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If you google “effective sales conversations,” you’ll probably see a ton of results with a list of communication tactics that will help you close more deals. 

But there’s one that doesn’t get discussed very much, and it’s not a tactic. It should be part of your entire mindset around selling.


When most people hear that word, they think of some stubborn person, arms crossed, shaking their head, and unwilling to listen or believe anybody.

That’s not what we’re talking about here.

A healthy level of skepticism is what will actually open your mind and help you listen to your prospects better than you ever have before.

Shifting Skepticism from a Bad Thing to Good

We’re all guilty of walking into a sales conversation with a head full of assumptions about how badly they’re doing without your services, how much they need help, and how you can provide it. Since we want to close the deal, we need them to need us.

But when you hold onto those assumptions, you’ll miss a lot. Plus, no one really wants to work with a salesperson who is too eager. It makes them feel like there is a hidden trap. Or, even worse, they’ll take advantage of your neediness and try to get a deal or some freebies. 

The salesperson who is too eager is one who is constantly talking at the prospect, and not listening to or talking with a prospect. 

Talk less…

Studies show that salespeople who close more deals than others talk less. A lot less! The golden ratio is described as a roughly 60/40 split of listening to talking. That means that the salesperson should be listening over 60% of the time and only talking about 40%. This rule comes as a shock to many salespeople, but it holds true time and time again.

You might be thinking, “how do I have effective sales conversations if I only talk 40% of the time?”

Questions. You should be asking questions. You should be answering questions with more questions. 

We know that we have to dig in to find out what their pain is, what their needs are, what is, dare I say it, keeping them up at night. And we know that to do that, we have to ask them. 

But the trick of all of that is to maintain a level of skepticism that allows you to dig a little deeper.

If you ask, “what is the biggest issue you’re dealing with in your business right now?” and they answer with something that perfectly aligns with what you do, STOP! It’s easy to get excited and say, “well, great, I’ve got just the solution for you!” Don’t fall into that trap!

Instead, keep digging. “How is that affecting you?” “How would things be better if you weren’t dealing with this?”

Keep asking…

The more you ask, the more you might find that their needs don’t align as much as you think.

If it goes the other way, “Everything is great. No problems at all.” Don’t hang your head and do the Charlie Brown walk back to your car. Keep digging. 

So many people will tell you that everything is fine when the truth is, they just don’t want to deal with a salesperson. 

But your skepticism will save you in those situations. It’s a superpower that keeps you from getting ahead of yourself in a sales conversation. Whether you’re about to jump the gun and take on a poorly fitting client or walking away from a potential sale because they haven’t opened up yet, use that powerful tool to stop yourself.

Skepticism Helps Your Sales Conversations Be Much More Effective

It’s really about not being so tied to the results. When is it easiest to ask difficult questions? When we’re not hoping for a specific answer or attached to the outcome of a conversation.

In other words, the most effective sales conversations occur when we treat every answer with a hint of skepticism.

A skeptical salesperson will always have better results than the salesperson who makes assumptions, talks too much, and can’t accept the fact that a prospect might have a good reason to say no. You don’t have to be stubborn or argumentative, and you certainly don’t want to call out your prospect or throw them under the bus. That doesn’t help anybody.

Having a high enough level of skepticism to ask more and more questions will significantly impact being able to close more and better-qualified deals. 

Learn about other SHERPA traits and how to have the most effective sales conversations below: 

Find out what being a Sales Sherpa means and how this sales strategy can help you improve all of your relationships. Read more here.

The S in SHERPA stands for Skeptical, the (positive!) mindset you need to have effective sales conversations. Find out how here

H stands for Helpful because that’s what the best salespeople are. Click here to find out how this intention can help you sell so much more. 

Empathetic is the E in SHERPA. When you lead conversations with empathy, your prospects will grow to trust you more. Read more here

The R stands for Resolute. And no, that doesn’t just mean stubbornly sticking to your guns. But it makes your job a lot easier when you do it right. Discover how here

P represents Practiced. Sorry, practice doesn’t just apply to learning an instrument or sport. The more reps you have in anything, the better you are. Learn how salespeople can get more practice here
The last letter in SHERPA stands for Accepting because everybody, not just salespeople, could stand to be more accepting. Find out what that means for you in sales here.

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