The historic prisoner swap offers a case study in what it takes to succeed at making complex, high-stakes deals.

For most businesses, high-stakes deals involve not lives but livelihoods, affecting dozens or even hundreds of individuals. Negotiations are often fierce. Looking at the prisoner swap completed on Aug. 1, 2024 in hindsight, there are a few key principles that underlie complex deals of all kinds and what it takes to break through when you are dealing with tough people on the other side of the table. When you focus on all of them, you are in a good position to get seemingly impossible things done.

It took two and half years and countless hours of diplomacy to return 27 people detained abroad to seven different home countries. The person in the prisoner swap who demonstrates all of these principles is Ella Milman, Evan Gershkovitz’s mother. Reading accounts of how the deal came together as the months stretched out, it’s easy to see how she was the driving factor behind the successful effort to get her son home.

  1. Alignment is essential. Bringing different parties together to achieve a common goal starts with aligning the goals of each party. This is not always easy, but it is essential to get high-stakes deals to completion. Ella Milman wanted her son freed. It didn’t take her long to figure to figure out that Russia also wanted a prisoner back, Vadim Krasikov, a Russian hitman and personal friend of Putin, serving a sentence in Germany for murder. Knowing what Putin wanted was the key to success. In hostage negotiations as in business, it’s not just about what you want. It’s about finding the sweet spot where the deal is win-win for every side. Everyone is going to have to give up something to get something they want more. Success means figuring out what others are willing to trade to get a deal everyone can sign off on.
  2. Understand the players. Whether you are dealing with governments or other companies, every negotiation ultimately comes down to people, each of whom has their own wants, needs, powers, and opinions. In order to get alignment, start by learning everything you can about stakeholders before you talk to them. Go past titles, check your assumptions at the door, and find out about the individual you are talking with. What has worked for them in the past? What drives them now? What powers or influence are they likely to have? Ella Milman researched everyone, their connections and powers. She also knew that their motivations and abilities could shift over time, so she checked back to see where they were now and what they could offer as pieces moved around. Knowing the players helped her approach each one with an argument or emotional pitch that built respect and connection everywhere and ultimately led to success.
  3. Use every channel and opportunity you can think of. Don’t limit yourself to the obvious or easy channels. Don’t be timid about seeking out new opportunities to make your case, no matter how high you have to go. Ella Milman never passed up an opportunity to advocate for her son and to keep his case top of mind. When she scored a ticket to the White House Correspondents Dinner, she approached Blinken and Biden to make her case directly. Her emotional pleas to Biden proved to be a motivator for the President to make this high-stakes deal happen. When she went to Russia for her son’s arraignment, she didn’t hesitate to sit down for questioning with the intelligence community there, even knowing that she too could have been taken prisoner. Making your case to everyone everywhere demonstrates a grit that others respect and admire in ways that motivate them to give what they can.
  4. Passion and courage are the secret sauce. What drove Ella Milman is, of course, her love for her son. We all know how fierce maternal love can be. What we often don’t recognize is the emotional attachment many of us have to our work. It’s not uncommon for an entrepreneur to see the organizations they found as their baby. Even in a corporate job, many people build networks and achievements that they see as their own creation, giving them an emotional tie to the work and the organization that is hard to break. For most people, work provides a sense of meaning and purpose and even identity. When you are truly connected in an emotional way to your cause, you will find strength that you didn’t know you had. When others have less of an emotional attachment to their work, they sometimes give in in the face of that fierceness.   
  5. Keep going. This high-stakes deal started taking shape long before Evan Gershkovich was taken prisoner. In fact, some have argued that Russia detained Evan as a bargaining chip in the deal that was already beginning to take shape. Russia needed to give Germany and the US a compelling reason to trade away a convicted murderer like Krasikov. For a time, Germany wanted Navalny, the jailed opposition leader in Russia. When Navalny died in detention, Germany remained open to the swap because by that point, there were too many lives on the line to go back. Things change. Keep going. When the stakes are high enough and you feel you have to make the deal, it’s just a matter of finding the way.

If you are involved in high-stakes deals, expect obstacles and keep going no matter what comes your way. Keep working to find everyone’s motivation, use every opportunity you get, maintain your passion, and keep going, and find that sweet spot where everyone’s interests align. That is the deal making moment.

OTHER RESOURCES

Washington Post’s excellent account of the deal: Inside the Secret Negotiations to Free Evan Gershkovich

Other great negotiating advice from the Harvard Negotiation Project: Getting to Yes and Difficult Conversations.

Learn more about emotional intelligence and decision making here.

Are you in a high-stakes negotiation? Contact me to learn how emotional intelligence can help you succeed.