Closed Won

🦙 The Problem Isn’t Enough

Brian LaManna

March 8, 2026

Read Time: 3 minutes

HighSpot and Seismic are merging in a major software deal.
When two fierce competitors merge, it signals that market is commoditized.
Both aren’t thriving independently. So they combine.
Their platforms have immense product overlap, so it’s hard to know how this’ll play out from a tech perspective.
My bet: More significant M&A will unfold soon.

NEWS TO KNOW

📚 – The AI replacing sellers irony… 
📝 – Don’t be a “nice guy” or you’ll finish last
💸 – How to ask “a hard thing in a soft way”

BEST FROM LAST WEEK

Don’t Sell the Problem. Sell the Cost of Ignoring It.

Here’s what most sellers get wrong: they find a problem, nod along, and then pitch their solution.

The buyer says “yeah, our forecasting is pretty manual” and the rep immediately jumps to “well, our platform automates that!”

But here’s the thing. Your buyer already knows they have a problem.

If they didn’t, they wouldn’t be talking to you.

What they often haven’t yet identified is what it’s actually costing them to live with it.

The difference between average and elite

Average reps stop at pain validation.

They ask “what challenges are you facing?” and “how is that impacting you?” Then they move on.

Elite reps go three layers deeper. They turn vague frustrations into dollar signs, missed opportunities, and career risks the buyer can’t unsee.

Think about it. “Our reporting is slow” is a problem.

But “you’re spending 40 hours a month on reports that could be automated, which means your analysts are doing data entry instead of the strategic work that could drive an extra $2M in revenue” is a consequence.

One is annoying. The other is expensive.

The Cost Ladder Framework

When you uncover a problem, climb this ladder with your questions:

Level 1: Time Cost How much time does this actually take?

Not just one person. The whole team. Every week. Then multiply it out over a year.

Example questions:

  • “Walk me through the last time you did this process. How long did each step take?”
  • “Who else gets pulled into this? How much of their week does it eat up?”
  • “If you add it all up, how many hours per month is your team spending on this?”

Level 2: Money Cost What’s the financial impact? Lost revenue, wasted budget, higher costs. Get specific numbers.

Example questions:

  • “What’s the hourly rate for the people doing this work? So we’re talking about X dollars per month just in labor?”
  • “How many deals have slipped because of this? What’s the average deal size?”
  • “What are you currently spending on the workaround? Tools, contractors, overtime?”

Level 3: Opportunity Cost This is where it gets real. What aren’t they doing because they’re stuck dealing with this problem?

Example questions:

  • “If your team wasn’t spending 40 hours a month on this, what would they be working on instead?”
  • “What initiatives are sitting on the back burner because you don’t have bandwidth?”
  • “Where could that budget be going if it wasn’t tied up here?”

Level 4: Risk Cost What could go wrong if this doesn’t get fixed? Compliance issues, customer churn, competitive disadvantage, missed targets.

Example questions:

  • “What happens if this breaks during your busy season?”
  • “Are you at risk of losing customers over this? How many?”
  • “What does your CEO say when they see these numbers?”

The magic question

After you’ve walked through the costs, ask this: “So if nothing changes, what does this look like in six months? In a year?”

Let them paint the picture. Let them feel the weight of inaction.

Because people don’t buy solutions to problems they can live with.

They buy solutions to consequences they can’t afford.

Your homework

Pick your last three deals. Go back and look at the problems you uncovered.

Now ask yourself: did you validate the problem or quantify the consequence?

If you just validated, you’re probably competing on price. If you quantified, you’re probably winning on value.

Stop selling problems. Start selling the cost of ignoring them.


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