Too much positivity wipes out healthy skepticism in sales

In Northern Colorado, we live in a positive place: 300 days of sunshine per year, low unemployment and America’s playground all around us. It’s a happy place to live, and as a result, folks are pretty positive. Positivity is a healthy quality in most aspects of our lives.

However, there’s one area where positivity can create real problems: selling. Before I had learned about a selling system that differentiated my team and me from our competitors, I was a student of traditional selling that stressed the importance of being positive and upbeat on a sales call. I remember one lesson in particular called, “The YES System,” that advised to smile and nod your head up and down a lot in a sales call to get your prospect to do the same.

While positivity is not necessarily a bad thing in selling, it can wipe out one of the most helpful traits a salesperson can leverage to successfully manage a sales opportunity and close the sale: healthy skepticism. Unfortunately, the worst of traditional salespeople have conditioned prospects to beware their cheesy sales tactics, question their honesty and avoid having honest conversations. As a result, many prospects are less than honest with salespeople.

The skeptical salesperson understands this, without contempt for the prospect, and will use questions to get to the truth. During the Decision Step of a sales call, it might sound like this: Salesperson: “Alice, when you go about making an investment in programs like the one we’re talking about, who do you bring in to help you make a decision?” Prospect: “Oh, it’s just me, I run the office, and I make all of those decisions.” This is the point in the sales call where the traditional positive salesperson gets great big “happy ears,” and says, “that’s great Alice.”

At the end of the sales call, when the salesperson asks their closing question, when the prospect says, “it sounds good, but now that I think about it, I should probably run this by the regional manager just to make sure I have her buy-in,” the salesperson is painted into a corner. Then, in their pipeline review with their manager, some eight weeks later, the salesperson is still hanging on to the opportunity, telling their manager, “I’m going to close this one, Alice loved it and is just trying to get an OK from the regional manager.”

Had the salesperson been better-trained on their questioning skills and the importance of a skeptical mindset, they might have asked this follow-up question: Salesperson: “I understand Alice, but I should ask, do you mean that you don’t get any feedback on things like this from your CEO or maybe even some other key people in your organization whose support is important to you?”

When asked the additional follow-up probing question, it’s quite possible that the prospect may have rounded out their decision-making process, sharing that other people would be involved. With this information, the salesperson now has a choice as to whether they wanted to make their presentation to someone whom could not or would not make a decision, instead, opting to request time to present to both people together. Unfortunately, all too many salespeople have trained themselves to take the first answer, avoid the skeptical mindset that says “let’s double-check what the prospect just told me, as many times there is more than meets the eye when it comes to a prospect’s decision-making process.”

In your next coaching session, debriefing calls with your salespeople, give them permission to check their traditional “positive salesperson” outlook in favor of a mindset of curiosity, skepticism and emotional detachment and watch their selling cycle shrink and their closed sales increase.

Bob Bolak is president of Sandler Training. He can be reached at 303-579-1939 or