When Everything You Know Is Wrong
Why the smartest sales leaders question their own success
You’ve built a successful sales team. Your processes work. Your numbers are solid. But here’s an uncomfortable question: What if your biggest strengths are actually invisible weaknesses waiting to sabotage you?
The French philosopher Jacques Derrida spent his career proving that our most basic assumptions about meaning and truth are built on shaky ground. His insights reveal why even successful sales leaders need to regularly deconstruct their own methods—before the market does it for them.
The Dangerous Certainty of Customer Needs
We train our teams to identify customer pain points and solve them efficiently. But what if customer needs aren’t as clear-cut as they appear?
Derrida argued that meaning is never fixed—it’s always shifting based on context. Your customer says they need “better efficiency,” but efficiency compared to what? For whom? Under which circumstances? The real opportunity often lives in these unexplored spaces.
Try this: In your next discovery call, when a prospect states a clear need, resist the urge to immediately position your solution. Instead ask: “That’s interesting—when you say [their stated need], what does that look like in practice?” Then ask it again about their answer. Most reps stop at the first layer. Go deeper.
The Win-Lose Trap
Traditional sales thinking divides the world into binary opposites: win or lose, rational or emotional, qualified or unqualified. But these categories can blind us to unexpected opportunities.
Consider the prospect who seems “unqualified” because they lack budget. What if they could become your champion for a larger initiative? What if they could connect you to the real decision-maker? The space between qualified and unqualified might be where your best deals begin.
Make it practical: Challenge your team to identify one binary assumption they make about prospects. For the next month, deliberately explore what exists between those opposing categories.
The Myth of Perfect Presence
Here’s where Derrida gets really useful for sales leaders. We’re taught to project confidence and expertise. But what if admitting uncertainty actually builds more trust?
Derrida showed that authentic communication happens not when we have all the answers, but when we acknowledge what we don’t know. Your prospects live with uncertainty every day. When you pretend everything is simple and clear, you separate yourself from their reality.
Action step: Train your team to say “I don’t know” when they actually don’t know something. Follow it immediately with “but here’s how we’ll find out together.” Watch how this changes the dynamic of your customer relationships.
When Your Process Becomes Your Prison
Every sales organization needs repeatable processes. But Derrida pointed out that repetition without adaptation leads to failure. Each customer interaction happens in a unique context, even when following the same general framework.
The best sales teams standardize their principles while customizing their approach. They understand that yesterday’s winning move might be today’s losing strategy.
Weekly exercise: Ask your team to identify one assumption they made about a prospect that turned out to be wrong. What did they learn? How can that insight improve future interactions?
The Competitive Advantage Illusion
What makes you competitive today? Your product features? Your process? Your relationships? Derrida would ask: what happens when those advantages become standard in your market?
The most sustainable competitive advantage might be your team’s ability to continuously question and adapt their own assumptions. In a world of constant change, the capacity to learn and evolve becomes more valuable than any specific knowledge or skill.
Building Anti-Fragile Sales Teams
Instead of building teams that resist change, build teams that get stronger from disruption. This means:
Regular assumption audits: Monthly team discussions about what you thought you knew about customers that turned out to be incomplete
Productive confusion: Celebrating moments when prospects surprise you rather than trying to force them into familiar categories
Learning metrics: Tracking insights generated and assumptions challenged alongside traditional sales metrics
From Theory to Action
Philosophy is only valuable if it changes how you work. Here’s what to do this week:
Pick one customer conversation where you felt certain about their needs. Schedule a follow-up call focused entirely on understanding what you might have missed.
Identify your team’s strongest belief about what makes prospects buy. Spend 30 minutes brainstorming ways that belief might be incomplete or situational.
Choose one “failed” opportunity from last quarter. Reexamine it through the lens of “what assumptions did we make that we never questioned?”
The goal isn’t to become paralyzed by uncertainty. It’s to develop the intellectual agility that keeps you ahead of change instead of behind it.
Your competitors are probably reinforcing their existing beliefs and doubling down on what’s always worked. While they’re building stronger walls, you can be building better questions. In sales, the team that adapts fastest wins.