Hi there! It’s Heather Stevenson.

Happy Wednesday and thanks for being here! Here’s what’s covered in today’s issue:

  • A word from today’s sponsor, Latitude. For over a year, I’ve relied on Latitude lawyers as an extension of my lean legal team—providing high quality overflow support and stepping in as fractional counsel for certain portfolio companies;

  • The single biggest communication mistake smart lawyers make and practical steps for how to fix it;

  • Links you’ll love;

  • And More.

Let’s dive in.

Trusted Attorneys for the Work Ahead

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Latitude provides experienced former Big Law attorneys and in-house counsel who can step in on a flexible basis to support your team. Every Latitude attorney is thoughtfully vetted for skills, judgment, professionalism, and the ability to step in and contribute meaningfully to sophisticated and complex legal matters.

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Deep Dive

The Single Biggest Communication Mistake Smart Lawyers Make

Here it is: delivering information the way you would want to receive it.

It seems obvious when you say it out loud. Of course you should think about your audience. You do it in your legal work all the time. You write differently for a board than you do for an engineer, and you explain risk differently to a CFO than to a product manager. You've internalized that adapting your legal communication is part of the job.

But something shifts when it comes to the day-to-day — updates to your boss, feedback to your team, briefings to your internal clients. In those moments, a lot of us default to communicating the way we think clearly and feel most comfortable. We communicate the way we would want someone to communicate with us. And it costs us, often without our even realizing it.

You don’t need to shapeshift to please everyone around you. But you do need to recognize that doing this job well requires understanding what the individuals around you actually need and how they most effectively receive communication. What can be surprising is how much it varies, not just role to role, but person to person.

Two Bosses, Two Completely Different Playbooks

I've had the privilege of working for some really talented leaders, and two of them couldn't have been more different in how they want information.

One boss wanted the details. He was a careful thinker who liked to understand the full picture before forming a view. Sharing in writing worked well, and he wanted my thoughts thorough, organized, and highlighting the key considerations. He read them carefully. He engaged with them. When I came to him with a complex issue, the more context I could give him, the better the conversation we had. That's how he operated, and once I understood that, supporting him became significantly easier.

The second boss was the opposite. He wanted the headline and the confidence that it was handled. Detailed written analysis wasn't just unnecessary for him — it was actually counterproductive, because he considered it a distraction. He preferred clarity and momentum over comprehensiveness. His ideal written format to receive would be a single PowerPoint slide with the issue, the recommendation, and the next step. Verbal updates were his preferred mode. He trusted me to have done the work, and didn't need or want to see all of it.

Neither of these approaches is better. Both were excellent leaders. But if I had brought boss number two the same playbook I used with boss number one — long memos, thorough written analysis, detailed briefings — I would have frustrated someone who relied on me to make his life easier, not harder. The content of my work would have been exactly the same. The delivery would have been completely wrong.

When managing up, doing great work isn't enough if you're packaging it in a way that doesn't land for your audience.

Managing Down is the Same Skill

One place where a lot of good managers, myself included, can miss the mark is by thinking that adapting our communication style is something we do for people who have power over us. But it matters just as much in the other direction, with the people who work for you.

I had a direct report at one point who needed more feedback than I was giving. I thought I was doing right by this person. I made a huge effort not to micromanage, by letting them do their work, not hovering, and trusting their judgment. What I didn't realize was that they read the space I was giving them as silence, and they read that silence as uncertainty. They didn't know if they were on the right track. They were working harder to compensate for the lack of signal, and they were less confident doing it.

When I adjusted and started giving more feedback, faster and more directly, everything changed. The quality of the work, which was already solid, didn't change. But the pace, confidence, and honestly, how much they seemed to enjoy the job improved measurably. They thrived on direct, timely input. I just hadn't been giving it to them, because it wasn't what I would have needed.

That one is a little uncomfortable to admit. It's easy to think of a struggling team member as someone who needs to develop a skill or step up in some way. It's harder to consider that the problem might be in how you're managing them. But it's worth asking the question.

What This Looks Like In Practice

I'm not suggesting you conduct a communication preferences audit before every interaction. That's not realistic, not the point, and frankly it could come across as a little intrusive.

What I am suggesting is that over time, as you build working relationships with your boss, your team, and your internal clients, you intentionally develop a read on what each person actually needs. Then make what you learn part of how you work — not a separate checklist you run through. Over time, it should become an instinct already baked into how you prepare for a meeting, how you structure an update, and how you deliver a piece of feedback.

Some people need the bottom line first and will ask for the details if they want them. Others need the context before the conclusion or they feel like they're missing something. Some people want feedback in the moment; others need a little processing time before they can receive it well. Some of your internal clients will want you to walk them through your analysis; others trust your recommendation and just want to know what to do.

You pick up on these things naturally over time. The question is whether you're actually acting on them, or defaulting back to what's comfortable for you.

There are formal frameworks that can help sharpen this awareness if you're interested — personality models like the Big Five (OCEAN) are one example, and tools like DiSC are another. But you don't need a framework to start. You just need to pay attention and be willing to adjust.

A few things worth noticing about the people you work with most closely:

  1. Do they want the details or the headline? Watch how they engage with information. Do they ask follow-up questions that dig deeper, or do they move quickly once they have the key point?

  2. How do they prefer to receive updates — written or verbal? Some people read everything. Others won't read a long email, no matter how good it is.

  3. How do they respond to feedback? Do they engage better with direct and immediate input, or do they seem to do more with it when they've had time to sit with it?

  4. What's their threshold for detail before a decision? Some decision-makers want to understand the full analysis. Others trust the recommendation and just need to know the risk.

None of this requires a personality test or a formal conversation. Most of it, you already know if you've been paying attention. You just need to decide to act on it.

The Actual Differentiator

We spend a lot of time in this profession developing technical skills, building substantive expertise, and learning how to navigate complex business situations. All of that matters enormously.

But some of the most effective in-house lawyers I've seen — and some of the ones who've advanced the fastest — aren't necessarily successful because they are the deepest legal experts in the room. What sets them apart is that they understand the people around them, adapt without being asked, and make everyone they work with feel personally well-served.

Call it a soft skill if you want. It's one of the most game-changing ones there is.

That’s it for today.

But before you go, here are a few links I think you will enjoy.

Each week, I share content from across the web that will help make your life as an in-house lawyer better. Let me know your favorite.

  • An Aspirational Framework for Hiring and Onboarding in the AI Era- AI expert Allie Miller improved up on this framework, and I've borrowed it as I think about where my team and I are headed. It lays out what it looks like to use AI effectively at work — not just frequently, but in a way that improves outcomes and expands what you're capable of.

  • When Your ChatGPT Chats Are Work Product - If you’ve been following AI at all, you are likely aware that Judge Rakoff recently warned that AI chats could be used against litigants. A federal magistrate judge in Michigan came to the opposite conclusion, ruling that a pro se litigant's AI chat logs were her own work product — not fair game for the other side. Cat Moon weighs in, and I agree with her: telling people who can't access a lawyer that they also can't use a tool to help themselves is a problem worth talking about.

  • In-Person in Boston - The Legal Mentor Network’s next in person event in Boston is coming up next Tuesday, April 28 at DLA Piper. If you are in Boston, this is a great opportunity to spend time with other lawyers in a friendly and supportive setting. And if you’re not in Boston, check out some of our other in person and online events.

  • On Grit and Jellyfish - This is a great post on doing hard things from litigator Susan DuMont. As she said in the comments, “Type 2 fun leads to more Type 2 fun! And better performance in all the rest of life I think!” I could not agree more.

Thanks for reading! Look out for the next issue in your inbox next Wednesday morning.

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