How the Right Questions Shape Outcomes and Unlock Success

Negotiation is a fundamental pillar in the world of business and enterprise leadership. Whether you are an entrepreneur building a startup, a manager leading a team, or a professional navigating partnerships and contracts, your ability to negotiate effectively is a key driver of progress. At its essence, negotiation is the art and science of reaching agreements—often in situations where interests differ—by employing dialogue, persuasion, and compromise. It is about finding common ground, resolving conflicts, and crafting outcomes that create value for all involved.

Negotiation is not restricted to formal settings like boardrooms or contract signings. It permeates everyday interactions: aligning on project timelines, setting priorities, determining budgets, resolving team disagreements, or deciding strategic directions. Any conversation in which two or more parties have the power to shape an outcome is, at its heart, a negotiation. Even conversations regarding resources, coalition-building, or vision alignment within your enterprise rely on your negotiation acumen.

So why is it so important to become an effective negotiator? The answer lies in the ability of negotiation to shape your enterprise’s future. Effective negotiators break through impasses, unlock opportunities, and build trust. They move their organization’s vision forward not by force or authority, but by skillfully guiding discussions, understanding needs, and forging agreements that benefit all sides. This ability enhances collaboration, strengthens partnerships, and ensures long-term success.

As we explore the nuances of negotiation, I encourage you to consider reading “Never Split the Difference” by Chris Voss. Drawing from his experience as a lead international kidnapping negotiator for the FBI, Voss distills powerful lessons about human psychology, communication, and tactical negotiation. One of the most valuable takeaways is the recognition that negotiation is not a zero-sum game—it is an intricate dance requiring empathy, strategic questioning, and the ability to shape the conversation. If you aspire to sharpen your negotiating skills, this book is an indispensable resource. Many of the techniques discussed here have been elaborated upon in Voss’s work, and I highly recommend you add it to your reading list.

“Why?” Questions—Accusations

One of the most overlooked aspects of negotiation is the framing of questions. The way you pose a question can transform the tone of a discussion, influencing whether it becomes collaborative or contentious. Let us begin with questions that start with “why.”

At first glance, “why” questions seem logical; after all, seeking to understand someone’s rationale appears reasonable. However, as Chris Voss explains, “why” questions are often received as accusations rather than invitations to share information. The moment you ask, “Why did you do that?” or “Why are you requesting these terms?”, you may inadvertently trigger defensiveness. The word “why” carries an implicit judgement, suggesting that the recipient must justify or defend their choices, actions, or beliefs.

This subtle dynamic communicates suspicion or challenge. The counterpart may infer that you are questioning their motives, doubting their intentions, or implying blame. Instead of fostering openness, “why” questions tend to provoke anxiety, self-protection, and a reluctance to share further insights. In the context of negotiations, this is problematic. Defensive postures can lead to stonewalling, escalation of conflict, or a breakdown in trust.

Consider these examples:

• “Why are you asking for such a high price?”
• “Why can’t you deliver the project sooner?”
• “Why did you choose that supplier?”
• “Why don’t you want to expand the budget?”

In each instance, the recipient may feel as though they are being interrogated, not invited to collaborate. This perception can shut down dialogue, causing the person to guard information or respond tersely. The overall effect is detrimental: the negotiation becomes rigid, with both sides digging into their positions rather than exploring solutions.

Let’s illustrate further. Imagine you are negotiating a joint venture, and you ask, “Why aren’t you willing to increase your investment?” The other party might interpret this as criticism, leading them to justify their stance rather than reveal their actual constraints or concerns. As a result, the conversation stalls, and opportunities for compromise are lost.

As an educator in negotiation, I advise professionals to avoid “why” questions unless trust is high and the relationship is strong enough to withstand potential defensiveness. Instead, seek alternatives that invite dialogue without accusation. For example, replacing “Why is your price so high?” with “How did you arrive at this pricing?” opens the door to discussion rather than confrontation.

“What” Questions—Limiting

Let's now turn our attention to “what” questions—another common form of inquiry in negotiation. These questions are typically used for clarifying details, establishing facts, or narrowing down options:

• “What is your bottom line?”
• “What are your terms?”
• “What do you need to close this deal?”
• “What will it take to get this proposal approved?”

While such questions are useful for obtaining specific pieces of information, they tend to limit the conversation’s scope. By asking “what,” you direct your counterpart to provide a particular answer, which can restrict the sharing of context, rationale, or underlying interests. The result is a transactional exchange, where parties trade facts but rarely uncover the deeper motivations or constraints behind those facts.

In negotiation, limiting information can be risky. You may fail to understand the full picture, overlook creative possibilities, or miss signals about flexibility. For example, if you ask, “What are you willing to pay for this service?” the answer might be a single figure. Yet the counterpart’s willingness to negotiate on payment terms, scope, or timing remains undisclosed.

The subtle message of “what” questions is that you are focused on outcomes, not processes. The recipient may feel pressure to commit to a position, rather than collaborate on alternatives. This can lead to rigidity, with both sides adhering to stated demands and missing the chance to discover mutually beneficial solutions.

Let’s explore a scenario: You are negotiating a merger, and you ask, “What would it take for you to agree to this deal?” The other party might respond with a list of demands, but the answer may not reflect deeper concerns, such as cultural fit, integration risks, or strategic priorities. By focusing solely on “what,” you may miss the opportunity to explore areas of flexibility or innovation that could unlock agreement.

Instead, strive to use “what” questions judiciously. They are valuable for clarifying boundaries or requirements, but should be supplemented with inquiries that invite broader discussion. For instance, pairing a “what” question with a “how” question—“What are your priorities for this partnership, and how do you see them being addressed?”—can encourage your counterpart to share more context and engage in creative problem-solving.

“How” Questions—Opening the Door

Among all forms of inquiry, “how” questions reign supreme in their ability to foster collaboration, elicit valuable information, and drive negotiations forward. “How” questions are inherently open-ended, inviting the other party to share their process, reasoning, concerns, and ideas. They signal genuine curiosity and respect, creating an atmosphere conducive to constructive dialogue.

When you pose a “how” question, you communicate several key messages:

• You are interested in understanding the other party’s perspective.
• You value their expertise and want their input.
• You seek to work together, not merely exchange demands.

This approach transforms the negotiation dynamic from adversarial to cooperative. The counterpart feels heard and respected, making them more likely to share information, reveal constraints, and participate in joint problem-solving.

Consider these examples:

• “How can we structure this agreement to benefit both sides?”
• “How did you develop your proposal?”
• “How would you address the timing issues that concern us both?”
• “How do you envision overcoming the challenges in implementation?”
• “How might we adjust the scope to fit within both budgets?”

Each question encourages the recipient to explain their reasoning, voice concerns, and suggest solutions. This openness paves the way for creative options, breakthrough ideas, and deeper trust. It also allows you to uncover motivations that may not be stated directly.

Let’s look at a practical example: Suppose you are negotiating a strategic alliance and ask, “How can we ensure our teams are aligned throughout the partnership?” This question not only prompts discussion of specific strategies, but also invites the other party to share their experience, preferences, and perceptions of potential risks. The result is a richer conversation, more innovative solutions, and an agreement tailored to both sides’ needs.

Moreover, “how” questions help diffuse tension. When discussions become heated or reach an impasse, shifting to “how” reframes the negotiation as a joint effort. Asking, “How can we move forward given our current constraints?” signals your willingness to collaborate and adjust, rather than demand or judge.

In my years teaching negotiation, I have seen “how” questions unlock powerful shifts in attitude and outcome. They transform negotiations from transactional exchanges to opportunities for partnership and mutual growth—precisely the mindset needed to move your enterprise vision forward.

Sharpen Your Negotiation Skills to Move Your Vision Forward

Negotiation is the driving force behind progress in any enterprise. It occurs whenever parties must reconcile differing interests, and the success of your business vision depends on your ability to negotiate with skill and sensitivity. The questions you use in negotiation profoundly shape the course and outcome of those conversations.

“Why” questions, though common, are often received as accusations, triggering defensiveness and limiting dialogue. “What” questions can help clarify facts but risk constraining the flow of information and creative opportunity. “How” questions, by contrast, invite openness, collaboration, and the co-creation of solutions—yielding richer insights and stronger agreements.

As professionals and leaders, our challenge is to master the nuances of questioning and conversation. By integrating these principles—especially the strategic use of “how” questions—you will empower yourself to build trust, unlock innovation, and move your enterprise’s vision forward.

To deepen your expertise, I encourage you to read “Never Split the Difference” by Chris Voss. The lessons in this book will complement what you have learned here and equip you with advanced tools for negotiation success.

Are you ready to take your negotiation skills to the next level? I invite you to schedule a complimentary 30-minute strategy session. Together, we will analyze your negotiation challenges, identify opportunities for growth, and develop a personalized action plan to ensure your enterprise thrives. Click here to book your free session and begin your journey to negotiation mastery.