In this episode of Creating Confidence, Heather Monahan and negotiation expert Chris Voss examine the sophisticated dynamics of successful deal-making, with emphasis on tactical empathy and stakeholder management. Voss explains why many negotiations fail due to hidden decision-makers who sabotage deals after discussions conclude, and shares strategies for identifying genuine commitment early in the process. The conversation covers practical techniques for transforming difficult stakeholders from adversaries into allies through recognition and involvement.
Voss and Monahan also explore the role of emotional intelligence in negotiation, discussing four core emotional states that build resilience and connection. They address common misconceptions about soft skills in business, particularly how women have been encouraged to suppress empathy in professional settings. Throughout, both experts emphasize reframing adversity as opportunity, sharing examples of leaders who thrived after setbacks by adopting flexible mindsets and practicing tactical empathy in low-stakes everyday interactions.

Sign up for Shortform to access the whole episode summary along with additional materials like counterarguments and context.
Negotiation experts Chris Voss and Heather Monahan explore the sophisticated dynamics of successful deal-making, focusing on tactical empathy, stakeholder engagement, and reframing adversarial relationships.
Voss explains that modern negotiations often fail not because of disagreements at the table, but due to secondary stakeholders—excluded decision-makers who sabotage deals post-discussion, often motivated by internal politics or feeling undervalued. He calls this the "agreement graveyard." Another pitfall is mistaking interest for intent, as roughly 20% of business negotiations are never meant to close. Instead, negotiators may be used as "rabbits"—competing bids to drive down prices elsewhere. The key is assessing "proof of life" early: determining if there's genuine commitment to making a deal with you.
To navigate these challenges, Voss recommends deploying strategic "what" and "how" questions with all stakeholders, especially potential deal-killers. Questions like "What are the obstacles here?" serve two purposes: they inflate the respondent's sense of control and force them to invest mental energy, increasing their psychological ownership of the process. Bringing problematic decision-makers into discussions early makes them feel valued and involved. Monahan adds that publicly praising difficult stakeholders improved their collaboration in subsequent interactions.
Rather than viewing tough stakeholders as adversaries, Monahan advocates approaching them with gratitude and recognizing their contributions. Both experts agree that adversarial attitudes often stem from insecurities and a desire for meaningful involvement. By addressing these deeper motivations with empathy and recognition, negotiators can transform risky relationships into sources of strength.
Voss identifies gratitude, curiosity, playfulness, and being present as emotional superpowers that keep people in the moment and prevent anxiety-driven calculations that undermine negotiations. These emotions are interdependent: curiosity naturally makes someone present, which in turn fosters gratitude and playfulness. Voss emphasizes that curiosity cannot co-exist with anger, and in high-tension situations, channeling curiosity prevents destructive emotions from taking hold. Drawing from Viktor Frankl's work, he notes that survivors of extreme stress often adopted curious outlooks, which bolstered their psychological resilience.
Voss shares a practical tool: ask people what they love about where they work or live. Monahan explains that when people speak about things they love, their brains release [restricted term], creating a positive emotional tie to the person who asked. This neurochemical boost happens unconsciously but elevates mood and connection remarkably. Even in brief interactions, giving someone the opportunity to share their passions forges instant rapport.
Voss observes that the real power of empathy and emotional intelligence is largely invisible. While the recipient experiences neurochemical benefits, these changes aren't visible to bystanders. Because empathy works so subtly, it frequently goes unrecognized and is difficult to learn through observation alone. Without explicit mentorship, people are unlikely to discover these techniques, making intentional practice and guidance essential.
Voss emphasizes that self-talk makes all the difference during difficult moments like job loss. He advocates repeating, "This is not happening to me, it's happening for me," to shift from feeling like a victim to seeing adversity as opportunity. Monahan shares her own experience of being fired, acknowledging the pain but recognizing it as the best thing that happened to her. Both argue that job loss often becomes a springboard to better opportunities.
Voss introduces the concept of a "two-millimeter mind shift"—a small perspective change that can alter life's momentum. He compares leaving a bad job to leaving a bad relationship: sometimes job loss frees you from situations where you weren't valued or able to grow.
Bob Iger, former CEO of Disney, provides a clear example of thriving amid corporate turbulence. Voss highlights Iger's consistent ability to succeed after multiple takeovers by adapting and showing respect for new authority rather than resisting change. This flexible attitude enabled Iger to not only survive but also architect transformational deals like the Pixar-Disney agreement. Voss also references Harvey Mackay's book "Fired Up," which collects stories of successful people whose careers took off after being fired. Both experts agree that job loss, while initially painful, often becomes the catalyst for personal and professional transformation.
Voss observes that women typically adopt tactical empathy techniques more quickly than men, not because they're inherently better, but because they more readily embrace soft skills like empathy. Women are educated in these skills from a young age, while men often regard them with suspicion. Men tend to seek perfection before trying new techniques, while women experiment sooner, facilitating faster skill development.
Monahan reflects on widespread advice for women to hide emotion and empathy—qualities branded as weaknesses—to succeed in male-dominated industries. Voss points out that in the past, successful women were encouraged to suppress their femininity, often to their detriment. Now, many highly effective executives are thriving by remaining authentic and disproving the idea that only masculine business styles bring success.
Voss also highlights that men restrict their business potential by constantly comparing themselves to competitors rather than focusing on growth. He uses Tiger Woods as a counter-example: Woods' relentless self-improvement, rather than comparison with others, exemplifies a mindset that leads to excellence. To overcome fear and build skill, Voss advocates small-stakes practice in everyday low-stakes interactions, like chatting with grocery store cashiers. Monahan describes this as a "pattern interrupt" that removes pressure and proves the value of the skill in action, building confidence through repeated, low-pressure practice.
1-Page Summary
Negotiation experts Chris Voss and Heather Monahan delve into the sophisticated dynamics that define successful deal-making—especially the crucial roles of tactical empathy, stakeholder engagement, and reframing adversarial relationships.
Modern negotiations often stall or collapse not due to disagreements at the table, but because of secondary stakeholders—decision-makers or influencers removed from the negotiation itself—who sabotage the deal post-discussion. Chris Voss refers to this phenomenon as the "agreement graveyard," where promising deals are derailed by individuals who wait in the wings, often motivated by internal politics, jealousy, or a perceived lack of involvement. For instance, corporate in-house counsels who were excluded from negotiations may feel compelled to justify their role by rigorously scrutinizing and potentially undermining deals, regardless of their objective merit.
Another frequent pitfall is mistaking genuine interest from a counterpart for authentic intent to close a deal. Voss shares that about 20% of business negotiations are never intended to reach fruition. Instead, negotiators may be used as “rabbits”—competing bids or reference points to drive down prices from a favored provider, or simply for due diligence. The key is to assess “proof of life”: determine early if there is true commitment to making a deal with you, not just collecting pricing information to leverage elsewhere.
To navigate these hurdles, Voss recommends employing strategic "what" and "how" questions with all stakeholders, especially those notorious for derailing deals, like general counsels or other powerful internal figures. Such questions, for example, "What are the obstacles here?", "What's the biggest challenge?", or "How can we ensure success?" serve two vital purposes. First, they inflate the respondent’s sense of control, making them feel respected and in charge, which satisfies their psychological need for significance. Second, these questions force stakeholders to invest mental energy and thought, which, in turn, increases their psychological ownership of the process and its outcomes.
Bringing problematic decision-makers into the process early is essential. By engaging them with strategic questioning from the outset, these stakeholders feel involved, valued, and even cast in the role of mentors or guides. This sense of ownership decreases their likelihood of becoming barriers at the final hurdle. Monahan underscores that when she praised difficult stakeholders publicly, their willingness to collaborate improve ...
Advanced Negotiation Strategies: Tactical Empathy and Stakeholder Management
Emotional intelligence lies at the heart of effective connection and negotiation. Chris Voss and Heather Monahan discuss how cultivating gratitude, curiosity, playfulness, and presence can transform conversations, foster resilience, and build powerful rapport, even in moments of stress or perceived conflict.
Chris Voss identifies gratitude, curiosity, playfulness, and being present as four emotional superpowers that help people remain in the moment. These emotions prevent the anxiety-driven calculations that can undermine negotiations and relationships. Playfulness, in particular, he highlights as a superpower for keeping perspectives fresh and open. Curiosity, according to Voss, forces individuals into the present, helping them engage positively, see patterns more quickly, and connect more genuinely with others.
The interplay between these emotions is critical. Curiosity naturally makes someone present, which in turn can seed gratitude and playfulness. When a person is genuinely curious about another, they become more attentive, which leads to deeper connections—people are likely to share things they haven’t told anyone else.
Voss emphasizes that curiosity cannot co-exist with anger: "You can't be angry and curious at the same time." In high-tension negotiations or difficult conversations, channeling curiosity occupies the mind, preventing space for destructive emotions to grow.
Drawing from Nassim Nicholas Taleb’s concept of anti-fragility and Viktor Frankl’s "Man’s Search for Meaning," Voss points out that people surviving extremely stressful environments, such as Holocaust survivors, often did so by adopting a curious outlook—wondering curiously about what would happen next helped them withstand overwhelming horrors. Curiosity, therefore, bolsters psychological resilience in the face of adversity.
Voss shares a practical tool: ask people what they love about where they work or live. He demonstrates this by recounting a grocery store scenario, where a simple question—"What do you love about working at Albertsons?"—elicited a heartfelt, detailed response from the cashier. She shared her positive feelings about her benefits and workplace, resulting in a genuine, emotional connection during what would otherwise have been a routine transaction.
Heather Monahan explains that when people speak about things they love, their brains release [restricted term]. This neurochemical boost improves happiness and creates a positive emotional tie to the person who asked the question. The act is biological; the recipient is often unaware of it happening, but it indisputably elevates mood and connection.
Voss reflects how even in brief or transactional interactions, giving some ...
Emotional Intelligence and Mindset: Building Conversational Superpowers
Reframing setbacks like job loss as catalysts for growth requires conscious mental shifts. Chris Voss and Heather Monahan explore how internal dialogue and role models can help turn adversity into a launchpad for greater success.
Chris Voss emphasizes that the inner chatter in your mind—your self-talk—makes all the difference during difficult moments like job loss. He advocates repeating the phrase, “This is not happening to me, it’s happening for me,” as a mental exercise to shift from feeling like a victim to seeing adversity as a turning point. Voss explains that although this mindset shift is challenging and takes practice, it can change the way you experience and respond to your situation. Rather than thinking only of what’s lost, reframing the narrative allows you to look for growth and new possibilities.
Heather Monahan echoes this, sharing her own experience of being fired after she outgrew her company. She acknowledges the pain and fear in the moment, but with hindsight, she sees it as the best thing that happened to her. Both experts argue that people often feel anxiety and dread after job loss because the vision of the future has vanished, but that future-casting negative outcomes is often untrue—these events can be a springboard to a better life.
Voss introduces the concept of a “two-millimeter mind shift”—a small change in perspective that can alter the entire momentum of your life. He compares leaving a bad job to leaving a bad relationship: sometimes job loss frees you from a situation where you weren’t valued or able to grow. He points out that job loss may stem from circumstances beyond your control, like company mismanagement or a bloated, failing organization. Embracing this shift speeds up moving from processing loss to seeking out new opportunities, helping individuals thrive rather than suffer after setbacks.
Bob Iger, former CEO of Disney, provides a clear example of surviving—and succeeding—amid corporate turbulence. Voss highlights Iger’s consistent ability to thrive after multiple takeovers, in stark contrast to others who refused to adapt and were shown the door. When Disney acquired ABC Sports, Iger faced budget slashes, loss of creative independence, and a radically different culture. Instead of resisting, he adapted, showing respect for new authority, and committed to doing things “their way” as long as it was within the rules. This flexible, respectful attitude enabled Iger to not only survive repeated acquisitions but also shape transformational deals, such as the historic Pixar-Disney agreement.
Iger’s career demonstrates the value of respecting authority and shifting with new corpora ...
Reframing Adversity For Growth: Shifting Your Mental Narrative
Chris Voss and Heather Monahan discuss how gendered perspectives and business culture have shaped the development and application of soft skills—particularly emotional intelligence—in negotiation, and how fresh approaches can unlock everyone’s potential.
Voss observes that women typically pick up emotional intelligence-based negotiation tactics, which he refers to as tactical empathy, more quickly than men. This is not because women are inherently better at the skill, but they more readily embrace soft skills such as empathy, comprehending the other side's perspective, and demonstrating understanding. Voss notes that women are educated in these skills from a young age, while men are often less familiar and thus regard them with suspicion or fear. Men tend to hesitate and delay using empathy-based techniques, as they want to perfect them first before trying. In contrast, women are more willing to experiment and try these new skills right away, facilitating faster skill development.
Voss notes that even within his team, male trainees are more reluctant to use new negotiation techniques because they seek perfection from the outset, while women naturally try them sooner, which speeds up their learning process.
Monahan reflects on her own career in male-dominated industries and the widespread advice for women to hide their emotion and empathy—qualities branded as weaknesses—to succeed. In fields like radio, she was taught to "be one of the guys" and conceal her femininity, which conflicted with her natural inclination to connect authentically. Voss points out that in the past, successful women were encouraged to suppress their femininity and lost their authentic selves, often to their detriment. Now, many highly effective executives are challenging these old norms, thriving by remaining true to themselves and disproving the idea that only masculine business styles bring success.
Voss highlights that men, in particular, restrict their business potential by constantly comparing themselves to competitors. Instead of focusing on growth, they are satisfied with being better than the next person without realizing how much more effective they could become. He likens this to "vog guys" who, while seeking the comfort of a group, reinforce their own mediocrity and perpetuate it as mentors. Mediocre mentors encourage others to mirror their approach, ensuring that neither they nor their mentees rise ab ...
Soft Skills and Learning: Debunking Gender Myths
Download the Shortform Chrome extension for your browser
