Your Experience Can Become Your Biggest Blind Spot
There are a handful of deals from my career that I still think about years later.
Not because they were the biggest.
Not because they were particularly painful.
They're the ones that quietly changed the way I think.
This was one of them.
I can still picture the parking lot as I walked back to the rental car after the meeting. It had been one of those long enterprise sessions where everyone left feeling good. We had the executive sponsor in the room. The technical team was engaged. Procurement had started asking commercial questions, which usually meant we'd made it through the hardest part.
As I tossed my laptop bag into the passenger seat, I remember thinking, I've seen this movie before.
At the time, that thought felt reassuring.
I'd been selling enterprise software long enough that fewer things caught me by surprise. I knew what healthy buying committees looked like. I knew when legal was simply doing legal's job and when they were becoming an obstacle. I could usually tell when a champion was genuinely influential and when they were just enthusiastic.
That confidence had been earned over a lot of years.
The problem was, confidence slowly became certainty, and I didn't notice the difference.
A few months later we lost the opportunity.
I've replayed that deal in my head more times than I care to admit. For a while I blamed all the usual things. Maybe we'd missed a stakeholder. Maybe the competitor had a relationship we didn't know about. Maybe the budget had disappeared.
Eventually I realized none of those explanations sat quite right.
The truth was less dramatic.
Somewhere during that sales cycle I'd stopped paying attention to the customer in front of me and started paying attention to every customer I'd sold to before them. It happened so gradually I never saw it happening.
That realization eventually became the inspiration for this week's lesson, Your Experience Can Become Your Biggest Blind Spot, because I suspect I'm not the only seller who's confused experience with understanding.
Somewhere Along the Way...
"Experience doesn't just give us answers. It quietly teaches us which questions we stop asking."
When you're new to enterprise sales, every customer feels different.
Every meeting demands your full attention because you don't have enough experience to predict what's coming next. You're listening carefully because you have to. You haven't built enough mental shortcuts yet.
Those shortcuts eventually arrive.
That's one of the gifts experience gives us.
You begin recognizing buying behavior almost instinctively. You can sense when a deal has real momentum. You recognize procurement tactics before they're used. You hear an executive ask a question and immediately understand why they're asking it.
Most of the time, those instincts are incredibly valuable.
The problem isn't pattern recognition.
The problem is forgetting that patterns are only a starting point.
That's the central idea behind this week's Forge lesson: experience is one of the greatest advantages you'll ever develop—but only if you continue questioning the conclusions it leads you to.
Customers aren't patterns.
Organizations aren't patterns.
Buying committees certainly aren't patterns.
They're people, each carrying their own incentives, pressures, politics, and history. No two combinations are ever exactly the same, even when they look remarkably similar from the outside.
I don't think I appreciated that enough early in my career.
A Question I Couldn't Answer
"What evidence do we have... or are we filling in the blanks?"
Several years later I found myself in an internal account strategy meeting discussing another large enterprise opportunity.
On paper, it looked familiar.
Global customer.
Strong technical validation.
An engaged champion.
Procurement beginning to circle.
I'd seen this sequence enough times that I was already explaining to the team how I expected the rest of the sales cycle to unfold.
Security would finish.
Commercial negotiations would begin.
Procurement would slow things down while trying to improve their position.
Eventually the executive sponsor would step back in and we'd work toward a final agreement.
I wasn't guessing...Or at least I didn't think I was.
After I finished walking everyone through my thinking, one of the newer account executives who had been sitting quietly through the conversation spoke up.
"Can I ask you something?"
"Of course."
"What makes you think procurement is driving this deal?"
I answered almost immediately.
"They always do."
He smiled.
"I know they usually do. I'm just wondering what we've actually seen that tells us that's true here."
It wasn't a challenge. It wasn't disrespectful. If anything, it was curiosity.
I wish I could tell you I immediately realized what he was getting at...I didn't. I spent the next few seconds mentally searching for proof. Not assumptions...Proof.
There wasn't much. Nobody had actually told us procurement was holding things up. We hadn't heard it from our champion. We hadn't heard it from the executive sponsor.
Nobody inside the customer's organization had ever suggested procurement was the issue. I'd simply filled in the blank because I'd seen dozens of deals where that had been true.
So we stopped debating what we expected to happen and started reviewing what had actually happened.
We went back through meeting notes. We reread emails. We looked at executive conversations we'd almost forgotten about. We challenged each other's assumptions instead of reinforcing them.
About twenty minutes later someone noticed something that completely changed the direction of the discussion. Procurement had already finished almost everything on their side. The real bottleneck wasn't commercial at all.
It was finance.
The CFO hadn't decided whether the initiative would survive a broader budget reprioritization, and while we were busy preparing negotiation strategies, we weren't having conversations with the one executive who actually controlled the outcome.
I remember sitting there thinking how close we'd come to spending another month solving a problem that didn't exist.
Not because we lacked experience.
Because we relied on it too quickly.
The Best Teams I've Been Part Of
"Championship organizations don't protect assumptions. They challenge them."
That meeting has stayed with me for years, and not because a younger seller happened to notice something I missed. If you spend enough time around great people, that should happen.
What stayed with me was the environment. Nobody in the room cared whose idea turned out to be right. Nobody defended their position simply because they'd said it first.
The goal wasn't to win the discussion. The goal was to understand the customer better than we did thirty minutes earlier.
I've noticed that's true of almost every high-performing sales organization I've been fortunate enough to work with. People ask uncomfortable questions.
Someone challenges the obvious conclusion...An SE sees something the account executive missed...A first-line manager notices a risk nobody else has mentioned.
Experience matters in those organizations, but it isn't treated as authority. It's treated as another input.
Curiosity carries just as much weight.
Maybe more.
Looking Back...
"Expertise isn't collecting better answers. It's becoming harder to fool."
I still catch myself doing it.
I'll leave a meeting and think, I've seen this before.
Whenever that thought shows up now, I try to slow myself down instead of speeding myself up. Sometimes the deal really is following a familiar path. Sometimes it isn't.
The only way to know the difference is to keep asking questions long after your experience tells you to stop. That's probably the biggest change in my thinking over the years.
When I was younger, I thought expertise meant needing fewer questions because you'd already accumulated enough answers.
Today I think expertise looks almost the opposite. The people I trust most are usually the ones who have enough experience to recognize a pattern... and enough humility to wonder if they're wrong.
Sometimes I think that's the real gift experience gives us. Not certainty...Perspective.
And if we're lucky, just enough humility to keep earning it.
If this idea resonates with you, I'd encourage you to spend a few minutes with Your Experience Can Become Your Biggest Blind Spot. It's a short companion lesson that explores the same idea from a different angle—and might leave you thinking differently before your next customer conversation.