What Executive Teams Actually Want From In-House Legal

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Deep Dive

The In-House Lawyer Executives Can’t Imagine Working Without

Ask most in-house lawyers what their job is, and they'll tell you some version of the same thing: protect the company from legal risk. And they're right. That is the job. But it's not the whole job, and the lawyers who stop there are leaving real value, and real career opportunity, on the table.

The executives you work with want more than a legal service provider. They want a thought partner. Someone who brings clarity when things are complicated, stays calm when things go sideways, and tells them the truth even when it's not what they want to hear. That's a different skill set than what law school trained you for, and it's worth developing intentionally.

Here's what executives are really looking for from their in-house teams.

1. Clear Guidance Over Analysis

Law school memos and exams taught us that nuance is everything. We were awarded more points on our exams for spotting more issues in a fact pattern. When we wrote memos in law school and as junior associates in firms, we were encouraged to list out and explain all the potential issues on both sides.

Guess who doesn’t want a list of 50 potential issues with a new company partnership or product? Or an in depth analysis of how 5 different regulations might be a blocker to a new deal?

The executive team. They want clear guidance.

If there are 50 material, unsolvable problems with a partnership, don't list them all. Tell the executive team the deal is likely a bad idea, share the two or three biggest reasons why, and propose one or two alternative paths to the same business goal. That's it. That's what they need.

If the problems are real but manageable, do the work to figure out how to mitigate them first. Then lead with the bottom line: it's okay to move forward, here's what we need to put in place, and here's a quick read on the tradeoffs. Executives can work with that. They can't work with a 50-point issue list.

Action Step: Distill your guidance into a clear recommendation, and lead with that. Then provide a brief explanation of the key reasons for that recommendation. Remember that less is often more.

2. “Help me understand” over “No”

As an in-house lawyer, colleagues will come to you with ideas that you know will get the company sued, cause it to lose money, or worse. Saying “no” protects the company from risk, but is a missed opportunity for legal.

Instead, try starting your response with “help me understand.”

Those three words do something that "no" never can: they buy you time, signal respect for the business goal, and almost always surface information that changes the conversation. Try it once and you'll use it forever.

“Help me understand the business goals here.”

“Help me understand how you came up with this approach.”

“Help me understand what aspects of your proposal must be acceptable in order for this to work, and which ones might be more flexible.”

Action Step: Practice intentionally pausing when you hear an idea that seems problematic. This helps avoid your natural, but not always helpful, instinct to immediately shut it down. Then, get curious and try asking some of the above questions. You may just come to a great solution.

3. Solid Practical Solutions Over “Perfect” Impractical Ones

The most perfectly buttoned-up option isn't always the right one. When the "perfect" solution protects the company but requires an administrative overhaul or introduces unnecessary complexity, it may not be so perfect after all.

I saw this firsthand early in my career. I negotiated an advertising contract with a revenue share component for a new partnership. The contract was thorough, well-reasoned, and a genuine win-win. But the draft had multiple teams sending reports back and forth, too many audit requirements, and was administratively heavy. We ended up settling on a simpler structure that made the company slightly less money on paper, but that people could actually run. It was the right call.

The best in-house lawyers think through implementation as part of the work, not as an afterthought. Before you deliver a recommendation, ask yourself: can the people who have to execute this actually do it? Do they have the bandwidth, the tools, the authority? If the answer is no, you don't have a solution yet.

This requires staying close enough to how the business operates that your guidance lands in the real world, not just on paper. Sometimes that means talking to a product manager or operations lead before you finalize your advice. The goal is guidance the business can actually use.

Executives are builders. When legal hands them something they can't act on, it reads as out of touch, even if it's technically correct. The lawyers who earn a seat at the table deliver advice that is both sound and doable.

Action Step: Before you finalize your next recommendation, ask yourself: if I handed this to the business team tomorrow, could they actually implement it? If the answer is no, keep working. The goal isn't perfection on paper. It's a solution that actually solves the problem.

4. Calm Over Chaos

Any lawyer who has been in-house for more than a few years has experienced a moment when it felt like the proverbial sky was falling.

The biggest customer is trying to cancel their contract. HR just received a letter from a recently terminated employee's lawyer alleging discrimination. And the merger that's been 18 months in the making is threatening to fall apart. All on the same day. It happens.

We can't prevent days like that. But we can control how we respond to them.

The CEO does not want a breathless phone call from their in-house lawyer reporting that everything is a disaster. They want a calm, clear heads-up on what's happening, paired with one or two concrete proposals for how to move forward. The difference between those two versions of the same conversation is enormous, both for the outcome and for how you're perceived as a lawyer and a leader.

This is where in-house lawyers can really distinguish themselves. Staying composed when things go sideways is a skill, and it's one that gets noticed. It signals that you have judgment, not just knowledge. It tells the people around you that they can bring you their worst problems without making things worse.

The way to build that reputation is simple, though not always easy: when something goes wrong, slow down before you pick up the phone. Take a few minutes to think through what you actually know, what you don't yet know, and what the most likely paths forward are. Then make the call. You don't need to have all the answers. You just need to show up as the steady, clear-headed person in the room.

Action Step: The next time something urgent lands on your desk, resist the urge to immediately escalate. Give yourself ten minutes to organize your thinking first. What's the actual issue? What are one or two ways to address it? Then bring that to your executive, not the chaos.

5. Honest Negative Opinions, Even When They’re Unpopular

The most dangerous person on an executive team, to the company and to the CEO themselves, is a lawyer who always says what the team wants to hear.

Executives are surrounded by people who tell them what they want to hear: direct reports who want to stay in their good graces, vendors who want to close the deal, board members who don't want to rock the boat. You have a choice: be one more voice that validates whatever is already in motion, or be the person who tells them the truth. The lawyers who become truly indispensable choose the latter.

This is harder than it sounds. When a senior executive is visibly excited about a new deal or initiative, it takes real confidence to say "I think we have a problem here." The instinct to soften, hedge, or stay quiet is understandable. But when you give in to it consistently, you stop being a trusted advisor and start being a rubber stamp. Executives, even the ones who seem to want agreement, almost always know the difference.

Delivering an honest, unpopular opinion doesn't have to mean killing the deal or raining on every parade. Lead with the business goal you're trying to protect, not the legal technicality. Be direct, be brief, skip the lecture. Say it once, and if the decision goes the other way, get behind it and help make it work.

What you want to avoid is staying quiet in the room and then documenting your concerns in a carefully worded email afterward. If something matters enough to put in writing after the fact, it mattered enough to say out loud in the moment.

Executives don't need a yes machine. They need someone honest enough to push back, and composed enough to do it without being preachy. That combination is rarer than you'd think.

Action Step: Think about a concern you have right now that you haven't fully voiced. Maybe you've softened it or told yourself it isn't your place. Find a moment to say it directly. You don't have to be confrontational. You just have to be honest.

Bringing it all together

None of this requires a new title or a bigger team. It requires a shift in how you think about the job. The lawyers who rise, and who genuinely love their work, are the ones who stopped seeing themselves as legal service providers and started showing up as business partners. That starts today, with the next conversation you have.