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The Questioning Edge: A Guide to Better Conversations

Writer's picture: David OteyDavid Otey

Updated: Feb 9


Great conversations don’t just happen. They are built with thoughtful, intentional questioning. Asking the right questions at the right time can uncover valuable insights, build stronger relationships, and ultimately drive meaningful discussions. But what separates an average question from an extraordinary one? The secret lies in understanding the purpose, context, and desired outcome of each question you ask.


In my years of experience managing some of the largest Personal Training Departments in the country, a few common topics resonated from facility to facility - no matter what demographic. 


Here are some of my best tips:



It’s a Question, Not an Interrogation

Effective questioning is about fostering a dialogue, not conducting an interrogation. When questions feel like an inquisition, people shut down. The goal should always be to create an open, collaborative environment where the conversation flows naturally.


The challenge for a coach to get “deep” information is a tall task. You are asking someone to strip back their wall and tell you all of the things they are most insecure about regarding their health, physique, and lifestyle. To have any chance of getting quality information, you can have curate an environment that breeds trust and compassion.


Rather than grilling someone with rapid-fire inquiries, approach questioning with curiosity and empathy. Think of it as an opportunity to explore ideas together rather than extracting information like a detective. This mindset shift leads to richer conversations and deeper connections.



The Recipe for Great Questions

Just like a well-prepared dish, powerful questions require key ingredients:


  • Purpose: What is the reason behind your question? Are you gathering information, uncovering needs, or driving action? Defining the purpose ensures your questions serve a clear objective.

  • Context: Consider the situation, the people involved, and the environment. Tailoring your questions to fit the moment increases their impact.

  • Desired Outcome: What do you hope to achieve? Whether it’s deeper insights, stronger engagement, or a clearer understanding, your goal will shape how you ask questions.



More Questions = Better Conversations

Want to have a truly engaging conversation? Ask more questions. Research consistently shows that the more questions you ask, the more interested the other person perceives you to be. It’s not just about quantity, though—it’s about crafting the right kind of questions that encourage thoughtful responses.


An effective conversation should be weighted in favor of the other person speaking more. Ideally, they should be talking 80-90% of the time while you guide the conversation with strategic questions. This approach ensures that you uncover the full story rather than just surface-level responses.



Types of Questions and Their Power

Different types of questions serve different purposes. Mastering when and how to use them is key to an effective dialogue. These concepts are broken down in depth in the Career Trainer Mentorship.



Open-Ended Questions: Digging for the “Why”

Open-ended questions allow for expansive answers and deeper insights. They encourage storytelling, uncover emotions, and reveal motivations.


Examples:

  • Tell me about yourself.

  • What does success look like to you?

  • You said you want to be healthier—what does that mean for you?

  • If you were to wake up tomorrow and look exactly the way you wanted to, what would be different about you?


Discovering the context makes all of the difference.


People often struggle to articulate what they want, and open-ended questions help them clarify their thoughts. They also reveal the emotional drivers behind their answers—whether it’s confidence, fear, or excitement—that ultimately influence their decisions.



Yes or No Questions: Setting Up Depth

Yes or no questions provide clarity and validation. They are useful when confirming details or setting up deeper discussions.


Examples:

  • Have you worked with a coach before?

  • Do you have experience in this area?

  • Would you be open to a new approach?


While these questions are useful, they shouldn’t dominate the conversation. The yes or no question is the fork in the road that pushes you down another path. The last thing you want to do is end a yes or no question with a response like “Okay, awesome”


You are leaving so much on the table without digging in.


Use them as stepping stones to deeper discussions.



Rating Scale Questions: Quantifying Insights

Using numerical or qualitative scales helps gauge opinions, preferences, or satisfaction levels.


Examples:

  • On a scale of 1-10, how committed are you to achieving your goal?

  • On a scale of 1-5, how comfortable are you with this process?


These questions provide measurable data, but the real power comes in the follow-up. If someone rates their commitment a 5 out of 10, ask, What would need to change for that number to be an 8 or 9? This simple follow-up transforms a number into an actionable insight.


Additionally, rating scale questions can reveal discrepancies in self-perception. People may overestimate or underestimate their abilities, readiness, or understanding of a situation. 

By asking them to justify their rating, you gain valuable context.


 For instance, if someone rates their fitness level as an 8 out of 10 but struggles with basic exercises, you can gently guide them toward a more realistic assessment and actionable next steps. On the flip side, if someone rates their confidence at a 3 but demonstrates strong capabilities, you can highlight their strengths and encourage them to see their true potential.


By probing deeper into the reasoning behind their number, you help people gain clarity on where they actually stand and what steps they need to take to improve.



Gauging Expectations and Building Buy-In

Understanding what someone expects from an interaction allows you to meet them where they are. It also helps align goals and avoid miscommunication.


Examples:

  • What are you hoping to get out of our conversation today?

  • How can I ensure you leave this meeting with clear next steps?


By addressing expectations early, you set the stage for a productive conversation and reduce potential friction.



Disarming and Planting Seeds

Sometimes, people resist new ideas or commitments due to concerns about time, money, or effort. By asking strategic questions, you can help them overcome these mental roadblocks.


Examples:

  • How does your current schedule align with your goals?

  • Have you considered different ways to invest in yourself?

  • What would it take for you to feel fully committed to this plan?


A coaches responsibility is to figure out how to effectively get from Point A to Point B. Identifying some common roadblocks or objections in advance can lead to a more clear and direct conversation when you get to the program recommendation at the end.


 These questions invite people to explore possibilities rather than shutting down due to perceived limitations.



Bringing It All Together

Effective questioning is both an art and a science. It’s about understanding human nature, listening intently, and guiding conversations toward meaningful outcomes. When done well, questioning not only uncovers valuable information but also builds relationships, fosters trust, and drives action. We are in the relationship business and your intentions in that first interaction set the stage for the future interactions.


So the next time you find yourself in a conversation, remember: the power lies not in the answers you provide, but in the questions you ask.


Want to upgrade your Training Business? Download a free trial of the Career Trainer Mentorship to get your career on track!

 
 
 

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