Questions can make or break a negotiation, yet it is an element that many negotiators get wrong.
Come in too strong and you could put the other party on the defensive (e.g., Do you want this deal or not?) Fail to assert your proposal strongly enough and you might miss out on a good deal (e.g., Is there any chance you could improve the terms?).
With the right questions, though, you can open up discussion, defuse tension, and get the other party's perspective. Let's see how negotiation questions are strategic, what the best types of questions to ask are, and why some are to be cautious about.
According to a 2025 study of over 180,000 AI negotiations by Cornell University, "positivity, gratitude, and question-asking (associated with warmth) were strongly associated with reaching deals."
Why is this?
It is no wonder that negotiations have a reputation for being tense. Faced across from someone at a negotiation table, you might feel like a grandmaster battling it out on a chessboard. Opening the game with a question helps break the ice and move the game from a competitive to a collaborative approach.
Questions help clarify the other individual's perspective by surfacing their needs, constraints, and motives. With an understanding of their priorities, it is easier to manage expectations and persuade them towards a mutually beneficial agreement. At Scotwork, we call this stage of the negotiation process the Argue step, in which both parties attempt to ferret out the most useful information.
If the negotiation keeps stalling on minor details, questions could be the jumpstart that gets you back on the road. This is because you may get stuck because of unaddressed concerns: with good questions, you can find out what these are, and keep the conversation moving forward.
Questions give you greater control in negotiation, allowing you to subtly drive the discussion without appearing confrontational. This can be particularly powerful if you are in a weaker negotiation position. In a salary negotiation, for example, it could be effective to ask your employer a hypothetical question like, "What would happen if we looked at a performance-based bonus structure?"
Novice negotiators often fail to prepare for anything other than the perfect scenario: blinkers on, they are often blindsided when the other party doesn't respond as expected.
An experienced negotiator, on the other hand, prepares for multiple scenarios and anticipates that the other party may throw in a curveball. They use questions to move with the flow of the negotiation, striking a balance between securing important provisions and leveraging opportunities for valuable compromise.
Here are five types of questions that will keep you in control, even when the negotiation takes an unexpected turn.
A classic case of a closed-ended question is when a parent asks their teen, "Did you have a good day?" only to be met with a one-word response and a lapse into silence.
Open-ended questions, on the contrary, are those that require an answer beyond a basic "yes" or "no." Also known as calibrated questions, they usually begin with "how" or "what" and are an effective means of encouraging dialogue and building rapport.
To illustrate, when former FBI negotiator Chris Voss was sent into high-stakes hostage negotiation situations, he would use questions like "What are we trying to accomplish here?" and "How am I supposed to do that?" to get to the heart of the issue, aiming for a solutions-based approach that saved people's lives.
A subset of open-ended questions, probing questions help uncover extra information from the other party. Use probing questions as a way to draw out a deeper answer if you feel that the other party is displaying emotional resistance and holding back useful information.
Imagine a person in the process of buying a second-hand car. They notice that the car has been sold three times in the space of two years, so they bring it up to the car salesperson, asking, "Can you elaborate on that?" In the process, they may uncover information about the car that leads to a discount in the price.
In high-stakes deals, you can't afford misunderstandings. Clarifying questions help to confirm whether you have understood the other side's proposal correctly, or not, before you sign on the dotted line. This also demonstrates that you have been listening, and makes it more likely that the other party will remain open to your concerns for the remainder of the negotiation.
For instance, your client tells you that they "need more flexibility." Rather than assume what they mean, you ask, "When you say flexibility, are you referring to timeline or scope?" to clarify the details.
In the "negotiator's dilemma," you are caught between the necessity of remaining open and collaborative, while pushing to strike the best possible deal. According to a study from Harvard's Negotiation Journal, hypothetical questions can be used as a strategic device to combat this, allowing you to successfully broach uncomfortable yet relevant information without offending.
While trying to secure a job offer, for example, you may be asked about your salary expectations. In response, it can be effective to ask questions of your own, such as, "What would it look like if we explored what success in this role is worth to the business?"
It might sound counterintuitive, but introducing no-orientated questions into the state of play can yield some positive results. By giving the other person an "out" (permission to say no), they are likely to feel more in control and, as a result, more positively disposed towards you for the duration of the negotiation.
For example, a soon-to-be father wants to discuss paternity leave with his employer, so he tests the water by asking HR, "Are you against 12 weeks of paternity leave for employees?"
One potential answer is, "No, but we have a few concerns..." which opens up the negotiation in his favour, while revealing any hesitations on the part of the employer–essential information that will help him negotiate more effectively going forward.
The alternative is that yes, they are against it, "but may be open to discussing other options." Again, a positive start to what could be a difficult negotiation.
Having strong communication and negotiating skills means not only knowing what to say, but also what not to say. The following types of questions are unlikely to serve your negotiation and may even damage it.
In a negotiation, confidence (or at least the appearance of confidence!) is key. Vague questions don't only make you seem nervous and unprepared, but they also merit a vague answer. Neither is conducive to gaining the thorough details you need for a formal written agreement.
Vague questions might sound like:
"Is that okay?"
"If that makes sense?"
"Can we sort something out?"
A 2022 study by Frontiers Psychology found that while expressing anger in negotiation can lead to short-term positive economic returns, it does so at the cost of relationship in the longer term. These aggressive questions should be treated with caution:
"Do you want this deal or not?"
"Are you seriously asking for that?"
"Why are you being so difficult?"
A wise man once said...nothing at all. Staying calm and collected despite the pressure and potentially negative communication from the other side is essential for staying in control of a negotiation. These aren't questions you should be asking to begin with. And if someone does ask, resist the urge to give them a piece of your mind.
"Don’t you care about quality?"
"Why would you even suggest that?"
"Are you trying to make me look bad?"
Our capability survey shows that only 32% of negotiators know what questions to ask before entering a negotiation. Are you part of the majority that unfortunately doesn't?
You can change this by leveraging Scotwork's 8-Step Approach© for negotiation, so next time you are at the negotiation table, you will be comfortably seated to ask questions with purpose and poise. Get in touch today.
