Radical Candor Podcast

Stuck In a Ruinous Empathy Rut 5 | 11

On this episode of the Radical Candor podcast, the team delves into a mash-up of Ruinous Empathy and Manipulative Insincerity. Ruinous Empathy—being “nice” but ultimately unhelpful and unkind—is rampant among new managers, including this new manager who wrote to us asking for advice about how to break out of a Ruinous Empathy rut. This new boss also veers into Manipulative Insincerity when they become too tired to care or argue anymore. This person dreamed of being a boss and now realizes it’s nothing like they imagined. Kim and Jason role-play how this new manager could approach a Radically Candid conversation with a direct report.

Listen to the episode:

Radical Candor Podcast Episode At a Glance

*The question:

When I recently transitioned to a dream job where I am a manager, my obsession became a commitment to taking matters into my own hands to foster cultural change. But, I’ve never been the boss before and I feel like a teenager testing out my new voice and observing it coming out awkwardly, and at times not aligned with the situation.

While I joined this organization amidst massive changes, I have experience with well-structured organization processes and change management, and I’m also deeply committed to the people. 

Upon joining, I was quick to establish meaningful relationships with my staff. I have a positive relationship with all of them except one who has been with the organization for over a decade. Other than the founder/CEO, they are the longest employee and their relationship is clouded by this devotion/fidelity that is hurting the organization. 

They are stuck at the time when this organization was a small operation when manual work was possible. We have grown so much that now they are overwhelmed and hyperventilate during our one-on-ones as I ask questions. They are so resistant to any change in process even when it will benefit them directly. 

I asked this person to meet to discuss their workload so we could find ways to manage it. They got angry and offended. I am positive they have been failed by the system and the organization, left alone to build processes that fit their way of doing the work but are not centered on the organization or other employees’ needs. 

When I concluded that they are no longer the right person for the job and consulted a peer leader, they told me this person cannot be fired.

A couple of days ago when we met for our one-on-one, they pushed back at all my attempts to offer Radical Candor. I made sure to be compassionate, noting that I know they are overwhelmed and care for the organization to the detriment of their health and that they need to be well in order to perform well at work. 

I brought up the need to share their workload with the newly hired staff and questioned why they are consistently refusing that help. After an intense emotional conversation, they told me they need kindness and space from me. 

Inside I was furious because that is me being kind and trying to give them space, but I said nothing. Instead, I told them how excited I was to support their re-distributing their workload. 

Two days later, they failed to attend a meeting for a project they were leading that the team and I spent hours preparing for. Not only that, they deleted the meeting appointment from their calendar and then said they never received it.


@simplescaling Break free from ruinous empathy: How to save your business from obnoxious aggression #radicalcandor #obnoxiouslyaggressive #ruinousempathy #empathyatwork #brendanmcgurgan #scalexinsiderpodcast #inspiration #fyp #businessgrowth ♬ UNDERWATER WONDERSCAPES (MASTER) – Frederic Bernard

Again, furious, I couldn’t bring myself to say anything. A few hours later they show up for a walk we’d planned a few days earlier stating that they just want us to share some quality time together. Because it’s raining we walk into the lounge room. They know I teach mindfulness and ask me to guide a meditation practice. I say how much I notice they need that and start leading the meditation.

On my way home, I was pissed at them for lying. But later I realized I’m angry at myself for saying nothing, day after day. For realizing the organization failed them—protecting their feelings instead of giving true guidance about their performance, and that I too have fallen into the same pattern and practice. 

I arrived home in tears, overwhelmed by my Ruinous Empathy. 

I’m letting their feelings of overwhelm guide my approach and by trying to be respectful of their time I’m actually hurting them even more. It’s also not fair to the rest of the team. It’s 5:30 a.m. and I’ve been up for over an hour crafting this email and thinking through all the missed opportunities to be the kick-ass boss I long to be. 

I need help; how do I get out of this Ruinous Empathy pattern?

*(These submissions are edited to remove any identifying characteristics.)

Radical Candor Podcast Checklist

Radical Candor Podcast

  1. Remember the Radical Candor Order of Operations: Get it, Give it, Gauge it, Encourage it. Practicing the steps in this order is important. You have to start by asking for feedback. When you as a manager start making changes that feel small to you, your team may experience those changes as unsettling chaos with unintended consequences—but you don’t know unless you ask.
  2.  With these difficult conversations, have some patience and give yourself some space. While you’re part of this challenge, you’re a big part of the solution too. Ask for help from other people and don’t expect a difficult situation to resolve itself immediately. Try to seek out little wins—start by getting the perspective of the person you’re having a challenging relationship with.
  3. Use one of your 1:1 meetings to have Career Conversations with your employees. If you’re a new manager on a well-established team, it’s important to assure them you are actually curious about their career goals and dreams and you’re not gathering information to use against them but instead to help them take a step in the direction of their dreams.
  4. Your ego is not your amigo. When you become the boss your ego can hijack your brain and take you to a bad place.

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Radical Candor podcastThe Radical Candor Podcast is based on the book Radical Candor: Be A Kickass Boss Without Losing Your Humanity by Kim Scott.

Episodes are written and produced by Brandi Neal with script editing by Amy Sandler. The show features Radical Candor co-founders Kim Scott and Jason Rosoff and is hosted by Amy Sandler. Nick Carissimi is our audio engineer.

The Radical Candor Podcast theme music was composed by Cliff Goldmacher. Order his book: The Reason For The Rhymes: Mastering the Seven Essential Skills of Innovation by Learning to Write Songs.


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