The ability to ask great questions is one of the most undertrained, undervalued skills in professional communication. Yet for salespeople, it is often the single factor that separates a forgettable conversation from one that actually moves a buyer forward.
Consider this: of all the courses Jeff Bloomfield, CEO and founder of Braintrust, has created on LinkedIn Learning, the most-viewed by a wide margin is "Asking Great Sales Questions" — with over 60,000 views and more comments than any of his other programs. When LinkedIn and Microsoft curated their "Top 10" courses to provide free learning resources during COVID-19, that course made the list. That's not an accident. It's a signal about how starved most sales professionals are for real, practical guidance on this skill.
Why Questioning Gets Undertrained
We ask questions every day. Because it feels natural, we assume we're doing it well. But there's a significant difference between asking questions habitually and asking them with intention. In professions where questioning determines outcomes, that gap is everything.
Lawyers, physicians, TV interviewers, school counselors, and sales professionals all depend on their ability to ask questions. But here's what's worth noting: each of those professions asks questions toward a fundamentally different goal. And the goal behind your questions shapes everything about how the other person responds.
The Lawyer vs. The Doctor
Think about the famous courtroom scene in A Few Good Men. Lieutenant Kaffee's relentless pressure on Colonel Jessup is a masterclass in interrogative questioning. Every question is engineered to extract information that serves the lawyer's case. The agenda is his. The goal is his. The outcome he's driving toward is his.
That approach works in a courtroom. It has a place, and it serves a purpose.
Now contrast that with the final scene of ER. The questions being asked in that emergency room are completely different in character. They're fast, focused, and entirely in service of the patient. What's wrong? Where does it hurt? What happened? The clinician's agenda is subordinated to the person in front of them.
Both questioning styles accomplish something. The critical difference is whose interests are being served by the questions. The lawyer serves himself. The doctor serves the patient.
Now think about your own sales conversations. Think about the last ten customer interactions you've had. Were you the lawyer or the doctor?
Self-Serving vs. Other-Serving Questions
Most salespeople, if they're honest, ask a mix of both. They ask discovery questions that are genuinely curious about the customer's situation, and they ask questions designed to steer the conversation toward the product they want to talk about. The ratio matters. Buyers feel the difference, even if they can't articulate it.
When your questions serve you, they create pressure. When your questions serve the other person, they create trust. And trust is what moves deals forward in complex, high-consideration sales environments.
The shift from self-serving to other-serving questions isn't just tactical. It's a mindset change. You have to walk into the conversation genuinely curious about the customer's story rather than focused on advancing your own narrative.
What Hot Ones Teaches Us About Preparation
Here's a less obvious example worth paying attention to: Sean Evans and his YouTube series Hot Ones, where he interviews celebrities while they eat increasingly spicy chicken wings.
What makes Sean remarkable as an interviewer isn't the format. It's the questions. Guests who have done hundreds of press junkets and media appearances consistently remark that Sean asks things no one else has asked. He surfaces stories, memories, and opinions that high-profile publicists and handlers haven't managed to lock down. Guests don't just answer his questions; they thank him for them.
How? Preparation and genuine curiosity. Sean and his team research each guest deeply. They understand the person's story before the cameras roll. They design questions that open up, not ones that confirm what Sean already thinks he knows. The result is a level of candor and connection that other formats rarely produce.
That's the same discipline that separates a great sales conversation from a mediocre one. Know the customer's story. Ask questions that let them tell it. Build from there.
Three Practical Tips for Better Questions
Asking great questions is a learnable skill. It takes knowledge, preparation, and consistent practice. Here are three places to start:
- Prepare your questions in advance by understanding your customer's story. Before any customer conversation, do the work. Know their business, their challenges, their industry context. Your questions should reflect that you've already invested in understanding their world — not that you're starting from zero.
- Audit whether your questions are self-serving or other-person serving. After each conversation, review the questions you asked. How many were designed to move the customer's thinking forward? How many were designed to move your sales process forward? The ratio reveals more about your approach than you might expect.
- Practice your questions consistently. Write them out. Test them in lower-stakes conversations. Refine what opens people up and what closes them down. Great questioning isn't improvised; it's a habit built through repetition.
The Standard Worth Holding
The best sales professionals ask questions the way a great doctor conducts a consultation: with focused attention on the person in front of them, genuine curiosity about what's really going on, and the discipline to listen to the answer rather than formulate their next point.
It's a standard worth holding. And the good news is that it's entirely learnable.
We'll go deeper on the art of provocative, insightful questioning in future posts. For now: prepare your questions, serve the other person with them, and practice until it's second nature. The wings are optional.
If you'd like to explore how Braintrust helps sales teams build this skill at scale, start a conversation with us here.
