Why Asking Better Sales Questions Won’t Help You Close More Deals.


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One of the most popular recent theories about business development is that if you ask better questions of your clients, you can uniquely uncover pain points that allow you to negotiate a more efficient close.

According to the experts, you improve your chances of closing the deal if you ask open-ended questions rather than asking questions that simply have a yes or no answer.

For instance, according to the experts it is better to ask “What has worked in the past?” over the simplistic “Did this work in the past?”.

Over the last decade, this theory has become a widely taught sales tactic. Sales trainers all over the world have developed programs that help sales teams (both on the phone and in front of clients) ask questions that tip the odds in the favor of the salesperson closing the deal.

And after decades of proposing these ideas the experts still can’t explain why that strategy doesn’t seem to work consistently.

Better questions don’t lead to better sales performance.

Oh sure, there are always a few “big fish stories” where that tactic paid off and a salesperson emerges as a hero. But overall, why aren’t better questions helping us close bigger deals question

Why is it harder than ever right now to have meaningful conversations with potential prospects? Why is it so hard to generate revenue?

Well, the sales experts are well-meaning, but the behavior they prescribe is simply misguided. The true impact of asking better questions is minimal on increased deals. Sometimes this behavior even backfires, costing the company and the sales rep valuable business they would have otherwise landed.

So what does work?

And why is this focus on asking better questions so flawed?

Simply, the questions don’t really matter.

Caring matters. That’s the secret to more sales.

Instead of teaching sales reps how to care about a prospect, sales experts teach you how to ask questions that help you pretend like you care. That’s a huge difference.

But your business prospects are just as discerning as you are. You don’t want to be around people that don’t really care about you. You detest fake friends.

And so when you sit in front of a potential client and make your way through a list of questions that are designed to trap the client, is it any wonder that you fail to close the deal?

You expect more of the people that you interact with.

So do your prospects.

The solution then isn’t to train your team (or yourself) to ask questions that are more caring or kind. The solution is to be a caring person. To be humble yet confident. To see people not as potential revenue but as fellow humans.

Instead of trying to close deals, close wounds. Prospects don’t really care about your presentation that much,. They just want their pain to go away.

Heal them.

Help them.

Along the way, you’re really helping yourself.

Republished with author's permission from original post.

Dan Waldschmidt
Speaker, author, strategist, Dan Waldschmidt is a conversation changer. Dan and his team help people arrive at business-changing breakthrough ideas by moving past outdated conventional wisdom, social peer pressure, and the selfish behaviors that stop them from being high performers. The Wall Street Journal calls his blog, Edge of Explosion, one of the Top 7 blogs sales blogs anywhere on the internet and hundreds of his articles on unconventional sales tactics have been published.


  1. None of the questioning trickery you described does any good in the long run. I think sales trainers create all this open-ended, closed-ended angst for self-serving purposes. It does little other than to baffle salespeople about how to engage in sales conversations.

    What’s lacking in much of the questioning hype is how to help salespeople develop a clear understanding of what they’re after in the first place. The late Mike Wallace knew exactly what he was after in his interviews. I suspect that focus led him to asking the right questions. Had he gotten hamstrung over the questions themselves, his interviews would have failed to uncover the truth. Successful salespeople are equally adept at the same thing.

  2. I agree, dude.

    The problem with most sales training is that we teach new activities without teaching new attitudes. So our results are marginal, at best. And over the long run it actually seems to have a negative impact.

    We’re just confused and seem to jump from tactic to tactic — never sticking with anything long enough to realize the benefits of it. Almost anything works if you stick with it long enough.

    Know what you want. Relentlessly pursue it.

  3. I also think that what goes along with caring is letting go of the outcome. The belief that you can close a deal gets your head in the wrong space.


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