How a Simple Probability Method Can Turn Sales Uncertainty Into Predictable Wins

Three weeks ago on a Friday afternoon, Cheryl Jackson—our own Cheryl at Hartmann & Co., the one who helps sales reps keep their pipelines in order—was on a Zoom call with astruggling sales rep, Tim (not his real name).


Two important facts:

  1. Cheryl’s spirit animal is a lamb. She’s one of the kindest, gentlest people you’ll meet.
     
  2. These weekly Zooms had become more frequent. Tim was 68% behind pace. Everyone knew the stakes: he had to produce or he’d be gone—by resignation or termination.

Twelve minutes into their thirty-minute session, Cheryl finished updating deals from Tim’s current customers. Then she moved to prospects and began her usual line of questioning.

Cheryl: “Any new opportunities, Tim?”
Tim: “Tough to say.”
Cheryl: “Which ones are you focusing on?”
Tim: “All of ’em, I hope.”
Cheryl: “How can you advance the best opportunities?”
Tim: “Depends what fires I gotta put out.”
Cheryl: “Okay, for MVD Homes, what dollar value would you assign?”

This last question lit the fuse.

“Dammit, I don’t know, okay! There’s an inherent level of unknowability to selling. My customers are different. They’re not cookie-cutter, tract builders. So, you want me to just throw out a number, Cheryl? Is that the game?”

The meeting ended soon after.

The next Wednesday, I called Tim. He’s smart, hardworking, and unaccustomed to failure after thirty years in construction. His frustration was real. But so were the flaws in his reasoning. So, we unpacked them.

“There’s an inherent level of unknowability in sales.”

True. Selling involves a maddening lack of certainty. That’s why probabilistic thinking matters. In Tim’s case, the issue wasn’t that the information didn’t exist—it did. The problem was he didn’t have it.

In our Simple Sales Pipeline™, uncertainty is captured by probability: HOT (90% likely to close this month), IN PROGRESS (33%), TARGET (10%). That’s how we classify the unknown.

“My customers are different.”

This is a common defense mechanism among under-performers. Every market offers the same binary choice: your product or the competitor’s. High performance is measured by results, not excuses. The scoreboard doesn’t lie.

“Want me to just throw out a number?”

Yes. That’s forecasting—an educated guess, informed by dataand pattern recognition. Forecasts let us test, evaluate, and improve month after month. But forecasting also requires vulnerability, a trait Tim admitted he struggles with.


“I hear more and more that vulnerability is good,” Tim said. “No, it’s not. Being vulnerable means you can get killed.”

I chose to address the practical over the philosophical. “Tim, if the fear of being wrong thirty days from now is stopping you from making predictions, you’re choosing to protect your ego over feeding your family.”

Print out a list of open quotes less than 45 days old. (If they’re older, move on—your prospect probably already has.)

Label each: HOT (90%), IN PROGRESS (33%), TARGET(10%).

Multiply the dollar value by its probability of closing in 30 days. Rank them in descending order. Follow up on each within the next five business days.

That’s pipeline prioritization—no software required. For asimple document to help you organize this process, download the Sales Pipeline Organizer here

Tim said he felt like Sisyphus, condemned to push a boulder uphill for eternity.

“Been there,” I told him. “That’s sales. We roll the boulder uphill every day. If you’d rather be the guy who waits at the bottom of the hill for it to roll into your lap, you can probably transition into that role: it’s Operations.”

In Sales, we initiate.
We push.
We predict.

We fight through randomness and uncertainty to drive the business forward.

That’s the game.

Tim’s smart enough to succeed anywhere. But in sales, that success starts with forecasting—accepting some vulnerability and embracing full accountability.

The goal isn’t to nail the perfect number every month, it’s to find out if you were right, why you were right, and how you can improve over time.

Yes, there’s an inherent level of unknowability in life. But if you approach sales—and your colleagues who rely on you to generate the revenue that drives your business—as if next month’s results are just as unknowable, you risk ending up like Tim: snapping at the Cheryls in your world, the very people trying to help you win.

Thanks for reading.
I’ll be back next Thursday.

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Bradley Hartmann & Co.
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Contact Bradley Hartmann:
bradley@bradleyhartmannandco.com