One of the best parts of being in-house counsel is that we get to be business partners, problem solvers, and strategic advisors. One of the hardest parts? Most people don’t ask for legal advice until they absolutely have to.

And look, I get it. No one wants to slow things down with legal questions when there’s a deal to close, a product to launch, or a contract to sign. But sometimes, just a quick check-in with legal before making a decision can save everyone a lot of headaches later.

So, consider this a friendly, preemptive guide to the legal advice you might not think to ask for—but definitely should.

1. “Yes, your personal texts can be subpoenaed.”

I know, it feels like texts, WhatsApp messages, and Slack DMs should be off-limits. But in reality, if it’s relevant to a legal dispute, it’s fair game.

So before you fire off a message like “Don’t worry, we’ll cover any losses” or “Just sign it, we’ll sort out the details later,” take a pause.

✅ Better move: If it’s important enough to discuss, put it in the contract—not a group chat. And if you ever type, “Let’s not put this in writing,” you’ve just created a very interesting piece of evidence.

2. “Just because another company does it doesn’t mean it’s legal.”

We’ve all heard it: “But [insert competitor’s name] does it this way!”

That’s great for them, but unless they’re willing to personally cover any fines or lawsuits on your behalf, it’s not a strong defense.

✅ Better move: If you see a competitor doing something risky, let’s take a minute to double-check whether they’re getting away with it, or just haven’t been caught yet.

3. “Contracts are not ‘just boilerplate.’”

The phrase “Don’t worry, it’s just standard boilerplate” has the same energy as “Just click ‘I agree’ without reading the terms.”

Here’s the thing: the most “boring” parts of a contract, like indemnification, liability caps, termination clauses, are usually the ones that matter most when something actually goes wrong.

✅ Better move: Read the whole contract. Or, at the very least, flag anything that feels unclear before signing. Future you will thank you.

4. “Verbal agreements are real agreements… they’re just really hard to prove.”

Yes, a handshake deal is still legally binding. But unless it’s recorded (which, let’s be honest, would be weird), it’s your word against theirs.

The problem isn’t that verbal agreements don’t count, it’s that they’re nearly impossible to enforce if someone changes their version of events later.

✅ Better move: At minimum, send a quick follow-up email: “Just confirming what we agreed to…” That way, you have something to reference if memories suddenly become very different.

5. “If the deal sounds too good to be true, it probably is.”

That vendor promising “unlimited support” with no fine print? The contract that’s “super light on terms”? The sales rep who swears “there’s no downside”?

If something feels too easy, too generous, or too much in your favor, it’s worth asking why. Because there’s usually a catch, you just haven’t found it yet.

✅ Better move: Take an extra five minutes to check for any surprise clauses before celebrating.

6. “Your indemnification clause actually matters.”

I get it. Indemnification sounds like one of those legal terms that probably won’t come up, so why stress about it?

Well, this is the clause that determines who pays when things go sideways.

• Who covers the cost if a third party sues?
• Who takes the financial hit if there’s a major breach or dispute?
• Who is stuck writing the check if the unexpected happens?

✅ Better move: If you’re not sure how indemnification works in your contract, ask legal before signing. Because finding out later is much less fun.

7. “A termination clause is like a prenup; you don’t need it until you do.”

Right now, everyone’s excited about the partnership. Everything is sunshine and synergy. But contracts don’t exist for when things go right, they exist for when things get complicated.

If you don’t negotiate an exit strategy up front, you might find yourself stuck in a deal you can’t get out of.

✅ Better move: Make sure you understand how and when you can walk away from an agreement before you sign it.

8. “Just because they said it in an email doesn’t mean it’s enforceable.”

It’s great when a vendor promises special terms or a sales rep guarantees a discount, but unless it’s actually in the contract, it doesn’t count.

Courts don’t enforce verbal promises or wishful thinking. They enforce what’s written down.

✅ Better move: If it’s important, make sure it’s part of the actual agreement, not just a friendly email exchange.

9. “Compliance is not optional.”

“Oh, we’ll deal with privacy compliance later.”

Oh, will you? The thing about regulations like GDPR and CCPA is that they don’t wait until it’s convenient for you. Just because you haven’t been fined yet doesn’t mean it’s not coming.

✅ Better move: If your company handles personal data, let’s make sure it’s compliant before regulators decide to make an example out of you.

10. “If legal is raising concerns, there’s a reason.”

If your in-house lawyer is visibly stressed, if we’re pushing back hard, or if we say, “We really need to talk about this,” — it’s not because we enjoy slowing things down.

We’re not here to make your life harder. We’re here to protect the company, protect you, and make sure a small issue doesn’t turn into a big one.

✅ Better move: If legal is waving a red flag, don’t ignore it. We’re not here to stop progress, we’re here to make sure progress happens without unnecessary risk.

Final Thoughts

Legal isn’t about saying “no” for the sake of it, it’s about helping the company move forward while staying protected.

A quick check-in with legal before making a major decision can save a ton of time (and stress) down the road. But since we know that’s not always going to happen, hopefully this list helps highlight the key legal questions that are worth asking before things go sideways.

What’s the best piece of legal advice you wish more people asked for? Let’s swap stories in the comments!