The mindset shift lawyers need to make

Your legal training isn't the problem. Knowing when to use it is.

A tourist stops you on the street asking for directions to Times Square. Most people would say something like “go down this way five blocks, then turn left.” That’s what I would’ve said too, before I became a lawyer.

But legal training changed how I answered simple questions. My instinct became to give context, to surface nuance, to protect against wrong turns. “Walk down two blocks and look for the McDonald’s on your left so you know you’re on the right street. There’s an alley a couple blocks after that you should avoid because the foot traffic is unpredictable. When you get to the intersection before your left turn, don’t take the street that angles diagonally—that’s not the one. After you turn, you’ll pass a Starbucks. There’s a Taco Bell after that but keep going past it.”

I felt like a good counselor. I was helping the tourist remove risk through comprehensiveness. I was being thorough and professional and protective. What I was actually doing was overwhelming them. By the time I finished, they’d forgotten the basic instruction and were too deep in the weeds to move.

Legal training made me better at spotting issues. It made me much worse at giving the answer someone actually needed.

What Law School Taught Me

In law school, I learned one thing above all else: issue spotting. Read a case, find the legal problem buried inside it. Miss an edge case, you fail. Catch something everyone else missed, you excel. Nuance was sophistication. Comprehensiveness was virtue.

I got rewarded for it. A one-issue exam answer would get a B. An exam answer that caught the angle the professor was testing for—all the nuance, all the possible interpretations—would get an A. So I optimized for thoroughness. I trained myself to consider all angles, flag all risks, leave nothing unsaid.

After three years of that (plus the bar exam) it became how I thought about giving advice on anything.

The Lesson Reinforced in Biglaw

Law school was just the beginning. The real reinforcement happened as a junior associate.

I’d research case law on an issue and come back to the partner with “There’s nothing on this.”

The partner would look at me skeptical. How do I know there’s nothing? What databases did I check? What about these cases—why aren’t they on point? How do I know I did the work carefully and not just missed something because I was sloppy?

So I had to prove it. I’d explain what I searched, identify the cases that looked promising but actually didn’t apply, describe my legal reasoning for why they didn’t. I’d build a case for why my “nothing” was credible.

I realized I wasn’t just giving an answer—I was demonstrating competence by showing the rigor behind it. Nuance and explanation became my proxy for quality. The partner couldn’t directly verify my research, so thorough explanation signaled diligence. That signal mattered more than the answer itself.

This happened over and over. By the time I was a more senior associate, I’d spent years learning that nuance and explanation were valuable commodities. That’s how you prove you’re good at your job.

That’s how you build credibility.

In the Biglaw world, that training made sense. Nuance and explanation were real signals of quality. But once I left, that proxy collapsed. A client asking me a question doesn’t need me to prove my diligence. They need an answer they can act on.

I didn’t realize how deeply the training had gone until I pivoted to sales.

After leaving the practice of law

A few years after my pivot, I found myself trying to convince buyers to purchase our AI-powered contracts system. I was in my element—selling legal technology to legal professionals. Surely my legal background and thoroughness would be an advantage.

It wasn’t. It was the opposite.

I would walk into a demo and my instinct was to explain the full picture. Here’s how the AI works. Here’s the machine learning model underneath it. Here’s why it’s better than the competitor’s approach. Here’s all the nuance around when it works well and when you need human review. Here’s the implementation timeline and the edge cases and the training requirements.

The buyer would sit politely and nod. By the end of forty-five minutes, I’d covered everything I thought mattered. By the end of forty-five minutes, they’d tuned me out.

Then I had an epiphany.

The buyer didn’t care how the AI worked. They didn’t care about the technical sophistication or the competitive differentiation or the implementation nuance. They cared about one thing: “Will this catch auto-renewal clauses we might miss?”

That was it. That was The One Thing.

I stopped preparing comprehensive demos. I started by listening. “What’s keeping you up at night with your contract management right now?” Listen to the answer. Show how the system handles that specific problem. Stop. “Does that solve it?” Yes or no. If yes, we move to the next conversation. If no, what else are you worried about?

My demo got dramatically shorter, but my close rate went up. The buyers felt like I actually understood what they needed instead of just throwing information at them.

And I realized: My legal training was getting in the way. The thing law had rewarded me for—comprehensiveness, nuance, covering all the angles—was actively getting in the way of helping the person I was trying to help.

The Pattern Everywhere

Once I saw it, I couldn’t stop seeing it everywhere else. As a sales leader, I watched it happen over and over—but from the other side.

My own in-house counsel would advise our team on contract risk. Legal training says: “Here are all the ways this could go wrong. Here’s the nuance around X. Here’s what we’d want to negotiate ideally, here’s what we can live with, here’s the tail risk if this clause gets interpreted this way.”

The sales rep’s question was simpler: “Can we sign this MSA or not?”

Legal went into comprehensive mode. The sales team got frustrated and checked out. Legal felt like they’d done rigorous work. The sales team felt like legal was protecting the legal function instead of helping them close the business.

Same pattern. Different context.

Whether you’re selling contracts software or advising an internal stakeholder or counseling a client, legal training has taught you to optimize for the wrong thing: comprehensiveness instead of clarity, accuracy instead of focus, covering everything instead of identifying what actually matters.

Why This Matters

Don’t get me wrong, law provides incredible training that’s useful beyond law. I still believe that. But it does requires a mindset shift when you move into client-facing work.¹

Inside law, comprehensive thinking protects people. You’re supposed to see the edge cases and flag the risks. But once you’re advising a client or prospect, comprehensiveness becomes a distraction. They need clarity on what actually moves the needle, not proof of how thoroughly you thought about it.²

That’s the shift most lawyers struggle with. They learn the comprehensive thinking and think that’s the job. It’s half the job. The other half is knowing what to leave out.

That’s why I ended up writing Talk Less Win More, by the way. Because once I saw the pattern, I realized it wasn’t about the training being wrong. It was about deploying it differently depending on who I’m talking to and what they actually need.

Once you see this, you can’t unsee it. You notice every lawyer going into comprehensive mode when someone just needed a yes or a no. You notice how the system rewards explaining the work instead of making the work clear. And you realize: Legal training gave you something valuable. You just have to learn when to show it and when to hold it back.

What Changed

What I learned to do instead was listen more. Study what actually mattered to the person I was talking to. Understand their constraints, their timeline, what they were trying to optimize for.

Over time, I could show up differently. Not with comprehensive risk analysis, but with prescriptive, succinct advice. Or, in the in-house lawyer’s framework: “There are ten risks here, but only two matter. And only one is a dealbreaker. Ask for A, and if you can’t get it, ask for B.”

One thing. Maybe two. That’s it. Everything else is context.

The Mindset Shift

What changes when you realize the thing that made you successful in your career is making you unsuccessful at helping the people who you need to advise?

I spent years unlearning comprehensiveness. I’m still not sure I’ve got it all the way. Every time I’m advising someone, I feel the pull back toward the Times Square explanation—the context, the nuance, the edge cases. It’s the groove the training cut.

But I know what works. Stop explaining. Listen harder. Study your counterpart until you understand what actually matters to them—not in theory, but to them, right now. Then give them the one or two things that move the needle, with the precision you learned in law school but directed at what they need instead of what you can explain.

It’s harder than being comprehensive. It requires more judgment.

But it’s how you can translate all that judgment to impact.³

1. On judgment: The real question isn’t just when to surface an edge case, but whether you’ve developed the judgment to know when it matters. A lawyer without judgment defaults to flagging everything because issue spotting is the virtue. But surfacing every possible issue paralyzes the decision-maker. True judgment requires understanding your counterpart’s world—their constraints, their timeline, what they’re actually optimizing for. At first you learn this through questions. But if you want to get better, you anticipate. You read the situation before it’s explained. You understand whether they’re under time pressure, whether they’ve already decided emotionally and just need permission from legal, what their natural tendency is (overthink or move too fast). That’s when you develop real judgment about whether to bring something up or leave it alone.

2. On the value of comprehensive thinking: Legal training teaches you to think through all the angles, understand the risks, see what could go wrong. This is genuinely valuable. Most people don’t think that carefully. The difference isn’t that internal legal work should be comprehensive and client-facing work should be simple. It’s that comprehensive thinking should happen before you step into the room. Once you’re advising, you make a clear choice about what to surface and what to hold back. Rigor is what you do beforehand. Clarity is what you do in the conversation. Most lawyers skip the second part.

3. Further reading: The skills law didn’t teach you