Why The Most Successful Sales People Are Pessimists

It may sound counterintuitive, but I believe the best salespeople are pessimists.

Before you disagree with me—yes, I’ve read all of the “feel good” studies that state we should only focus on positivity. This thought process has been prevalent for years. Back in 1982, MetLife paid a psychologist, Martin Seligman, PhD, to help them learn how to hire more effective salespeople. The conclusion Dr. Seligman came to was to hire sales teams full of optimists. His research revealed that optimists make more sales than pessimists, are more persistent in the face of rejection, and are less likely to give up when things don’t go well.

Conversely, 22 years of research from New York University’s Gabriele Oettingen found that pessimism can improve productivity. Oftentimes pessimism is a better motivator for getting things done. And as we all know, getting things done equates to closing more deals.

No matter which side of the fence you are on, I believe there is no room for optimism or blind hope when selling. While pessimism tends to be associated with negativity, for many it is a way to mentally and emotionally prepare for all types of selling situations. Whether that’s identifying buying personas, asking decision questions, or even forecasting. By looking at every conversation, meeting, and/or communication with the prospect at all angles—what could happen, what could go wrong with strategy, tactics, and/or players—it prepares you to never be surprised or shocked. By asking more questions we have a better picture of true reality, not the picture we paint with the brush called hope. Let me explain my perspective:

I’ve taught thousands of financial services professionals the fundamentals of The Sandler Selling System. I work directly with top producers, teams, and agencies to reinforce these techniques with the goal to increase referrals, sales, or new hires. I do this because this type of sales process works. It literally changed my professional path and helped me to become one of the leading training and coaching experts in the financial services industry. Once I adopted the thought process of being realistic, curious, and pessimistic, I became confident in always knowing where I stood in every selling situation.

The system removes the pie in the sky, utopic perspective in which the salesperson can easily fall prey, which causes them to have the classic syndrome “happy ears.” The Sandler Selling System is based on techniques and principles that focus on asking meaningful questions, getting to the root of the prospect’s emotional and financial needs, and knowing when to walk away. Let’s review a few key Sandler Rules that reinforce the importance of pessimism:

1. Sandler Rule #37 - All Prospects Lie All Of The Time:

Salespeople tend to have their selling show. When a person believes they just became a prospect, their role has changed. They want to maintain control of the conversation, so they mislead their answers. I’m sure you’re as guilty of this as the last prospect who lied to you. Haven’t you found yourself just outright lying to those in selling roles asking you questions like “Have you found what you’re looking for today?” or “Is there anything I can help you with?” I’m certain you have often responded with “Oh, I’m just browsing” or “No, I’m fine,” just so you don’t have to share the details of your situation with the salesperson. Instead of taking what the prospect says at face value, be a little pessimistic. Dig a little deeper by asking meaningful questions to get to the truth.

2. Sandler Rule #3 - No Mutual Mystification:

Assumptions have caused more sleepless nights than any one wants to admit.

Mutual mystification occurs when the buying and selling parties are on two different pages regarding where they are and/or where they are going. People have a tendency to use “safe words” or wishy-washy words. Words with different meanings. Easy ones are things like “Sounds good,” “I like what I see,” “Seems like there could be a fit,” or any version you or your team hears. Managers, do you hear “I will try this week to…,” “I’m gonna do better at . . .,” or “This should close by the end of the week.” Honestly, what does “should” mean?

People using wishy-washy words is bad enough, but what makes it worse is to add happy ears to the mix. The salesperson or manager hears what they want, not what was said. Have you ever showed up to a joint call and the prep you got from the producer is not the reality of what the prospect is expecting?

Clearing up wishy-washy words is the key to understanding what was intended versus what was heard.

3. Sandler Rule #13 – Don’t Assume Facts Not in Evidence a.k.a. No Mind Reading:

Don’t misread between the lines. Instead, directly ask what the prospect means.

Prospect says, “This looks very good, I think this is an excellent chance of doing work together.” Or, “We are hoping to have the investment be less (or your fees were less).” Guess what Managers? The producer thinks either “I have a deal” or “I better lower my fees to win the deal.”

They are guilty of mind reading—assuming facts not in evidence and misreading between the lines.

What does “very good chance” mean? We have no idea. We need to find out. Regarding the fees, is it a demand or is the prospect talking out loud? Here’s a crazy statistic—more than 71% of fee reductions were based on happy ears, not reality. There is no way to truly understand unless you ask for clarification.

When you are a pessimist, you’re not falling prey to hope and happy ears. You ask more questions to ensure clarity, which also reduces anxiety on the buyer.

Managers, to improve your development of your people stop mind reading. “I’m gonna try to focus more on sourcing new recruits.” Unfortunately, many managers hear “I will do” versus what they really said, “I’m gonna try.”

Do you want to impact the results of your one-on-ones? Then stop mind reading and ask a ton more questions.

By the way, I think it’s important to note that being a pessimistic does not mean having a bad attitude, nor does it mean that you only focus on doom and gloom. Taking a pessimistic approach to sales gives you a competitive advantage—it removes uncertainty and introduces consistency.

My challenge is for you to be pessimistic the next time you are preparing for a sales call, recruiting meeting, or forecast discussion. Be consistently pessimistic, and remove hope from the equation. Hope for the sake of hope is not a sales strategy—successful sales professionals know where they stand and are not afraid of truth even if it’s a no. Pessimism is a key ingredient in that success.

Remember to do a little bit all of the time, not a lot some of the time.

I’d like to hear how adopting a pessimistic approach to your sales process is working for you. Please reach out to me via LinkedIn and let me know how it’s going.