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When Empathy Becomes Ruinous

When Empathy Become Ruinous | Make Your Supervision Effective

Sometimes being a manager feels like being less human. I hate confrontation – so much so that I don’t even like uncomfortable conversations, let alone actual confrontation. Unfortunately, managing others calls on me to have uncomfortable conversations on a near-daily basis. But I believe in being human first. Can the two coincide?

Kim Scott, entrepreneur, manager, and author, says most of us have internalized two messages for most of our lives that work against those of us who are managers. First, we all learned: “If you don’t have something nice to say, don’t say anything at all.” Second, in adulthood, we learned to be “professional,” which means leaving your feelings at home.

In her work, she learned over many years that in fact the best managers are able to break through these social pressures to offer a combination of:

  1. Directly challenging their employees (meaning sometimes they have not-so-nice things to say)
  2. Caring deeply and personally about their staff (meaning they bring their whole emotional selves into the work place)

This combination of qualities, she calls Radical Candor, which is also the title of her book on the subject. In a remarkably simple and effective graphic (right on the cover of the book), she maps out four different types of managers two perpendicular axis: caring personally and challenging directly.

Ruinous Empathy

When I first heard about the book, I was most drawn to it because of the upper-left quadrant – the combination of caring personally but not challenging directly. This quadrant is called “Ruinous Empathy.” The term alone resonated deeply with me and the more I learned about it, the more I knew it was describing me. And I’m sure millions of other women are in the same category.

I never struggled with this antiquated definition of “professionalism.” I’m very lucky to work in the nonprofit sector, which is all about heart and feelings. Add to that being raised right on the cusp of the Gen X and Millennial generations, I always believed I was supposed to reject these antiquated stodgy old ideas of what “professional” is about. Not to mention… that old definition of “professionalism” was really about men. I’m not sure who let me in on that nugget of wisdom, but I learned it early on. I never thought I had to keep my feelings out of the equation – that was an outdated definition of masculinity and never had anything to do with me.

But oh that other part of the equation – challenging directly – was so far out of my comfort zone. I internalized this notion of “If you don’t have anything nice to say” early in childhood. I can’t remember a time when I didn’t know and embrace this old adage.

Is My Empathy Ruinous?

I devoured Scott’s book and I listened to her podcast. It resonated deeply with me. Empathy is both the blessing and the curse I bear every day. I have never been able to shut my empathy off. There have been so many times when this has been a great gift – connecting me to others and driving me to do work that helps others. But it has also been a great trouble-maker in my life – preventing me from honesty with others I care deeply about and spiking my anxiety and depression when others around me are feeling similarly.

And it’s been the same at work. While I saw that members of my team had plenty of room for improvement, I held back on my feedback. I delivered it in small, vague, suggestions. After all, I wouldn’t want to hurt someone’s feelings, right? How horrible would that be?

It turns out that hurting someone’s feelings is not the most horrible thing I could do at work. I learned – through this book and my real-life experience – that the worst thing that could happen is that a person could lose her job. It took me more than a year of being a manager before I understood that withholding feedback that could help a person grow might protect her feelings in the short term, but in the long term it would be ruinous.

Redirecting the Empathy

Anyone who has managed other people knows bad news has to be delivered. It’s not a fun part of the job, but it is part of the job nonetheless. After reading Radical Candor, I knew I had to find a way to challenge directly. But, I felt comforted knowing that according to Scott, you must also care deeply and personally to successfully manage others. Challenging directly without caring personally (the lower right quadrant) is called “Obnoxious Aggression.”

So, I realized I had to take that empathy I had used to protect my colleagues’ feelings and redirect it. In one of my self-coaching sessions (otherwise known as talking to myself in the car… don’t judge! I drive almost an hour each way every day. I have to talk to someone sometimes!), I told myself:

Do you care more about feelings or whether they have jobs?

Well, the answer was clear. If I actually cared about these folks, I had to put my own discomfort aside. I had to make sure they would all keep their jobs.

Problem Solved? Yeah Right…

I wish I could tell you this has become easy now. Not even close. I’d still prefer to hide in my comfortable little empathetic shell. But my eyes were opened and I know now that it’s not an option. I won’t let others’ lives be ruined because I would prefer to avoid uncomfortable conversations. Instead I’m working on choosing true empathy.


Ordinary Days, Meaningful Life is a labor of love geared toward working moms ready to embrace the chaos and find meaning in it. If you found this post meaningful, please share it with someone you think would enjoy it too! I’d love to stay in touch with you! Leave a comment below, contact me, or sign up for the mailing list. I can’t wait to hear from you!

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