Dear Crucial Skills,

I’m a judge, and every year I hire new law clerks. They’re smart, but they’re new, so they make mistakes. That’s normal. The problem is that when I give them feedback, they get defensive or shut down. It feels like there’s a real generational gap between us. How do I give feedback my clerks will actually hear?

Signed,
Minding the Gap

Dear Minding the Gap,

Have a conversation before the conversation. Have you told your clerks that feedback is going to be a normal part of working for you?

Consider that your clerks were raised and taught differently than you. We don’t need to get into all of that, but it may be that they don’t see feedback as normal. That’s your opportunity. What looks like a generational gap is often an expectations gap.

So if you haven’t set that expectation, that’s partly on you. I don’t say that to blame you, just to be realistic. People hate being held accountable to a standard they didn’t know existed.

Prepare the soil before you plant the seeds. When a new clerk starts, have a conversation like this: “I’m glad you’re here. Where are you hoping to grow over the next few years?” (Then listen.) “One of my main jobs is to help you get there, so I’m going to give you a lot of feedback, maybe more than you’re used to. I’ll never share it to blame or shame you. I won’t be perfect, but my goal will always be to help you succeed and to help all of us get the results we need here in chambers.”

Once you’ve prepared the soil, here’s my specific advice.

Do the Full Math

When we face a moment of feedback, we run a quick calculation, and we’re bad at it. We ask, “What will it cost me to say something?” It’ll be awkward. They’ll get defensive. We rarely ask what it will cost to stay quiet: the habits that stick, the bigger conversation later, the work that goes out with your name on it.

And if you don’t talk it out, you’ll act it out. You think you’re biting your tongue, but you raise an eyebrow when they share an idea. You don’t laugh at their joke. When someone brings in birthday cake, you cut their piece a little smaller. They can feel it, even if they can’t put their finger on it.

Remember that Comfort Isn’t the Goal—Safety Is

Comfortable people rarely grow. Your job isn’t to make your clerks comfortable. It’s to help them get better. But they do need to feel safe. We’ve all gotten feedback that stung and still been grateful for it, because we trusted the person giving it.

Humans are threat monitors. We scan for two things: Does this person intend to hurt me? And can they? When you’re the boss, the answer to the second question is always yes. So they need to be very sure about the first.

That makes your first job to suck fear out of the room. You may be a genuinely nice person, but people defer to the leader in the room, even when that person isn’t scary. You have to go further than you think. A few ways to start:

• Don’t share your opinion first. Once you do, everyone anchors to it.
• Ask lots of questions, and listen to the answers.
• Don’t ask questions that nudge them toward your view. “Don’t you think this section runs long?” isn’t really a question.

Build Safety Before You Need It

Safety is created much more by what you do day in and day out than by what you say at the start of a tough conversation. In fact, it’s built more when things are going well than when something goes wrong.

One of the simplest ways to build it is to say thank you. I know the old story: nobody thanked our generation for doing our job, because that’s what the paycheck was for. I understand it. But these are human beings. I’m not saying butter them up. I’m saying that when someone goes above and beyond or catches something you missed, take ten seconds to name exactly what they did and why it matters to you: “Thanks for catching that bad citation. That saved us a correction, and I really value it.”

When people feel seen, they give you more. And you build a relationship that can bear the weight of the candor you’re going to deliver.

You Don’t Need a Perfect Script

I could give you steps for exactly what to say (and I have, in articles like How to Deliver Feedback Effectively). But the real benefit of preparing the soil and creating safety is that it gives you room to be human. You don’t have to say things perfectly. If they trust your intent, you’ll probably be fine.

I once managed a guy who was likable and tried hard, but things kept falling through the cracks. I was dreading the conversation. He was so happy-go-lucky that I didn’t want to burst his bubble. In one of our weekly meetings, I just said, “Look, nobody likes giving tough feedback, me included. But if I didn’t care about seeing you do well, I might take the easy way out and say nothing. I hope you know that the fact that I’m bringing this up is evidence that I want you to succeed.”

It felt a little awkward, and I wasn’t using my most refined skills. He was taken aback at first. Then I saw his face relax, and I could tell he wanted to hear it.

Speak Up Early—Both Ways

Once you’ve set the expectation, don’t let small things become patterns, because patterns can become friction. A small issue is far easier to bring up than a trust issue.

And this goes for praise as much as correction. Speak up early when you see something wrong, and just as early when you see something right. If you only speak up to correct, your clerks will get worn down, though it will seem to you they don’t want feedback. They need to feel built up by what they’re doing well, too.

Best of luck,
Justin