Welcome to the final issue of Stacked Seller for 2025.

We’re two weeks out from EoY.

You know what that means.

OOOs are about to start rolling in and deals that looked “done” suddenly stall right before the finish line.

If you've got anything hanging for Q4, this is your last shot to get after it.

This week we’re sharing the most persuasive thing you can say in a sales negotiation.

It’s dead simple. Wildly effective. Yet heavily underused.

Let’s get into it.

FEATURE

Buyers ask for a lot.

Better pricing. Favorable terms. Custom SLAs.

The list goes on.

When reps get hit with these requests, they immediately go into problem-solving mode.

They fight internally to get as many concessions approved as possible.

Then present to the buyer, hoping it’s enough to move things forward.

Sometimes it is. Often it’s not.

Either way, it’s the wrong approach.

Here’s why…

First, you train bad behavior. The buyer learns they can ask for more and you'll deliver without pushback.

Second, you give away all your leverage with zero guarantee of commitment. Once the concessions are gone, you've got nothing left to negotiate with.

There’s a better way.

Treat every request from the buyer as an opportunity to get more skin in the game.

When they ask for something, use the most persuasive phrase in sales negotiation: "If I, will you?"

Here's how it works in real conversations.

1/ Discount Requests

Buyer: “We're interested, but we need at least 20% off to make this work with our budget.”

Rep: “Finance already gave me their floor but I can make one final ask. If we get approval for 20% can you commit to signing by the 31st?”

2/ Redlines

Buyer: “I've attached the redlines for the contract. Can you get these added to the agreement?”

Rep: “Before I take this back to legal, are these all the redlines you needed? If approved, are we done with legal review?”

3/ Payment terms

Buyer: “Our CFO won't approve monthly payments. We'll need to do quarterly.”

Rep: “I've exhausted all my options with finance on this. Our VP has more authority on payment terms. If I can get her on our next call, can you bring your CFO as well?”

4/ Custom Demo

Buyer: "Can we schedule a custom demo for our engineering team?"

Seller: “Happy to set that up with our solutions team. Can you provide an outline of what features and workflows the team would like to see?”

5/ Support escalation

Buyer: “Can you get this support ticket resolved ASAP?”

Seller: “I can request a one-time escalation to pull this ticket out of the free support queue. Can we set up time this week to review our premium support packages?”

This works in the negotiation phase where buyers are already engaged. For early stages, you often have to give relentlessly without expecting anything in return.

As the deal progresses, you need someone on the buyer’s side motivated enough to push through the friction within their org.

That's why "If I, will you?" creates a win-win.

The buyer knows you'll fight internally to get what they need.

In return, you get micro-wins. One milestone at a time.

*Note: we are taking a break for the holidays. See you again in January!

YOUR TWO CENTS

➡ Which part of your deal stalls most often?

  1. Pricing

  2. Security review

  3. Legal

  4. Final sign-off

*Reply with your number. I’ll share the poll results in the next issue.

LAST WEEK’S POLL RESULTS

➡ How many pricing options do you typically present on calls?

  1. One - 3%

  2. Two - 28%

  3. Three - 41%

  4. Four or more - 28%

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