Why Your Best Reps Can’t Forecast

What Don Moore’s Research Reveals About the Gap Between Confidence and Accuracy

In last week’s forecast meeting, I asked a rep why he had a major opportunity sitting in “commit.” He smiled and said, “I just feel really good about it.”

Nothing kills accuracy faster than that sentence.

Later that same day, another rep tried to explain why she refused to commit a deal with clear budget alignment, executive sponsorship, and an agreed timeline. She looked down at her notes and said, “I don’t want to jinx it.”

Both reps were working the same size opportunities. Both were seasoned. Both were talking to the right stakeholders. And both were wildly miscalibrated—just in opposite directions.

That’s the problem psychologist Don Moore has spent decades studying: we don’t struggle with too much confidence or too little confidence. We struggle with miscalibrated confidence. A mismatch between how sure we feel and what’s actually true.

Most sales teams don’t have calibrated confidence. Most leaders don’t teach it. And every quarter, the gap between what reps believe and what actually closes creates chaos in the roll-up.

This is the gap worth closing.

The Real Problem Isn’t Optimism or Pessimism

Moore’s research shows that people are remarkably bad at knowing how well they know something. We anchor to hope. We lean on past experience. We imagine best-case scenarios. We undervalue contrary evidence. We fall in love with our own impressions.

Overconfidence leads to inflated forecasts. Underconfidence hides real revenue. Both create noise that cascades up through every layer of the organization.

Here’s Moore’s core insight: confidence should rise and fall with evidence, not emotion.

The goal isn’t to make reps optimistic or cautious. It’s to make them accurate. Not because accuracy is virtuous, but because it’s the only thing that makes forecasting useful.

Think about your own team. You probably have both types.

The overconfident rep commits early, often, and loudly. They talk about “great conversations” and “strong momentum.” Their Salesforce notes look like summaries, not evidence. Thin next steps. Vague budget alignment. Unclear buying process. No written confirmation from the customer. They’re leaning on intuition shaped by past wins that may have nothing to do with current reality.

Their forecast looks strong. Their close rate does not.

Then there’s the underconfident rep who holds back even when the indicators are positive. They keep deals in “best case” until the PO hits their inbox. They underestimate buyer excitement and overestimate risk. They worry that confidence itself will somehow jinx the deal or expose them to embarrassment. These reps surprise you with end-of-quarter wins, but they weaken your roll-ups and planning models along the way.

Neither type has a forecasting problem. Both have confidence calibration problems.

And here’s what most leaders miss: neither problem gets solved by telling reps to “be more realistic” or “trust your gut.” Those aren’t instructions. They’re platitudes masquerading as coaching.

What Calibrated Confidence Actually Looks Like

Moore argues that calibration is a learnable skill, but not through encouragement. Through structure.

The reps who forecast most accurately on your team are never the most optimistic or the most cautious. They’re the ones who think in evidence, not feelings. They know the difference between a buyer saying “We love this” and a buyer booking the implementation kickoff. They know that access to the superintendent means nothing if the CFO hasn’t seen the budget line.

In K12 sales, this matters even more because deals involve so many stakeholders across such long timelines. A curriculum director’s enthusiasm in March doesn’t predict a July purchase order when the board still hasn’t voted on the budget and the superintendent just announced a hiring freeze.

Your reps aren’t selling to a single decision-maker with a clear buying process. They’re selling into a system where cabinet members have competing priorities, superintendents approve but don’t drive purchases, and board politics can derail a done deal in the final week of June.

That complexity makes calibration harder. It also makes it more valuable.

Here’s how to build it.

Replace Single-Number Confidence With Ranges

Forecast submissions fall apart when reps treat confidence as a single point. “I’m 90% sure this is closing.” That number is almost never grounded in anything.

Instead, train reps to think in confidence ranges supported by evidence. What’s the worst-case scenario where this slips? What’s the most likely outcome based on actual signals? What could accelerate it?

This simple shift resets the conversation from belief to probability.

Moore notes that experts become more accurate when they think in ranges because ranges force them to consider alternative scenarios. Sales is no different. When reps think in ranges, they stop anchoring to the best or worst story in their head and start mapping the actual possibility space.

In your next deal review, try this. Instead of asking “When will this close?”, ask “What are the three scenarios that could play out here, and which one do you think is most likely?” Watch how the conversation changes. Suddenly you’re not debating optimism versus pessimism. You’re evaluating evidence.

Teach Reps to Red-Team Their Own Deals

Moore emphasizes that experts become overconfident when they rely on intuition more than data. The fastest way to counter that is through what he calls counterfactual thinking—arguing against yourself.

In deal reviews, ask three red-team prompts. What would have to be true for this deal to slip? What signal would make you increase confidence? If this doesn’t close, what will be the reason?

These questions force reps to imagine alternative futures. If a rep cannot imagine a slip scenario, they’re overconfident. If they imagine too many, they’re underconfident. If they give realistic, specific answers tied to buyer behavior, they’re calibrated.

I tried this with a rep who had an opportunity committed in her forecast. I asked what would make it slip. She paused, then said, “Honestly, nothing. The CAO already got board approval for the line item.”

I asked if she knew that for certain or was inferring it. She realized she was inferring based on the CAO’s confidence. I asked if she’d seen the board minutes. She hadn’t. We moved the deal to “best case” until she confirmed it. Two weeks later, she found out the board had tabled the vote pending a budget audit.

That’s the value of red-teaming. It exposes the gap between what reps believe and what they can verify.

Shift From Buyer Enthusiasm to Buyer Action

One of Moore’s strongest insights is that people overweight verbal cues and underweight actions. Sales reps do this constantly.

A buyer saying “We love this” is not evidence. A buyer booking the next meeting is. A buyer introducing you to the CFO is. A buyer sharing their internal timeline is. A buyer correcting your proposal is.

Replace “buyer enthusiasm” with observable behaviors. Has the district brought in additional stakeholders? Did they share their decision process? Did procurement get looped in? Are they giving you access or limiting it?

I worked with a rep who kept a deal in commit because the assistant superintendent told him, “This is exactly what we need.” But when I asked what actions the district had taken, he couldn’t point to anything concrete. No follow-up meetings scheduled. No internal advocates identified. No timeline shared. Just positive sentiment.

Sentiment doesn’t close deals. Process does.

When reps shift attention from tone to action, their confidence shifts with it. Forecasts become cleaner. Roll-ups become steadier. And you stop getting surprised by deals that “felt great” but went dark.

Make Calibration Visible and Measurable

If you want reps to get good at this, they need regular reps. Moore recommends giving people repeated opportunities to test and adjust their judgments. You can do the same.

Pick three deals every week in your one-on-one. One the rep feels great about. One they feel unsure about. One they’re underplaying. Have them walk through the evidence supporting their confidence level. Then revisit those same deals the following week.

Over time, the reps who get closest to their own predictions also become the most consistent performers. The drill itself becomes part of the culture. And “perfect confidence” stops being about feeling certain. It becomes about aligning confidence with reality.

Adjust Your Roll-Up to Reflect Calibration History

Most leaders adjust roll-ups based on dollars. Moore suggests adjusting expectations based on confidence accuracy instead.

If a rep is historically 40% accurate when they say 90%, your roll-up shouldn’t take their 90 at face value. If a rep who “feels uncertain” ends up closing 75% of that category of deals, you should weight their hesitation differently.

You’re not adjusting based on personality. You’re adjusting based on calibration history. This prevents one rep’s bias—positive or negative—from distorting your total forecast.

It also creates accountability. Reps start to notice when their forecasts consistently miss in one direction. That awareness, by itself, begins to correct the miscalibration.

Stop Rewarding Bluffing and Punishing Honesty

Moore writes that miscalibration persists when people receive social rewards for confidence itself. Sales culture often reinforces this. Overconfident reps get praise for “big forecasts.” Underconfident reps get punished for caution, even when accurate.

If you want calibration, you must reward accuracy, not bravado.

Change your language in deal reviews. Instead of “Why isn’t this in commit yet?”, ask “What evidence do you still need before committing this?” Instead of “Looks like a big number—nice,” say “Show me the signals that support this number.”

Confidence becomes a byproduct of clarity, not performance theater.

What Happens When Your Team Gets Calibrated

The payoff is enormous, but it’s not flashy.

Your roll-ups stop swinging wildly. Deals close when they should. Fewer surprises. Fewer fire drills. Reps move deals with intention instead of parking stalled opportunities in mid-stage limbo hoping something changes.

More importantly, trust improves—up, down, and across. Reps trust your feedback. You trust their assessments. The organization trusts your forecast.

Deal reviews shift from reps selling you on a story to working through evidence, alternatives, and ranges together. It’s calmer. It’s clearer. It’s more objective.

And it’s exactly what Moore means by “perfect confidence.” Not the absence of doubt. Just the alignment of belief with reality.

Where to Start Tomorrow

You don’t need to overhaul your entire forecast process overnight. Start with one change.

Replace single-number confidence with confidence ranges. This alone raises accuracy.

Add one red-team question to every deal review. What would make this slip? That simple prompt forces reps to consider alternatives and expose overconfidence.

Track rep-level calibration over time. Compare what they predict to what actually happens. Then forecast to their historical accuracy, not their enthusiasm.

Praise accuracy more than optimism. Model what calibrated confidence sounds like. When a rep says “I’m not sure yet—I need to see X before I can commit this,” celebrate that clarity instead of treating it as hedging.

Perfect forecasting will never exist. But perfectly calibrated forecasting is possible. It’s learnable. It’s repeatable. It’s stable. And it’s one of the most powerful traits a sales leader can teach.

Don Moore’s research gives us the vocabulary. Sales gives us the application. Together they point to a simple truth: Great sales leaders don’t build confident teams. They build calibrated teams.

Those are the teams that win more deals, miss fewer signals, and deliver forecasts executives can trust.