In a recent LinkedIn post, Christine Carrillo shares a compelling anecdote illustrating a powerful negotiation strategy, highlighting how a shift in perspective can salvage deals on the brink of collapse. Carrillo, who was dubbed the “negotiating Jedi” by her board, emphasizes that success in negotiation stems not from aggression, but from a genuine desire to find a mutually beneficial outcome rather than a win-lose scenario.
Carrillo recounts a high-stakes situation where she was raising $50 million and had secured multiple term sheets. Just as a deal was set to close, the lead investor unexpectedly balked. While her board and legal team reacted with panic and escalation, Carrillo adopted a different approach.
“I picked up the phone and called him directly. ‘I don’t want you to worry. I’m not upset. We’re going to get a deal done. Just tell me what’s happening.'”
This direct, empathetic outreach, Carrillo explains, immediately disarmed the investor. Instead of facing an adversary, he encountered someone seeking understanding. As Christine Carrillo notes, this allowed the real issue to surface:
Uncovering the ‘Black Swan’ Through Empathy
Carrillo elaborates on how this approach led to the revelation of the core problem, distinguishing it from mere positional bargaining. She explains that the investor’s guard came down, allowing him to share the genuine obstacle his team faced, rather than a hardened negotiation stance.
Referencing the concept of the “Black Swan” popularized by Chris Voss, Carrillo argues that this hidden, critical piece of information is rarely revealed when the other party feels defensive. According to Christine Carrillo, true breakthroughs occur when the other person believes you are aligned with their interests.
“You’ll never get it if the other person is defending themselves. You only get it when they believe you’re on their side.”
This philosophy, Carrillo suggests, is about prioritizing the deal’s completion over personal ego or the need to be ‘right.’ She contrasts this with common negotiation pitfalls:
Common Negotiation Pitfalls Highlighted by Carrillo
- Correcting rather than understanding the underlying issues.
- Raising one’s voice instead of ensuring the other party feels heard.
- Prioritizing winning a point over closing the deal.
Carrillo’s strategy involved genuine curiosity and a focus on partnership rather than adversarial tactics. As Christine Carrillo states:
“I stopped trying to be right. I meant it when I said I wasn’t upset. I got curious about what was scaring him. I wanted the deal more than I needed to protect my ego.”
The outcome was a swift resolution to the problem, saving the deal. Carrillo concludes by reflecting that many lost deals could have been salvaged with a similar approach – a single, empathetic conversation that treats the other party as a partner, not an opponent.
“Every deal you’ve lost had a moment where one phone call could have changed everything. You just didn’t make it.”
Ultimately, Christine Carrillo’s insights underscore the power of empathy and a collaborative mindset in navigating complex business negotiations, transforming potential conflicts into opportunities for successful outcomes.
📝 About This Content
This article is based on insights shared by Christine Carrillo on LinkedIn.
📅 Originally posted on April 13, 2026 | View original post on LinkedIn →