30 of the Best Questions to Ask in Any Negotiation

Introduction

Asking the right questions is one of the most important parts of any successful negotiation – next to preparation. Great questions drive the conversation, uncover needs and reveal hidden interests. The quality of your questions determines the quality of the information you gather, the solutions you co-create, and ultimately, the agreements you reach. This is why we wrote this article ’40 of the Best Questions to Ask in Any Negotiation’.

Think about it, when you are communicating, there is so much hidden value that you are able to unlock with your questions.

In this article we dive into the most effective questions to ask in any negotiation and frankly in any interaction. I like to refer to these questions as High Quality Questions. We focus on the Rules for Asking Great Questions and list “How” “What” and “Why” questions, as well as essential phrases that every negotiator should have in their toolkit. This will guide you through discussions, resolve disagreements, and reach meaningful outcomes.

What We Will Cover

In this article, we will explore the importance of asking high-quality questions in negotiations. You’ll learn:

• Four key principles for framing your questions effectively.
• The power of “How,” “What,” and “Why” questions to uncover needs and hidden interests.
• Practical phrases and active listening strategies that will transform your negotiation approach.
• A set of 30 questions to guide your discussions and reach better outcomes.

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The Rules for Asking Great Questions

Before diving into the specific types of questions you should use in negotiations, it’s important to pause and understand why the quality matters so much. Asking great questions is not just about curiosity – it’s about strategy. High-quality questions are tools that unlock insights, foster collaboration, and pave the way for creative solutions.

Many negotiations fail not because of a lack of preparation but because one side fails to ask the right questions or listens poorly to the answers. By mastering the way you ask questions, you show confidence, demonstrate that you value the other person’s perspective, and gain access to critical information that can tip the scales in your favor.

However, asking effective questions requires discipline. It’s not just about what you ask but how you ask. To guide you, we focus on the four key principles to keep in mind.

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Ask Open Questions – Avoid ‘Yes’ or ‘No’ Questions

Open-ended questions are one of the most powerful tools in a negotiator’s toolkit. Questions that can be answered with a simple “yes” or “no” tend to shut down conversations rather than open them up. For example:

• Instead of asking, “Do you agree with this price?” or “Did you have a nice holiday” etc
• Try, “What are your thoughts on this pricing?” or “Tell Me About Your Holiday“.

The second approach encourages the other party to elaborate, giving you valuable insights into their reasoning, concerns, or hesitations. Open-ended questions invite dialogue, uncover motivations, and often reveal opportunities to find common ground.

When you ask open-ended questions, you position yourself as someone genuinely interested in understanding the other side, which builds trust – a crucial element of any negotiation.

See this great article “Asking Open-Ended Questions Increases Personal Gains in Negotiations” from Matteo Di Stasi, Alison Wood Brooks, and Jordi Quoidbach on this subject.

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W.A.I.(S.)T. – Why Am I (Still) Talking?

This principle is simple yet often overlooked: ask your question, then stop talking. Silence may feel uncomfortable, but it’s one of the most effective tools a negotiator can use. Many people sabotage their own questions by filling the silence with explanations or, worse, answering the question themselves.

For example:

• Asking, “How does this align with your goals?” is a great. However, if you then immediately add for example, “I mean, I assume it does not fully align, but we can discuss…?” undermines the power of the question.
• During contract negotiations you might ask: “Does this new wording in Art X work for you?” and then immediately filling the silence with assumptions like, “I assume it’s probably not fully aligned with your proposed wording, but I am sure we can work something out….” would again not be advised. Ask your question and wait for your answer. Wait and allow the other side to respond. Their answer might surprise you, such as: “Actually, the wording is fine, except for this one word. Would this alternative work for you?”

By think about the concept “W.A.I.S.T. – Why Am I Still Talking?” – you give the other party space to think, process, and provide a meaningful answer. The silence you leave can be a powerful motivator for the other person to fill it with their thoughts, which often reveals more than you might expect. Insight: by staying quiet, you avoid creating problems that don’t exist and let the real issue surface.

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Land the Plane

The concept of “W.A.I.S.T.” and “Land the Plane” comes from Alexandra Carter’s book, “Ask For More – 10 Questions to Ask to Get What You Want. It’s about asking a clear, concise question and then stopping—giving the other party space to respond. Many negotiators undermine their own questions by “circling the runway,” over-explaining, or talking too much.

For example:

• Instead of asking, “How does this price fit within your budget?” and then nervously adding, “I mean, if it doesn’t work, we can look at discounts, or we can split it into payments…”
• Simply ask: “How does this price fit within your budget?”

Why does this work?

When you “land the plane,” you:

• Avoid diluting your message. Adding extra words or unnecessary suggestions often weakens the strength of your question.
• Give the other party room to think and answer. Negotiations require processing time. Silence often encourages deeper responses.
• Project confidence. A clear question followed by quiet shows that you value their input and are comfortable waiting.

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Active Listening

Active listening is a very powerful tool that I learned from the Harvard Program on Negotiation, but a lot has been written about the subject. s not just about hearing words – it’s about understanding, processing, and responding thoughtfully. Effective negotiators don’t just wait for their turn to speak; they listen carefully and build their follow-up questions based on what was said.

What Is Active Listening?

As mentioned in a recent Harvard Business Review article, active listening is when you not only hear what someone is saying, but also attune to their thoughts and feelings. It turns a conversation into an active, non-competitive, two-way interaction. Robin Abrahams and Boris Groysberg from Harvard Business School describe active listening as having three aspects: cognitive, emotional, and behavioral. Here’s how they define each aspect in their article, “How to Become a Better Listener”:

• Cognitive: Paying attention to all the information, both explicit and implicit, that you are receiving from the other person, comprehending, and integrating that information
• Emotional: Staying calm and compassionate during the conversation, including managing any emotional reactions (annoyance, boredom) you might experience
• Behavioral: Conveying interest and comprehension verbally and nonverbally

For example

• If the other party says, “We’re concerned about the delivery timeline,” an active listener might follow up with, “What part of the timeline feels unrealistic to you?”
• When your counterpart mentions: “We are particularly concerned about your liability clauses so we will need to go with our standards”, instead of going into a discussion why you should your standards (or not), ask what part of the clause they are concerned about and what the reason is of the concern.

This approach achieves two things:

1. It shows the other party that you are engaged and care about their perspective.
2. It gives you the chance to gather more information and address their concerns directly.

Active listening also helps avoid assumptions, which are a common pitfall in negotiations. When you listen deeply and ask relevant follow-up questions, you reduce the risk of misunderstanding and strengthen the quality of the dialogue.

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Why These Rules Matter

The reason we reiterate these rules is that asking great questions is both an art and a skill. It requires intentionality, focus, and practice. When you master the art of asking clear, open-ended questions and combine it with active listening, you gain a huge advantage in any negotiation.

Think of it this way: questions are like keys. Some questions unlock doors to hidden opportunities, while others keep those doors firmly shut. By avoiding closed questions, staying silent after you ask, being concise, and actively listening, you ensure that you’re asking the right questions in the right way.

These rules serve as the foundation for all the “How,” “What,” and “Why” questions we’ll explore in this article. Use them consistently, and you’ll find that your conversations become more insightful, your relationships stronger, and your outcomes more favorable.

In short: ask well, listen better, and negotiate smarter.

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30 Questions to Improve Your Negotiations

1. “HOW” Questions

“How” questions are powerful because they focus on process, possibility, and solutions. They encourage the other party to think constructively and collaboratively, which can shift negotiations from conflict to cooperation.

As Chris Voss explains in Never Split the Difference, “How” questions work particularly well because they force the other party to engage with your perspective without feeling attacked. For example, asking “How am I supposed to do that?” puts the burden of providing solutions back onto the other party.

Examples of “HOW” Questions

• How am I supposed to [do that/pay this]?
• How does this violate our agreement?
• How do we know?
• How can I help make this better for us?
• How on board are the people who are not here today?
• How would you feel if…?

Further Reading:

• How to Use “How” Questions in Negotiations – YouTube explanation from Chris Voss – The Black Swan Group (Book: Never Split the Difference).
• Getting to Yes: The Art of Collaborative Negotiation – Harvard PON.

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2. “WHAT” Questions

“What” questions are neutral, open-ended, and non-confrontational. They work because they invite the other party to explain themselves without feeling defensive. According to negotiation theory from Getting to Yes, “What” questions help you uncover key interests and concerns.

For example:

• “What challenges do you see with this proposal?” encourages the other party to express their concerns openly, allowing you to address them proactively.
• “What is your biggest concern?” cuts through surface-level objections and gets to the root of the problem.

“What” questions also create opportunities for exploration and creativity, two elements that experts agree are critical in creating value during negotiations.

More Examples of “WHAT” Questions

• What else would you like us to know?
• What is the reason…?
• What if we tried…?
• What are your views on…?
• What challenges do you see with…?
• What is your biggest concern?
• What brought us into this situation?

Further Reading:

• Getting to Yes: The Power of Questions – Harvard Program on Negotiation.
• How to Ask Powerful Questions in Negotiation – Harvard Business Review.

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3. “WHY” Questions

“Why” questions are excellent for uncovering motivations, values, and hidden interests, but they must be used carefully. While they can dig deeper into someone’s reasoning, poorly phrased “Why” questions may come across as accusatory or confrontational.

The key to using “Why” questions effectively, as emphasized in negotiation literature, is tone and intent. According to Fisher and Ury in Getting to Yes, asking “Why is this important to you?” encourages the other party to share their underlying interests without feeling attacked.

Additionally, “Why” questions help you test assumptions and challenge objections diplomatically. For example, “Why would this solution not work for you?” invites constructive feedback instead of resistance.

As mentioned by Chris Voss, you should avoid asking too many “Why” questions and use other high quality questions as ‘Why’ questions could have a negative connotation.

Examples of “WHY” Questions

• Why is this so important for you?
• Why is this unacceptable to you?
• Why should we consider…?
• Why should we delay an answer on this?
• Why would this solution not work for you?
• Why is this part of the article crucial for you?

Further Reading:

• See this video “The Secret Way To Use “Why” & “No” in Your Next Negotiation | Chris Voss”.
• The Psychology of ‘Why’ Questions in Negotiation – Psychology Today.

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4. Great Phrases You Can Use

Also part of asking high quality questions is using effective phrases that create an atmosphere of collaboration and understanding. These phrases are excellent for encouraging dialogue, clarifying positions, and keeping the negotiation constructive.

Examples of Great Phrases

• Is there anything I am missing…?
• Have you given up on this…?
• Is it okay if…?
• I am curious…
• It sounds like…
• Tell me about…
• OK, help me understand…

These phrases demonstrate humility, curiosity, and a desire to understand, which are key elements of building trust and achieving better results.

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Conclusion

Asking high-quality questions is a game-changer in negotiations. By focusing on “How,” “What,” and “Why” questions, and complementing them with great phrases, you can steer conversations toward productive outcomes. Whether you’re addressing objections, seeking clarification, or exploring solutions, it allows you to gain insights, uncover motivations, and move closer to a successful agreement.

Also see the importance of great questions in this article ‘The Surprising Power of Questions’..

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About AMST Legal

At AMST Legal, we provide negotiation and contract advice to help businesses achieve better results. Contact us at lowa@amstlegal.com or book a meeting here for help with a negotiation or for (team or individual) training to become a better negotiator.