I started asking deeper questions - and became a better communicator.

If you're struggling to make your professional conversations more meaningful, you're hardly alone. Most people miss the real key to connection. It’s not about talking more—it’s about asking better questions.

Effective communication is so core to business that some people say that without it, you'll never succeed in business. Yet, many interactions feel transactional or unproductive. Meetings go on and on without clear outcomes, employees feel like no one's hearing them, and trust within teams is... well there is none.

The solution? Learn the art of asking deep questions. Unlike surface-level questions, deep questions dive down into motivations, emotions, and values of the people you're having a conversation with. They don’t just exchange information—they build connection and understanding.

Here’s how you can make your communication game stronger and actually connect with people on a whole new level.

The Problem with Surface-Level Communication

Most business conversations stick to logistics, updates, or surface-level facts. And I can understand that. After all, we're busy and we need to get things done.

While these kinds of conversations are necessary, they rarely create any kind of genuine connection or uncover meaningful insights.

I remember a time when I asked a colleague, “How’s the project going?” It was a perfectly valid question, but their answer was short and factual.

But what I really wanted to know was how they were going with the project.

I figured out much later that I asked the wrong question.

What I needed to ask was, “How are you feeling about how you're going with the project?”

The response? It could have been a far more enthusiastic explanation of their ideas, challenges, and goals.

That one shift could have changed the dynamic of our conversation and strengthened our working relationship.

Shallow conversations keep relationships stagnant. Deep questions, on the other hand, help unlock the potential of every interaction.

Why Deep Questions Work

Deep questions are transformative because they:

1. Bring Forward Authenticity: They encourage people to share who they are, not just what they do.
2. Build Trust: Vulnerability creates stronger connections in professional relationships.
3. Uncover Motivations: They reveal what matters most to the other person.
4. Encourage New Thoughts: They inspire critical thinking and fresh perspectives.

Charles Duhigg, in his TEDx talk The Science Behind Dramatically Better Conversations, explains that every interaction falls into three categories:

• Practical Conversations: Focused on solving problems or achieving specific goals.
• Emotional Conversations: Centred on sharing feelings and seeking empathy.
• Social Conversations: About identity, belonging, and how we relate to others.

Effective communicators match their approach to the type of conversation the other person needs. Misaligned conversations—like offering advice when someone needs empathy—often lead to frustration and misunderstanding. I think most married men have come up against this one with their wives.

A while back, I managed a team member who came to me feeling overwhelmed. My first instinct was to offer solutions on how to be productive and get organised to relieve the stress. This was not what they were looking for at the time.

They just wanted to be heard. When I heard myself going into "Messiah Mode" I paused and changed my approach to first, apologise for trying to fix everything and then asked, “How are you feeling about all of this?” Her entire demeanour shifted. She opened up, and we found a way forward together.

5 Steps to Better Business Communication Through Deep Questions

1. Ask Beyond the Surface

Replace standard questions with open-ended ones that explore motivations and values.

• Instead of “How’s the project going?” ask, “What excites you most about this project?”
• Instead of “What’s the next step?” ask, “What’s the biggest challenge we haven’t addressed yet?”

These questions encourage deeper reflection and provide richer insights. I’ve used this technique in client meetings, and it’s amazing how much more engaged and creative people become when you ask the right questions.

2. Match the Conversation Type

Using Duhigg’s “matching principle,” align your response to the type of conversation at hand:

• Practical: “What resources would help you overcome this challenge?”
• Emotional: “How are you feeling about this situation?”
• Social: “How does this project align with your personal goals?”

Recognising what someone needs ensures you’re meeting them where they are, rather than imposing your assumptions.

I recall a mentoring session last year with a young professional with a background as an international student, who was unsure about his career direction. He didn’t need advice at first—he needed to articulate his fears and goals. By asking, “What does success look like for you?” we discovered what truly mattered to him.

3. Encourage Vulnerability

Deep questions invite people to share their values and beliefs, but this requires a safe environment. Show genuine curiosity and avoid judgment.

For example:

• Instead of “Where did you work before this job?” ask, “What inspired you to pursue this career?”
• Instead of “What’s your background?” ask, “What’s one experience that shaped your approach to work?”

I’ve seen this approach work wonders in networking events. People light up when you show real interest in their stories. But like I said, this requires a safe environment. No one is going to want to open up in a group meeting or to a manager who is constantly belittling them.

4. Listen Without Fixing

One of the most common mistakes in communication is focusing on your response rather than the other person’s message.

After asking a deep question, resist the urge to jump in with solutions or advice. Instead, respond with prompts like:

• “That’s really interesting—what made you feel that way?”
• “Can you elaborate on what that experience was like for you?”

True listening makes people feel valued, which fosters stronger relationships.

I remember a senior executive at Optus back in the 90s once told me, “The best conversations I’ve ever had are the ones where I felt truly heard. It’s rare, but it’s unforgettable.”

5. Share Your Story

Reciprocal vulnerability strengthens bonds. When someone shares a challenge or personal insight, consider offering a relevant experience of your own.

For example:

• A colleague says, “Balancing work and life has been tough lately.” You might respond, “I’ve felt the same at times. Setting clearer boundaries really helped me. What’s been working for you?”

I’ve had moments where sharing my struggles with work-life balance turned a tough conversation into a collaborative problem-solving session.

Deep Questions in Action: A Case Study

Dr Behfar Ehdaie, a surgeon specialising in prostate cancer, initially struggled to convince patients to choose less invasive treatments. Despite presenting compelling medical evidence, patients often insisted on unnecessary surgeries.

The breakthrough came when he started asking deep questions. Instead of jumping into medical advice, he began consultations by asking, “What does this cancer diagnosis mean to you?”

One patient shared fears about his legacy, how his family would cope, and concerns about being judged by colleagues. By addressing these emotional and social concerns, Dr Ehdaie built trust and helped the patient feel confident in a non-surgical treatment plan.

The result? Most of Dr Ehdaie’s patients now follow his advice, demonstrating the transformative power of understanding through deep questions. You can read more about it at?Understanding Patients Better.

Practical Applications for Business Settings

Deep questions can improve communication across all professional scenarios:

• In Team Meetings: Encourage participation and innovation by asking, “What’s one thing you’re proud of this week?”
• In One-on-Ones: Build trust by exploring motivations. Try, “What’s something you’d love to achieve that we haven’t discussed yet?”
• With Clients: Strengthen relationships with questions like, “What’s your biggest priority for this project, and why is it important to you?”

These questions don’t just gather information—they signal that you genuinely care about the other person’s perspective.

Meanwhile, back in the real world...

It’s easy to prioritise efficiency over connection when we're busy and we need to get a lot of things done. But true leadership and collaboration come from understanding and valuing the people you work with.

Deep questions are more than just communication tools—they’re a mindset. They help you uncover the motivations, values, and feelings that drive others. And like all mindset changes, you're going to have to work at it a bit.

Start small.

Next time you’re in a meeting or conversation, skip the small talk. Ask a deep question like, “What’s been the highlight of your work this month?” Then, listen.

Because at the heart of great communication isn’t what you say—it’s how deeply you connect.