Adapted Growth

Do You Want More Effective Sales Conversations? Lead With Skepticism!

Effective sales conversations involve a lot of questions, and a healthy dose of skepticism will make asking those questions a lot easier.
Photo by Karsten Winegeart on Unsplash


You’ll find tons of tactics and techniques when you want to learn how to have highly effective sales conversations. Some will be great; others might be pushy and manipulative. And that doesn’t sit well with everybody.

And sales training doesn’t often help because that’s more focused on the products or services, not how to start a sales conversation.

Fortunately, there might be only one thing you’re missing, and it’s not manipulative or just another 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 will actually open your mind and help you listen to your prospects better than you ever have before.


Shifting Skepticism from Negative to Positive


We’re all guilty of starting a sales conversation with a head full of assumptions. They usually include hopes 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 wants to work with a too-eager salesperson. 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’s champing at the bit talks at the prospect instead of listening or speaking with them.


Talk Less…

Studies show that salespeople who close more deals than others talk less. A lot less! The golden ratio is a roughly 60/40 split between listening to talking. That means the salesperson should listen over 60% of the time and only talk 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. Sometimes, you even want to answer questions with more questions. 

And not just any questions either. Asking open-ended questions allows them to open up to you without the possibility of you skewing their answers.

We know that we have to dig in to find their pain points, their needs, and what keeps them up at night. And we know that to do that, we have to ask them. 

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


The more you dig into your prospect's pains and needs, the easier it'll be to have effective sales conversations.
Image by Mark Miller from Pixabay


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 things are okay 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 walk away from a potential sale because they haven’t opened up yet, use that powerful tool to stop yourself.


Skepticism Helps You Close More Deals


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. It’s really about not being so tied to the results.

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

A skeptical salesperson will always have better results than one who makes assumptions, talks too much, and can’t accept 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 your ability to close more and better-qualified deals. This mindset will also make it easier to develop sales processes that will lead to more productive sales conversations every time.

Your sales training might not have taught you how to start a sales conversation or ask the right questions. But this soft skill can develop with enough time, practice, experience, and a skeptical mindset. Once you have it, you’ll find out more about what your prospects need, and they’ll be happier with the results.


Learn how other SHERPA traits help you have effective sales conversations:

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

H stands for Helpful because your intent drives your ability to be the best salesperson you can be.  

One of the most important characteristics of successful salespeople is Empathy.

Another trait that makes a sales rep successful is being Resolute.

P represents Practiced since learning anything new takes practice, including becoming a successful sales rep

The last letter in SHERPA stands for Accepting because it’s one of the most valuable traits a successful salesperson can have.