Skip to Content
Sales

Why Top-Performing Reps See Their Pipeline as Half Empty

The best sales reps know that they will fail more than they win, be down after they're up, and that no deal is certain until it's signed.

Sales rep smiling while wearing a headset and looking at his laptop: pessimism in sales
Address your customer's needs by cutting out the pretense and be as blunt as possible about what you can offer them. [Kobus Louw /Getty Images]

A whopping 90% of sales reps describe themselves as optimists, according to veteran sales strategy professor Steve W. Martin. That’s likely no surprise. This is, though: nearly two-thirds of high-performing reps actually exhibit a healthy dose of pessimism in sales. 

Every salesperson remembers the deal that didn’t happen. We are gluttons for punishment sometimes.

Jennifer Lagaly, SVP, Enterprise, Salesforce

When it comes to closing a deal, it pays to look at your pipeline as half empty. A healthy dose of pessimism in sales can help you avoid “Happy Ears” syndrome, where the desire to believe a deal will close can keep reps from hearing client objections or identifying roadblocks. It can also help reps candidly assess which deals went wrong and why — and how to stay strategic and smart — from the first pitch to closed deal. Most opportunities don’t close. That’s okay.

“Every salesperson remembers the deal that didn’t happen,” said Jennifer Lagaly, senior vice president, Enterprise, Salesforce. “We are gluttons for punishment sometimes.”

Let’s take a closer look at why a more pessimistic outlook can be a sales performance booster.

1. You can spend your energy on deals that will close

“You deal with a lot of failure as a rep,” said Belal Batrawy, veteran sales coach and Head of Go-to-Market at GTM Buddy. “Most people’s close rates are somewhere between the teens to 30%.” The best way to improve your numbers is not to spend all your time focusing on the majority of leads that aren’t going to come through — but on the leads that most likely will. And that means being a bit pessimistic about the likelihood of any given deal.

Twenty years of research from New York University’s Gabriele Oettingen backs this up, showing a little pessimistic thinking is a better motivator than an optimistic outlook for getting things done.

It’s a lot easier to lose less than to win more. And by losing less, [you] will win more. It’s a question of efficiency.

Belal Batrawy, Head of Go-to-Market at GTM Buddy

In her early career, Zagst spent a lot of time chasing down clients who only communicated with her every few months. Now, when a client ghosts or seems hesitant, she looks at the deal more pessimistically and assumes they’re unlikely to close. Instead of writing endless check-in or nurture emails, she shifts focus to more engaged prospects.

It’s what Batrawy calls “losing less.” “It’s a lot easier to lose less than to win more,” Batrawy adds, “And by losing less, [you] will win more. It’s a question of efficiency.”;

2. You can better anticipate customer objections and needs

Objections are inevitable in the sales process. A little pessimism in sales prepares you to view the deal from the prospect’s perspective, take on the pessimism they likely have about the deal or product, and use it to prepare to address any objection that comes up in a deal. Back in 1983, renowned Harvard marketing expert Theodore Levitt posited that in a world of uncertainty and intangibles, it can be valuable to weave a bit of pessimism into both your selling strategy and your narrative — advice that rings true nearly 30 years later. 

“It’s very common that an elite seller already knows what their buyer is thinking and can bring it up before they say it,” Batrawy said. “There’s a superpower in that because you show you’re relevant.” 

According to Batrawy, one of the fastest ways to recognize and address your customer’s needs is to cut the pretense and be as blunt as possible about what you can offer them. This will encourage a blunt response — one that’s likely to include objections that you can then address. You can ease the tension by directly addressing your client’s most likely concerns before they have a chance to articulate them. 

“You can talk about pricing; you could talk about implementation; you could talk about product shortcomings; you can talk about competition — all things that typically a seller would withhold,” Batrawy said.

A good rep will acknowledge an unspoken bid around pricing and bring it up proactively. If the price is right, great. If not, it’s an opportunity to either negotiate or cut your losses.

3. You can be more human and realistic

No matter what your marketing says, there’s no perfect product or end-all-be-all solution for everyone. A little pessimism in sales will help you understand the limits of the solution you’re selling and craft a pitch with benefits outweighing product shortcomings. Pessimistic sellers know you can’t just get this done with positive vibes and glad-handing. Realistic people recognize that the relationship is fundamentally transactional. You’ve got to engage honestly and be a little pessimistic about how effective your solution will be. Then, lean into what you do well.

… [a] lack of authenticity ruins the social bids, or interrupts them. Just be more blunt, more forward. Stop walking on eggshells. And don’t sound like a cheesy seller.

Belal Batrawy, Head of Go-to-Market at GTM Buddy

There are two advantages to this. First, you’re being honest with your prospect — and building a foundation of trust that can easily lead to customer loyalty. Second, you’re being authentic, which is much easier to engage with than over-enthusiastic hawking.

“You’re just saying that because you want to sell them something,” Batrawy said. “That lack of authenticity ruins the social bids or interrupts them. Just be more blunt, more forward. Stop walking on eggshells. Use the social bids and leverage them. And don’t sound like a cheesy seller.” 

For Zagst, this looks like having a conversation rather than a smarmy sales pitch. Acknowledge the prospect’s pain points candidly and demonstrate how you can solve their specific problems. Write up a business case with their decision-maker or collaborate on a solutions document that turns the relationship into something with a tangible benefit. 

4. You can build failure into your forecasting

You may be having the best quarter of your career, on pace to crush your quota and close some big deals. Don’t get too comfortable. A little pessimism will help you stay on the offensive, anticipate objectives and roadblocks, and be smart about moving deals forward. 

No matter what product or service you’re selling, there are always things that can get the way of a deal. Upcoming holidays, budget cuts, personnel shifts, and more can foil even the best-laid plans. Instead of planning your pipeline for perfect conditions, plan like a pessimist and include some room for hiccups, slowdowns, and failures.

Ultimately, it’s about reminding yourself that you are not your number. You can ‘fail’ at certain things and still celebrate what you did well.

Ashley Zagst, Account executive, Chili Piper

Pessimism in sales isn’t about sandbagging, though. And it’s not about intentionally lowballing your forecasts to give the appearance of overperformance. It’s about questioning in order to be better. “It’s about asking, ‘What else could I find out? How can I poke holes in my own theories’,” Zagst said. “Ultimately, it’s about reminding yourself that you are not your number. You can ‘fail’ at certain things and still celebrate what you did well.”

The first move is to stop pursuing leads that aren’t going anywhere. The second is to be realistic and build failure into your forecasting. The third might be to ditch your quota entirely. A Stanford study found sales quotas promote a short-term mindset, can damage morale, and can even undercut profits, and more organizations are taking a pessimistic second look at quotas.

All pessimism in moderation

A pessimistic outlook can help you communicate effectively and close elusive deals. The trick is to not let pessimism spiral into a defeatist mentality, which can become sales performance quicksand. The best sales reps know that they will fail more than they win, be down after they’re up, and that no deal is certain until it’s signed.

“Hearing hard things to fix or to solve — that is the challenge. And so many are afraid of it,” said Lagaly. “But you have to get to ‘no’ before you get to ‘yes.’”

Thinking beyond pessimism in sales

A little pessimism is only one characteristic that can help reps optimize their pipeline. To ensure ongoing success, stay in the know on the latest and greatest sales wisdom. Our new video series, Think Outside the Quota,” features insights on how to approach.

Take a peek at episode five of our “Think Outside the Quota” series, “You Are Not Your Number,” to learn why reps who miss their quota today can win big tomorrow. Or, stream the entire series on Salesforce+.

Think Outside the Quote, “You Are Not Your Number”

Related Stories

Astro

Get the latest stories from The 360 Blog, every week.

Get the latest stories from The 360 Blog, every week.

Enter a valid e-mail address
Select your Country
Select a state
Please read and agree to the Master Subscription Agreement

Yes, I would like to receive the Salesforce Weekly Brief as well as marketing communications regarding Salesforce products, services, and events. I can unsubscribe at any time.

Salesforce values your privacy. To learn more, visit our Privacy Statement.