The Biggest Mistake I Made Was Thinking Deals Moved Forward.. It took me years to realize they almost never do.
There was a deal years ago that drove me absolutely crazy.
Not because the customer was difficult. Not because we got blown out by a competitor. In fact, if you'd asked me halfway through the opportunity how I felt about it, I probably would've smiled and told you it was one of the healthiest deals in my forecast.
Everything looked exactly the way you'd want it to.
The meetings were productive. Our champion was engaged. The technical team liked what they'd seen, and every conversation ended with another meeting getting scheduled. It felt like the deal had momentum, and if you've been in enterprise sales for any length of time, you know how reassuring that can be. A full calendar has a funny way of convincing you everything is moving in the right direction.
Then a vice president joined the evaluation.
He wasn't hostile. He wasn't trying to kill the project. If anything, he was thoughtful and genuinely curious. The problem was that he immediately started asking questions I thought we'd already answered months earlier.
We found ourselves talking about the business problem again. The urgency. The impact. Why the customer wanted to change in the first place.
I remember driving back to the airport feeling frustrated because it honestly felt like we'd gone backward. We'd already had these conversations. We'd already agreed on this. Why were we starting over?
Looking back, I don't think the deal ever went backward.
I think I misunderstood how complex buying decisions actually happen.
I Was Following the Process. The Customer Was Following Reality.
Early in my career, I believed deals progressed the same way they appeared inside Salesforce.
Discovery.
Qualification.
Evaluation.
Proposal.
Negotiation.
Closed.
Every methodology I learned reinforced that picture. The terminology changed depending on the company, but the underlying assumption stayed the same. Move the opportunity from one stage to the next until the customer signs.
It made forecasting easier.
It made pipeline reviews cleaner.
It also created a mental model that had very little to do with how enterprise buying actually works.
Customers don't make decisions in straight lines because organizations aren't linear. Every executive enters the conversation with different priorities, different experiences, and different risks they're trying to manage. Finance evaluates a decision differently than Security. Operations sees the world differently than Legal. Procurement often joins long after everyone else believes the hard work is done.
For a long time, I interpreted those moments as regression.
Eventually I realized something embarrassingly obvious.
The deal wasn't moving backward.
Someone new had simply started their journey.
The Loop Isn't the Problem
Once I saw that, I started noticing it everywhere.
A technical evaluator would become completely convinced while Finance was hearing about the initiative for the first time. An executive sponsor understood the strategic value immediately, while the operational leaders were still trying to decide whether the problem was important enough to solve. Legal would enter near the end of the process and suddenly introduce concerns nobody had discussed during the previous six months.
None of those people were wrong.
They were simply arriving at the conversation from different starting points.
That's what makes enterprise selling difficult.
You're not guiding one buyer through one decision.
You're helping a dozen people reach the same conclusion, each at their own pace.
That realization eventually became one of the biggest shifts in how I think about pipeline management. I explored this idea much more deeply in Deals Don't Move in a Line. They Move in Threads, because once I understood that buyers move independently before they move together, forecasting, stakeholder management, and executive conversations all started making a lot more sense.
Explore the full lesson here:
https://forgeforsellers.com/pages/deals-dont-move-in-a-line-they-move-in-threads
The CRM Quietly Taught Me the Wrong Lesson
I don't blame the CRM.
I don't blame the methodology either.
They're valuable tools.
The mistake was mine.
Somewhere along the way, I stopped using stages to organize my opportunities and started using them to explain customer behavior.
Those aren't the same thing.
Once that happened, every reopened conversation felt like lost momentum. Every new stakeholder felt like unnecessary friction. Every difficult question made me wonder whether the deal was slipping away.
Now I see those moments completely differently.
When someone wants to revisit the business problem, I don't assume we're losing control.
I assume someone important hasn't reached the same conclusion everyone else already has.
That's not failure.
That's information.
Somewhere Along the Way, I Stopped Asking About Stages
If you'd listened to one of my forecast calls fifteen years ago, you would've heard me talking almost entirely about where each opportunity sat in the sales process.
Stage Two.
Stage Three.
Proposal.
Negotiation.
Those labels felt incredibly important.
Today, I ask myself completely different questions.
Who still doesn't believe the problem is worth solving?
Who's quietly worried about risk?
Who's agreeing publicly but hasn't committed privately?
Who's supporting the initiative... but still isn't willing to own the decision?
Those answers tell me infinitely more than a CRM stage ever will because they reveal where alignment actually exists and where it doesn't.
If you've ever wondered why a forecast looked healthy while a deal quietly fell apart anyway, this way of thinking is exactly what led me to write Deals Don't Move in a Line. They Move in Threads. It's one of the lessons I return to most often because it fundamentally changed how I evaluate pipeline health.
You can explore that lesson here:
https://forgeforsellers.com/pages/deals-dont-move-in-a-line-they-move-in-threads
The Best Sellers Don't Fight the Loop
One thing I've noticed about the strongest enterprise sellers I've worked with is that they almost never become frustrated when a deal circles back.
Years ago, I thought that confidence came from experience.
Now I think it comes from expectation.
They expect executives to see the world differently than practitioners.
They expect priorities to shift over the course of a nine-month sales cycle.
They expect new stakeholders to challenge assumptions because that's exactly what responsible leaders should do.
Nothing about those moments surprises them.
Instead of resisting the loop, they become curious about it.
They aren't asking, "Why did the deal go backward?"
They're asking, "What is this conversation trying to teach me about the buying process?"
That's a very different question.
Looking Back, I Was Measuring the Wrong Thing
When I think about that opportunity now, I don't remember losing it.
I remember what it taught me.
Movement isn't progress.
Meetings aren't momentum.
Stages aren't alignment.
Those things can exist together, but they aren't the same thing.
If I could sit down with the younger version of myself who walked out of that meeting frustrated because the vice president wanted to revisit conversations we'd already had, I'd probably tell him something simple.
"The deal didn't go backward."
"Someone important just started catching up."
That single realization changed the way I forecast, the way I coach, and the way I navigate complex enterprise opportunities.
If this perspective resonates with you, I unpack it much more deeply in Deals Don't Move in a Line. They Move in Threads. It's the companion lesson to this story and one of the ideas that has had the biggest impact on my own career because it completely changed how I think about momentum inside enterprise deals.
Read the full lesson here:
https://forgeforsellers.com/pages/deals-dont-move-in-a-line-they-move-in-threads
Once you begin looking at enterprise sales this way, something interesting happens.
You stop trying to move deals forward.
You start helping people move together.
And those are two very different careers.