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Ep 3: The Question Behind the Question

Published: November 9, 2026

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Sam McKenna: My first job at 16 was as a lifeguard at Disney's Typhoon Lagoon. In training, they taught us about the concept of the "question behind the question," using the one that was most frequently asked in their theme parks, which is, "What time is the 3:00 parade?". Now, if you're like most sales reps, you're going to say, "It's 3:00, right? Does that answer your question?".

The key is that the question a buyer asks you is rarely the real question, and it's our job to uncover the real one. I once coached a rep who told me that he was great at open-ended questions, so I listened to a stack of his calls and he hadn't asked a single one. When I asked, "Give me an example of what you think an open-ended question is," he gave me one that you could answer with a yes or a no. When I said that's not open-ended, his response was, "Sure it is, because it can go in a bunch of different directions.".

Here's what I want your reps doing instead. When a buyer asks about a feature, give a short answer and then ask another question. Here's what I mean: if someone asks me, "Sam, do your trainings live on an app that we can integrate with?" my move isn't to answer the question at length. It's to say yes, no, or maybe it depends, and then say, "I have a few more things to tell you about that, but tell me a bit more about why you're asking or why this is important.". In an instant, you're going to hear something like, "The reason I asked is..." and then a treasure trove of details that will help us identify the data points behind the question.

That's the goal. But here's what it usually sounds like when a rep misses the "why" completely.

Paul (the buyer): "I mean, that all sounds great. One thing we were wondering, do you guys have an app we can integrate with?"

Sam (the seller): "Yeah, we do. We have an app you can integrate with, and we can do single sign-on as well. Does that answer your question?"

Paul (the buyer): "Uh, it does. Thanks."

Sam (the seller): "Cool. Yeah. You bet. A couple of other things to tell you, too, about what we can offer you."

I answered the question perfectly and again learned nothing. Here's a bonus coaching tip: listen for the phrase "Does that answer your question?" or worse, "Does that make sense?". Both of those are as useless as questions come because they don't tell us anything. We get a yes or no and we leave it at that. Instead, our job here is to keep digging. The more the buyer speaks, the more we learn, and the more we can pivot our recommendations to their specific challenges. Now watch how this approach shifts the buyer into sharing mode.

Sam (the seller): "Yeah, great question. And so do we. We get asked by basically every customer. A couple of things I can tell you about it, but tell me a little bit more about why you're asking. Do you guys use one now? Are there frustrations with it? Is there an issue? It's important. Tell me a little bit more."

Paul (the buyer): "Yeah, I'm glad you asked. The CRM integration angle here is going to be really important. We're kind of doing some broader tech work. So let me tell you about what's going on there because it'll inform my move."

The asked question is never the question. What sits behind it tells you whether it matters at all. If I had just answered, I might have spent four minutes on the app and missed that Paul already has one that he can't stand, or he doesn't care about it, or that it's the entire reason he took the call to begin with. Two phrases to flag on the recording: "Does that answer your question?" or "Does that make sense?". Both of them mean your rep could use some coaching on how to ask better active listening and/or "question behind the question" questions. That was a lot of questions.

Your rep can answer a buyer’s question perfectly and still learn nothing about why they asked.

In this episode, Sam McKenna, founder of #samsales, shows you how to coach reps to uncover the question behind the question. Good and bad role-playing scenarios show two responses to the same feature request: one sends the rep back into a product explanation, while the other gets the buyer explaining a broader business need. Learn what to flag and what to have your reps try instead.

What you’ll learn:

• ​Answer briefly, then ask: The follow-up that helps reps understand why a capability matters before explaining it at length.
• ​Two phrases to flag: Why “Does that answer your question?” and “Does that make sense?” can end discovery too soon.
• ​Coach for context: How to help reps understand what the buyer is dealing with today so they can make a more useful recommendation.

Plus, get the free Discovery Call Playbook

Bring all four frameworks into your next call review with The Discovery Call Playbook for Sales Coaches. Get Sam’s talk tracks, common mistakes to listen for, and specific coaching fixes, plus ways to put the frameworks into practice with Salesloft.

Fill out the form to get your copy.

\ \ Ep 4: The Close November 9, 2026

\ \ Ep 3: The Question Behind the Question November 9, 2026

\ \ Ep 2: The Opening Script November 9, 2026

\ \ Ep 1: Show Me You Know Me® November 9, 2026