The Real Reason You Lose Deals You Should Win

Uncovering the Need Behind the Need

I once had an enterprise salesperson tell me after losing a deal:

“Kenneth, I don’t get it. I showed the executives we could save them a million dollars. A 10x return. And they still said, ‘talk to us in six months.’ What the hell happened?”

He was shocked.

Maybe you’ve been there too.

You feel like everything lines up. Strong ROI. Full executive buy-in. Killer demo. Then the deal goes dark.

Why?

That’s what this lesson is about. And honestly, this might be the most important discovery skill you ever learn.

Because until you understand the need behind the need, sales will feel like a coin toss. One day you’re closing a monster deal. The next day you’re losing something that felt like a guaranteed win.

You don’t have to keep guessing.

You can control the outcome a lot more than you think.

Money Follows Pain

People don’t spend because something is interesting. They spend to stop pain.

But in business, executives only spend on serious pain. The kind that:

• Threatens revenue

• Threatens cash

• Threatens their goals

• Threatens their job

Executives aren’t short on money. They are short on time and attention.

If the problem isn’t burning hot, it’s not getting budget. Simple.

Peel the Onion

In discovery, imagine the buyer hands you an onion.

Your job is to peel it.

Layer by layer.

Because most reps stop at the first sign of pain. Something like:

“We need more visibility.” “We want to improve branding.” “Our follow-ups could be better.”

Surface-level pain = small deals or no deals.

You need to dig until you get to the business pain that money follows.

This is the need behind the need.

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You Know You’ve Reached the Core

Two signs:

1. It’s a problem your solution actually solves

2. It’s a top priority for a decision maker

When those two line up — you’re in business.

How to Peel Deeper

Buyers rarely give you the real problem right away. You have to earn your way there.

And the easiest tool?

Ask some version of:

“What’s driving this to be a priority right now?”

Not “why” — that can sound like interrogation. Just keep peeling…

A Real Example

A Trembi rep and I were talking to a VP of Sales and a Sales Enablement Manager.

I asked:

“What motivated you to look at Trembi?”

First answer:

“We need visibility into sales conversations.”

Weak. Visibility alone doesn’t unlock budget.

So I asked:

“What’s making visibility so important right now?”

They said:

“Our reps struggle to sell to decision makers, so we need to coach them.”

Better… but still not deep enough.

Another layer:

“What’s driving that to be a priority over everything else happening right now?”

This time the VP jumped in:

“A 9-month sales cycle means an 11-month cash cycle. That puts our cash position at risk. If we don’t fix it, we’ll need to raise capital — which will dilute us heavily.”

Bingo.

Now we’re talking about:

• Cash flow

• Funding risk

• Shareholder dilution

• Metrics the VP owns personally

That’s a problem worth paying for.

And Trembi can solve it.

The Signal You’re Deep Enough

If the pain…

✅ Ties directly to a hard metric

✅ And that metric is owned by a decision maker

Then you’ve hit the core.

That’s when deals move fast. That’s when budgets appear magically. That’s when you win what others lose.

Skill > Luck

Master this one skill and your sales results change forever.

No more “I thought this was a slam dunk…”No more guessing. No more deals going cold for no reason.

Your success isn’t years away. It’s skills away.

Start peeling. That’s how you uncover the need behind the need.

— Kenneth

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