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

Workloads shift. Priorities change. Legal teams need ways to stay ahead without overextending themselves.

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.

With the right flexible legal talent in place, legal leaders can amplify strategic impact—leading nimble, high-performing teams that protect the business, fuel growth, and drive value across the organization. Latitude attorneys help in-house legal departments add capacity when workloads shift without sacrificing quality. Legal departments of all shapes and sizes rely on Latitude attorneys for leave coverage, backfill support, special projects, surge and overflow support, and fractional needs.

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

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