Podcasts > Creating Confidence with Heather Monahan > Confidence Classic: Master Negotiation to Get What You Deserve with Chris Voss, Alex Carter & Molly Fletcher

Confidence Classic: Master Negotiation to Get What You Deserve with Chris Voss, Alex Carter & Molly Fletcher

By Heather Monahan

In this episode of Creating Confidence with Heather Monahan, negotiation experts Chris Voss, Alex Carter, and Molly Fletcher share strategies for effective negotiation that go beyond tactics and counteroffers. They emphasize that successful negotiation depends on building strong relationships, understanding the other party's perspective, and asking the right questions to uncover true needs and concerns.

The conversation covers several practical techniques, including the use of open-ended questions that begin with "tell me," the strategic value of triggering "no" responses to help people feel in control, and the power of silence in negotiations. Fletcher and Voss particularly stress how pausing—whether for seconds or weeks—demonstrates confidence and often leads the other party to make concessions. Throughout the discussion, the experts highlight that thorough preparation and genuine listening are essential foundations that enable negotiators to use these techniques effectively.

Confidence Classic: Master Negotiation to Get What You Deserve with Chris Voss, Alex Carter & Molly Fletcher

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Confidence Classic: Master Negotiation to Get What You Deserve with Chris Voss, Alex Carter & Molly Fletcher

1-Page Summary

Rapport Building and Understanding Perspectives In Negotiation

Negotiation experts emphasize that success depends on building rapport, understanding perspectives, and asking the right questions—not just tactics and offers.

Strong Relationships Key to Negotiation Success

Molly Fletcher stresses that negotiation is fundamentally a conversation where strong relationships drive better and faster outcomes. She explains that approaching negotiation relationally rather than transactionally leads to healthier connections and future opportunities. Fletcher shares that stronger relationships with industry contacts consistently resulted in more effective deals throughout her career as an agent.

Chris Voss echoes this, noting that adversarial tactics can damage future opportunities. He explains that maintaining professionalism and respect is crucial, even in high-stakes situations like hostage negotiations. When people feel understood and cared for, they're more likely to feel satisfied even without major concessions. Alex Carter demonstrates how leveraging existing relationships and building trust-based networks can effectively mobilize groups and close deals. Heather Monahan emphasizes that negotiation is ultimately rooted in deepening and leveraging all types of relationships.

Open-Ended Questions Uncover True Needs and Concerns

Voss advises that the biggest mistake negotiators make is not hearing the other side out first. He notes that listening calmly and empathetically, even adjusting vocal tone to a calming cadence, can resolve most issues before they escalate.

"Encourage Openness With 'Tell Me'"

Alex Carter advocates replacing yes/no questions with open-ended prompts starting with "tell me." These conversational commands prompt people to share more information. Carter cites research showing that 93 percent of negotiators fail to ask the right questions to maximize deal value, and using "tell me" places negotiators in the top 7 percent who do. Fletcher reiterates that discovering what matters most comes from genuine preparation and active listening, which uncovers real concerns and forges deeper connections.

Strategic Questioning to Gather Information and Build Connection

Chris Voss and Heather Monahan discuss techniques that deepen understanding and build genuine rapport through strategic questions that make the other party feel understood.

Triggering "No" Can Provide Insights and Advance Negotiations

Voss argues that traditional "yes momentum" backfires by violating people's sense of autonomy. Instead, triggering a "no" response can be more productive. He intentionally asks questions like "Is this a bad idea?" because when people reply "no," they feel safe and in control, allowing them to be candid about concerns.

Monahan clarifies that this works because saying no allows the other person to take ownership, often leading them to defend the merits of the idea. Voss adds that after a "no," people are much more likely to reveal their true objections, providing invaluable information. He gives an example of suggesting potential clients might be better off with competitors—if they're committed, they'll explain why his team is the right choice, and if not, he can end the conversation respectfully.

Summarizing the Other Party's Viewpoints Shows Understanding

Voss stresses the power of summarizing the other side's position until their only possible response is "That's right." This thorough summarization demonstrates empathy and validation. He considers this emotional validation a tremendous advantage in negotiations, crediting his hostage negotiation background for teaching him to always hear out the other side first using a calm tone and full listening.

Leveraging the Power Of Pausing In Negotiation

Pausing during negotiations is a powerful yet often overlooked tactic that both Molly Fletcher and Chris Voss emphasize.

Silence in Negotiation Can Lead To Breakthroughs

Fletcher identifies failing to pause as the biggest negotiation mistake. Silence demonstrates firmness and comfort with one's position. She shares a story where she paused for a minute and a half after making an ask, resisting the urge to make unnecessary concessions, which ultimately secured the deal. Voss builds on this, noting that in high-stakes negotiations, remaining silent after the other side speaks often leads them to make the concessions you desire.

Silence Encourages Reflection and Concessions

Both negotiators agree that silence is critical thinking time, allowing the other side to reflect and often fill the void with information or concessions. Fletcher likens it to handing over a medicine ball—let the other side hold it.

Patience in Negotiation Yields Better Results

Fletcher discusses the courage needed to pause confidently. A pause can last minutes, days, or weeks, signaling that the negotiator stands firm.

Time Spent On Preparation and Understanding Enables Confidently Pausing Negotiations

Preparation is key to pausing confidently. Fletcher emphasizes doing extensive work in advance—understanding needs, building relationships, and clearly communicating positions. When negotiators have settled all groundwork, they can pause without feeling pressured to fill the void or make concessions. More preparation equips negotiators to handle unpredictable turns and gives them confidence to let silence do its work.

1-Page Summary

Additional Materials

Counterarguments

  • While building rapport and relationships can be beneficial, some negotiations—such as one-off transactions or highly competitive bidding processes—may not allow time or opportunity for relationship-building, making transactional tactics more practical.
  • In certain cultural or industry contexts, directness and assertiveness may be valued over relational approaches, and attempts to build rapport could be perceived as insincere or manipulative.
  • Not all parties are receptive to open-ended questions or empathetic listening; some may prefer clear, concise, and direct communication, especially in time-sensitive or high-pressure situations.
  • The emphasis on emotional validation and summarizing the other party's viewpoint may be less effective when negotiating with parties who are primarily motivated by objective criteria, data, or legal constraints.
  • Silence and pausing can be misinterpreted as indecision, lack of preparation, or disinterest in some cultures or business environments, potentially undermining the negotiator's position.
  • Over-reliance on relationship-building and empathy may lead to negotiators making unnecessary concessions to preserve harmony, potentially sacrificing optimal outcomes.
  • In highly adversarial or zero-sum negotiations, such as certain legal disputes or labor negotiations, relational approaches may be less effective than assertive or competitive tactics.
  • Some negotiators may exploit open-ended questioning and empathetic listening to manipulate or extract information without reciprocating, leading to imbalanced outcomes.

Actionables

- You can keep a negotiation reflection journal to track your interactions, noting what you learned about the other person’s perspective, how you built rapport, and what questions or pauses led to breakthroughs, so you can spot patterns and improve your approach over time.

  • A practical way to strengthen relationships before negotiations is to schedule informal check-ins (like a quick coffee chat or a friendly message) with people you might negotiate with in the future, focusing on learning about their interests and communication styles outside of any deal-making context.
  • You can practice using silence by setting a timer during everyday conversations—after making a request or suggestion, pause for a set number of seconds before responding, and observe how the other person reacts or what new information emerges, gradually increasing the pause length as you get more comfortable.

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Confidence Classic: Master Negotiation to Get What You Deserve with Chris Voss, Alex Carter & Molly Fletcher

Rapport Building and Understanding Perspectives In Negotiation

Negotiation experts stress that success depends on more than just tactics and offers. Building rapport, understanding perspectives, and asking the right questions are essential for favorable outcomes and lasting relationships.

Strong Relationships Key to Negotiation Success

Molly Fletcher highlights that negotiation is essentially a conversation and that strong relationships drive better and faster outcomes. She emphasizes that approaching negotiation from a relational perspective, instead of a purely transactional one, leads to healthier, ongoing connections and opportunities for future deals. Fletcher recounts her own experiences as an agent, where stronger connections with manufacturers' reps, network executives, or athletic directors resulted in faster and more effective deals. She notes that trust becomes especially crucial when clients rely on her to navigate life-changing decisions within their finite careers. Maintaining connections within her industry allowed her to consistently serve her clients’ best interests over time.

Chris Voss echoes this, noting that using anger or adversarial tactics plants negative seeds in relationships—something that can come back to harm future opportunities. He explains that in high-stakes negotiations, such as hostage situations, all parties are repeat players in their environments. Maintaining professionalism and respect can lead to mutual esteem, as shown by a sociopathic hostage-taker later congratulating Voss on his skillful negotiation despite losing. Voss adds that when people feel understood and cared for, they are more likely to feel satisfied, even absent big concessions. Safety and trust are foundational; once established, only then can negotiators sincerely discuss needs and reach meaningful agreements.

Alex Carter demonstrates how leveraging existing relationships and building networks of “captains” in communities can mobilize large groups effectively, emphasizing the importance of strong, trust-based connections for spreading a message or closing deals. Heather Monahan sums up that the art of negotiation is rooted in deepening and leveraging all types of relationships—personal, professional, or otherwise.

Open-Ended Questions Uncover True Needs and Concerns

Chris Voss advises that the biggest mistake negotiators make is not hearing the other side out first. In both business and personal life, listening calmly and empathetically resolves most issues before they escalate. He notes neuroscience shows that even changes in tonal voice—like the calming cadence of a late-night FM DJ—can reframe conversations and reduce tension substantially, with many disputes calming down if this technique is used from the outset.

"Encourage Openness With 'Tell Me'"

Alex Carter advocates replacing yes/no questions with open-ended prompts starting with "tell ...

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Rapport Building and Understanding Perspectives In Negotiation

Additional Materials

Clarifications

  • A relational perspective in negotiation focuses on building long-term trust and ongoing partnerships beyond the immediate deal. It values understanding emotions, interests, and future collaboration potential. A transactional perspective treats negotiation as a one-time exchange, prioritizing immediate gains over relationships. Relational approaches often lead to more sustainable and mutually beneficial outcomes.
  • Molly Fletcher is a renowned sports agent and negotiation expert known for her work in high-stakes deal-making. Chris Voss is a former FBI hostage negotiator who applies psychological tactics to business and personal negotiations. Alex Carter is a leadership and communication coach specializing in negotiation and influence strategies. Heather Monahan is a motivational speaker and author who focuses on empowerment and effective communication in professional settings.
  • Networks of "captains" refer to influential individuals within communities who have trust and authority among members. They act as key connectors or leaders who can mobilize support and spread messages effectively. In negotiation, engaging these captains helps build credibility and facilitates consensus or agreement within larger groups. Their endorsement can accelerate decision-making and strengthen relational ties.
  • Changes in tonal voice influence the brain's limbic system, which regulates emotions and stress responses. A calm, soothing tone can lower cortisol levels, reducing anxiety and defensiveness in the listener. This creates a safer environment for open communication and cooperation. Neuroscience shows that such vocal cues help shift the brain from a fight-or-flight state to a more receptive, problem-solving mode.
  • "Tell me" statements are considered conversational commands because they direct the listener to provide information rather than simply asking a question. They create an open invitation to share details without the pressure of a yes/no response. This phrasing encourages elaboration and deeper dialogue. It shifts the dynamic from interrogation to guided conversation.
  • The statistic that 93% of negotiators do not ask the right questions likely comes from research in negotiation and communication studies highlighting common pitfalls in information gathering. Asking the right questions is crucial because it uncovers underlying interests and needs, which can lead to better deals. Many negotiators rely on closed or leading questions, limiting the depth of information exchanged. Using open-ended prompts like "tell me" encourages more detailed and honest responses, improving negotiation outcomes.
  • "Repeat players" are individuals or groups who frequently engage in negotiations within the same environment or context. Their ongoing interactions create a history that influences trust, reputation, and future dealings. In high-stakes situations like hostage negotiations, this means parties often encounter each othe ...

Counterarguments

  • While relationship-building and trust are valuable, some negotiations—such as one-off transactions or highly competitive bidding processes—may not benefit significantly from rapport, and a transactional approach could be more efficient.
  • In certain cultural or industry contexts, directness and assertiveness may be valued over relational approaches, and attempts at rapport-building could be perceived as insincere or manipulative.
  • Focusing heavily on relationship-building can sometimes blur professional boundaries or lead to favoritism, potentially undermining objectivity or fairness.
  • Open-ended questions and active listening require time and patience, which may not be feasible in fast-paced or high-pressure negotiation environments.
  • Not all parties are receptive to open-ended prompts or willing to share their true concerns, l ...

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Confidence Classic: Master Negotiation to Get What You Deserve with Chris Voss, Alex Carter & Molly Fletcher

Strategic Questioning to Gather Information and Build Connection

Chris Voss and Heather Monahan discuss negotiation techniques that deepen understanding and build genuine rapport. They emphasize the importance of asking strategic questions and making the other party feel understood rather than maneuvered into agreement.

Triggering "No" Can Provide Insights and Advance Negotiations

Voss argues that the traditional "yes momentum"—pushing people to say yes through micro-agreements—backfires by violating their sense of autonomy. He explains that when people feel trapped into saying yes, they often resent the process and the relationship suffers. Instead, triggering a "no" response can be far more productive. Voss and his team intentionally ask questions like "Is this a bad idea?" or "Are you against doing this?" rather than "Does this look like something that would work for you?" When people reply "no," they feel safe and in control, which allows them to be candid about any concerns.

Monahan clarifies that this approach works because saying no allows the other person to take ownership, and often they begin defending the merits of the idea. Voss adds that after a "no," people are much more likely to lay out their true objections or problems with the proposal, which provides invaluable information for moving the conversation forward. This candidness stems from the feeling that they are not being pushed or trapped into commitment.

Voss gives another example: if a potential client calls his company, he might list major competitors and suggest the caller might be better off working with them. If the potential client is committed, they offer reasons why Voss’s team is the right choice. This allows Voss to gauge their level of commitment or get clarity on their intentions. If it's not a fit, he’s quick to end the conversation respectfully, preserving goodwill and efficiency.

Summarizing the Other Party's Viewpoints Shows Understanding

Voss also stresses the power of summarizing the other side’s position as a technique to build connection. He coaches his te ...

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Strategic Questioning to Gather Information and Build Connection

Additional Materials

Counterarguments

  • While triggering a "no" response can make people feel safe, some individuals may interpret such questions as manipulative or insincere, especially if overused or perceived as a tactic rather than genuine inquiry.
  • In certain cultures or contexts, directness in summarizing or inviting "no" responses may be seen as confrontational or disrespectful, potentially undermining rapport rather than building it.
  • Some negotiations require clear commitments and affirmative agreements; focusing too much on "no" responses might delay decision-making or create ambiguity.
  • Not all parties are equally comfortable or skilled at articulating their objections after saying "no," which could limit the effectiveness of this approach in some situations.
  • Offering alternatives, including competitors, may risk losing business if the other party interprets it as a lack of confidence or interest in their ne ...

Actionables

  • You can create a personal negotiation journal where you record each time you ask a question designed to get a no, then note the other person’s reaction and any new information you learn, helping you refine your approach and spot patterns in how people respond.
  • A practical way to build rapport and demonstrate care is to set a reminder before important conversations to spend the first few minutes asking about the other person’s current challenges or priorities, then paraphrase what you hear to confirm understanding before moving to your agenda.
  • You can practice offering at least two alt ...

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Confidence Classic: Master Negotiation to Get What You Deserve with Chris Voss, Alex Carter & Molly Fletcher

Leveraging the Power Of Pausing In Negotiation

Pausing during negotiations is a powerful tactic that both Molly Fletcher and Chris Voss emphasize as essential yet often overlooked. Mastering the art of silence and patience can lead to breakthroughs and yield superior outcomes.

Silence in Negotiation Can Lead To Breakthroughs

Molly Fletcher identifies the biggest mistake in negotiation as failing to pause. She asserts that silence sends a strong message—demonstrating firmness in one's position and signaling that negotiators are comfortable with where they stand. Fletcher illustrates its impact with a story: during a phone negotiation, she paused after making the ask. The silence stretched to a minute and a half, becoming uncomfortable for even her husband listening in. Yet, the other party eventually broke the silence, agreed to the deal, and emailed over the term sheet. Fletcher notes that in that prolonged silence, there was ample opportunity for her to make unnecessary concessions, but holding the pause helped secure the outcome she wanted.

Chris Voss builds on this idea, sharing that in high-stakes negotiations—even with hostile and dangerous parties—remaining silent after the other side speaks often leads them to make the concessions or offers you desire. If you simply hear them out and then "shut up," they often give you an answer you want.

Silence Encourages Reflection and Concessions

Both negotiators agree that silence is not merely empty space; it is critical thinking time. It allows the other side to reflect and, often, to fill the silence with information, concessions, or even acceptance of your terms. Fletcher likens it to handing over a medicine ball in a workout—let the other side hold it and "feel that you mean it."

Patience in Negotiation Yields Better Results

Exercising patience is closely linked with successful pauses in negotiation. Fletcher talks about the courage and confidence needed to pause: negotiation is a conversation, but that conversation doesn’t have to be continuous. A pause can last minutes, days, or weeks, and it often signals t ...

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Leveraging the Power Of Pausing In Negotiation

Additional Materials

Clarifications

  • Molly Fletcher is a renowned sports agent and negotiation expert known for representing high-profile athletes and executives. Chris Voss is a former FBI hostage negotiator and author of the bestselling book "Never Split the Difference," specializing in negotiation tactics. Their opinions matter because they have extensive real-world experience negotiating high-stakes deals and crises. Their insights are widely respected and applied in business and conflict resolution.
  • "Making the ask" in negotiation means clearly stating what you want or requesting a specific outcome. It is the moment you present your proposal, offer, or demand to the other party. This step is crucial because it sets the stage for the other side to respond or negotiate. Effective "asking" requires confidence and clarity to communicate your position.
  • In negotiation, the "medicine ball" metaphor means giving the other party the responsibility to respond or act, similar to handing them a heavy ball to hold. It implies making a strong statement or offer and then waiting silently, forcing them to "carry" the pressure of the decision. This tactic encourages them to engage thoughtfully and often leads to concessions or agreement. The metaphor highlights the power of silence combined with assertiveness.
  • Silence in negotiation creates psychological pressure, prompting the other party to fill the void, often revealing valuable information or making concessions. It signals confidence and control, showing you are not desperate to speak or concede. Silence also disrupts the natural flow of conversation, giving you time to think and the other side time to reconsider their position. This strategic use of silence leverages human discomfort with awkward pauses to your advantage.
  • Silence creates psychological discomfort, prompting the other party to break it to relieve tension. It signals confidence and control, implying you are not desperate to fill the gap. This can make them reveal more information or make concessions to end the awkwardness. The unspoken pressure arises because people naturally seek to avoid prolonged silence in conversations.
  • Patience in negotiation means being willing to wait without rushing decisions or responses. Pausing is the deliberate act of creating silence or breaks during the negotiation process. Patience supports pausing by allowing negotiators to remain calm and composed during these breaks. Together, they prevent impulsive concessions and encourage thoughtful responses.
  • "Settling all necessary groundwork" means thoroughly researching the other party’s interests, needs, and constraints before negotiating. "Internal alignment" involves ensuring your team or yourself fully agree on goals, priorities, and acceptable outcomes. This preparation prevents confusion and strengthens your position during pauses. It also helps you remain confident without feeling pressured to ma ...

Counterarguments

  • Pausing and silence may be misinterpreted as indecision, lack of preparation, or disinterest by some negotiation counterparts, potentially undermining credibility or rapport.
  • In certain cultural contexts, prolonged silence can be considered rude or disrespectful, which may damage relationships or hinder progress.
  • Some negotiations, especially those involving urgent timelines or high-pressure environments, may not allow for extended pauses without risking lost opportunities or appearing unresponsive.
  • Overreliance on silence as a tactic can be perceived as manipulative or passive-aggressive, potentially eroding trust between parties.
  • Not all negotiators respond to silence by making concessions; some may simply wait out the pause or become equally entrenched in their positions.
  • The effectiv ...

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