Why Thinking Like a Failure Can Make You a Sales Success.
You’re gearing up for a career-defining sales pitch. Your team is buzzing, your strategy feels airtight, and the energy in the room is electric. Then, just before you step into the spotlight, someone says, “Wait. What if this all goes wrong? Spectacularly wrong.”
Awkward silence. A few nervous chuckles. But imagine if that one question—as uncomfortable as it sounds—ends up being the reason you crush it in the pitch.
Welcome to the power of the premortem, a technique designed by psychologist Gary Klein that shifts your mindset from naive optimism to bulletproof preparation. It’s not about being a pessimist; it’s about being ready for anything.
What’s a Premortem Anyway?
The premortem turns traditional planning on its head. Instead of looking back after a failure, you imagine it before it happens. The question isn’t, “What if we succeed?” It’s, “What if we fail?”
Let’s say you’re pitching a game-changing solution to a big client. The team takes a moment to visualize worst-case scenarios: maybe the pricing is off, the client’s priorities shift, or a competitor swoops in at the last minute. By identifying these risks upfront, you’re not just prepared—you’re practically unstoppable.
Remember Google Wave? It had all the makings of a groundbreaking tool but failed because users couldn’t figure out its purpose. A premortem could’ve flagged this early on, saving Google millions and untold frustration.
Stoic Wisdom: Premeditatio Malorum
The idea of planning for failure isn’t new. The Stoics called it premeditatio malorum (premeditation of evils). Philosophers like Seneca and Marcus Aurelius used this practice to brace for life’s curveballs.
Seneca’s words still ring true: “Nothing happens to the wise man against his expectation… he reckoned that something could block his plans.” For sales professionals, this isn’t doom and gloom. It’s empowerment. Knowing what could go wrong keeps you agile, resilient, and one step ahead.
Why Sales Pros Should Fall in Love with the Premortem
Find Your Blind Spots: Optimism feels great but can leave you vulnerable. A premortem forces you to dig deep and uncover risks.
Bounce Back Stronger: Rejection is part of sales. Preparing for it makes you more resilient when it happens.
Collaborate Like a Pro: A premortem brings diverse voices together to poke holes in your strategy—and make it airtight.
Win Client Confidence: Addressing risks proactively shows clients you’re thorough and trustworthy.
How to Run a Sales Premortem
Assemble Your Team: Include everyone involved. Diverse perspectives are your secret weapon.
Paint the Failure: Define the nightmare scenario: “What is the worst thing that could happen in the presentation? What is the worst thing the client could say?”
Get Real About Risks: Encourage everyone to brainstorm potential pitfalls.
Plan Your Comeback: Turn each risk into a game plan.
Stay Flexible: Accept that surprises will happen. Focus on how you’ll adapt.
Turn Setbacks Into Superpowers: A Real-World Success Story
We were gearing up to pitch one of the biggest advertisers in our area: a massive car dealership group. Our goal? Convince them to boost their already significant advertising budget. Sounds simple, right? Big client, big spend—an easy win.
At first, we were laser-focused on showcasing the value of additional visibility. It seemed like a no-brainer. But then, someone on our team threw out a curveball: “What if they’re already selling enough cars?” Boom. That question stopped us in our tracks. This dealership already dominated the market. Would more ads really move the needle?
Instead of brushing it off, we dug deeper. We asked ourselves: What challenges might this client actually be facing? That’s when we uncovered something big. The dealership’s reputation had recently taken a hit due to some negative press involving the owner’s family. It wasn’t about selling more cars—it was about repairing their image.
So, we pivoted. We pitched a branding campaign that showcased the dealership’s positive contributions to the community. Sponsorships of local events, stories highlighting their charity work—we reframed the conversation to solve a deeper problem. The result? Not only did we secure the deal, but we also helped the client regain trust in their market. That’s the power of the premortem mindset.
Ready to Flip the Script on Failure?
Before your next pitch, try this:
Gather Your Team: Diverse perspectives matter.
Define the Worst: Don’t sugarcoat it.
Brainstorm Risks: No idea is too small.
Plan for Everything: Even the curveballs.
Stay Resilient: Remember, setbacks are setups for comebacks.
Failure isn’t the enemy—it’s your secret weapon. By facing it head-on, you turn potential pitfalls into your greatest opportunities for growth and success. A premortem isn’t just another exercise—it’s your ticket to selling smarter, leading better, and thriving under pressure. Don’t just react to what comes your way. Own it. Use it. And crush it. What’s stopping you from trying it out today?
