267 | AI First Drafts: What Your Clients Aren’t Telling You (and Why It Matters)

Hello to all 8128+ of you from around the globe.

This edition is about the fast growing “AI First Draft Dilemma” and what lawyers need to start doing and asking to save their a$$. See a helpful checklist at the end.

The scene:

You open the document your client just sent over. It looks polished. The formatting is clean. The tone is confident. It's even structured like a solid legal memo.

But something's off.

A few key facts are wrong. The structure, while familiar, doesn’t actually match the client's real situation. And there are a few assertions that sound plausible—but just don’t hold up under scrutiny.

You suspect this wasn't drafted by a human. Or at least not entirely.

Welcome to the new normal: the AI First Draft.

Clients—from everyday citizens to solo entrepreneurs to sophisticated in-house counsel—are increasingly using AI to create the first draft of legal documents before outside counsel even enters the conversation. Contracts, memos, emails, issue spotters, litigation narratives: AI can now do it all.

This means outside counsel is now navigating a very different kind of document review and client relationship. One that comes with hidden risks, awkward conversations, and new economic pressures.

Here are the three things every lawyer needs to start thinking about when reviewing client-generated work product.

1. The Prompt Problem: What Was Shared, and With Whom?

Most clients aren't disclosing when they've used AI. And even when they do, they often forget the more important part: what they told the AI to get the draft.

This matters.

If a client pasted confidential strategy, facts, or matter details into ChatGPT or another public LLM, there's a real chance they've waived privilege or confidentiality without realizing it. Many consumer-grade AI tools store prompts. Some even learn from them.

And here's the kicker: in three months, when you’re in discovery or deposition prep, no one’s going to remember what that original prompt said. But you might still be held responsible for how it shaped the draft.

What to do:

• Ask explicitly if AI was used. Every time!

• Ask for the prompts.

• Flag potential waiver risks early—and build a process for documenting this in your intake or engagement letter.

2. The Confidence Barrier: When AI Sounds Right, But Isn’t

AI generates documents that sound very lawyerly. Which gives clients—even smart, experienced ones—a false sense of confidence.

When you start to scrutinize the draft and pull it apart, the client may get defensive. After all, they already "did the work." They just want your blessing.

This dynamic can quietly erode trust. The lawyer is trying to protect the client. The client thinks the lawyer is trying to pad the bill, or worse, reassert control.

What to do:

• Acknowledge the value of the AI starting point.

• Focus your critique on tailoring the draft to the client's specific context.

• Use language that aligns you with the client against the problem: "Let's make sure this reflects your specific reality, not just a similar situation."

3. The Economic Shift: Why AI Work Can Cost More, Not Less

Here's the biggest surprise for many clients: that AI draft they think saved you time? It probably didn't.

It may have created more work.

When outside counsel receives an AI-generated draft, three things now need to happen:

1. The draft itself must be reviewed line-by-line, just like any client work.

2. The prompts need to be requested, read, and evaluated for privilege or factual error.

3. Time needs to be spent communicating with the client about what AI got wrong—and why that matters.

That’s not free. It’s not even neutral. It’s additive.

What to do:

• Set expectations early: reviewing AI drafts takes time, especially if risk is involved.

• Consider developing a policy or line-item for "AI work product review."

• Remind clients: you're not charging for what the AI did. You're charging for what it missed.

The Bottom Line

The first draft might be a landmine and timebomb. It's a document with unknown inputs, potential privilege risks, and subtle emotional baggage.

Outside counsel need to be ready with:

• A clear process for identifying AI-originated work

• A protocol for reviewing prompts and evaluating risk

• The language to explain, without condescension, why review still matters

Happening Now

This is happening right now. Inspired by this LinkedIn post where trademark attorney Josh Gerben described how clients were sending AI-generated emails and action plans that required 2-3x more attorney time to correct and clarify, I dove deeper into the issue.

Even before reading that post, I had conversations with practitioners across the spectrum who were already encountering AI first drafts and struggling with how to address them productively.

Often, just starting the conversation with the client feels awkward.

So, I put together a short and simple checklist lawyers can use. Is it foolproof in eliminating your risk? No. But by presenting these questions early, it opens the door to a more transparent, fruitful, and safer exchange with your client.

The AI First Draft Checklist for Outside Counsel

• ❑ Was AI in any way to draft this?

• ❑ Which tool was used?

• ❑ Do you have a copy of the prompts?

• ❑ Was confidential or privileged information entered into the AI tool?

• ❑ Are you comfortable with us reviewing, revising, or redrafting this from a risk standpoint?

• ❑ Do you understand that review of AI work may involve additional time and cost?

  Talk to you soon again . . .

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DISCLAIMER: None of this is legal advice. This newsletter is strictly educational and is not legal advice or a solicitation to buy or sell any assets or to make any legal decisions. Please /be careful and do your own research.