RevOps Champions Newsletter #21
I’ve always considered myself an empathetic leader. But I recently learned that empathy, on its own, can be dangerous.
“Ruinous empathy” is what happens when we avoid honest feedback—because we care. And it’s something I’ve been working hard to avoid.
Ruinous empathy. Sounds horrible doesn’t it?
This is how author and speaker Kim Scott describes what happens in a relationship when you might care personally about the other person, but you don’t challenge them directly by providing clear, direct, and specific feedback, even when it's critical.
Why do we sometimes not give honest feedback to people when we care about them, they know we care about them, and we know the feedback is important for them to develop?
Scott, who wrote “Radical Candor”, and more recently, “Radical Respect”, and who I had the privilege to hear speak in Minneapolis earlier this year, says it’s because we sometimes prioritize sparing that person’s (or our own) short-term feelings, over their long-term need for feedback that will help them grow and improve.
Most of us don’t take pleasure in hurting other people’s feelings, but Scott argues that we are doing more harm to that person in the long term by not giving the feedback that they need, and deserve.
So how can we ‘challenge directly’ as Scott calls it, and give direct feedback, in the nicest way possible?
Her framework is simple:
Care Personally (Y axis)
Challenge Directly (X axis)
The best feedback lives in the upper right: high care, high challenge.
The top left quadrant is the one she calls “Ruinous Empathy” and we do NOT want to land there. In her talk, she gave a great personal example of why.
She told us the story of a guy who had worked for her, we can call him Charlie. Everyone on the team had nice things to say about Charlie. He was the first person to make a new team member feel welcome, he was thoughtful with everyone, he was fun, had a positive attitude and good energy. The problem was that he wasn’t very good at his actual job. He didn’t hit his KPIs and that brought down the average KPIs for the whole team.
Scott shared that she was aware of his performance issues, but she was afraid to do anything about it because she knew the whole team enjoyed working with Charlie and she thought she’d be the one to receive backlash if she fired him. So she said nothing about his performance to him.
Until she couldn’t ignore it anymore. Her A players expected to work with other A players and they weren’t going to stay on a team that tolerated poor performance. So she finally had a conversation with Charlie to terminate him at the company. He was shocked (which should never be the case when you have to let someone go).
He couldn’t understand why Scott hadn’t told him his performance wasn’t up to scratch earlier. Had he known, he said, he would have tried to change and do better. But because she always just said nice things to him, he felt blindsided. This is “ruinous empathy”. It left both Charlie and Scott feeling terrible.
Scott’s 2x2 framework is so easy to apply that it’s guided numerous conversations I’ve had personally and professionally in the past few weeks since I learned about it. And which is why I was excited to hear about a completely different way to apply it from one of our recent podcast guests, Dick Polipnick, VP of Marketing at GoRout.
I’ve known Dick for a number of years, he’s extremely bright and driven. So I was not surprised to learn in the podcast that he’s also a fan of using frameworks and methodologies to help solve challenges, especially ones that companies who are trying to scale face on a regular basis.
During the podcast, he shares his appreciation for Scott’s “Radical Candor” philosophy. Dick lives in the Midwest though, where not everyone appreciates a ‘direct’ communication approach.
To get around that, he begins his new business relationships by sharing Scott’s TED Talk and explaining that’s his preferred style of communication. Giving people context about why he believes it’s important helps to set the table for a successful relationship, and it encourages his counterparts to communicate in the same way with him.
The most brilliant takeaway I learned from Dick though is how to help your customer-facing team members to apply ‘Radical Candor’ with customers.
GoRout is a very data-driven organization and they track what their product usage is by customer. They’ve set up dashboards in HubSpot to flag them internally when a customer’s usage is lower than expected, and then they use that data to trigger an email to the customer.
Dick shared that, “We tell them, based on our information, it looks like you are off pace. That's a huge red flag, right? Nobody wants to be off pace. Right? Because that tells them that their competitors are practicing more than them or using the system faster than they are.”
They’ve built a system that lets them challenge directly—but in a way that still feels supportive. It’s radical candor in action.
What GoRout found is that within 24 hours of getting that email, the customer’s usage skyrockets. And that additional usage helps their customers get more value out of GoRout’s product. Which leads to more renewals.
As I mentioned earlier, I’ve been working intentionally to incorporate more “radical candor” into my own conversations, but I’m going to take a page from Dick’s book and challenge myself to find ways for our whole team to incorporate more of it as well.
I think the key to that is using Scott’s framework to make sure we stay in the upper right quadrant. We won’t get it perfectly every time, but as our leadership team likes to say, we’re either winning or learning. And there’s no losing if we’re learning.
What conversation have you been avoiding?
This week, what would it look like to trade "nice" for honest?
Cheers,
Kristin
![]() |
Kristin Dennewill
|