Bad Empathy Guesses: An Aspirational Guide

[Please note: The views and opinions expressed in each post are those of the author and do not necessarily reflect the views and opinions of BayNVC as a whole.]


YEARS AGO, WHEN I FIRST started working as a leadership coach and consultant in Collaborative Communication, my nightmare fantasy was that during a business meeting, I’d make a “bad” empathy guess about my client’s needs and values. As a rookie, I was convinced that this one error would undermine any shred of credibility—revealing that I had no idea what I was doing.

I imagined that a client would tell me, for example, about some complicated conflict in which they were embroiled. I would listen diligently, taking careful notes about the perhaps lamentable actions of their coworkers. Finally it would be my turn to respond with empathy, strategies and solutions. I would prove I understood what had transpired and how my client saw the situation.

“It sounds like you wanted a little respect,” I might say. “Am I getting that right?”

“No!” my client would shout. “Of course it’s not about respect! How could you possibly think that? I bared my soul! Were you even listening? Who ARE you?”

And thus would end my fledgling career.

IN FACT, NOTHING REMOTELY LIKE THIS ever occurred. Instead, “Is it that you’re wanting respect?” I would query.

“YES, EXACTLY,” my clients often replied.

Or occasionally, “No, it wasn’t about respect at all. It was actually that I needed a sense of safety. Thanks for asking.”

“Got it. It’s about safety,” I would confirm. And then we moved forward with our conversation.

Contrary to my outsized fears (and the anxiety monsters squawking in my ear), making a “wrong” empathy guess didn’t seem to matter much. People hardly seemed to notice. Indeed, they simply corrected my language and our discussion continued without a ripple.

WHAT DID SEEM TO MATTER was my effort and intention–that I cared. That I was fully present and engaged. That I was trying to understand what really mattered to my client.

Of course it was lovely when my empathy guesses were accurate; it meant we were both on the same page. My client could see that I “got” where they were coming from, and this built a sense of partnership and trust. But my larger concern—that one misstep would destroy our working relationship—turned out to be overwrought.

WHEN I TEACH CONFLICT RESOLUTION, I distribute a handout with a menu of universal human needs. It’s a long list of about a hundred items—core values that we all share, such as freedom, safety, community, love, support, integrity, autonomy, beauty, meaning, understanding, mattering and of course, respect.

I encourage my students to use this page as a cheat sheet, so that as they listen to a surface-level narrative of who said what, they can also look for the deeper meaning of what has unfolded.

Collaborative Communication teaches us that every word we say, every action we take, is an attempt to satisfy basic human requirements. So when someone sits down to a meal, they’re meeting a need for sustenance–and perhaps also rest or companionship. If a partner yells that they’ve been betrayed, they may be longing for safety and trust. If a contractor asks to be paid on time, they’re probably seeking financial security.

In my workshops, we do role-plays where two people act out a scene of everyday dispute, while a third person practices mediating the conflict. Part of their job is to identify the underlying values and needs. Just like me, the facilitators-in-training want to be perfect. With furrowed brows, they spend long minutes studying the Needs List, searching for the very best empathy guess.

I don’t mind the time, but I wish I could alleviate their distress.

SOMETIMES I THINK I SHOULD tell my novices to look at the list and just choose a need at random. “Be bold!” I want to proclaim. “Make an arbitrary empathy guess! Is your best friend telling you a story about how that guy in marketing constantly hijacks the weekly staff meeting and dominates every discussion? Go for it. Make a patently ridiculous assessment: Ask your buddy if they were looking for a sense of spiritual connection.”

Right? Because there’s basically a 3% chance that this silly appraisal is correct versus a 97% likelihood that the best friend will give my student the side eye and say, “Um, noooooo, it’s not about spirituality. Really, I just wanted other people at the table to get a word in edgewise.”

“Ah,” my scholar responds, using their wisest voice. “So maybe you were hoping for a sense of inclusion and equity, because you want your team to build cooperation and make better decisions?”

“Exactly,” the friend replies. And their conversation moves on.

My own lingering addiction to the perfection game still trips me up at times. Author Heather Armstrong writes about wanting to be the valedictorian of everything: academics, vocation, parenting, washing the car. We all want to excel. We want to take pride in our work and that’s great.

BUT MAYBE CONNECTION AND KINDNESS matter more than precision. Maybe what our clients, coworkers, families and friends really want from us is curiosity, support and generosity of spirit.

As a mediator, one of the most effective things I ever said to a client was, “I’m so confused. I really want to understand what this means to you and I’m still not getting it. Will you help me fill in the missing pieces?” And they did. Which clarified the situation for both of us.

It’s taken a long time, but I think I finally figured out the secret: Making a perfect empathy guess doesn’t matter. Demonstrating care does.


LISA MONTANA came to conflict resolution from the business world where she witnessed frequent disputes, most of them handled in ways that nobody liked. With Collaborative Communication, she found a model in which everyone’s needs matter and against all odds, has seen wildly antagonistic foes find common ground.

Lisa works with individuals, businesses and organizations around the country. She provides leadership and personal coaching, conflict resolution, skills sessions, organizational development, DEI, and facilitation of group meetings and decision-making.

In her private practice, Lisa’s clients value her ability to solve problems efficiently and discern core issues in complex situations. Her workshops help participants strengthen their communication skills in an engaging, interactive and supportive environment.

Lisa is a trainer at Bay Area Nonviolent Communication (BayNVC) and the Center for Efficient Collaboration (CEC). She’s also been a lead trainer with a year-long mediation program based on Nonviolent Communication. And since 2013, she’s taught conflict resolution at San Quentin State Prison.

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Copyright 2022 Lisa Montana. Reprint with permission and attribution.