Attorneys and law firms are starting to look into running ads during AI chats.
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In today’s column, I examine the emerging trend of lawyers and law firms opting to place ads that will appear during everyday usage of generative AI and large language models (LLMs) by consumers and businesses.
Here’s the backstory. Hundreds of millions of people are tapping daily into the likes of ChatGPT, GPT-5, Claude, CoPilot, Gemini, Grok, and other major LLMs. The AI makers are keenly interested in monetizing their LLMs. One means of earning a buck consists of allowing ads to be displayed when AI chats are underway.
A potential advertiser approaches an AI maker to find out what advertising arrangements might be possible (or the AI maker reaches out to those that might want to advertise in the AI). Discussions about the nature of the ads, their wording, frequency, and other aspects are undertaken. If all goes well, the AI maker then sets up their AI to incorporate ads for that ad buyer.
Should lawyers and law firms go this route, placing ads that will appear during AI chats?
One perspective is that absolutely, lawyers and law firms ought to do so. They are reaching potential clients in a rather unique way. The AI can detect when a user is leaning into a legal topic and then, on a timely basis, display an ad for that lawyer or law firm, reaching the user at an ideal moment in time. This is far better than blindly buying ads on roadside billboards or in magazines. The AI is targeting the placement of your ad in just the right place at just the right time.
Whoa, comes the angry retort, it is unseemly for lawyers and law firms to be advertising amid AI chats. Users aren’t expecting to see ads by legal beagles, especially not while having a personal conversation with AI. It is outrageous. It is tantamount to ambulance chasing.
Let’s talk about it.
This analysis of AI breakthroughs is part of my ongoing Forbes column coverage on the latest in AI, including identifying and explaining various impactful AI complexities (see the link here).
As a quick background, I’ve been extensively covering and analyzing a myriad of facets regarding the intersection of AI and the law for many years. You can find my writings not only in my Forbes column but also as posted in Bloomberg Law, ABA Law Journal, The National Jurist, The Global Legal Post, Lawyer Monthly, The Legal Technologist, MIT Computational Law Journal, and so on. I give frequent talks on the latest trends of AI in the legal field, including having been the keynote speaker at the iTechLaw World Technology Conference.
There are two major perspectives on the mixture of AI and law:
Thus, you can apply the law to AI, and conversely, you can apply AI to the law. For my big picture overview of both of these exciting and rapidly evolving realms, see my discussion at the link here and the link here.
When it comes to applying the law to AI, the aim is to establish suitable regulations and provide appropriate governance on how AI should be devised and implemented. There are longstanding concerns that AI makers aren’t giving due attention to the ethical ramifications of their wares. Ethical issues are construed as “soft laws” and aren’t as formidable as legally enacted laws, known as “hard laws”. To level the playing field and keep AI makers on the up-and-up, some believe that we need more AI laws.
On the other side of the coin is the application of AI to the law. This consists of using AI to aid legal activities. Lawyers tap into the latest AI to devise legal strategies, brainstorm to find creative legal arguments, draft court filings, and prepare for cases by having the AI pretend to be an able adversary. For my extensive coverage on AI for legal reasoning (AILR), see the link here.
Shifting gears, you might generally know that some of the AI makers are inching their way towards incorporating ads into their AI chats. The AI makers are doing this cautiously. They know that users might turn on them. If a user can easily switch from one AI to another one, they might abandon an AI that has ads, opting to use an AI that doesn’t include ads.
Another concern for AI makers is that running ads might bring new laws and stern regulators into the picture. Lawmakers might decide that LLMs should not willy-nilly include ads. All sorts of legislation and regulations could readily come down the pike and restrict how ads can be legally utilized by AI companies. AI makers don’t want that kind of heat. As such, they are gingerly making their way toward ads. For more about my coverage of where the new AI laws are appearing and what they encompass, see the link here.
Part of the reason that ads are attractive to AI makers is due to the desire to make money and turn a profit. Most AI makers have some of their AI available for a monthly subscription; they also offer a less-capable version for free usage. It sure would be handy if they could run ads, particularly in the free version, allowing them to bring in some nice dough.
Why would a business or entity want to run ads that appear during AI chats?
First, there is a huge and untapped market of millions and on the order of billions of people that are regularly undertaking AI chats. As the old saw goes, the reason that crooks rob banks is that’s where the money is. If you want to advertise to the public, doing so via ads placed into AI chats is extremely alluring.
Second, the AI maker can tune their AI to best choose when to display an ad. This aids in reducing wasted spending on ads. The AI will display an ad that befits the topic of an AI chat. A chat that discusses how to fix a car might get an ad from a car dealer or a mechanic’s shop. The right ad, at the right time, for a particular user, is something that you cannot readily get in any other venue, especially not at scale.
Let’s see how the ads topic applies to the legal field.
Lawyers and law firms already advertise in lots of venues. You probably have seen legal ads on billboards, bus benches, inside subway cars, during online searches, on social media, and in many other places. If ads in general are going to be appearing in AI chats by businesses of all sizes and shapes, the legal field would naturally be curious about and potentially interested in doing likewise.
Advantages of doing so include:
Downsides are also important to consider, including:
I’ll keep you posted on what state bars are saying about AI chat ads for lawyers and law firms, along with positions formulated by the ABA. For some of my prior coverage about ABA positions on AI topics, see the link here, the link here, and the link here.
Now that we’ve covered a macroscopic viewpoint, let’s dig into the nitty-gritty.
A common approach to displaying lawyering ads during a chatbot conversation consists of triggering an ad based on these two factors:
Notice that the two factors are considered independent of each other. A user prompt might trigger a lawyering ad. The AI-generated response might trigger a lawyering ad. If both the user prompt and the AI-generated response happen to invoke triggers, that’s fine, but it only needs to be one of the two that does so.
Another important aspect is that the AI is not influencing the AI-generated response, in the sense that the response isn’t based on whether the user prompt has triggered a lawyering ad. The AI-generated response is determined separately from any ad triggering that is going on. It is the same AI-generated response regardless of whether any triggering occurs in the user prompt or in the AI-generated response itself.
The lawyering ad is displayed after each turn of the conversation. A turn consists of a user prompt that is followed by an AI-generated response. Thus, once the AI-generated response is shown to the user, a lawyering ad can then be displayed. If there wasn’t any triggering during the turn, a lawyering ad would not ordinarily be displayed.
There are lots of exceptions and twists and turns on this conventional setup, but let’s use that straightforward approach first.
Here are some quick examples to illustrate this approach.
You can plainly see that the prompt and the response contained legal considerations. The AI detected those aspects and then ran an ad. The ad appeared after the turn had completed and did so before the next turn got underway.
The prompt and the response were obviously part of a legal consideration since the user asked overtly about taking legal action. But the AI doesn’t necessarily need to have the legal consideration be quite so obviously articulated.
For example, a subtle indication might be involved. Look at this turn:
Observe that the prompt did not directly ask about a legal topic, nor did the AI-generated response give a legal indication. Nonetheless, the AI was able to trigger from the mention of a car crash to then opt to display a lawyering ad.
The fluent customized version, which costs more, would say something like this:
The AI has peeked at the prompt and the AI-generated response, and accordingly devised an ad that tried to more fully match the chat that is taking place. This version mentions that it was a minor crash. Additional elements of the prompt and the response could also be dovetailed in the ad. There is a balance between elongating the ad with too much customization and keeping the ad relatively streamlined.
The beauty of this type of ad is that it is being done at a massive scale. In other words, it is an entirely customized ad that is crafted by the AI in real-time for however many thousands or millions of chats might be taking place at any moment in time.
A different and highly controversial approach to lawyering ads consists of infusing the ads into the internal processing of the AI. You might recall that so far, the lawyering ads have had no bearing on the AI chat itself. The AI chat is the AI chat. Lawyering ads are merely being triggered by whatever the AI chat is covering. In that sense, the lawyering ads have no direct influence on the AI chat.
As an aside, I might add that a lawyering ad can have an indirect impact on an AI chat.
Here’s how. A user sees the lawyering ad, and this stirs the user to start asking the AI about legal topics, even though that might not have been the path of the chat up until that juncture. Consider the example of the person who got into a car crash. They weren’t focusing on legal aspects. Nor did the AI-generated response focus on legal aspects. Perhaps, after the lawyering ad is displayed, the user might now start asking legal-oriented questions to the AI. The point being that a lawyering ad can potentially spur a user to veer into legal territory, despite the AI chat not previously being in that realm.
Spurring a user is a possible consequence of a lawyering ad. Still, the AI itself wasn’t being influenced by the lawyering ad. If we wanted to do so, it would be easy to have the AI take into account that a lawyering ad is at play.
There are two major routes:
Consider the first route. A handy example of infusing legal topics into chat, doing so to aid the prominence of a lawyering ad, would be this:
You perhaps noticed that the AI-generated response pretty much set aside the question about car insurance, and instead hammers away that the user should find an attorney.
That’s quite a different response from the prior one. Why? Because the AI was tilted to try to produce responses that match one of its advertisers. In this case, this becomes a nearly perfect one-two punch. The user gets the “unbiased” AI answer, and on the heels of that answer, the lawyering ad magically appears. Chef’s kiss.
The other route is even more blatant. In the second route, the AI actively names the lawyer or law firm within the content of the AI-generated response. No more footsie playing. The AI lays things right on the line.
You can clearly now see that the contents of the ad are completely incorporated into the AI-generated response.
Whether the actual ad is also displayed is up to the advertiser’s preference. Sometimes, it makes sense not to show the ad. This will make it seem that the AI has organically come up with the naming of the lawyer or law firm. Also, showing the ad might arouse suspicion in the user. Despite those potential pitfalls, there is value in showing the ad since it can double up and help reinforce to the user that they should make use of the lawyer or law firm.
There are plenty of ethical landmines and legal pitfalls to this unashamed approach.
Ads within AI chats are a bold move. Even bolder is the placement of ads by lawyers and law firms into AI chats. It is risky right now. Those with a weak stomach should wait until the air is cleared as to what the legal field considers permissible versus impermissible. Likewise, wait and see what society as a whole thinks of lawyering ad placements.
For those seeking a high upside in a high-ambiguity advertising channel, please proceed with due caution. I believe that this will initially be niche law practices. They customarily must make sure that their ad dollars are as effective as humanly possible. Maybe AI will help with that goal. Such law firms also tend to be eager to find ways to rise above the usual clutter.
Lawyers and law firms that are traditionally reputation-dependent are probably not going to swiftly wade into this swimming pool. It could be perceived as beneath the white-shoe law firms. Plus, if there is a backlash, they are usually highly averse to muddying their prized and hard-fought reputation.
Any legal beagle working in a tightly regulated space or spanning multi-jurisdictional areas will need to mindfully decide whether this is the right play for them. One other consideration is that if you do place ads, and if those ads hit the jackpot, you’d better be sure that you have a strong intake process already in place. A dour outcome would be to generate tons of client leads, but flounder trying to collect them, sort them, and be responsive to them. Be ready for a tsunami of responses, just in case.
AI makers are also going to be cautious about including lawyers and law firms as advertisers. The AI makers realize that those are hot potatoes at the get-go. It is much safer to start the ad bonanza with other professions. Also, sorry to say, law firms are generally known as being stodgy and not willing to try out new ways of doing business. Their outlook might not fit well with the AI developers who want to move fast and break things.
A final thought for now. Cicero famously made this remark: “The good of the people is the greatest law.” If running ads for lawyers in AI chats is good for the people, bam, ads ought to start flowing. But if such ads are bad for the people, well, we’ll have to wait and see what happens.
Consult with your trusty attorney before deciding.
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