Does it fit?

One of the most common problems in sales is not a lack of effort. Most salespeople work hard. They prospect, follow up, run demos, and push deals forward. The problem is often much more subtle than that. It begins with the mindset salespeople bring into an opportunity.

Too often, the moment a salesperson identifies a potential deal, their focus immediately shifts to winning it. The internal dialogue centers on a single question: How do I close this deal?

At first glance, that might seem like the right mindset. Salespeople are paid to win business, after all. But approaching every opportunity with an intensity focused on winning the deal can create a serious problem. It encourages the salesperson to look for ways to make the opportunity fit instead of determining whether it actually should.

Great salespeople approach opportunities differently. Their intensity is not focused on closing the deal. Their intensity is focused on understanding the customer’s problem.

They want to know what is really going on inside the organization. They want to understand what is preventing the company from achieving its goals. They want to uncover the obstacles, inefficiencies, or strategic challenges that are holding the business back.

In other words, they start with curiosity rather than persuasion.

The Real Starting Point: Customer Pain

This is where the MEDDIC framework becomes so powerful. At the center of MEDDIC is the concept of PAIN.

Pain is the reason companies change. Pain is what justifies investment. Pain is what brings executives into the conversation and pushes initiatives forward.

Without real pain, change rarely happens.

But uncovering true pain requires patience and discipline. Instead of jumping quickly to a demo or pitching features, the salesperson must spend time exploring the customer’s situation.

Key discovery questions might include:

• What is the problem the organization is facing?

• Why does it matter to the business?

• Who inside the organization is impacted by it?

• What happens if nothing changes?

These questions are not simply part of a discovery checklist. They are the foundation of determining whether the opportunity is real.

Unfortunately, many salespeople rush through this process because they are eager to move the deal forward. They hear a surface-level challenge and immediately begin connecting it to their product.

The conversation quickly shifts from understanding the problem to presenting the solution. When that happens, the salesperson may believe they are building momentum, but in reality they are skipping the most important step in the process.

The Dangerous Question: “How Do I Make This Fit?”

Once a salesperson decides they want to win a deal, confirmation bias begins to creep in.

Confirmation bias is a simple but powerful psychological effect. Once we decide something is true, we naturally start looking for evidence that supports it.

In sales, this often shows up in subtle ways.

A vague problem becomes a major business challenge. A loose alignment becomes a perfect use case. A curious prospect becomes a highly qualified buyer.

Instead of objectively evaluating the situation, the salesperson begins shaping the story so the deal makes sense.

The question quietly changes from:

“Are we the right solution?”

to

“How do I make this solution fit?”

This is where bad deals begin.

Sometimes the deal still closes. But the product only solves part of the problem. Expectations between the buyer and seller are misaligned. Implementation becomes more difficult than expected.

Eventually, the organization feels the consequences. Customer frustration increases, support teams struggle, and renewals become more difficult.

From the outside, the deal looked like a win. In reality, the problem started much earlier when the opportunity was approached with the wrong mindset.

The Discipline of Determining Fit

Elite salespeople approach opportunities with a different objective. Their primary goal is not simply winning the deal.

Their primary goal is to determine FIT.

FIT means the problem is real.

FIT means the problem matters to the business.

FIT means the organization actually wants to solve it.

FIT means your solution can truly solve that problem.

When those elements are present, the sales process becomes dramatically easier.

The conversation shifts from persuasion to collaboration. Instead of trying to convince the customer to buy, the salesperson and the buyer begin working together to solve a shared problem.

This dynamic creates much stronger deals. The value of the solution is clear, expectations are aligned, and both sides are working toward the same outcome.

The Courage to Walk Away

Sometimes the discovery process reveals something uncomfortable. Sometimes, the problem the customer is facing is not something your solution can solve.

This is where many salespeople struggle.

Walking away from a potential opportunity feels counterintuitive. Pipelines look smaller, and forecasts feel weaker. But recognizing poor fit is one of the most valuable skills a salesperson can develop.

When salespeople remove poor-fit opportunities, they improve the overall quality of their pipeline. Instead of chasing deals that are unlikely to succeed, they focus on opportunities with strong alignment and a higher probability of success.

Even more interesting, walking away can actually strengthen the relationship with the prospect.

When a salesperson openly acknowledges that their solution may not be the best option for the customer’s situation, it builds credibility. The buyer recognizes that the salesperson is focused on solving problems rather than simply closing deals.

Trust grows quickly in that environment.

And trust often leads to future opportunities where the alignment is much stronger.

The Feedback Loop Most Sales Teams Miss

There is another benefit to identifying a poor fit that many organizations overlook.

Information.

When a deal is not a good fit, the conversation should not simply end. That moment contains valuable insight about the market.

Salespeople are on the front lines of customer conversations. They hear directly from organizations about the problems they are trying to solve and the capabilities they need. When a deal does not move forward because of a product gap, that insight should be captured and communicated back to the company.

Important questions to capture include:

• Why was the solution not the right fit?

• What requirement could not be met?

• What capability was missing?

• What problem remained unsolved?

When sales teams consistently provide this information to product and leadership teams, something powerful happens.

The organization begins to learn.

Patterns start to emerge. Product gaps become visible. Market needs become clearer. Product teams can prioritize improvements that align directly with real customer problems rather than assumptions.

Sometimes the changes required are smaller than expected. A capability may already exist but needs improvement. A feature may only require a modest adjustment.

Deals that were once impossible suddenly become winnable. If you don't take this step, the information never finds its way back to the product, and the struggle will continue.

Sales as Market Intelligence

This perspective changes the role of the salesperson.

Salespeople are not simply responsible for revenue. They are also the organization’s connection to the market.

Every customer conversation provides insight into industry trends, operational challenges, and competitive dynamics. When that intelligence flows back into the company, it strengthens everything.

Marketing messaging becomes clearer.

Product strategy becomes smarter.

Sales conversations become more effective.

Over time the company becomes better aligned with the problems the market actually cares about solving.

Start With the Right Question

At the beginning of every opportunity, there is a simple but powerful choice.

A salesperson can approach the conversation asking:

“How do I win this deal?”

Or they can approach it by asking:

“What problem is this company trying to solve, and are we truly the right partner to solve it?”

The first question often leads to pressure, forced alignment, and fragile deals.

The second question leads to clarity, trust, and long term success.

Great sales organizations train their teams to start with the second mindset.

Because the goal of sales is not to win every opportunity.

The goal is to win the right ones.