Growing up, I used to get very upset with my mom. Every time we got in the car as a family, she and my dad would argue about his driving. She was constantly telling him how to drive and worrying that we would get into an accident. Her high degree of anxiety, especially in the car, put a wedge between us because I found that anxiety genuinely difficult to be around.
The Question That Changed Everything
Fast forward to my early 30s. One night, as I sat with my mom drinking a late-night cup of tea, I got curious. I decided to ask her a question, one that would change our relationship forever.
As I watched my mom quietly sip her steaming drink, I asked: "Mom, when you think back on your life, if there was one thing you would change, what would it be?" A very somber look came over her face. She stared at the tea, then at me. "I would have forced Tom Burns to go home."
That single question opened a door that had been closed for years.
What Tom Burns Taught Me About People
She went on to tell me the story of her first date with Tom Burns. She was 16, he was 17, and both attended Jamaica High in Queens, New York. Since Tom had his license, he picked her up at her house, and they went to the local cinema to watch the movie "Tea and Sympathy." After the film, Tom drove my mom home and walked her to the door, where he was greeted by my mom's mom, Big Grandma. Big Grandma insisted that Tom come into the house for some cake and coffee. My mom tried to spare him the trouble. Big Grandma would not be deterred, and she rarely lost an argument. About two hours later, Tom headed home and my mom went up to bed.
The following morning, as my mom walked to school, she saw some police activity ahead. Approaching the scene, she saw Tom's car had been totaled, and about 50 feet from the wreck was a body covered with newspapers. It was Tom. He had been killed by a hit-and-run on his way home from her house.
"If I'd only forced Tom to go home earlier, he'd still be alive today," she said, admitting to carrying that burden of blame for all those years. At that moment, all the pieces clicked. My mom's anxiety in the car, her fears about death and dying: it all began to make sense. I went on to ask more questions about her childhood and learned about many more challenges she had lived through that shaped who she had become as an adult.
That night, over steaming chamomile at the kitchen table, my relationship with my mom changed forever. We grew so much closer, and my respect for her grew exponentially, all because I got curious and asked one good question.
The Skill Nobody Teaches Us
Most of us spend our entire lives learning how to talk. We practice presentations, polish our pitches, and rehearse answers to tough questions. What we almost never practice is how to ask a genuinely good question and then sit in the silence long enough for the real answer to emerge.
In personal relationships, this shows up as surface-level connection. We stay in the shallow end of what we know about people we have known for decades. In professional relationships and in sales, the cost is more tangible. Sellers who dominate a conversation with their own value propositions rarely earn the kind of trust that builds a long-term client relationship. Leaders who always have the answer in the room rarely build the psychological safety that unlocks their team's best thinking.
The skill of asking better questions is learnable. It starts with three principles, each of which applies just as directly to a conversation with a client as to a conversation with your mom over tea.
Principle One: Genuine Curiosity
Walt Whitman wrote: "Be curious, not judgmental." It is one of the most usable pieces of advice in human communication, and almost nobody actually practices it.
Genuine curiosity means approaching every person as a mystery to be explored: each client, each prospect, each colleague, each family member rather than a problem to be solved or a profile to be confirmed. It means assuming nothing and questioning everything, in the best possible way.
In practice, this looks like asking about someone's experience before offering your own. It looks like following a thread when the other person hesitates, rather than filling the silence. It looks like tailoring your questions to what you already know about them rather than recycling the same five questions you ask everyone.
When I sat down with my mom that night, I did not ask her what I always asked: "How was your day?" or "How are you feeling?" I asked her something I genuinely wanted to know, and I gave her the space to answer it fully. That is the starting point for every meaningful conversation, in business or in life.
Greet each customer or client as a mystery to be explored. Assume nothing. Inquire about their interests and experiences within the context of the conversation. Tailoring your questions to their specific background or the purpose of the relationship fosters a connection that generic questions never can.
Principle Two: Openness
There is a structural problem with most of the questions people ask in professional settings. They are either closed (answerable with "yes" or "no") or leading, pointing toward an answer the asker already wants to confirm. Neither of those builds a relationship.
Openness means crafting questions that invite the other person to bring something of themselves into the answer. Open-ended questions, the kind that begin with "what," "how," "tell me about," "walk me through," or "what was it like," create the conditions for honest, unexpected communication.
In a sales conversation, this matters a great deal. A question like "Is budget a concern?" is closed and typically generates a defensive response. A question like "What does the decision-making process look like when you are evaluating something like this?" is open. It invites the other person to reveal how they actually think, rather than presenting a wall for you to push against.
Open questions take longer to answer. That is the point. The depth of the answer is the signal that the relationship is deepening. Avoid leading questions or those that can be answered with a simple "yes" or "no." Instead, ask questions that invite the other person to share their thoughts, feelings, and experiences more fully.
Principle Three: Empathy
The third principle is the hardest one. Not because empathy is rare (it is not) but because practicing it under pressure requires a level of self-awareness that most people do not bring to professional conversations.
Empathy means showing genuine interest in the other person's perspective and feelings. It means asking questions that allow them to express their emotions and concerns, and then being a compassionate listener in response: not a problem-solver, not a solution-pitcher, not a devil's advocate. A compassionate listener.
My mom did not need me to fix what happened to Tom Burns. She needed someone to ask her about him, and then to sit with her in what that story meant. That willingness to hold space for someone else's experience is what closed the distance between us.
In a business context, empathy looks like asking a client what is keeping them up at night, then actually listening to the answer before pivoting to your solution. It looks like asking a direct report what is making a project feel hard before telling them how you would approach it. It is the practice of orienting yourself toward understanding before you orient toward action.
Show genuine interest in the other person's perspective and feelings. Ask questions that allow them to express their emotions and concerns, and be a compassionate listener in response.
One Question at a Time
You do not need to overhaul how you communicate overnight. You need one question.
Think of a few relationships you have in your personal and professional lives. How can you use the skill of asking great questions to deepen and strengthen them? Think about what you do not know about the person on the other side of one of those conversations. Think about what you have never asked.
Then ask it.
Use genuine curiosity as your orientation: approach this person as a mystery to be explored. Use openness as your structure: frame the question in a way that invites them to bring themselves to the answer. Use empathy as your posture: commit to listening fully before you respond.
The people who build the deepest, most durable relationships in their professional lives are not the people with the best answers. They are the people with the best questions. My mom and I grew closer that night not because I told her something meaningful, but because I asked her something meaningful.
Use more intentional question-asking in your conversations and watch your relationships deepen and strengthen faster than you imagined possible. It is one question away, and worth starting today. If you are curious what that looks like inside your sales team, start a conversation with Braintrust.
