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Stop Discounting: Why "Difficult" Founders Win Bigger Deals

pricing reclaim the trait sales show

The call goes quiet for a second. Then comes the line: "Can you do a bit better on the price?"

The yes comes out fast. It feels like good service. Nobody wants to look difficult.

The deal closes. It is just smaller than the one you walked in with, and it leaves a bitter taste for weeks.

This is part 2 of a series sparked by Wild Courage, the book by ex-Google executive Jenny Wood. She reclaims nine traits people get told to hide (weird, selfish, bossy and more) as strengths.

We are doing the same for sales. Today's trait: "difficult."

The habit that shrinks your deals

🐬 Somewhere along the way, B2B sales picked up a rule: be easy to buy from, at any cost.

So the discount goes out to keep the mood friendly. The extra scope gets a yes, because a no feels rude. The price lands in a proposal before the buyer has said what the problem costs them.

Each move feels polite. Together they tell the buyer your number is soft.

And a soft number gets pushed. You can feel it give, every time.

Twenty percent off one deal is a bad week. Twenty percent off every deal this year is the gap between you and your annual target.

Underneath it all sits control. Whoever sets the order of the conversation sets the size of the deal.

Difficult is the wrong word

What people call "difficult" is usually something else. It is standards.

Standards sound like this: "Before we talk price, help me understand what this problem costs you today."

That is not rude. It is the order a serious buyer expects. Doctors diagnose before they prescribe. Nobody calls that difficult. They call it the expert.

🐯 Your price is not too high. It is standing alone, with nothing next to it.

A price with no comparison looks big. A price next to the buyer's own number looks small.

The mechanism: Step 4 before Step 6

In the 8 Steps of the Repeatable Sale, two steps decide your deal size.

Step 4 is Cost of Inaction. Step 6 is Investment. The order is the whole point.

Here is how it runs:

  1. Ask the cost question. "What happens if you do nothing about this for another 12 months?" Then stay quiet. Let the silence hang until the buyer fills it.
  2. Let them name the number. Lost deals, a slipping target, a sales hire with no process to run. The number has to come from their mouth, not your slide.
  3. Repeat it back. "So doing nothing costs you around X a year." Now it is on the table, in their words.
  4. Talk investment in order: time, people, money. How many hours a week. Who on their team is involved. Then the price, which now sits next to their X.
  5. Hold the number. If they want a lower price, cut a deliverable, not the price. Never the same scope for less.
  6. Be willing to walk. A buyer who will not name the cost is not ready to buy. Saying so out loud is a standard too.

You stay in control because the buyer did the math, not you.

Picture Daniel

Picture Daniel. Made-up name, very common founder. He runs a B2B consulting firm and wants $40,000 for a sales project.

Old Daniel sends the proposal first. The buyer stares at $40,000 with nothing beside it. The thread goes stale for a week. Daniel discounts 20% to "keep it moving." The deal closes at $32,000.

New Daniel asks the Step 4 question first. The buyer says three deals a year slip because nobody follows up properly. Each deal is worth $50,000.

So doing nothing costs $150,000 a year.

Now $40,000 sits next to $150,000. It looks like the cheap option. Daniel holds his price. That is $8,000 more on one deal, from one question asked earlier.

🌴 Same founder. Same offer. A different order.

What standards feel like from the other side

I learned this as a buyer, not a seller.

I once had three high-intensity Pilates studios to choose from. I picked the most expensive one. Better teachers, better playlists, better interior, better ventilation.

Right after paying, I felt a few seconds of buyer's remorse. Then a WhatsApp message welcomed me into their community. That one message made me feel sure I had chosen right.

Neither of the cheaper studios did anything like it.

🐬 The expensive studio did not try to be the cheapest. It charged more and then delivered from day one. From the buyer's side, that does not feel difficult. It feels safe.

Your move this week

🐯 Take the next deal in your pipeline that is heading toward a proposal.

Before you send a single number, book 20 minutes and ask the Step 4 question. Write down the buyer's answer in their words.

Then put your price next to it and say it out loud. Hear how much calmer your voice sounds. Run it on every proposal this month, until the question comes out on its own.

You do not have a pricing problem. You have an order problem. And order is something you can fix this week.

🌴 Standards are how you get bigger deals, calmer calls and your evenings back. That is the Sprintlife: you lead the conversation, and the business funds the life you want.

Practice the 8 Steps with other founders inside Sprint Club. 7-day free trial: https://www.strategysprints.com

Ready to accelerate now? Book a Discovery Call: https://calendly.com/strategysprint/discovery-call

Happy hunting.

Simon & The Sprinters 🐬⚡️🐆

Lead your next deal, first call to signature. 🌴

The 36 Sales Gaps Checklist: 36 places a deal dies, and the fix for each. Free, one page.

Free. You get the checklist, then more sales tools like it by email from Strategy Sprints. Leave in one click, any time.

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