Have you ever received praise from your boss, only to discover that was just a lead-in to talk about the real issue: some negative piece of feedback they wanted to deliver? The idea is that people will be more receptive to negative feedback if you “wrap” it compliments, like a sandwich. However, in practice, this technique tends to backfire. Especially when you deliver compliment sandwiches to the same person multiple times, it begins to appear inauthentic. They’ll begin to question if your praise is really praise or just a warm-up for something more dire. And from the perspective of the feedback giver, making these sandwiches can be frustratingly dishonest and indirect.

Ben Horowitz, a prolific businessman and executive, suggests overcoming this tendency by constantly offering feedback, both positive and negative. He even goes so far as to say that “as CEO, you should have an opinion on absolutely everything. Let people know what you think. If you like someone’s comment, give her the feedback. If you disagree, give her the feedback. Say what you think. Express yourself.”

Although I imagine few of my readers are CEOs, this advice resonates with me as a judge. Giving feedback on a regular basis reduces or even negates the personal nature of the feedback. When your feedback is negative, being known for simply presenting things as they are helps everyone focus on the actual issues at hand, rather than making it personal. And when your feedback is positive, judges you’re working with can accept that praise at face value, without having to worry that it’s a convoluted setup for major problems.

Stepping back a little, Horowitz’s advice aligns well with last week’s post on practicing radical candor. From the context of radical candor, offering feedback frequently is a great way to challenge directly more often. Although showing that you care personally about someone is hard in its own way, I personally feel that challenging directly is the harder skill to master.

For most of us, challenging directly requires to overcome our social conditioning towards niceness, not to mention our general desire to avoid conflict. Although it’s easy to poo-poo people who are conflict-averse, let’s not forget: From an evolutionary standpoint, critiquing someone is simply unnatural. We are social creatures, and our brains are wired for survival. We want to do things that make people like us — but challenging someone is probably going to make them dislike us. In order to really practice radical candor, we need to overcome this instinct. Riki calls this quality a willingness to be “the villain of this piece.”

What happens when someone screws up, but we don’t work up our nerve to “be the villain” and really tell them how they’re doing? Kim Scott has a name for this, too: ruinous empathy. Ruinous empathy is the result of caring for your team, but being unwilling to really be honest with them. In her presentation, Scott tells the story of how ruinous empathy led to the worst moment of her career.

“Bob” was one of Scott’s direct reports. Bob was charming, and Scott genuinely enjoyed working with him. But Bob was absolutely terrible at his job…and he sort of knew it. Whenever Bob came to Scott and asked if he was doing all right, though, she gave into her natural instinct to reassure him and affirm he was doing well. (I know this is an instinct that many judges have felt as well.)

Unfortunately, this pattern wasn’t sustainable. After ten months of this, Scott finally realized the adverse effect that coddling Bob was having on her whole team, when she learned that several of her team’s truly great employees were going to quit if Bob remained.

And so, after nearly a year of trying to be nice to Bob, Scott found herself in the utterly not nice position of firing him. When Scott told Bob the news, he pushed his chair back, looked at her, and said, “Why didn’t you tell me? Why didn’t anyone tell me?”

A fair question. Scott absolutely failed Bob by letting things get that bad. Her praise had been nothing but empty reassurances. She hadn’t even given him a compliment sandwich, with real feedback layered in the middle. Maybe if Bob had received some genuine and honest feedback, he would have been able to change course and improve his position in the company — or maybe not. At least Scott could have then fired Bob for being unable to receive and act on feedback. But because of ruinous empathy, she’ll never know.

Does “Bob” sound like anyone you know in the judge program? If so, I challenge you to open up a conversation with them. In person, if possible — but don’t let time and distance be excuses. If you truly care about someone, you owe it to them to be honest about how you feel they’re doing, to point out their mistakes and where they can improve. The essence of being human is that we can improve and change. Even if your feedback is something you think they already know, you’d be surprised how often everyone except “Bob” knows what Bob is doing wrong.

Channeling Kim Scott’s own excellent strategies for practicing radical candor, I have three pieces of advice for having these difficult — but, ultimately, rewarding — conversations.

First, rather than making this conversation about feedback, try approaching it from the perspective of guidance. Offering feedback can sound patronizing and hierarchical, like we’re being graded and measured — but guidance is something we crave.

Second, don’t make it personal. Don’t label people. There’s a huge difference between telling someone “you’re stupid” and “you sounded stupid when you said ‘um’ so much.” The former is just name-calling; the latter is actual, relevant advice that can be acted on.

Finally, make sure you’re actually having a conversation. When you give feedback, you may have the best of intentions, but you won’t always be right. Don’t let “Bob” just brush off your observations, but also be willing to discuss and defend your conclusions.

If this sounds difficult, that’s because it is. But I can assure you that it’s worth it. Over the past few weeks, I’ve been pushing myself to be more honest than I previously have been, and I’ve been grateful every time.

But I’m not perfect. Even at GP Oakland, for example, I encountered opportunities for radical candor…and let them slide. It feels awkward to climb up on my soapbox and preach something that I don’t perfectly practice. And yet — I’m going to continue doing so. Because what really matters is striving to improve.

Like any habit, radical candor is a muscle that we each need to develop. And the sooner we start, the easier it will be.

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Continue your journey of practicing radical candor by visiting the official Radical Candor website.