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Sales Leadership with Jim Pancero

Jim Pancero has been influencing, guiding, and inspiring sales professionals in more than 80 different industries to increase sales, market share and profitability. Jim's combination of humor, larger-than-life personality, outstanding research and real-world examples that hit home, provide even experienced sales pros who think they've heard it all, with strategies and concepts that work! Your sales team will be charged up and ready to go...and your company and customers will reap the rewards. Time with Jim is time well spent. Watch your productivity and profitability soar! https://pancero.com

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Sales Leadership with Jim Pancero

Are your reps asking enough “Why” questions?

September 21, 2026 • Jim Pancero • Season 5 • Episode 55

0:00 | 1:27

One of the best questions a sales rep can ask a buyer at any time in their selling process is “Why?” Too many times we only ask buyers a lot of “What” they want and “How” often they want it questions.

If a buyer shows interest in your products, how many of your reps immediately assume their buyer has valid reasons and go right into their “Features & Benefits” pitch without asking any additional questions?

Your buyer says, “We're wanting to add this new product.” A great first question to ask is, “Why is that important? Why do you want to make this change?”

To win more business in today’s hyper-competitive markets, your team needs to be asking more probing questions to better understand your buyer’s motivations for wanting to make changes or to do something different. Listening to their “Why?” answers can help you deliver a better presentation of the “What’s?” and “How’s?” of your proposal, and answering their original “Why?” answer.

Think your next sales meeting is a good time to discuss what they can do to ask more “Why?” Questions about their prospects and customers?

Today’s video talks about how asking more “Why?” questions can help your team sell even more!

Are your sales reps asking enough why questions? Hi, I'm Jim Pancero, helping you and your team be more effective in selling a day. And one of the best questions a sales rep can be asking a customer at any time in the selling process is why. Too many times we ask them what do they want and how often do they want it? But we don't really get into asking what's their motivation for wanting it. So the customer says, "I'm interested in buying something." We go on the assumption there's valid reasons and we immediately start trying to sell them on why we've got a better alternative than the others for what they're looking for. But I found one really great question that can help probe and really start to understand customers pain and opportunities they're looking for is to ask why. So if they say we're looking at adding this new product, a great first question for the sales rep is to say why. Why is that important? Why are you why are you ch making this kind of change? And because that might tell you the motivation behind so that you can be more effective selling to the what and to the how. The reality of the process is today we need to ask more probing questions to really understand the motivations of customers of wanting to make changes or to do something different. So as part of that great question when a customer says they need or want something say of course we can help you get it. Why? Why do you need that? Why do you see that's going to be an opportunity to help your business? Because when we understand the why, I bet you'll tend to sell even more.