How to Ask Better Questions | The Art of Listening & Communication
Chris Do explains why asking the right questions, not having the right answers, is the key to building empathy and authority.
Chris Do
Founder, The Futur™ · December 3, 2023
Your Credentials Are Not the Answer
An illustrator, a former student, approaches educator Chris Do in a state of deep frustration. “Chris, how do I charge the kind of money that you’re able to get?” she asks. It’s a question that echoes a common anxiety among creative professionals and entrepreneurs: the chasm between their price and their perceived value.
She believes the answer lies in credentials. “You have awards… you have this body of work and you have all these logos,” she insists. It’s a logical assumption. We are taught that experience, accolades, and an impressive portfolio are the currency of expertise. They are the tangible proof that allows one to command a premium.
Do challenges this logic with a simple thought experiment. “Why don’t we switch portfolios?” he proposes. “I’ll give you my portfolio, I’ll take yours, and let’s go and present to the same client. What do you imagine would happen?”
She knows the answer instantly. “No,” she admits. She still wouldn’t be able to command his price.
The portfolio is not the variable that matters. The logos are not the differentiator.
So, what is?
The next logical guess is confidence. An audience member at the Hot Sauce Conference in New York, where Do is speaking, suggests it. “Speaking confidently about your… whatever it is… makes you seem like more of an expert.”
This creates a classic paradox. You need experience to build confidence, but you need confidence to be seen as an expert and gain experience. It’s a self-defeating loop, a mental trap that keeps aspiring professionals from ever reaching the next level. If you believe your lack of a portfolio or a long client list is what holds you back, you have designed an internal belief that guarantees your own failure.
The real key is not what you present. It is how you listen.
The Question No One Can Answer Correctly
To expose this baked-in cognitive bias, Do poses a seemingly simple question to the room: “What is more valuable, questions or answers?”
The response is immediate and overwhelming. By Do’s estimate, a full 80% of the audience calls out in unison: “Questions.” It is the enlightened, modern response. It signals an appreciation for curiosity, discovery, and dialogue.
The justifications are sound. “You learn more from questions,” one person offers. “Questions frame the answer,” says another. A third astutely notes, “People like talking about themselves.” These are all correct observations about the power of inquiry.
But then comes the twist.
Do turns to the 80% who championed questions and asks them a direct question himself. And in that moment, he asks them to observe a critical detail. “If questions are more valuable than answers,” he posits, “why did you answer a question with an answer?”
The room goes silent. The trick has been revealed. Despite intellectually valuing questions, the audience’s reflexive, deeply ingrained behavior was to provide an answer. Instantly.
This is not a personal failing. It is a product of our social and educational conditioning. Do explains, “I think we’re rewarded in our society, at least Western society, for answers.” From a young age, the student who shoots their hand up fastest with the correct answer is praised. They get the A, they are labeled the teacher’s pet. Those who are more reserved, who might doubt their answer, learn to stay quiet. “I would rather not give the wrong answer or be humiliated and I’ll just keep quiet,” Do recalls of his own experience.
We are compelled to give answers. It is a social and professional reflex. The expert is seen as the one with the answer, not the one with the clarifying question. This is the fundamental error that keeps us from building deeper connections and solving the right problems.
The Art of Deliberate Discovery
Breaking this habit requires a conscious and deliberate shift in behavior. It means choosing to be slower to give answers and staying curious for a little longer. It’s a principle powerfully articulated by Michael Bungay Stanier in his book, The Coaching Habit.
Do explains the profound benefits of adopting a question-first mindset.
- It empowers the other person. When you jump to provide a solution, you rob the other person of the chance to think for themselves. By asking questions, you guide them to their own insights, building their confidence and resourcefulness.
- It prevents you from becoming a bottleneck. For managers and leaders, being the sole source of answers creates dependence. Your team cannot move forward without you. By teaching them to solve problems through inquiry, you develop a more autonomous and capable team.
- It ensures you solve the real problem. Clients and colleagues often present a solution disguised as a problem. They say, “I need a new website,” when their real problem might be a lack of leads, a confusing message, or a broken sales process. Answering their request directly can lead to expensive and ineffective work.
As Do learned from his own business coach, asking simple questions is what truly changed his business. When a client approaches you, resist the urge to pitch ideas. Instead, begin a process of deliberate discovery. Exploring a client's needs is a key part of how to close more deals in your sales calls.
The questions themselves are not complex. They are the kind a fifth grader could understand. What do you want to accomplish? How will you measure success? What has worked in the past? Where did this go wrong before? Who else needs to be involved in this decision?
Simply getting permission to ask these questions, instead of feeling pressured to provide immediate answers, can transform your professional relationships. It is the foundation of empathy and the starting point for creating meaningful connections. As has been noted, advanced communication tactics are often rooted in simple, fundamental shifts in approach.
The Anatomy of a Powerful Question
Not all questions are created equal. To be effective, you must understand the difference between a question that opens a conversation and one that shuts it down.
Do leads his audience through an exercise to define the attributes of good questions versus bad ones. The results provide a clear map for anyone looking to improve their communication skills.
Stop asking questions that are:
- Binary. These are questions that can be answered with a simple “yes” or “no.” They kill conversation and provide very little information. Example: “Should I focus on my personal brand?” A simple “yes” ends the interaction.
- Leading or Biased. These questions have an agenda and push the other person toward a specific answer. They are about confirmation, not discovery. Example: “Don’t you think The Futur is awesome?”
- Ambiguous. Vague or unclear questions lead to confused or irrelevant answers. The other person has to guess what you’re really asking.
- Long-winded or Complex. Overly complicated questions are hard to follow. They often contain multiple questions in one, forcing the other person to dissect your query before they can even begin to answer.
Start asking questions that are:
- Open-ended. These questions invite stories, explanations, and deeper thoughts. They often start with words like “what,” “how,” or “why.”
- Neutral or Impartial. Powerful questions are free of judgment or a desired outcome. They create a safe space for the other person to share their honest perspective.
- Clear and Direct. A good question is easy to understand. It is precise and focuses on a single idea.
- Concise. The best questions are brief. They get straight to the point without unnecessary preamble.
The ideal question, Do suggests, is both clear and concise, yet invites an infinite number of possible answers. This combination allows each individual to bring their unique context to the table without being led down a predetermined path.
Diagnosis Before Prescription
Theory is one thing. Practice is another. To demonstrate the power of this method in real time, Do invites an audience member to ask a big, important question.
A woman steps up. “What is the number one thing you suggest for someone to elevate their personal brand?” she asks.
It’s a great question, relevant to many in the room. The old model of expertise would demand a direct answer. A top ten list. A silver bullet strategy. Do provides none of these.
Instead, he begins to diagnose. “What is the challenge for you right now about elevating your personal brand?” he asks. “What’s getting in the way?”
The answer reveals a tangle of issues: low engagement on Instagram and LinkedIn, a desire for more speaking engagements, and a general lack of confidence. The problem is not one thing; it is a collection of related symptoms.
Do focuses the conversation. Let’s talk about Instagram. He asks for specifics. What does “low engagement” mean?
“I want to get to 5k followers,” she replies. She is currently at 3,500 and has been stuck there for a while.
The problem is now concrete and measurable. This is a critical step many consultants skip. They hear a vague goal like “elevate my brand” and immediately jump to prescriptions. But without a proper diagnosis, any solution is just a guess. The difference between a business brand and a personal brand strategy often hinges on this level of diagnostic clarity.
Do continues to probe. Why does she think she is stuck? He solicits ideas from her and the room. The potential culprits are familiar to any content creator:
- A niche audience that has been saturated.
- A lack of focus or clear content pillars.
- Inconsistency in posting.
- Content that is not entertaining or valuable.
In the space of a few minutes, Do has given zero answers. Yet, the audience member and everyone watching now has a much clearer understanding of the actual problem. They have moved from a vague aspiration to a specific set of potential issues that can be addressed systematically. He didn't offer tactics on what successful personal brands do differently; he helped her find her own path to an answer.
This is the work. This is what experts do. They don't just solve the problem you bring them. They use questions to help you find the real problem you need to solve.
A Framework for Strategic Listening
This intuitive process of diagnosis can be structured. Do shares a powerful model called the PRO•A•C•T Framework from the book The Visual MBA by Jason Barron. It’s a way to listen and make decisions that is perfectly suited for sales, consulting, and any high-stakes conversation.
The framework breaks down a conversation into five distinct phases, ensuring you move from a surface-level request to a deep understanding of the situation.
- P - Problem. What is the *real* problem here? People often present false problems or solutions disguised as problems. Your first job is to dig deeper and find the root cause.
- O - Objective. What does success look like? What specific outcome is the person trying to achieve, and how will it be measured? You need a clear finish line.
- A - Alternatives. What are all the possible ways to reach the objective? Creative people excel at this divergent thinking. Brainstorm every option, from the expensive and complex to the simple and cheap.
- C - Consequences. What are the potential positive and negative outcomes of each alternative? Consider the cost in time, money, and even professional reputation.
- T - Trade-offs. If we say yes to this path, what are we implicitly saying no to? Every decision involves an opportunity cost. Making this explicit helps in making a fully informed choice.
By moving through these five steps, you avoid the costly mistake of executing on a flawed premise. For years, Do’s agency would pitch idea after idea, trying to wear clients down with creativity. It was only after learning to ask these fundamental questions that his business transformed.
The Empathy Engine
If you want to be more empathetic, if you want to build meaningful connections, it starts with a simple change. Learn how to ask better questions. And just as importantly, learn to actually listen to the answers.
These two skills are inseparable. Do points out the all-too-common experience of being a guest on a podcast where the host is clearly just working through a checklist. “Whatever I say means nothing to you because you’re more concerned about getting to question 2, 3, 4, and 5,” he says. “Is that how you want to build empathy and a deep, meaningful relationship with me?”
Answering a question before listening invalidates the other person. The question becomes useless because you are not willing to receive new information, update your thinking, and follow up with a relevant, thoughtful inquiry.
Listening is not waiting for your turn to talk. It is an active, engaged process of discovery. It is the engine of empathy.
To deepen this practice, Do recommends several resources, including Stanier's The Coaching Habit, Thomas Wedell-Wedellsborg's What's Your Problem?, and Marshall Rosenberg's classic work, Nonviolent Communication, which teaches a language of compassion and understanding.
The path to becoming a trusted advisor, a valued partner, and a highly-paid expert is not paved with more credentials. It is paved with better questions.
Stop providing answers. Start the conversation.
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“We're rewarded in our society for answers.”
— Chris Do
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