When Business Teams Don't Take Legal's Advice

Deep Dive

Setting the scene . . .

When I talk with friends about their biggest challenges as in-house lawyers, one issue comes up again and again: business colleagues—from the CEO to the sales rep—don’t take their advice. And when that happens repeatedly, it creates frustration and limits legal’s influence and impact.

Sometimes that looks like outright ignoring legal guidance.

Other times, it looks like nodding along, thanking you for the input, and then doing the opposite.

And sometimes, it looks like legal being cut out of the conversation entirely or looped in only after decisions are effectively locked.

All of this is incredibly frustrating. Especially when you’re confident the advice is legally sound and genuinely aimed at protecting the company.

It’s tempting to throw up your hands and say, “They just don’t get it.” But that response doesn’t help the business, and it doesn’t help your career.

Moments like this call for self-assessment, ownership, and a more strategic approach. Here’s what to do.

1. Honestly assess the situation

When we’ve put in real effort, it’s easy to assume our advice should be followed. But that isn’t always the right lens.

For example, did you flag a legal risk that a colleague consciously decided was worth taking in exchange for meaningful business upside? You might not agree with their call, but it also could be reasonable.

Or did you raise issues in a contract negotiation that were technically legal, but primarily business risks, like termination for convenience, pricing flexibility, or a vendor’s ability to change terms in ways that might (or might not) ever matter? Maybe they assessed and decided they can live with those risks.

Not every ignored comment is a failure of influence. Sometimes it’s a rational tradeoff.

The first step is being honest about which situation you’re actually in.

2. Take responsibility for your role in being ignored

Maybe they’re difficult. Maybe they distrust lawyers. Maybe they root for the wrong football team.

There are plenty of reasons a business colleague might resist legal advice, and many of them are unfair.

But “unfair” doesn’t mean “out of your control.”

Can you build a relationship that helps them see legal differently? Have you asked about their prior experiences with lawyers and genuinely listened if those experiences were bad?

It’s worth taking a hard look at whether their behavior is not fair, but at least understandable.

• Did your feedback take so long that the project moved on without you?

• Do most of your interactions focus on what they can’t do, rather than where legal can help them move faster or smarter?

• Have you been stretched thin, stressed, or short-tempered, and letting that spill into your conversations?

Once you’ve taken ownership of your role in the dynamic, the next question is whether your advice is actually landing the way you intend.

3. Assess and update your communication approach

Even when your advice is right, how you deliver it matters more than most of us like to admit.

Legal training rewards precision, completeness, and spotting every issue. Business decision-making often rewards clarity, speed, and judgment. When those styles collide, legal advice can be technically correct and still get ignored.

Take a close look at how you’re communicating:

• Are you leading with the risk, or with the recommendation?

• Are you explaining why something matters in business terms, or defaulting to legal analysis?

• Are you presenting options or just problems?

Many business colleagues don’t need (or want) a memo-length explanation. They want to know:

• What’s the real risk?

• How likely is it?

• What happens if we do nothing?

• What do you recommend?

If your feedback is landing as overly cautious, overly long, or overly theoretical, it may not be because they don’t respect legal; it may be because they can’t quickly translate what you’re saying into a decision.

To fix this, you need to reframe theoretical legal advice into practical, concrete guidance the business can actually use.

For example, instead of saying:
“This provision creates significant legal risk and we shouldn’t agree to it,”

Try something like:
“This provision gives the customer a termination right that could cost us ~$500K if exercised. It’s not market, but we’ve seen it enforced about 10% of the time. My recommendation is to accept it if this deal is critical to hitting this quarter’s number, and push back if it’s not.”

Same legal issue. Very different outcome.

Clear, concise, business-oriented communication is one of the fastest ways to rebuild credibility and to shift legal from being seen as an obstacle to being seen as a trusted decision partner.

4. Use tools of influence

When clear communication isn’t enough, it’s time to think about how influence works. It rarely comes from just being right. It comes from trust, timing, and alignment with what the business actually cares about.

Start by anchoring your advice to shared goals. If a team is focused on speed, revenue, or customer experience, frame your guidance in those terms. Legal risk matters, but it carries more weight when it’s explicitly connected to outcomes the business already prioritizes.

You can also borrow credibility from others. Sometimes advice lands better when it’s reinforced by:

• a prior incident (“We saw this exact issue cause problems in X deal”),

• external market practice (“This is why most companies our size handle it this way”), or

• leadership expectations (“This is consistent with how the CEO has asked us to approach risk”).

Timing matters, too. Advice delivered early, when options are still open, feels collaborative. Advice delivered late can feel obstructive, even when it’s correct.

And don’t underestimate the power of offering a path forward. When people feel stuck, they push back. When they see a workable solution, they’re far more likely to engage.

5. Work on building your relationship

If you want your advice to be taken seriously, the work can’t start only when there’s a problem.

Influence is built in the common, day-to-day moments outside of high-stakes deals and tense negotiations. If the only time a business colleague hears from legal is when you’re saying no, pushing back, or flagging risk, it’s not surprising when they tune you out.

Invest time in understanding how they operate. What pressures are they under? What does success look like in their role? What are they measured on and what keeps them up at night?

Small, consistent actions matter more than grand gestures:

• Checking in early on projects, before opinions harden

• Offering quick, informal guidance before something becomes urgent

• Following up after a decision to help implement it, not just approve it

Over time, this builds a track record: you’re not just a risk-spotter, you’re a thought partner.

It also means being human. Remembering context. Giving grace when things are messy. Acknowledging when the business made a tough call, even if it wasn’t the one you would have chosen.

6. Let it go

Even if you do all of the above, there will still be times when your advice isn’t followed.

That’s part of working in-house.

Your role is to advise: to surface risks, frame tradeoffs, and make thoughtful recommendations. You don’t control every outcome and you’re not supposed to. Once you’ve clearly weighed in, it’s often both appropriate and necessary to let the business make the call.

Strong in-house lawyers know when to push, when to influence, and when to step back. They conserve their credibility for the moments that truly matter.

Ironically, the ability to let go often increases your influence over time. It signals confidence, judgment, and alignment with the business; qualities that make people more likely to seek out your advice the next time around.

Wrapping it up . . .

Taken together, these steps won’t guarantee your advice is always followed. But they will increase your influence, protect your credibility, and help you show up as a trusted partner rather than a last-minute gatekeeper.

That’s an ideal position to be in as an in-house lawyer, and the benefits compound over time.

This is issue #52 of In-House: Outside the Box!

I hit “send” on the very first issue from a hotel room during a Red Cell all-hands week almost exactly a year ago. Since then, this newsletter has gone out while I’ve been standing up new companies, supporting financings, deep in board prep, and occasionally on vacation.

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