I Used to Think I Was Losing Deals One Conversation at a Time... Looking back, I was really designing the outcome months before I ever realized it.

One of the most frustrating seasons of my career wasn't when I was losing a lot of deals.

It was when I couldn't explain why.

I'd walk out of a customer meeting feeling good. The discovery had been thoughtful. We'd identified a real business problem, agreed on next steps, and another meeting was already on the calendar. If you'd asked me that afternoon how I felt, I probably would've said the opportunity had real momentum.

A few months later, it would quietly disappear.

Sometimes the customer stopped responding.

Sometimes priorities shifted.

Sometimes another project took precedence.

Every deal seemed to have its own explanation, but after enough years I started noticing something uncomfortable.

The reasons were different.

The pattern wasn't.

I Kept Looking at the Wrong Part of the Deal

Like most sellers, I naturally focused on the place where the pain showed up.

If a late-stage deal stalled, I studied the last executive meeting.

If a forecast slipped, I replayed the final conversations in my head.

If a customer went quiet, I wondered what I should've said differently during the previous call.

I was trying to solve problems where they became visible.

Not where they were created.

That distinction took me years to appreciate.

Enterprise sales has a funny way of hiding cause and effect.

The conversation where everything finally falls apart is rarely the conversation where the deal actually started drifting.

That happened much earlier.

Somewhere Along the Way, I Realized Selling Behaves Like a System

One opportunity in particular finally forced me to see it.

We spent weeks preparing for an executive presentation. Everyone internally was focused on the meeting because it felt like the defining moment of the opportunity. We rehearsed messaging, refined the presentation, anticipated objections, and walked into the room feeling prepared.

The meeting went...

Fine.

Not bad.

Not great.

Just... fine.

Driving back to the airport, I remember wondering why it hadn't landed the way I'd expected.

Months later, after the deal was over, I realized I'd been asking the wrong question.

The executive meeting wasn't where we'd lost momentum.

We'd simply discovered it there.

The real problem started much earlier.

We'd entered the account through a stakeholder who cared about solving the problem but couldn't create organizational urgency around it. That shaped every discovery conversation that followed. Because we never fully established why the initiative mattered across the broader organization, every subsequent meeting required us to recreate momentum instead of building on it.

By the time we reached the executive presentation, we weren't fixing a meeting.

We were exposing a system that had quietly been working against us for months.

That realization eventually became one of the ideas I explore more deeply in Selling Is a System, Not a Moment. Once I started looking upstream instead of downstream, opportunities became much easier to understand because I stopped evaluating isolated conversations and started evaluating the system producing them.

Explore that lesson here:

https://forgeforsellers.com/pages/selling-is-a-system-not-a-moment

Looking Upstream Changed Everything

That experience made me rethink almost every part of how I approached enterprise selling.

Prospecting stopped being about filling my calendar.

It became the way I decided which conversations deserved months of my life.

Discovery stopped being a checklist of thoughtful questions.

It became the place where conviction was either built or quietly borrowed.

Forecasting stopped feeling like administrative work.

It became the clearest reflection of whether my selling system was actually functioning the way I believed it was.

Those activities had always existed.

I'd simply been treating them like separate jobs instead of connected parts of the same process.

The Best Sellers Rarely Chase the Fire

One thing I've noticed over the years is that experienced enterprise sellers almost never panic when a deal becomes difficult.

That doesn't mean they ignore problems.

It means they instinctively look for the source instead of the symptom.

If an executive suddenly isn't engaged, they don't immediately redesign the presentation.

They ask what happened earlier that prevented executive alignment from forming naturally.

If discovery feels shallow, they don't simply ask more questions.

They wonder whether they entered the account through the wrong conversation in the first place.

Their instinct isn't to work harder.

It's to think farther upstream.

I unpack that philosophy much more deeply in Selling Is a System, Not a Moment, because I eventually realized the strongest sellers don't spend their careers reacting to individual events. They quietly improve the system that produces those events.

You can continue the story here:

https://forgeforsellers.com/pages/selling-is-a-system-not-a-moment

Looking Back, Forecasting Was Trying to Tell Me the Truth

For years I thought forecasting existed to predict revenue.

Now I think it serves another purpose.

It exposes systems.

An unstable forecast usually isn't a forecasting problem.

It's often a prospecting problem that happened months earlier.

Or a discovery problem that never became obvious until late in the buying process.

Or a qualification assumption that quietly survived far longer than it should have.

Forecasts don't create surprises.

They reveal them.

That's a very different way to think about pipeline reviews.

Forge Was Built Around This Idea

When people ask what Forge is really about, I usually tell them it's about helping sellers think more clearly.

This is one of the reasons why.

There are already countless places to learn how to run a better discovery meeting or build a stronger executive presentation.

Those things matter.

But what changed my own career wasn't learning how to perform individual moments better.

It was learning to recognize how those moments were connected.

Once I understood that, I stopped asking,

"How do I fix this deal?"

I started asking,

"What part of my system produced this outcome?"

That question has probably taught me more than any sales methodology I've ever learned.

Looking Back, I Was Spending Too Much Time Looking Downstream

If I could sit beside the younger version of myself driving away from that executive meeting, I don't think I'd spend much time talking about the presentation.

He'd replay it enough on his own.

I'd probably ask him one question instead.

"How long ago do you think this meeting was actually won... or lost?"

I don't think he would've had an answer.

Neither would I.

Not yet.

Years later, I finally realized the meeting had simply revealed what the system had been creating all along.

That's why this idea has become one of the foundations of how I think about enterprise selling. If this perspective resonates with you, I unpack it much more deeply in Selling Is a System, Not a Moment, where I explore how prospecting, discovery, deal navigation, and forecasting are really parts of the same story.

Read the full lesson here:

https://forgeforsellers.com/pages/selling-is-a-system-not-a-moment

These days, when a deal starts feeling difficult, I still pay close attention to the conversation in front of me.

I just don't assume that's where the story began.

Most of the time, the answer is waiting somewhere much earlier.

You simply have to be willing to look upstream.