Ask yourself these 3 questions next time you’re negotiating

Most people think a negotiation is a battle of offers.

But here’s a little-known truth:

The best negotiators don’t start with offers. They start with questions.

The more you ask, the more valuable info you uncover—and that’s where the real power lies.

The Problem

If you’ve ever pitched an idea in a meeting or asked for more resources, it’s easy to focus only on what you want.

But negotiating without understanding the other person’s priorities is like driving with a blindfold.

You risk missed opportunities, pushback, or worse—a flat-out no.

The Big Small Thing

Want a raise, project resources, or extra support? Use these questions to reveal what really matters to the other side in your next negotiation.

You’ll be better positioned to make your case and secure a win-win.

1. “What does a successful outcome look like for you?” (aka Clarity Compass)

This flips the focus to their priorities, giving you insights to tailor your pitch.

Example:

If you’re asking for a bigger budget, they might care more about ROI than the actual dollar amount. You can then focus on how the added resources will drive results they care about.

Real life:

When I book speaking events, customers are surprised to learn bulk book sales are actually my priority—not just my speaking fee. Unless I tell them, they assume fee negotiation is my focus. When we both know what matters, we can strike a deal that’s better for everyone.

2. “What flexibility do we have on this?” (aka Flex for Success)

Don’t assume everything is set in stone. Often, flexibility is there if you ask for it.

Example:

If a pay increase isn’t possible, they might offer a one-time bonus, one work-from-home day, or professional development funds.

Real life:

When I negotiated for a new role, I asked for $10,000 more. They said I was at the salary cap—but offered an extra week of vacation. I’ll take it. Hawaii, here I come!

Stumped about what you can negotiate? Here’s a list of 76 things from another powerhouse negotiation pro and former McKinsey strategist, Kathryn Valentine.

3. “What challenges are you facing on this?” (aka Challenge Accepted)

This reveals pain points—and ways you can help solve them.

Example:

If you’re pitching yourself for a leadership role, and they say mentorship is a gap, you can highlight your strengths in mentoring. Now you’re not just asking—you’re solving their problem.

Real life:

When I pitch my keynotes, I always start by asking: “What’s one challenge your employees face? What’s another?” If they say their issues are apples, bananas, and oranges, I’ll show how my talk solves those challenges.

But here’s the key: I don’t mention pears or plums unless they bring them up. Tailoring your pitch to their exact needs shows you’re listening and makes it harder to say no.

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How This Helps You Chase What You Want

Asking smart questions shifts the control to you.

It helps you avoid assumptions, guide the conversation, and position yourself as a savvy, solution-oriented team member.

Because you’re someone who understands and delivers on the bigger picture.

Try these questions in your next negotiation. And watch the conversation shift in your favor.