Right Questions in Negotiations | RED BEAR Negotiation Company

Asking the right questions is a game-changer in any negotiation. 

Just this past week, I spoke with a procurement leader at a technology company who was brought in to support his team on a rather tense negotiation with a leading CRM organization.

It didn’t take a lot of digging to discover that internally, they weren’t clear on the true needs, wants, expectations, and motivations of the other party. 

They hadn’t gotten past the rehearsed elevator pitch. 

So that’s where he started. 

And through the productive conversations that followed, they were able to meet their savings targets and maintain the relationship with their supplier. 

How can you ask the right questions in any negotiation? 

Let’s open the playbook. 

WHY ASKING THE RIGHT QUESTIONS MATTERS

In negotiation, asking the right questions is the difference between blindly accepting information and steering with purpose. When you rely on critical thinking and critical analysis, you move beyond simply memorizing or simply accepting information. 

Instead, you dig for significant information—context, motivations, and the behind-the-scenes drivers that shape the other party’s decisions. This is how you spot rival causes, challenge descriptive assumptions, and close the gap between what’s on the page and what’s still left to be discovered.

The right questions don’t just help you gather data—they show the other side you care, that you’re genuinely interested in their perspective. This builds trust and strengthens the relationship, which is key in any negotiation, whether you’re dealing with suppliers, customers, or internal stakeholders. 

Think about it like an interview: a bad interview is flat, uninspired, and forgettable. A good interview is dynamic, engaging, and often leads to unexpected insights. 

The same holds true in negotiation—good questions create energy, reveal alternative points, and help both sides reach reasonable conclusions grounded in evidence, not just opinion.

WHAT MAKES A “GOOD” QUESTION?

Sometimes you won’t know what works if you don’t know what doesn’t work, right?

So let’s start with a bad question:

“Do you agree with our proposal?”

On the surface, you may think this sounds fine, but it’s really not doing much for you. Why? 

It’s closed, invites a one-word answer, and gives you nothing to work with. It doesn’t challenge assumptions, doesn’t encourage critical analysis, and certainly doesn’t help you develop a solid foundation for your strategy. 

Closed questions like this don’t help you spot fallacies, explore rival causes, or uncover omitted components.

Now, let’s flip it.
“What concerns do you have about our proposal, and how do you see those affecting your decision?”

This question is open, invites the other party to share significant information, and encourages them to think critically about their own position. 

It’s not just about gathering facts—it’s about exploring issues, testing assumptions, and developing a deeper understanding of the other side’s reasoning.

EXAMPLES OF GOOD QUESTIONS IN A NEGOTIATION 

The key difference? Good questions are open, nonjudgmental, and focused on eliciting real, actionable information. 

They help you challenge assumptions, spot manipulations, and develop a negotiation strategy that taps into the greater challenge of critical analysis and evidence. 

In short: If you want to make better personal choices, reach reasonable conclusions, and create value in every negotiation, start by asking the right questions.

BEST TYPES OF QUESTIONS TO ASK IN A NEGOTIATION 

Not all questions are created equal, especially in a negotiation. The best negotiators know how to use questions strategically to uncover critical information, build relationships, and shape the conversation. 

Broadly, these questions fall into two major categories: Situational Questions (Stage 1) and Discovery Questions (Stage 2). 

Each serves a distinct purpose and plays a crucial role in driving the negotiation forward.

SITUATIONAL QUESTIONS

At the start of a negotiation, you need to understand the lay of the land. This is where Stage 1 Questions come in. 

These are situational questions designed to get the other party to share existing information about their situation, challenges, needs, and goals. 

The goal here is simple: listen and learn.

When you ask these questions, the other party becomes the expert in the room. They explain their context, inform you about their priorities, and relate their perspective—all while giving you valuable insight into what’s driving their decisions. 

The result? You gain clarity on their situation, and they feel heard and understood—a critical step in building trust.

Here are some examples of effective Stage 1 Questions:

• “What are the biggest challenges you’re currently facing with your supplier?”
• “Can you walk me through your decision-making process for this project?”
• “What outcomes are most important to your team?”
• “How would resolving this issue impact your operations?”

These questions encourage the other party to open up while allowing you to gather significant information without appearing pushy or aggressive.

The power of Stage 1 Questions lies in their ability to establish a solid foundation for the negotiation. 

By understanding the other party’s situation clearly, you can tailor your approach to address their specific needs and concerns. 

Moreover, these questions help create a dynamic where the other party feels like they’re educating you—a subtle but effective way to build rapport.

DISCOVERY QUESTIONS

Once you’ve established a clear understanding of the situation, your greater challenge is to dig deeper.

Stage 2 Questions, or discovery questions, are designed to move beyond the surface and uncover new information—especially around motivations, priorities, and underlying needs. This is where the real value in negotiation emerges.

With discovery questions, you’re not just collecting facts; you’re encouraging the other party to envision possibilities, compare alternatives, and share what truly matters to them. 

These questions prompt reflection and often lead to new insights for both sides. The customer starts to see their situation from a fresh angle, and you gain a deeper understanding of what will drive a successful outcome.

Here are some powerful Stage 2 Questions to use in your next negotiation:

• Get them to prioritize: “If you had to rank your top three priorities for this agreement, what would they be?”
• Push them to think in hypotheticals: “Suppose we could address that delivery timeline—how would that change your view of the proposal?”
• Encourage them to thoughtfully compare: “How does our solution compare to others you’ve considered in terms of value and support?”
• Bring out their emotions: “What concerns you most about making a change right now?”

These questions go beyond simple information gathering to help both parties challenge assumptions, spot rival causes, and explore alternative points. 

The result is a conversation that’s not just transactional, but transformative. The customer feels you’ve helped them think more critically about their own needs and options, and you walk away with insights that can shape a more compelling, mutually beneficial agreement.

By weaving discovery questions into your negotiation, you move from simply accepting information to actively developing new value. This is where real breakthroughs happen.

WHEN TO ASK EACH TYPE OF QUESTION

Timing is everything in negotiation. Even the best questions fall flat if you ask them at the wrong moment. 

Knowing when to use each type of question is just as important as knowing what to ask. The right sequence helps you build a solid foundation, avoid misunderstandings, and guide the conversation toward real value.

Start with situational questions (Stage 1) at the very beginning of the negotiation. This is your information-gathering phase. You’re laying the groundwork, building rapport, and showing genuine interest in the other party’s context and challenges. At this stage, you’re not pushing for commitments or solutions—you’re listening, learning, and making sure you have all the facts before moving forward.

Once you’ve established trust and have a clear understanding of the basics, it’s time to shift gears. Discovery questions come into play when the conversation gets more complex—when you’re in the thick of the negotiation, relationships are established, and you’re ready to move beyond surface-level details. 

For example, if the other party starts pushing hard on price, that’s your cue to pivot to Stage 2 questions. Instead of getting stuck in a numbers game, you can steer the conversation back to value, priorities, and what really matters to both sides.

Remember, effective negotiators don’t wing it—they plan their questions in advance. By mapping out when to use situational versus discovery questions, you ensure you’re always a step ahead. This approach helps you avoid blindly accepting information, spot gaps in reasoning, and respond strategically as the negotiation unfolds. 

Laying this groundwork means you’re ready to adapt, dig deeper, and ultimately drive the conversation toward a stronger, more sustainable agreement.

LEARN TO ASK THE RIGHT QUESTIONS, EVERY TIME

Mastering negotiation isn’t about having all the answers—it’s about knowing how to ask the right questions at the right time. 

When you approach each conversation with critical thinking and a clear strategy, you uncover important information, challenge assumptions, and create real value for everyone at the table. 

The difference between a stalled deal and a breakthrough often comes down to the questions you ask and how you listen to the answers.

If you’re ready to sharpen your negotiation skills and consistently drive better outcomes, RED BEAR’s negotiation training gives you the tools, techniques, and real-world practice you need. 

Don’t settle for surface-level conversations—learn how to dig deeper, spot rival causes, and build agreements that last.

Contact RED BEAR today and start asking the questions that move the needle.