The Problem with Fishing

When I was twenty years old, I spent two years in Michigan as a missionary for my church. Most of my days were spent going door to door, trying to find people interested in hearing a message about faith.

It was an exhausting exercise in human psychology. We had about twenty seconds at each door to convince someone not to close it. We didn’t know their priorities, struggles, or beliefs — we were simply hoping that something we said might connect.

Most of the time, it didn’t.

It wasn’t that the message wasn’t meaningful; it was that we were pitching it to people we didn’t understand.

The most productive conversations didn’t come from door knocking — they came from people who had seen one of our commercials, talked to a friend, or expressed genuine interest in learning more. Those people already had a need or curiosity; they were looking for help connecting the dots.

Years later, in sales, I realized how similar those two worlds were. Too often, we treat demos and presentations like going door to door with our “features,” hoping someone invites us in.

When Demo Becomes the Default

When I joined a new company early in my sales career, they handed me a slide deck with 180 slides. I remember staring at it in disbelief.

“This,” my manager said, “is the corporate presentation. It has everything you’ll ever need.”

He wasn’t joking. The deck included every product, every capability, every diagram, and every customer logo we had ever earned. It was impressive — but it was also overwhelming.

During my first few customer meetings, I did exactly what I was told. I opened the deck and started from slide one. By slide twenty, I could already see the customer’s eyes glaze over. By slide forty, they were checking email. And by slide sixty, they were gone — mentally, if not physically.

I didn’t realize it then, but I was doing what so many sales teams still do: I was fishing for pain. I wasn’t guiding a conversation; I was hoping something on slide 87 might stick.

Later in my career, I sat on the other side of the table — as the customer. And I hated it. I watched vendors run through endless decks and demos, throwing features and buzzwords into the air, hoping one would land on a real need.

They were working hard, but they weren’t working smart. The truth was simple: they didn’t understand my business, my pressures, or what actually mattered to me. They were guessing.

That’s what most “deep demos” really are — not discovery, but guesswork with slides.

The Door-to-Door Problem

Selling this way feels productive. You’re doing something. You’re talking. You’re showing value — or so it seems. But underneath, it’s just motion without direction.

When we lead with a demo instead of discovery, we hand control of the conversation to chance. We hope the customer connects the dots between our features and their problems, rather than connecting those dots ourselves.

It’s the sales equivalent of saying, “Here’s everything we can do — tell me which part matters.”

That approach might occasionally stumble into a win, but it’s rarely repeatable, and it doesn’t build credibility. Customers don’t want a fishing trip; they want a guide who already knows where the fish are.

The Psychology of Why Fishing Feels Good

We don’t fall into “feature fishing” because we’re bad sellers — we fall into it because it feels good.

Our brains love dopamine hits from perceived progress. Clicking through slides, explaining features, and seeing heads nod gives us the illusion of success. It feels like momentum, even when it’s not.

There’s also laziness at play. Discovery takes effort. It requires thoughtful questions, active listening, and the willingness to slow down. Demoing, on the other hand, gives us a sense of control. We’re in our comfort zone — talking about what we know, not what we don’t.

This is why many sales teams confuse activity with progress. They’re avoiding discomfort, not creating opportunity.

Real discovery requires courage — the willingness to ask questions you don’t know the answers to.

A Tale of Two Meetings

In another account, I took a different approach. Before the meeting, I asked the rep what the client’s business priorities were. He didn’t know — so we spent time framing questions to uncover them.

When we sat down with the client, instead of launching into a demo, I asked, “When your team talks about success this year, what projects will matter most to your leadership?”

That single question shifted everything. Instead of nodding politely through a slide deck, the executive leaned forward and began to talk about the projects that mattered most to his leadership — the ones tied to delayed product launches, missed revenue targets, and risk exposure. The work that helped him hit his KPIs.

By the end of the meeting, we didn’t just have interest — we had urgency. The next week, they invited us to co-develop a pilot.

Pain Is the Currency of Change

Customers don’t buy because we have features; they buy because they have pain.

Every successful deal begins with a clear, quantifiable problem — something that costs money, time, or opportunity. Yet in most demos, we never get to that level of conversation. We spend time explaining “how it works” when what really matters is “why it matters.”

Identifying pain is the key to a sale. Without it, we’re guessing. And unless we quantify that pain — turning it into measurable business impact — we’re not building urgency. We’re wasting time.

Pain is the fuel of change. It’s the reason a business is willing to reallocate budget, shift priorities, or take risk. No pain, no change — and no deal.

The Psychology of Real Discovery

1. Curiosity Builds Trust – Asking open questions like “What’s making this a priority now?” signals genuine interest. It moves the focus from your product to their reality.
2. Pain Creates Focus – Once the customer articulates their pain, they naturally want resolution. That’s when your product becomes relevant.
3. Empathy Drives Connection – Listening without interrupting or defending creates psychological safety. People buy from those who make them feel understood.
4. Ownership Inspires Action – When customers verbalize their pain and quantify its impact, they’ve already started to own the problem — and they’re more likely to take steps to fix it.

Practical Exercise: From Fishing to Guiding

Before your next demo, take ten minutes and try this exercise.

1. List your top five features. Then, for each one, write the business problem it solves — in measurable terms.
2. Create one discovery question for each problem. Example: “When projects get delayed, what’s usually the cause?” or “How are you measuring the cost of downtime?”
3. Start your meeting with those questions, not your slides.
4. Listen deeply. Let their answers guide what you show, not the other way around.

By the time you open your demo, it won’t be a fishing trip anymore — it’ll be a targeted, trusted conversation.

Coaching the Curiosity

Great sales leaders know that curiosity isn’t just a personality trait — it’s a discipline.

When leaders consistently model discovery in their reviews and deal inspections, it reinforces that asking “why” is more important than saying “how.” It trains teams to think in business language, not product terms.

But coaching curiosity requires more than encouragement — it requires awareness. Many organizations unintentionally signal the opposite behavior.

When inspection meetings, forecast calls, or deal reviews focus only on answers — “What’s the close date? What’s the amount? What’s the next step?” — it sends a subtle message: uncertainty is bad. That message creates fear, and fear drives people to avoid pain.

And avoiding pain is one of the strongest human motivators. It’s what keeps reps from asking the tough discovery questions, from probing deeper, from risking the “no” that might save them weeks of wasted effort.

Leaders must create environments where curiosity and uncertainty aren’t punished but expected. Where not knowing is a sign of learning, not weakness.

Culture changes when curiosity becomes habit — when reps know they’ll be asked what pain they uncovered, not what slides they used.

Closing Reflection

Fishing feels busy. It feels safe. But it’s rarely effective.

True selling happens when we stop casting features and start catching meaning — when we understand the pain beneath the surface and connect our value to solving it.

Discovery is not a pre-sales activity; it’s the sale itself.