This article was originally published in our LinkedIn Newsletter “Leaders @ Law“

Does this sound familiar? An associate sends you a careful summary of the research. Sometimes, that’s where it ends: “Here’s what I found.”

Or maybe they go a step further. They lay out two possible approaches, then finish with, “Which one would you like me to take?”

You’re between calls. You scan the research, choose a direction, and get back to your own deadline.

Later, another question arrives. Then another.

Nothing is obviously wrong with the associate’s effort. They’re responsive, thorough, and willing to do what you ask. But you’re still doing the thinking that determines what happens next. 

You want them to develop judgment. You also need the matter to move. And some days, giving the answer feels like the only practical choice. But consider what the associate gets from that exchange. They know what you decided. Do they understand why?

Drawing on my own experience as a BigLaw attorney and nearly 15 years of coaching law firm partners on how to manage and develop their people more effectively, I’ve found that these relatively simple strategies can make a real difference:

1. Find Out What’s Keeping Them From Exercising Judgment

Before deciding that an associate lacks initiative or, worse, is not capable, ask them to take a position: “Based on what you’ve found, what would you recommend, and what’s your main reason?”

You are not looking for a perfect answer. The recommendation can be tentative. What you are trying to understand is whether they have formed a view at all. And, if not, you need to understand what might be getting in the way.

An associate who has a reasonable recommendation but hesitates to share it needs something quite different from one who understands the law but struggles to connect it to the client’s business priorities. And if the associate is missing context that you never provided, telling them to “use your judgment” is unlikely to accomplish much. 

Unless you understand where they’re getting stuck, you risk correcting the wrong problem and having the same frustrating conversation the next time you assign them work.

2. Let Them Hear Your Thinking Process

When you’ve been practicing law for years, much of your judgment becomes almost automatic. You recognize patterns, anticipate risks, recall something the client said three weeks ago, and quickly narrow down the available options. What might take an associate an hour to think through may take you only a few minutes.

Researchers have studied this difference between experts and novices for decades. In How People Learn: Brain, Mind, Experience, and School, the authors explain that experts recognize patterns that novices often miss, organize knowledge around deeper concepts, and retrieve relevant information with relatively little conscious effort. Interestingly, the research also points out that being an expert in something doesn’t necessarily make you good at teaching it to someone else!

This is sometimes referred to as the Expert Blind Spot. As experienced professionals, we can become so accustomed to our own knowledge and ways of thinking that we forget how much we’ve learned along the way. We assume certain things should be obvious, underestimate how difficult an assignment might be for someone with less experience, or skip over explanations because the reasoning seems self-evident to us.

For example: Let’s say you’ve decided that the client needs a narrower analysis rather than a comprehensive review of every potential issue. To you, the choice is straightforward. You understand the client’s immediate business objective, know what’s at stake in tomorrow’s meeting, and recognize that some legal questions, while interesting, can wait.

But how much of that thinking does the associate actually see?

Next time, rather than simply giving the direction, you might explain: “I’m recommending the narrower approach because the client needs to make a decision tomorrow. The other issue could become important, but it won’t change what they need to decide right now. Let’s flag it for the next stage.”

In less than a minute, you’ve shown the associate how you weighed competing considerations, connected the legal analysis to the client’s business needs, and decided what deserved attention now versus later.

Of course, you don’t need to explain every decision, and there will be times when an urgent matter calls for immediate direction. But when an opportunity presents itself, let the associate hear some of the reasoning behind your decisions, not just the conclusions you’ve reached. You can even revisit a decision after the immediate pressure has passed.

Over time, these conversations give associates something they can’t get from simply following instructions: a better understanding of how an experienced lawyer approaches problems, evaluates tradeoffs, and makes decisions. And you can build that understanding through the supervision you’re already providing, without adding another formal training session to anyone’s calendar.

3. Be Clear About What They Can Decide

Sometimes an associate keeps coming back for direction not because they lack judgment, but because they aren’t sure how much authority they have to make decisions. They may have a perfectly reasonable recommendation but hesitate to move forward because they assume the partner needs to make the call.

You can avoid some of this uncertainty by being explicit about what you expect them to decide independently, when you want to be consulted, and what requires your approval.

For example: “I’d like you to recommend an approach and prepare the draft based on your recommendation. I’ll review it before anything goes to the client. If you uncover something that changes your analysis, let’s discuss it before you proceed.”

Of course, how much discretion you give an associate will depend on their experience, the nature of the assignment, and the risks involved. The goal isn’t to delegate decisions they aren’t ready to make, but to give them opportunities to exercise judgment within appropriate boundaries.

And when a similar situation comes up, pay attention to whether their thinking has evolved. Are they weighing the relevant tradeoffs more effectively? Are they considering the client’s objectives without being prompted? Can they explain not only what they recommend, but why? If they continue to struggle, you have a better sense of where additional guidance might help.

Ultimately, developing an associate’s judgment requires more than asking them to think independently. It requires giving them opportunities to make recommendations, helping them understand the reasoning behind your decisions, and gradually expanding their responsibility as they demonstrate readiness.

The payoff for you is an associate who can handle increasingly complex work with less direction and greater confidence, becoming someone whose judgment you can trust and whose contributions genuinely make your job easier.