How To Use Effective Questioning To Unlock Value In Negotiation

Good questions are like master keys—they have the ability to unlock many doors and open up vast opportunities, both professionally and personally. Given how important and powerful they are to negotiation, in particular, it’s surprising just how many common and damaging myths continue to persist around them.

This may be because “question asking” as a skill is not widely taught outside of fields that specifically require it, such as medicine, law, and journalism.

What’s worse, the teachings we receive about how to approach negotiations often totally overlook the value of effective questioning. We’re taught both subtly and overtly that we need to sell ourselves, demonstrate our value, talk ourselves up. The way to success is to list our demands and prove ourselves, not to inquire about the other party’s needs, wants, or desires.

Moreover, we’ve been taught to respect and admire the person who “plays hardball.” Commanding negotiators tend to steal the spotlight, leaving careful listeners and thoughtful questioners in the shadows. And so, many people enter a negotiation with the mindset that the most important priority is stating their case and arguing for it.

The truth is, getting people to like us and getting them on our side is a far easier task when we demonstrate an interest in them by asking them questions and letting them talk.

Dale Carnegie shared this truth nearly a century ago in his classic book How to Win Friends and Influence People and it has been echoed many times by many great thinkers since. And yet, so many of us still don’t put this key principle into practice.

The good news is, this is a skill that can be learned by anyone and has limitless potential for improvement.

So how can we begin asking better questions? Let’s start by considering why this is difficult in the first place.

Why effective questioning is difficult

This goes back to another prevalent perspective that isn’t always true: that negotiations are inherently adversarial.

When either or both sides approach a negotiation as a zero-sum scenario (that is, your gain is my loss and vice versa), questions will naturally raise hackles. Questions from the opposing party can trigger feelings of suspicion and vulnerability and thoughts of “is this person trying to expose or exploit me?”

Sidestepping this aversion to questioning requires a paradigm shift, from one of a battle over resources, with a clear winner and loser, to one of an opportunity to explore new possibilities and value that stem from collaboration. And it isn’t always easy to shed this kind of thinking.

Later on in the article, we’ll go into greater depth about how to handle competitive conversations versus collaborative ones, but before we do that, let’s explore why effective questioning is important.

Why effective questioning is important

One way to answer this question is to consider what happens when you don’t ask effective questions. In short, a lot of potential value is lost.

Asking the right questions can bring much crucial information to light and illuminate possibilities that benefit both parties. It’s probably one of the most reliable ways to get to the coveted “win-win” outcome that is so often mentioned in the context of negotiations but is so rarely achieved. Most negotiators fall into the trap of going on the defensive and if they do manage to pose questions, they do so in a way that, at best, fails to draw out useful information and, at worst, offends the other party.

This brings us to the other major benefit of asking questions (when done well): it takes the chill out of the room, helps build bonds, and puts people at ease. When people let their guard down, they’re much more likely to reveal information that could be useful in a negotiation. In any case, you have more information to work with than if they retreat into their shells.

It’s also important to note that multiple studies confirm that most people aren’t aware of this link between questioning and positive regard. While they may be able to remember being asked questions throughout a conversation, they generally don’t realize to what extent it’s responsible for increased cordiality. So, being an effective questioner not only helps you get the information you want and need, it does so in a way that doesn’t raise eyebrows or red flags.

And as we all know, negotiations tend to have better outcomes when they are amicable rather than not.

It’s clear that effective questioning isn’t utilized enough and it has the potential to yield untold benefits when done well. This brings us to the million-dollar question: how do we go about asking effective questions?

How to ask effective questions

The number one way to improve at asking questions is to just do more of it. This simple advice comes with a caveat, however. It’s crucial to pay attention to the type of questions you ask, the tone you use, the sequence in which you ask them, and how you frame them.

Here are some methods you can use to help you ensure that your questioning is high in quality as well as quantity.

Make good use of open-ended questions

Open-ended questions are ones that require more than a simple yes or no or limited answer. They are superior when it comes to information gathering for several important reasons. Firstly, they don’t put people on the spot the way that closed-ended questions can. So they help prevent and diffuse tension. Secondly, they invite elaboration. An open-ended question is one that naturally elicits elaboration and detail, as opposed to a one-word answer.

Closed-ended questions have their place, too. There are some points in a conversation or negotiation when it’s preferable to have a short, to-the-point answer. However, most of the time, a successful negotiation strategy leans heavily on open-ended questions, especially early on in the talk when both sides are still sussing out each other’s motivations and goals. 

Find ways to follow up

If the other party in a negotiation isn’t being as forthcoming as you would like, you can encourage them to divulge more by probing them with follow-up questions. Common ways to nudge for more information include asking “What happened next?” and “Could you tell me more?”

You don’t even necessarily have to ask questions. Statements that indirectly request more information can be just as effective, such as “I see.” Another tactic is to summarize and restate what you’ve heard and tack on a tag question at the end. An example might be “What I’m hearing is that the budget will need to be adjusted to include three additional staff and the deadline extended by three months. Would you say that’s accurate?” 

Yet another way to gently probe for more is through no question at all. Silence exerts subtle but powerful pressure on someone who is being reticent. By simply allowing the silence to continue after the other party has spoken, and using social cues such as nodding and keeping your pen poised to write, you communicate that you are expecting more information to be provided. That mere expectation alone is often enough to motivate the other person to say more.

Buffer questions with explanations

Offering background information can help avoid creating a situation where the other party feels interrogated. Giving an explanation provides helpful context that can make questions seem less targeted and abrasive. Rather than asking “Doesn’t this deadline seem unrealistic to you?” you could rephrase the inquiry with the following explanation: “We’ve found that projects of this scale typically require a minimum of three months. Could you talk about how you see the workflow being paced to shorten that timeline to two months?”

Navigating competitive conversations versus collaborative conversations

The strategies we covered above provide the groundwork for improving your skill as an effective questioner. You’ll need to fine-tune your approach depending on the nature of the conversation and the goals of the involved parties.

In general, discussions fall somewhere along a spectrum that has as its two ends cooperative conversations (in which both sides are seeking to form a relationship or achieve a joint outcome) or competitive conversations (in which both sides have mutually exclusive interests or are looking to expose specific information about the other).

Here are some of the challenges you may encounter in the different types of discussions and tactics for navigating them successfully.

Competitive Conversations

When you are asking questions in a competitive conversation, you may find the other party is hesitant about sharing information and is either evasive or untruthful. In these cases, you can try:

●     Asking direct yes/no questions to cut through equivocation

●     Asking detailed follow-ups, even at the risk of being repetitive

●     Couching difficult questions in pessimistic terms (ie. “We’re looking at a late payment situation, is that right?”), which reduces the likelihood that the other party will lie

●     Tackling the most sensitive questions at the outset to dispel discomfort and lay the way for subsequent questions to feel less pointed

Collaborative Conversations

When you are asking questions in a collaborative conversation, you may find that your counterparts are reticent in order to avoid conflict or to withhold bad news. In these situations, you can try:

●     Asking open-ended questions to encourage more discussion

●     Asking the other party to play devil's advocate to give them a way to speak frankly

●     Starting with softball questions to develop rapport and building up to trickier questions from there

●     Framing tough questions using pessimistic assumptions as noted for competitive conversations

In Closing

“Half of science is asking the right questions.”

Philosopher Roger Bacon could have just as easily been talking about negotiations when he made this statement. Effective questioning is fundamental to developing trust, discovering new opportunities for collaboration and progress, and arriving at mutually beneficial outcomes. In short, questions are key to unlocking all of the potential of negotiations.