In this episode of Empathy at the Table, I sat down with my good friend and seasoned negotiator Tony Shepherd—a lawyer, consultant, and straight-talker with over three decades of experience.
This conversation pulled no punches.We challenged a lot of the feel-good ideas people have around negotiation—like the myth of “win-win” and the danger of being overly collaborative.
Tony shared stories that made me rethink how I’ve handled certain business relationships—and honestly, how sometimes empathy is misunderstood or misused.
We unpacked:Why “win-win” can be unrealistic—and even harmfulHow large companies manipulate relationships under the guise of trustThe importance of clear boundaries—even when emotions are high.
The risks of being liked too much in negotiations, how to stay grounded in emotionally intelligent conflict, if you’ve ever felt used in a negotiation, struggled to stand your ground, or sacrificed too much in the name of “being nice”—this conversation will resonate with you.
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