Every sales leader I know obsesses over the same question: “How do we hit our number?” But the most successful ones I’ve worked with ask something completely different: “What would guarantee we miss it?”
That backward question—focused on failure instead of success—cuts through the noise faster than any strategy session, pipeline review, or motivational speech. It’s called inversion, and it might be the most underused mental model in sales.
The concept is simple: instead of asking how to win, ask what would make you lose. By mapping the path to failure, you eliminate the obvious mistakes that derail most teams. What remains is a clearer route to success.
Why We Think Backwards
Sales leaders are wired for optimism. We have to be. But unchecked optimism creates dangerous blind spots. We focus so hard on what could go right that we miss what’s already going wrong.
Inversion forces uncomfortable clarity. It makes you name the things everyone can see but nobody wants to say. The territory design that sets half your team up to fail. The qualification process that lets bad deals clog your pipeline for months. The single-threaded relationships that collapse when your champion leaves.
Here’s the thing: you can’t always control what guarantees success, but you can almost always control what prevents failure. And in sales, avoiding failure often is success.
The Three Levels of Sales Inversion
Let me show you how this plays out at three levels: your strategy, your process, and your deals.
Strategic Inversion: The Pre-Mortem
Most annual planning starts with growth targets and revenue goals. Try this instead: gather your leadership team and say, “Imagine we miss our number by 30%. What went wrong?”
The answers usually sound familiar:
We built quotas on wishful thinking, not pipeline reality
Half our territories are too small to generate meaningful results
We’re hemorrhaging existing customers while chasing new ones
We’re selling one product when customers need three
These aren’t mysterious forces. They’re structural flaws hiding in plain sight. Once you name them, you can fix them before the year starts.
I’ve seen teams spend months crafting elaborate growth strategies when a simple failure analysis would have revealed that their biggest risk was customer churn, not new acquisition. Fix the leak before you pour in more water.
Process Inversion: What Breaks the Pipeline
At the process level, inversion asks: “What behaviors destroy our pipeline?”
The usual suspects emerge quickly:
Discovery calls that feel like product demos
Qualification that’s more hope than analysis
Pricing conversations that start with discounts
Single-threaded relationships that one layoff can kill
Instead of training reps on “best practices,” train them to recognize and avoid these pipeline killers. It’s more concrete, more actionable, and frankly more memorable than most sales methodology.
Your pipeline reviews get sharper too. Don’t just ask, “How will this deal progress?” Ask: “What could kill this deal?” You’ll uncover risks while there’s still time to address them.
Deal Inversion: Why We’ll Lose
Individual deals benefit most from inversion thinking. Reps naturally fall into confirmation bias, seeking evidence their deal will close. The backward question cuts through that: “Why might we lose this deal?”
Suddenly the conversation shifts:
If we’re single-threaded, our contact’s departure kills us
If we haven’t identified the real decision-maker, we’re selling to the wrong person
If we can’t articulate specific business impact, we’re just another vendor
If we don’t understand the competitive landscape, we’re flying blind
By naming the reasons for loss upfront, reps can address them while the deal is still winnable. It’s the difference between hoping for the best and planning to avoid the worst.
Making Inversion Stick
This isn’t just an intellectual exercise. Here’s how to build inversion into your team’s habits:
Run quarterly pre-mortems. Before each quarter, ask: “If we miss our number, what will have caused it?” Your risk mitigation plan writes itself.
Flip your pipeline reviews. Don’t just focus on progression. Spend equal time identifying what could derail each deal.
Train on failure modes. New reps learn faster when you show them what always fails, not just what sometimes works.
Build loss reasons into your CRM. Track why deals fail as rigorously as you track why they succeed. Patterns emerge quickly.
The Psychology of Thinking Backwards
There’s something liberating about naming failure directly. Most people can quickly identify what doesn’t work, even when they struggle to articulate what does. Inversion leverages that natural insight.
For salespeople—who navigate constant uncertainty—this clarity is powerful. Instead of wrestling with abstract success principles, they get concrete failure modes to avoid. The path forward becomes clearer when you eliminate the obvious wrong turns.
From Failure to Success
Inversion isn’t pessimism. It’s realism in service of optimism. By confronting what could go wrong, you dramatically increase your odds of what will go right.
The teams that consistently hit their numbers aren’t the ones with the most sophisticated strategies. They’re the ones who’ve eliminated the most obvious mistakes. They’ve learned to think backwards their way to better results.
Try it in your next leadership meeting. Ask the failure question instead of the success question. You might find that the shortest path to hitting your number runs directly through understanding how you’d miss it.