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I signed up for a triathlon at the beginning of the year which will take place in August. I’m not worried about the bike or run portion, I got those.

But, the swim? That’s where I was freaking out because I’m not a strong swimmer.

I could figure out how to maneuver in a pool on a Memorial Day weekend but 500 meters in open water without walls to grab onto got me nervous.

So instead of winging it, I went looking for a coach.

If that coach had asked me why I was there, and I said "I'm not great at swimming, I want to get better," and they just said "got it" and moved straight into selling me a program, they'd have been guessing.

They might just hand me some generic 12 week swim plan built for someone trying to learn for the first time and figure that is what I need.

But, I’m not just trying to learn to tread water, I need to swim 500 meters efficiently and be somewhat competitive.

That gap between what I said and what I actually need is exactly what's happening on your sales calls right now, and it’s the reason your deals are falling flat.

Think back to some recent discovery calls. Someone tells you their problem and instead of asking more thoughtful, deeper questions, you start to pitch a solution to what they told you.

But, what they handed you is almost always a symptom. The real problem is sitting one or two layers beneath it, and most founders never go get it.

Instead, the more you ask stuff like, “Tell me more about that” or “Where is that coming from”, you start to uncover the deeper emotions behind the problem they shared and the impact on them and their organization.

Until you know the root problems and specifics around it, you can never get to a point to help them visualize the transformation.

And that visualization is how you tie their problem to your solution.

Where is this person today, and where do they actually want to end up?

When you can paint this transformation picture with specificity, your buyer can see themselves inside the story you're telling.

That's the moment they lean in and get bought in to the plan.

Here are the five things you need to uncover to get there.

Start with whatever they give you first. For me it was "I need to get better at swimming."

That’s a good start but the real good stuff is below the surface. What does better mean? Why do you need to?

→ (ICYMI: Remove ambiguity from your calls)

My result wasn't "become a faster swimmer." It was finish the 500 meters and get to the bike portion alive.

Vague goals get vague solutions.

The sharper the result, the sharper your offer can be. If your buyer says "I want more leads," that's good, "I want 10 qualified demos a month from outbound" is great.

→ Let’s not settle for good.

This is the layer almost everyone skips, and it's the one that actually closes deals.

Why does finishing that swim even matter to me? It’s partly physical and something new I’ve never done before. But, it’s a big mental hurdle to climb over. When I commit to something, I want to see it through, and I don't want this race to be the one that breaks that streak.

The why is what turns a transaction into a decision.

→ If they can't tell you why it matters, they're not ready to buy yet, no matter how good your demo was.

Race day was about 3 1/2 months from when I got a coach. That single date changes how the entire plan gets built. A coach building me a six month program isn't paying attention (or asking the right questions).

No timeline means no urgency, or worse, they have a timeline that you never uncovered so your offer doesn’t align.

→ Get the deadline, and build backward from it.

What is the cost of inaction? Is there any? If I don't finish that swim, I don't finish the race. Maybe I don't even start it. Does that affect me negatively? In what way?

For your buyer, the cost might be missed targets, a board meeting they're dreading, or sitting and looking at an empty pipeline for another month.

And, if nothing happens if the goal isn’t achieved, then you have a massive red flag that they might not even make a decision in the first place.

Find that cost.

→ People move away from pain faster than they move toward gain.

Stack all five together and the pitch changes completely. It's no longer "I'll help you become a better swimmer."

It's "I'll help you become proficient at swimming and get you ready to crush the 500 meter swim portion by race day.”

That's specific.

That's a transformation.

And that's the version that helps your buyer see their future in your hands.

If you've got a deal that feels like a great fit but won't move, don't look at your product.

Look at your discovery.

Go back to the problem they handed you in that first call.

Did you take it at face value, or did you go after the layers underneath it?

Show someone a clear before and after, and you've given them a reason to believe you're the one who gets them there.

Pull up two or three deals that have gone quiet. For each one, see if you can answer all five questions above using only what's already in your notes.

Wherever you come up blank, that's likely where the deal lost momentum.

Try to reenage, see if this is a problem they still need solving and ask those questions on your next conversation.

Deals gone quiet don’t mean they won’t make a decision, they just haven’t convinced themselves you’re the solution yet.

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