You present your strategy, and a stakeholder asks for something that seems to come out of nowhere.

They aren't saying "no" outright… but they're proposing something that would move the plan, or part of the plan, in a totally different direction.

You can't simply agree, because it conflicts with other choices that were made for good reasons.

So you start to explain. You know all the reasons you made the decisions you made, and it makes sense to try and close the gap. You might launch into reasons why their ask is technically unsound, or quote some industry standard to show why it won't work, or start walking them through all the downstream constraints they didn't know about.

They still don't budge.

Why?

It's often be because the change they're asking for isn't really what they care about.

Something in the plan worries them, but they can’t quite say what. So they latch onto something they can point to, and ask you to change that.

Positions vs. interests

In their classic book on negotiation, Getting to Yes, Roger Fisher and William Ury make a distinction that explains what's happening here: the difference between a position and an interest.

A position is what someone says they want, like that left-field request. An interest is the underlying reason they are asking for it: the practical need or concern they are trying to address. When you debate a position, you stall. When you uncover the interest, you find a way to move the room forward.

To get past their literal request and figure out what it will actually take to get a "yes," Fisher and Ury suggest asking two questions: Why and Why Not.

1. Ask "Why"

Start by asking yourself what problem the request is trying to solve. If you don’t know, ask them.

Fisher and Ury suggest asking the other side directly about their basic concerns. But tone matters. Asking a blunt "Why would you want that?" sounds like an interrogation and makes people defensive. Asking something neutral like "What's behind that request?" invites them to explain their underlying need rather than defend their solution.

2. Ask "Why Not"

When someone is having a hard time seeing beyond their ask, this is the more powerful tool. Fisher and Ury frame it as: Ask "Why not?" Think about their choice.

You don't ask this out loud as "Why won't you say yes?" You work it out in your own head by looking at the decision through their eyes, not yours.

Remember, people hesitate because, from where they sit, saying yes feels riskier than saying no. While you see the plan as the right way to hit an upside metric, they might see it as an unproven plan, an operational headache, or an unnecessary career risk. Those are very different choices.

Use your hypothesis to ask open questions that address the hurdle directly:

"What would you need to see in this plan to feel confident moving forward?"

Or test your guess simply and neutrally:

"It sounds like part of the concern is what happens if this takes longer to pay off than planned. Is that fair?"

By focusing on Why and Why Not, you shift the conversation from an adversarial battle of “who’s right” to a collaborative exercise in joint problem-solving.