentions behind them.

? It fosters openness. When people feel safe and heard, they’re more willing to share openly and collaborate.

? It strengthens trust. Trust grows when people feel that their voice matters and that their leader is invested in understanding them.

The Role of Asking Great Questions in Active Listening

While active listening is essential, it’s even more powerful when paired with the right questions. Thoughtful, open-ended questions encourage deeper conversations and signal to the other person that you’re truly interested in what they have to say.

Great leaders know that asking the right questions isn’t about interrogation—it’s about invitation. Inviting the other person to share more, think deeper, and reflect on their experiences, concerns, or ideas. When combined with active listening, questions are a powerful tool for building trust and fostering collaboration.

Types of Questions That Build Trust

To create meaningful conversations and strengthen trust, the questions you ask should be:

1. Open-ended: Avoid simple yes/no questions. Instead, use questions that encourage the other person to expand on their thoughts.

2. Show Genuine Curiosity: Ask questions that signal you’re genuinely interested in their perspective.

3. Encourage Reflection: Ask questions that prompt deeper thinking, helping the other person to gain clarity or insight.

Here are some examples of questions that, when paired with active listening, can build trust:

“How do you feel about the current direction we’re taking?”

This invites the other person to express their thoughts and emotions about the team’s or organization’s goals, signaling that their opinion matters.

“What challenges are you facing right now that I may not be aware of?”

This question invites transparency and says that you’re open to hearing about potential obstacles.

“What’s most important to you in this situation?”

This helps uncover core values or priorities, showing that you’re vested in understanding what truly matters to them.

“How can I support you in achieving your goals?”

Offering support through a question like this builds trust by demonstrating a willingness to help.

“What’s your perspective on this issue?”

This question invites the other person to share their unique viewpoint and shows that you value their insight.

Active Listening Techniques That Build Trust

Now that we’ve established the power of pairing questions with listening, let’s review some approaches on how to listen actively. These techniques ensure that your questions lead to meaningful exchanges and that the person feels truly heard:

1. Be Present

Active listening starts with being fully present. Put away distractions, make eye contact, and focus entirely on the conversation. This shows the other person that they have your full attention, essential for trust-building.

2. Listen to Understand, Not to Respond

Too often, people listen just enough to formulate their response. Active listening means focusing entirely on understanding what the other person is saying before you begin to think of your reply. This creates a more thoughtful, empathetic exchange.

3. Reflect and Clarify

Show that you’re engaged by reflecting back on what you’ve heard. Phrases like “It sounds like you’re feeling…” or “What I’m hearing is…” help clarify their point and show that you’re truly listening.

4. Ask Follow-Up Questions

After listening, ask follow-up questions to deepen the conversation. If someone shares a concern, for example, you might ask, “Can you tell me more about what’s behind that?” Follow-ups show that you’re interested in their deeper thoughts and feelings.

5. Acknowledge Emotions

When people share something that’s emotionally charged or important to them, acknowledging their feelings builds trust. Simple statements like “That sounds really challenging” or “I can see why that’s important to you” validate their experience.

The Thoughtful Leader Asks and Listens

When leaders combine active listening with thoughtful questions, they’re creating a culture where openness, trust, and collaboration can thrive. Team members feel safe to share ideas, offer feedback, and engage in constructive dialogue—all of which are essential for innovation and growth.

The result is a culture where people feel valued, understood, and empowered. Trust, collaboration, and innovation all stem from these meaningful conversations.

The next time you’re in a conversation, remember: What you ask is important, but how you listen will define the level of trust you build.