Before You Pitch, Diagnose. Here’s How.

Today’s Skill: Becoming a Better Problem Solver

Growing up, I loved watching a show called Matlock starring the great Andy Griffith during my “I want to be an attorney” phase. What Matlock did extremely well was seeing the edges of the case. He didn’t take things at face value and stayed skeptical until he had all the facts.

He was a problem solver as much as an attorney.

That’s exactly what’s missing in many of your sales conversations.

You assume without asking.

Or ask without prying deeper.

Or pry deeper without questioning what they just told you.

And I get it. Many of you have told me you struggle with low confidence and a fear of rejection. So anything that resembles confrontation? You run from it.

But what if we reframed “confrontation” and called it coaching with care?

Can you do that?

Would you trust me to try?

Here are 5 ways you can “coach with care” and help uncover the real problems your prospects are facing, along with why they might be ready to solve them now.

Lean into the painful discussions

Too often, we stop at surface-level symptoms. We hear, “We want to improve X,” and think, “Great, I can help you improve that. Let’s move on.”

Don’t.

I want you to keep probing. Yes, it might feel uncomfortable. You might feel like you’re interrogating, but you’re not. These questions help both you and the prospect think through what’s really wrong.

Examples of how it might sound:

• “Why do you want to improve “X”? What issues is it causing?”

• “How long has that been happening?”

• “What has it cost you in dollars, resources, or time?”

• “What happens if nothing changes?”

Real problems leave evidence. You just have to follow the pain until you hit something urgent, costly, or frustrating. It’s rarely sitting at the surface.

→ You can’t help if you don’t know exactly what’s broken.

Don’t Assume

Founders often confuse buyer politeness for genuine interest, or assume a feature solves the core pain.

That’s why you need to pause and ask:

“Is what they told me actually clear, or am I filling in blanks based on what I think they meant?”

If anything sounds fuzzy or feels off, ask for clarification.

You’re not a 12-year-old scared to ask a question in class anymore. These are business conversations.

→ There are no dumb questions. Only unasked ones.

Go Micro and Macro

Founders often jump to solve the first problem they hear without getting the full picture.

But the deeper the wounds go, and the more pain points you uncover, the more likely this is a serious buyer.

It might sound like:

• Zooming in: “What triggered this problem?”

• Zooming out: “Where else does this show up in your business?”

Bonus question: “Why hasn’t this been solved already?”

Maybe it’s a new issue. Maybe it’s a recurring one they’ve ignored. Either way, you won’t know unless you ask.

You’re looking for patterns. Is this a one-off issue, or something deeper they might not even see?

→ Doing both avoids band-aid fixes and reveals root causes.

Reverse engineer decisions

Don’t just ask where they want to go. Understand how they got to this moment.

Try questions like:

• “What made you start looking into this?”

• “Why explore now?”

• “What have you tried before?”

• “How did you handle this last time it came up?”

This gives you backstory, failed attempts, or internal politics that may not be obvious.

→ The more you understand their story, the easier it is to show how your solution fits into it.

Ask the “magic wand” question

“If you had a magic wand and could solve this problem instantly, what would that look like?”

This is one of the best ways to uncover what actually matters to your prospect. It forces them to define a clear before-and-after picture. And if they struggle, it’s a great way to ask clarifying questions to coach them to the answer.

Now you have a visual of their ideal outcome, which lets you map your solution to it instead of hoping they connect the dots.

→ When you know where they want to go, it’s easier to guide them on the right path.

Bonus Mindset Shift:

Play devil’s advocate with yourself.

During your pipeline audits, try looking at the deal from the outside in.

Ask yourself:

• What am I missing?

• Where could I be wrong?

• What might they not be telling me?

The clearer you are on those “missing pieces,” the stronger your deal confidence becomes. Most “close-date” anxiety or dragging sales processes are just a lack of information.

→ Fill in the puzzle pieces and you’ll start to see the full picture.

Your Action Item:

Pick one of the approaches above.

Which one haven’t you been using in your sales conversations?

Think through where it fits in your process. Prepare your version of it.

Then, try it on your next call.

Remember: You aren’t being confrontation.

You’re coaching with care.