In last week’s How To Sell Yourself workshop, one participant admitted he sometimes asks too many questions. He gets so caught in curiosity that he “gives away all his marbles” before ever making the ask. Another participant shared the opposite pattern: she avoids asking questions because she’s afraid of what the answers might reveal – especially when she’s afraid the prospect isn’t a fit.
Both patterns are a form of resistance. Whether we over-ask or under-ask, we’re avoiding the discomfort of discovering the truth.
The conversation inspired me to write an article about questions – why they matter, the different types of questions, and which to use when.
Why Questions Matter
There are several different kinds of questions, and the kind you choose determines the outcome — in sales, in conflict, and in life.
Asking questions demonstrates authentic curiosity about the customer, which allows you to build rapport and an emotional connection. And in asking questions you’re able to get to the heart of the customer’s issue.
Ask Questions as Training for Real Life
One of the most important interpersonal skills anyone can practice is the ability to ask questions. Whether you’re gathering information, selling, coaching, interviewing, or navigating a hard conversation, asking questions trains many other essential human skills.
How Questions Sharpen Your Thinking
There are no inherently right or wrong questions – only questions that are more or less useful depending on the outcome you want. Asking better questions improves your ability to listen, connect, persuade, and think clearly.
High-Pressure Conversations
Any situation that matters – a first date, sales call, job interview, or giving feedback to a colleague – brings uncertainty. Important moments require the ability to think while under pressure.
Most people become passive in high-stakes situations. They respond reactively or expect the other party to lead. But if you can stay curious and ask thoughtful questions, you change the dynamic. You become an active participant instead of someone being carried along by circumstances.
Thinking on Your Feet
High-stress conversations are unpredictable. Someone says something surprising and emotions get involved.
You have to respond in real time.
The only way to train for this is to practice before the stakes are high. Asking questions builds the habit of staying calm when it matters.
Practice Before the Moment
We all face pivotal conversations. Instead of waiting for the critical moment to arrive, you can practice the skill of asking questions every day. This might mean:
- asking a friend one more follow-up question
- pausing to clarify someone’s intention
- checking in during a difficult conversation
- being curious instead of defensive
These small practices prepare you for the moments when the pressure is real.
The Different Kinds of Questions
There are several different types of questions, and each serves a different purpose.
Blaming questions
These are the most common — usually asked in frustration: “Why did you do that!?” When used intentionally, blame can motivate action, but more often these questions land as an attack and create distance.
Manipulative questions
These are the pushy, sales-adjacent questions everyone dislikes. They steer someone toward a predetermined answer and usually feel transactional.
Research questions
These are questions that accelerate learning. By asking an expert specific questions about their discipline, you dramatically increase your speed of learning.
Consulting questions
These assume you’re the expert and help the other person see the problem the way you see it. They’re directive and designed to move someone toward your conclusion.
Leading questions
These guide someone toward an insight, a storyline, or an emotional shift. They’re useful for teaching, storytelling, and persuasion — especially when they contain an unexpected twist.
Connecting questions
These presume the other person is their own expert. They create space for introspection and help someone articulate what they think or feel. They’re the least common, and the most powerful for building trust.
Each of these types of questions has an appropriate context. Even blaming and manipulative questions can be useful. But each type shapes the relationship differently – and some build connection while others break it.
Know Your Intentions
It’s important to know your intentions before beginning to ask questions, and to leverage your intention to ask the right kinds. All too often, we are attached to a specific outcome – closing a sale, getting what we want from a family member, achieving our desired ends. That desperation is perceived as pushy and a lack of consideration.
If you are feeling urgency, stop. That urgency, which comes across as pressure, will ultimately not serve you or your desired outcome.
Regardless of what you are selling, or the knowledge that you have, your intention should be to help the person you’re talking to. If, through the course of discovery, you find yourself thinking that what you are selling is not a good fit for the person you are talking to, explain “I don’t think this is a good fit for you.”
Thank them for their time and move on.
Being clear about your intentions means that people are more likely to come back later and the goodwill you generate by being so straightforward outweighs the loss of a sale.
Putting It All Together
In order to sell anything – an idea, a changed behavior, or a product – you must first understand the other person’s challenge. But you also have to know your own intentions.
I once heard Tony Robbins say thinking is the process of asking and answering questions. As we learn to ask more refined questions, our thinking improves. By asking more questions, you train yourself to think more clearly, understand your intention, and get better at asking the right questions.
3 Things I’ve Loved This Week
Quote I’m Considering
“Thinking is just the process of asking and answering questions.” -Tony Robbins
Article I’m Loving
You’re Gonna Need This Now More Than Ever by Ryan Holiday
Leave it to Ryan Holiday to describe the upside potential and downside risks of relying on AI. As he writes:
The machines are getting better at sounding smart. Which means we need to get better at actually becoming smart.
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Snafu Conference is convening 250 reluctant salespeople on March 5, 2026 at the Oakland Museum of California. See you there?
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The next How to Sell Yourself workshop series just kicked off this week with 12 people from all over the world. I'll be hosting another cohort beginning January 2026. This is a new approach to selling for people who aren't quite comfortable selling themselves - yet!
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Until next week,
Robin
