Regardless of where we are in life, we can always develop better skills from reading. I learned something new by reading Chris Voss’s book Never Split the Difference. I’ll share some lessons I learned from this book, how I’ve applied them, and how you can do the same to transform your outcomes in life and business.
Why I read Never Split the Difference
My friend Justin Paperny told me that this book had a huge influence on him. He works in sales, and I wanted to learn the same lessons that inspired him. Since getting out of prison, I haven’t read many books. It’s easier to listen. Carole and I had to make several trips between our home in Orange County and the Sacramento area during the spring of 2025. Before driving, I downloaded several books to my Audible account. We both enjoyed listening to Never Split the Difference.
What I learned from reading Never Split the Difference
The author, Chris Voss, built a career as an FBI hostage negotiator. He told stories about his career, and lessons he learned while negotiating better outcomes in high-stakes situations. For example, when criminals and terrorists took people hostage, Chris Voss frequently led teams to get the best resolution. I learned that he didn’t value compromise. Instead, he recommended that negotiators develop empathy. They should learn more about the reasons behind a person’s decisions. By listening closely, and mirroring statements, they can influence the way the person thinks. In the process, negotiators can get the outcome they want.
Chris Voss described this concept as “tactical empathy.” He encouraged negotiators to put themselves in the other person’s position—not just intellectually but emotionally. That strategy required good listening skills. Those who succeeded could uncover the person’s fears, desires, and motives.
As I listened to this book, I remembered being in prison. I constantly had to navigate rules or disputes with prison staff or other people serving time. When people felt as if they were being heard, more opportunities opened for a resolution. By using tactical empathy, we can build bridges to lead us out of the immediate crisis, or help us get closer to what we want.
Lessons That Apply Everywhere
Chris Voss distills negotiation into practical strategies that anyone can use. Here are three of my favorite tactics from the book, along with how I see them benefiting not just corporate executives but anyone determined to turn adversity into opportunity:
Ask “Calibrated Questions”
Instead of making demands or issuing ultimatums, Voss teaches us to use open-ended, calibrated questions. These questions start with “how” or “what” and encourage the other person to collaborate toward a solution. For example, rather than saying, “I need this done now,” try asking, “What can we do to have this resolved by today?”
Even in situations as challenging as incarceration, this approach works wonders. I used these kinds of questions to keep constructive conversations flowing, whether I was advocating for better resources or simply trying to create harmony with others in my environment. The key is to make the other person feel involved, not under attack.
Action Step: The next time you face a conflict, pause before responding. Replace a “why” question with a “how” or “what” question. Notice how this shifts the dynamic.
Use Mirroring to Build Rapport
This technique is almost deceptively simple. Mirroring means repeating the last few words the other person said, which signals that you’re paying attention. For instance, if someone says, “I just feel like no one listens around here,” you could respond, “No one listens around here?” This technique encourages them to open up more, giving you critical insights into their mindset.
During my time inside, I learned the value of mirroring before I even had a name for the technique. It was a way to show respect and understanding, particularly in tense environments. Building trust was essential, and by reflecting their words back to them, people felt acknowledged.
Action Step: Practice mirroring during your next conversation. You’ll be amazed at how people open up when you reflect their thoughts back to them.
Label Feelings
Voss emphasizes labeling emotions as a way to defuse tensions and build trust. For example:
- “It sounds like you’re frustrated with how things have been going.”
- “It seems like this situation has been overwhelming for you.”
Labeling someone’s emotions doesn’t mean you agree with them; rather, it shows that you recognize how they’re feeling. This, in turn, helps them feel validated and fosters cooperation.
When I was working to change my own circumstances in prison, I had to become skilled at managing interactions with everyone around me. Labeling emotions became a critical tool, whether I was talking to a peer struggling with family issues or advocating for myself with prison staff.
Action Step: The next time someone expresses strong emotions, resist the urge to argue or defend your position. Instead, try labeling what they’re feeling. They’ll feel seen, and you’ll have built trust.
Why Labeling Matters
Whether you’re navigating a legal system, trying to rebuild relationships after hardship, or advocating for opportunities in your career, negotiation is everywhere. The principles in Never Split the Difference show us how to approach every interaction strategically and empathetically.
For example:
- Justice-impacted individuals can use these tools to advocate for programs or opportunities that support their reentry process.
- Entrepreneurs can apply these strategies to strike better deals, negotiate with vendors, or resolve team conflicts.
- Leaders can strengthen their communication, resulting in more productive teams and a positive work culture.
If you’ve been through challenges, you already understand resilience. Negotiation skills add a crucial layer to that resilience, empowering you to influence outcomes and build healthier, more constructive relationships.
Applying the Lessons
If you’re ready to build your negotiation skills, here’s a quick guide to get started today:
- Practice Tactical Empathy: Seek first to understand the other person’s emotions and perspective. Reflect what you hear to ensure you’re on the same page.
- Prepare and Plan: Before entering a negotiation, list key questions you can ask to steer the conversation productively.
- Role-Play Situations: Find a partner or mentor to practice potential conversations, whether it’s advocating for a raise, resolving a dispute, or asking for help.
Questions for Self-Reflection
- Think about a recent disagreement or negotiation. How could you have used calibrated questions or tactical empathy to improve the outcome?
- What steps can you take today to strengthen your listening skills?
Final Thoughts
Reading Never Split the Difference reinforced something I’ve always believed: To influence outcomes, start with connection. The person on the other side of the table, argument, or challenge is just that—a person. By listening empathetically and approaching negotiations strategically, we achieve more than just agreements—we build relationships.
Remember this truth I always share at Prison Professors: success in any pursuit demands preparation, strategy, and discipline. Master negotiation, and you’ll find opportunities where others see roadblocks.
