The Questions That Will Tank Your Negotiation (and What to Ask Instead)

If you’ve been in any negotiation, you know that the questions you ask aren't just about gathering information—they’re tools that shape the dynamics of the conversation. Over the years, I’ve seen negotiators make or break deals based on how they wield their questions. Here’s my take on what makes a question good or bad in a negotiation and why the timing and purpose of those questions matter.

The Trap of Bad Questions: Why Closed-Ended and Yes-Oriented Questions Fail

Let’s start with the bad questions. These are your closed-ended, yes-oriented questions, or (with one exception) anything that starts with “why.” These types of questions can shut down your counterpart and derail the negotiation.

1. Closed-Ended Questions: These are the questions that can be answered with a simple “yes” or “no” or any other one-word answer.   They kill the flow of the conversation and rob you of the chance to learn more. When I hear a closed-ended question, I respond with a short, one-word answer to make my point. If you ask me, “Can we move forward?” I’ll say, “No.” I do this to drive home the fact that you asked a lazy question that did nothing but close the door on a deeper discussion. Closed-ended questions stifle dialogue, and they miss opportunities to dig into the details that matter.

2. Yes-Oriented Questions: Here’s the thing about yes-oriented questions—they sound like they’re creating agreement, but they’re actually just pushing your counterpart into a corner. Questions like, “Do you agree this is a good idea?” are used to drive the person to say, “Yes.”  It is about building what is often referred to as “Yes” momentum.  The idea is that if you can get the person to say yes multiple times during a conversation, the more inclined to say “yes:” when you make your big ask.  This approach is fundamentally flawed. “Yes” is a commitment, and commitments shouldn’t be forced. The moment someone feels pushed into saying yes, they start getting defensive, hesitant, and resistant. You think you’re creating momentum, but you’re actually creating pushback. Instead of feeling involved, your counterpart feels like they’re being led somewhere they didn’t volunteer to go.

3. Why Questions: “Why” is usually the worst question you can ask because it puts your counterpart on the defensive. No matter the language or culture, a “why” question implies judgment. It suggests that there’s a right answer that they don’t have, setting up a dynamic where the person receiving the question feels inferior. The only time “why” has any value is when you specifically want them to defend your position, like in a Proof of Life® scenario, where you’re trying to get them to explain why they value working with you. Otherwise, “why” is almost always a waste of breath.

The Power of Good Questions: Calibrated

Good questions are all about opening up the conversation and drawing the other side in. They’re designed to get your counterpart thinking, talking, and engaging with you. These questions are typically open-ended (referred to as Calibrated Questions by BSG), starting with “what” and “how,” and they serve a purpose far beyond just filling in the blanks.

1. Calibrated Questions: These questions invite your counterpart to think out loud, which is exactly what you want in a negotiation. Instead of asking, “Are you willing to move forward?” a Calibrated Question might be, “What would have to be true before moving forward?” or “How does proceeding with us align with your overall goals?” You’re not just seeking information; you’re shaping the conversation. These questions push your counterpart to reveal their thought process, and that’s where you find the real value in a negotiation.

2. Implementation Calibrated Questions: These are some of my favorite questions because they force your counterpart to troubleshoot future challenges and consider practical outcomes. For example, if I know a potential issue might arise, I’ll ask, “What happens if we fail?” or “How will this look six months down the road if we haven’t improved?” These questions are about getting the other side to look ahead and engage in problem-solving with you. They create a shared sense of accountability and drive the negotiation toward actionable results.

3. Time Travel Calibrated Questions: This is a technique that takes your counterpart back to a moment in time when things were working well or when an agreement was made. I’ll say, “When you agreed to X, what should my expectations have been?” or “When you said Y, what did that mean to you?” These questions are powerful because they hold the other side accountable to their past commitments without coming off as confrontational. It’s about bringing them back to a point where there was alignment, and from there, you can address any inconsistencies.

Shaping the Negotiation with Purpose-Driven Questions

Good questions are about more than just gathering facts—they’re about shaping your counterpart’s thinking in a way that benefits both parties. When you ask the right questions at the right time, you’re not just collecting data; you’re creating a collaborative environment where both sides feel heard, understood, and engaged.

I always say that the best questions can happen anywhere in the conversation, whether at the beginning when you’re setting the tone, in the middle when you’re exploring options, or at the end when you’re troubleshooting potential roadblocks. 

Every question you ask in a negotiation has a purpose—make sure it serves not only your objectives but also the needs of your counterpart. That’s how you turn a negotiation into a productive dialogue rather than a battle of wills. Remember, it’s not about getting the other side to say yes; it’s about getting them to think, engage, and arrive at a solution that works for everyone. That’s the real power of good questioning.