“These must indeed be splendid clothes! Had I such a suit I might at once…be able to distinguish the wise from the foolish.” — The Emperor’s New Clothes, Hans Christian Anderson
Remember the Hans Christian Andersen story The Emperor’s New Clothes? It’s about an emperor who is convinced by some vendors’ BS to buy a set of what’s described as a beautiful set of clothes. There’s only one problem; the clothes are imaginary. When the emperor wears (or actually doesn’t wear) the clothes in a big parade, his constituents are afraid to say that he’s wearing no clothes. Until a young child blurts out the truth: “The emperor is wearing no clothes!”
I can’t help thinking a bit about that story as I see AI tools that promise everything but may deliver questionable actual value.
A Siren Song for Email?
Many of these kinds of AI tools were on display last week at the AI Summit. I attended a presentation by Kyle Miller, Yahoo Email General Manager. Miller described an AI-based platform for managing, summarizing, and acting on emails.
Let’s face it, emails are the bane of most lawyers’ existence. We get hundreds of them every day. Many are routine. Many require no response. Many are marketing BS.
But some are critically important. I wanted to see if the Yahoo AI email management was something useful or just another AI tool that takes more time than it’s worth.
The goal behind the Yahoo platform is a good one: Leverage AI to create a more personalized email inbox experience. The idea is built around four pillars: The tool will catch what’s important in the email, will be able to act on it, will adapt as it goes along, and will evolve. “The goal,” said Miller “is that the platform would be more like a companion.” It’s similar to some other platforms offered by email providers.
I took a look at the present state of the Yahoo mail platform. It did a pretty good job of summarizing emails with offers and deals. It did not do quite as good a job at summarizing substantive emails.
The Verification Paradox
Miller made an interesting point: If it takes more time to create the prompt to get the output than it takes to get the output some other way, why use it? I was skeptical whether the platform Miller promoted would be the same way. Would it take more time to read the summary and what the AI agent planned to do than it would to just read the email itself?
It’s the same problem Melissa Rogozinski and I have written about with respect with respect to verification of AI-generated citations: The time savings are offset by the time needed to verify what the tool provided. In our rush to adopt the new and shiny AI toys, we forget whether they really do what’s promised. The ROI of AI is time savings. If it doesn’t save time, why use it? Why buy it?
ROI and Legal
Having said all that, I wonder about the use of these kind of AI email platforms in legal. I’m not sure these platforms pass the ROI test: I don’t think they save that much time in many circumstances.
First, any substantive email (or those that might be substantive) will need to be reviewed in total, irrespective of any summary. What could look like a simple reply-all might contain something the AI tool might miss.
More complex and detailed emails often require an understanding of context and nuance. They may require an understanding of the author, the business from which they come, past experiences, and the like. Perhaps someday, the AI platforms may be able to do this. But I don’t have enough confidence in them today to cede that understanding and not read the underlying email.
Think of it this way: You may know your client in ways the AI tool can’t. What they like. The latest book they read. Their politics. All of those things could make a difference in how you respond to a routine email.
Or how about this: you get an email from opposing counsel that appears to be routine case coordination but actually contains a subtle shift in their settlement position. An AI summary might characterize it as “standard case update” and miss the strategic implications.
And of course, if I have to read the underlying email, I haven’t saved time. I’ve actually spent more time. Let’s say it takes a minute to read the AI summary and a minute to read the email. That’s two minutes spent. If you just read the underlying email, it takes one minute total. Add that up over 100 emails and you’re talking real time. You’ve spent time you didn’t need to and may have even billed for it, much to your client’s dismay and state law ethics updates.
But that’s the paradox we find ourselves in today: Believing without question in the power of AI. Sometimes the emperor indeed has no clothes.
Unquestioned Reliance Leads to Compliancy
Without doubt, there are times that AI platforms save time. Significant time. They save time by separating out pure marketing materials. Or summarizing offers. Or ferreting out promotional materials masquerading as “newsletters.”
But the danger lurking is overreliance and complacency. The more we use the tool, the more we rely on it. We tend to get complacent and forget it can miss things. It doesn’t always get nuance. It doesn’t know, for example, the person sending the email might communicate using a blunt transactional style whereas another may use a softer, expressive one. Knowing that could make all the difference in how you react and respond.
I have worked with people on both sides of these styles by the way. I can read an email from someone with the blunt transactional style and if I’m not careful, since I’m a more expressive communicator, get really agitated. I have to make myself slow down and say, “That’s just Sam’s style, don’t take offense.”
If I didn’t do that? An email war between two lawyers could erupt costing everyone way too much time and energy.
An AI tool may be able to make that distinction after some training and seeing several Sam emails. But it might not and certainly might not early on. At the very least, it’s worth hitting pause first and asking the question.
And knowing that could make all the difference in the end result and your peace of mind. It’s akin to getting lazy about checking citations: The AI output looks good. It sounds good. To save time, it becomes tempting to rely on it.
I’m Not a Luddite
Don’t get me wrong. I am an AI fan. But in the age of hype and hyperbole, where vendors and pundits beat the AI drum over all else, it’s right to apply some lawyerly skepticism. To question some of what we are hearing. To take with a grain of salt that AI actually saves us time or whether we just think it does. To understand that just because a vendor says the clothes for the emperor are beautiful doesn’t mean they are or even that they exist.
In legal, where the margin for error is small and the stakes are high, we can’t afford to let AI vendor promises override our professional judgment. Before implementing any AI email tool, ask: What specific problem does this solve? How will I measure the time savings? What’s my fallback if the tool misses something critical?
Sometimes, the emperor is wearing no clothes.
Stephen Embry is a lawyer, speaker, blogger, and writer. He publishes TechLaw Crossroads, a blog devoted to the examination of the tension between technology, the law, and the practice of law.
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