Pro-Level AI for Law Firms

John McDougall breaks down why paid AI plans like ChatGPT Pro and Google Gemini deliver deeper research, fewer errors, and faster SEO workflows for attorneys. He covers file uploads, live web search, competitor analysis, and practical ways to get immediate time savings.

Why Paid AI Plans Beat Free Tools for Law Firms

John Maher: Welcome to AI SEO for Law Firms, the podcast that cuts through the tech noise to give you the exact roadmap for dominating search everywhere optimization and landing high value cases. From McDougall Interactive, I’m John Maher, and with me today is our founder, John McDougall. Today we’re talking about pro level AI for law firms. Welcome, John.

John McDougall: Good morning, John.

Maher: So, John, most attorneys have probably tried the free version of AI tools, but you’ve said that if a firm is really serious about growth, the paid tiers turn AI from being just…kind of a toy…into a true digital associate. What do law firms get from the paid version of tools like ChatGPT and Google Gemini that they maybe don’t get from the free versions?

McDougall: Number one, you’re saving a huge amount of time. And I think the lower end versions, obviously the free ChatGPT, for example, or I think even the $20 a month version, just don’t have the level of sophistication of really deep research with 5.2 Pro deep research and extended thinking. When you put it at that level of thought and it goes and spends 10 or 15 minutes every time you go have it do something, it’s coming back with really useful information, step by step, much less mistakes and hallucinations. And for a law firm, I mean, making a good amount of money, I think the 200 bucks a month for ChatGPT Pro and 250 for Gemini, I mean, those are small prices to pay, I think, to save time.

Maher: So, you’re basically getting these better models. And, like you said, this pro model is different than the basic model, and it’s going to have more thinking, more ability to do research and things like that, that you’re just not getting at that free tier.

McDougall: Yeah. The level of detail you get back and the accuracy, the level of quality basically is just so much better. Before I went to the pro versions, it was like, “yeah, AI is good”, but you’re kind of like, “geez, is this that exciting or usable”? Certainly when it was like…if you’re just getting the data based on old training data, that’s super lame, right? Especially when ChatGPT first came out, it’s like, “I’m getting these answers, but they’re outdated”, because they were using…

ChatGPT Pro vs Gemini: Different Strengths

Maher: Right, data from five years ago or something like that.

McDougall: Yeah, right.

Maher: You’ve said that ChatGPT and Gemini can also feel like kind of different personalities. Those two AI tools are a little bit different in the way that they work and the information that they give back to you. When should lawyers use one versus the other?

McDougall: Personally, I recommend using both. So ChatGPT Pro and the Gemini $250 a month version. I mean, obviously Claude for coding and there are a lot of different tools, but I don’t want to go into too many today. I think the main two that I’m using, ChatGPT Pro and the Pro version of Gemini, I use ChatGPT more for like drafting, structured thinking, reusable assets, and then you can then send those deep research documents and strategy things into get cleaned up in Gemini. And Gemini just in general is like a great SEO assistant. It is Google and the Google ecosystem. Not that they’re going to give away every last thing, but remember, Google has amazing help documentation on the Google blog about SEO, how to do SEO. I don’t know if people have looked at that stuff, but it’s really good. Like documentation on the Google Quality Raters guide.

It’s not like everything from the Google algorithm is private. I mean, they have a lot that’s private, but there are public patents that we’ve been reading for years about how the search engines work. And then just, again, the Google search docs and help files. So, when you’re asking Gemini, it obviously knows that stuff, right? And if that stuff’s public, I’m assuming that’s how that’s working is it’s able to give you really good answers about what’s going to work in Google because Google does want you to have helpful content that’s full of EEAT, expertise, experience, authoritativeness and trustworthiness, that whole EEAT thing. Google is encouraging you to have that kind of helpful content. And if you’re doing SEO type of stuff, title and meta descriptions, on page SEO, and you’re asking Gemini that, obviously it’s got all that background from the Google documentation.

So that SEO personality is really nice about Gemini. Not that ChatGPT is not decent at it too. There’s just like different flavors, I think, for each of them. So, draft in one, verify in the other is another way to look at it.

File Uploads, Privacy, and the Traffic Light Rule

Maher: File upload is a killer feature that you don’t get in the free versions of AI tools also. How can an attorney use that safely to analyze a competitor’s site or a marketing report or a Search Console report or things like that?

McDougall: I mean, a big win is to upload documents, CSVs, screenshots, and AI can find patterns that humans could miss. It’s just got such a big brain that it’s able to scan everything that you upload. But when you’re uploading, you’ve got to be very careful uploading privileged client data. You could think of it in terms of like the traffic light rule. So like green would be public competitor pages, your own public pages. Yellow would be internal marketing data, exported Google Search Console type of stuff. Red would be client info, case facts and privileged stuff. Don’t upload that stuff. But if you really need greater privacy controls, there are business and enterprise options you can look into.

Live Web Search for Keyword and Competitor Research

Maher: Okay. What about live web search? How is live web search within AI tools kind of changing things like keyword research or competitive analysis?

McDougall: Yeah. Again, I mean, the old, early days of ChatGPT were very frustrating because it was looking back at, what was it, 2021 training data or whatever. That was a lot less, obviously, way less useful, but just getting data back with links that it cites and then you have to do more research isn’t as easy as ask, verify, and site all in one motion. So the live mode is more efficient. You can ask, “what’s ranking today” for like a personal injury lawyer in Boston, “who’s showing up? What questions are people asking right now?” So you can do like keyword and prompt research. You might not get the exact data like you’d get from SEMRush, like monthly search volume, but you can get really good ideas for what people are asking and things like that. And then if you upload keyword research and continue to keep asking it, you’ll get even further.

So yeah, I think it’s just great that now you don’t necessarily have to upload like a screenshot of your competitor. It can go look at it. With that said, uploading screenshots of your competitors can make it very obvious like, “here’s a page I want you to analyze” kind of thing. But yeah, it’s just awesome to be able to say, “Go look at my competitors and give me ideas” live.

Maher: And just have it figure out for you who those competitors are, because it’s going to Google and it’s doing these searches and it’s finding … You might give it a phrase, a keyword phrase, or something like that and it’s going and finding, “Oh, okay. Well, based on that phrase, these are your competitors in your area and then let me analyze those and see what they’re doing that you’re not,” and that sort of thing. And that’s where that live search really comes in handy.

McDougall: Yeah. We did that yesterday on a training. We do the Workforce Training Fund. We’re certified by the state of Massachusetts to teach through the Workforce Training Fund, and one of our clients, we did that and we said…I actually scraped the homepage text because, again, I could say just go look at it live, but sometimes I like to be super exact. Take a look at this homepage text below of my AI SEO student and compare it. And I didn’t go and screenshot the competitors, that’s what…I used to do that a lot more, like go to three or four competitors, use a full page screenshot, grab the image of all those competitors and upload it and say, “compare it”. But now it’s nice. I don’t feel I need to do that now.

And it was pretty crazy what it came back with. I told my student, “See, in a way, you don’t need me anymore.” I mean, if you really wanted to go do everything on your own, and there are obviously a thousand steps to AI SEO now, but it was like, “Okay, here’s your homepage text and the top ranked sites for your main keywords, they have better geographic targeting in the headlines, they have longer text, they have FAQs, they have schema.” I mean, it just step-by-step came back with stating who the competitors were. “Competitor one has this”, kind of like SWOT analysis on the fly.

“This competitor has this that you don’t have, this one has this.” And if you add those key nice things that those five competitors have, all of those things, now you’re potentially beating all of them because you grabbed little gaps of things that you were missing, whether that’s paragraphs of text or better conversion optimization stuff like awards and affiliations or Super Lawyers or whatever badges of credibility. So, it did that for on page optimization mostly because that’s what we’re doing, but we also do that with the conversion stuff. And it kind of blended a little bit of that in there. It was like when you’re lengthening and deepening the page, it was suggesting a little bit of conversion stuff because again, conversion stuff really is now kind of part of on page SEO, because Google will rank pages better that have a good user experience and where people are satisfied with the page.

So if your page is really long for SEO and really boring with like just keywords all in it, that’s not exactly perfect on page SEO anymore, that might have worked 15 years ago, but now it came back…it was kind of a blend of conversion optimization stuff, but again, that’s because when Google was talking with the Department of Justice, they had to admit that user experience was in fact a part of a ranking factor, basically. It’s content, it’s links to your site, and how long people stay. Do they bounce off of your website? And if you’re just a bunch of on page SEO keywords and alt tags and interlinking, that’s not actually deep, on-page SEO, right? Deep, on-page SEO is keeping them there, which would involve some user experience/conversion stuff. So that’s what came back was like this unbelievable, not just old school SEO on-page stuff, but very current thinking.

So yeah, that’s amazing to get that live now. Hard to beat.

Quick Wins: Folders, Context, and Striking-Distance Keywords

Maher: Yeah. So if a firm wanted to start today, maybe they’re using the free version of ChatGPT and Google Gemini, but they say, “Yeah, this sounds great. I’m going to get the paid versions.” What would be a couple of things that they should do right away to maybe save an hour of their time this week?

McDougall: I mean, a first step would be learning how to upload files and give context. So, if you make a folder, it’s one of the awesome features of ChatGPT Pro, I think the Plus version has it, right?

Maher: Yeah, the folder structure.

McDougall: Yeah, you can have folders. Gemini doesn’t do that, so you have to keep everything in a thread. ChatGPT Pro and even Plus, having folders is awesome because you’re keeping the memory of the things, the various threads in that folder. So to pick, I would start with that, like learn how to make a folder and upload, for example, Google Search Console data about your site. I like to upload SEMrush data or Ubersuggest, whatever SEO tool you’re using with your ranking positions in Google, where you’re coming up, what your top pages are. Again, if you have Search Console set up and you can export that stuff, you can say, “I’m attaching various documentation on our ranking status, understand this stuff and then stop. Don’t do anything else.” So you just want to start there in that folder like, “I’ve attached a bunch of stuff that I want you to understand.”

Maher: “Read this”. And then it’ll come back. So, learn what I’m uploading, but then don’t do anything with it yet. Wait for me to tell you what to do.

McDougall: Sometimes it’s annoying like, “Oh, give me a stretch.” It comes back with this massive overblown thing and you’re like, “Oh my God, this is going to take me two weeks to read the reply. So, it’s like, “first just do this one thing”, and then it’s like storing it in context. So forever now in that folder, you don’t have to go back and re-upload that. Now that stuff’s going to change your ranking positions and things like that are going to change. But for the moment, you’ll be able to keep going back into that and do different things, like “give me a list of the places where I’m not top five in Google for keywords that you think would be meaningful”. Maybe I’m position 6 to 20 or something like that, or 8 to 20, where I’m coming up pretty good on the bottom of the first page or on the second page of Google, but not perfectly.

So go find those, what we call “striking distance” keywords that are going to be easier to get movement up to where it matters and tell me what to do next. Give me a strategy for some of the most important keywords where I’m just out of range. You’d be amazed because it’s going to find things that you might not have thought of because it’s looking at all the data. If you just ask it that to go look at the live internet, it doesn’t have all the background. You’re going to make it easier. Even though AI is super smart, what SEMRush and Ubersuggest and Search Console are going to give it for data is going to just be amazing. It’s going to give it fuel, basically.

The last thing I would say is just a little story of writing our next book. So, we’ve written numerous books on SEO over the years for people watching this, the Web Marketing On All Cylinders, that was a college textbook for five years, 420 pages.

We just got asked to speak today at Gordon College to the students. So sometimes we go into colleges and teach pro bono just to help out. Content Marketing and SEO for Law Firms, this book around COVID, and then Talk Marketing, our book about podcasting and SEO, podcasting and YouTube optimization as a mechanism to easily get talking content to better your SEO. And then we’ve written a lot of books for law firms.

So anyway, so I took my content marketing and SEO book and my talk marketing book, uploaded them into a folder called “AI SEO for Law Firms”. And I uploaded them one at a time and I said, “Understand this book and then stop.” And then I did that for those two books. I didn’t take the first book because that’s 15 years old. And then I put our first eight episodes of this podcast that we did intentionally with the concept of using it as a table of contents for our next book.

But what we would normally do would give that…I would go edit it or give it to a writer, “Hey, turn this into prose and then I’ll work with you on it and make it a book.” That’s how we did the talk marketing book. And that was very fast. I mean, way faster than writing books from scratch. Now, a book about AI SEO for law firms, you don’t want to only use AI, right? You don’t want like just push a button and write a book, but by uploading multiple books of my sort of brand voice, right? Like this is how I write, this is my style, this is my thinking, the AI understands that and the eight podcast episodes and then I said, “Okay, start by writing the prologue or the forward and things like that.” I mean, I usually have someone…like National Law Review wrote the forward to Content Marketing and SEO for Law Firms and Vignesh from Neil Patel Digital wrote it for Talk Marketing.

So, I’ll have a human do that, but more like a prologue, I said, “Write the introduction and background first.” So, step by step, that’s the key is, give it the context and the background in the folder and so “don’t overwhelm me.” And I tried this first and it failed. Even in Gemini with Gems or Opal, Google has this thing called Opal. It’s like a multi-step workflow and it understood that I was trying to upload all these documents, but it was really painful. I mean, it was not coming together. ChatGPT for that was amazing, but only when I realized even though AI is super smart, you’ve kind of got to go slow.

Maher: Step by step.

McDougall: “Do this one thing step by step”, and that changed everything. Now it’s just I need the time to sit there and finish it, but I’m not going to just, “Oh, here’s the book written by AI.”

Turning Podcast Episodes Into a Book With AI

Maher: You don’t tell AI, “just go write the book” and have it write the whole thing. You’re taking it a step at a time you’re saying, “Okay, write the forward here and now write the first chapter or something like that.” It can do like little chunks at a time, but it gets bogged down when you tell it to do some long, complex, multi-step process.

McDougall: That’s exactly right. It choked. Even with Gemini Opal it choked badly. I mean, it kept saying it was going to do it and hours later I’m like, “I’ll just go write it myself.” Remember, the talk marketing concept still applies here. Doing say 6 or 8 or 12 podcasts, I mean, 12 would be a lot. I mean, these kind of books that are…like we wrote Dog Bite Law for a personal injury law firm, I mean, you’re talking like maybe 100 pages, 120 pages, so that you have a little bit of a spine to it, it’s enough to have a gift book. Some people don’t want to read a massive book and things. AI SEO is changing so fast. I’m going to have it be like about 100 pages or so, 120 pages, I think.

But again, AI is not writing it out of the blue. It’s writing it using books that I wrote in the past. And if you don’t have books you wrote in the past, you could give it some style guides, of like how you think overall, into the folder. And I personally believe that uploading at least a half a dozen transcripts of podcast episodes where you specifically organize them in a table of contents using AI to generate the table of contents in kind of like topic cluster form, meaning like really well thought out, structured content that goes together. AI will do a great job giving you that outline, giving you the podcast questions. You then do the podcasts, upload them. Now your book is really based on you very deeply. So yeah, AI, I don’t mind AI helping me now with that. And when I’m done with the original, the first draft of the manuscript, I’m going to, either myself or pay one of my writers that ghost blogs for me for some of our content, I’ll give it that to that person.

Avoiding AI Slop and Detectable Content

So that’s a really good way to go because lawyers are busy and you don’t have time to do everything, but if you just think you’re just going to go right to basic ChatGPT, “Oh, write this blog post or write this book,” it’s going to be detectable as AI content, AI slop. It’s going to not be that deep or great, but if you do it this other way, if you’re writing it as a book, it’s okay if it’s AI, because it’s not being judged by Google, but if you’re going to put that content on your site, I think it’s still okay if the foundation of the concepts were from your original thinking and AI crafted it, but you would still need to go to originality.ai or Zero GPT type of tools to make sure it’s less than, say, 20% detectable as AI. So that’s the key.

But these folder structures and uploading the context is a game changer, especially with that 5.2 Pro deep research extended thinking. If you keep selecting that and yeah, it’s going to take 10, 15 minutes, each little thing it does, but you’re going to get results that are gold compared to the typical stuff people are doing.

Maher: All Right, well, that’s really great information, John. Thanks again for speaking with me today.

McDougall: Sounds good, John.

Maher: And thanks again for joining us on AI SEO for Law Firms. If you’re ready to stop losing high value cases because of outdated SEO, subscribe and follow us on Apple Podcasts, Spotify, or wherever you listen. And for a deeper look at your firm’s current AI strategy, visit mcdougalinteractive.com for a free audit.