"Soon, Not Using AI Will Be Malpractice"

Collin McKee

Welcome back to the Endeavors AI Podcast. I'm your host, Collin McKee, founder of Endeavors AI, where we explore what AI actually looks like inside a professional firm — small businesses trying to figure out where it fits, what it costs, and what it changes. Today's guest is Michael Carr, a business and estate planning attorney based in Florence, Alabama, part of what the locals call the Shoals area. Michael spent nearly a decade in solo practice before joining the firm where he works today. His practice covers business formation, M&A, commercial contracts, and trust and estate planning — the kind of work that touches people at real moments in their lives and businesses. What I want to talk about is something most attorneys don't discuss publicly: what running a lean practice actually teaches you about time, and what that lens looks like now as AI enters the picture for small firms. Michael, welcome to the show.

Michael Carr

Thank you, Collin. Thank you for having me.

Collin McKee

Before we get into it, give folks a quick picture of how you got here. You're originally from Birmingham, ended up in Florence following your wife — which I can relate to, moving for the right person. How did you land where you are today?

Michael Carr

I met my wife in law school — we were part of the statistical twenty-five percent of law students who meet their spouse in school. After we graduated in 2009, I went off to England for a year to get an LL.M., and my wife secured a position with a good regional firm here in Florence. So when the year was up and I came back, it made sense for me to follow her up here, because she was already established. I took the solo route — hung my own shingle and practiced what we call threshold law: anything that walks through the door, we'll take a look at. A little litigation, insurance defense, primarily some plaintiff's work. After a couple of years I decided I'd rather focus on transactional work, where I had more control over my calendar and my clientele, so I moved into business consultancy and transactional work — contracts, business formation, mergers and acquisitions. Then when COVID came along and the business world ground to a halt, I pivoted to estate and trust planning, not only for high-net-worth individuals but small business owners and anybody with protectable assets who needed a succession plan. That's what I've been doing most of my career — the estate planning since COVID, the business planning pretty much since day one.

Collin McKee

You mentioned in the pre-call that it wasn't that your solo venture wasn't working — you hit a ceiling. How did that happen?

Michael Carr

I'd say I hit a comfortable plateau. For right or wrong, I took pride in being a one-man shop. I had a paralegal I shared with another attorney I rented an office from. It was good and I enjoyed it, but I got to a point where I either needed to expand and hire a team, or join a team. At that point my daughter was about two, and I made the personal decision that I didn't want to be at the office eighty hours a week. I wanted to be there for first steps and first days of school and ball games. So I consciously moved out of solo practice into an established firm here in Florence and went of counsel.

Collin McKee

I wanted to touch on time management. You said something in our pre-call that stuck with me: you could get to your desk at eight o'clock, then look up around ten-thirty and realize you haven't done an ounce of legal work. How does that happen?

Michael Carr

I'm not sure how familiar you are with what I call the Eisenhower matrix — urgent and important, urgent but not important, important but not urgent. You'd come in with a to-do list of your top three priorities, sit down with the best of intentions, and then the phone would ring and it'd be a fire you needed to put out. You'd get that resolved, and then an email would come through. Particularly in this digital, connected age, we are all slaves to our notifications, and I've certainly been affected by that. These days when I'm working I do my best to close my email so I don't even tempt myself with the distraction — I check it first thing in the morning, when I get back from lunch, and at the end of the day. That seems to help a lot. I haven't found a great solution for the phone ringing, but I think that's the nature of the beast. As attorneys we serve at the privilege of our clients, and when they have urgent, pressing matters, as their trusted advisors we need to pick up the phone. It's a balancing act — a tightwire walk every day — but for the most part it's manageable.

Collin McKee

I agree. You can't shut all the notifications off, because people do need to reach you — but the lower-impact things need their time and place. So you ran what I'd describe as a fractional general-counsel model. Not subscription-based exactly, but you knew your clients would need roughly five to ten of your hours a month. How did that structure help you protect your time?

Michael Carr

In solo practice I was able to maintain a small book and a lean practice, and working with small business owners over the years you get a sense of the rhythm and seasonality of their individual businesses and needs. So I could informally time-block: this client usually needs about five hours a month through the summer, but they slow down in Q3 and I can take on new clients. A lot of it was trial and error, bumping along until you find your footing. But that was a good practice niche, where I could be available to small businesses who honestly didn't need a full-time payroll general counsel — they needed the security and confidence that when they had a legal issue, they could pick up the phone and an attorney would be available who was already familiar with their business, their structure, and their issues.

Collin McKee

And that seemed to work — was it adjustable when a client needed more of your time?

Michael Carr

Over the years I intentionally established some standing meetings or calls — touchpoints to check in and say, "What's coming down the pike? Is there anything new we haven't talked about since last month?" Really just trying to stay ahead of it. The easiest problems to fix are the ones you see coming, before they develop into full-blown problems. That's what we try to do when we can.

Collin McKee

Get the fires early. Let's shift to the AI piece. Your firm recently started using an AI tool through Clio — I understand the assistant is called Vincent. Walk me through how that happened. Was it a firm-wide decision, or did one member champion it?

Michael Carr

Our firm has used Clio as our client-management software for several years — it predates my association with the firm. They recently rolled out their AI program, and the chatbot itself is named Vincent. I did a demo and was impressed. The interface is very similar to ChatGPT or Claude. But the benefit for us and for other law firms is that it's self-contained: the database they use is vLex, which used to be called Fastcase, and it's a strictly legal database. So the model isn't going out and searching Google and the internet at large — it's all self-contained, and our hope and belief is that will not necessarily prevent, but maybe reduce, the chance of hallucination. The other benefit is that Clio already has our confidential, attorney-protected client information by virtue of being our client-management software, so we feel a little more comfortable that they're working on the back end to make sure it comports with the ABA model rules for confidentiality and privilege.

Collin McKee

Two benefits there — it's not pulling from everything out in the ether, and it's not pushing your information out into the ether either. I can see how that builds trust. To that point, you mentioned a phrase I love: trust but verify. What does that actually look like in your practice? Are you checking everything?

Michael Carr

Right now we have a simultaneous subscription with the Clio AI and Westlaw. As part of my due diligence, any citation, case, or rule of law, I will always go back and double-check it in Westlaw, KeyCite it, and make sure it's still valid. The other thing I've recently noticed — and I'm probably not going to use the right nomenclature — is that it shows you what the agent is doing. It keeps a log or ledger of the steps it takes, so you can go back and verify: this is where it pulled that case, this is where it found that clause. That's been very helpful. Maybe it's a peace-of-mind issue, but it lets me say, "Okay, it's not just a black box." When I type in a query, it shows its work and tells me what it's doing.

Collin McKee

Is there anywhere it's falling short right now?

Michael Carr

I'd probably say we're still on the upward slope of the learning curve. The more we use it and the more familiar we become with the technology, the better our results will be. The problem's in the chair, so to speak. I don't know that the AI has issues — I think it's user error.

Collin McKee

That's very well put and very humble. Most people would put the onus back on the technology, but I think you're spot on — people don't take the time to really learn and understand it, and to train it to understand what they want. That time and effort pays dividends. So let's turn to your clients, because what you described before we started recording genuinely surprised me: some clients now come into initial consultations with something they'd already talked through with ChatGPT. When did that start happening?

Michael Carr

It's been a very recent phenomenon, but I do think the sea change is underway. Last month I had an initial consultation — a couple wanted a trust to avoid probate. I went through my whole spiel about the difference between an inter vivos revocable trust and an irrevocable trust, the pros and cons of each. As the consultation was concluding, the gentleman said, "You said just what ChatGPT said." I didn't know exactly how to take that. I was somewhat relieved that it gave them the same information — I hope I said it better, or more particularly in compliance with Alabama law, than a general LLM answer. But I think we're already seeing, and it's only going to become more apparent, that our clients will come in better armed and equipped, with a printout from AI, having asked all these questions of the computer before they ever seek legal advice. Where we as lawyers can differentiate ourselves is with expertise, judgment, and the historical knowledge of an issue. The computer is great at research — it's got the entire annals of human history right in front of it — but it hasn't actually litigated that issue itself, and it doesn't know what a Lauderdale County jury will say. So to avoid legal advice becoming a commodity, the impetus is on attorneys to really stand out and say, "Here is my personal, professional experience with that, in this location, at this time — and that's how we can benefit you best."

Collin McKee

That almost answers my next question, but maybe there's more. Do you think an AI-informed client is a good development for the attorney-client relationship overall, or is it too early to tell?

Michael Carr

It's probably a little too early to tell, and I can certainly see it being a double-edged sword. It's cliché, but as attorneys we're in the relationship business, particularly in my practice areas. I hope I can be a trusted advisor and offer sound counsel in a way a machine can't. The AI can provide a generalized knowledge base, and I think that's good — particularly for client sophistication; it saves time on the front end. But on the back end you really want to be the human voice our clients come to know and trust. Time will tell, but I'm one of those who believes knowledge is power, and I would rather my clients weigh and measure my advice than follow it blindly. Other attorneys may say, "No, this is what you need, take my word for it." But there are no bad questions, and I want to make sure I'm asking the right questions so I fully understand your issues, goals, and objectives. I think that's one way attorneys can really get at the root of the issue that an AI can't — because it's only going to respond to the queries the client asks, and it's not going to know to ask the follow-up question.

Collin McKee

And as it stands today, a lot of the models are catered toward making you feel good — giving the answer it thinks you want. Another guest described the eighty-twenty problem: it's perfect on eighty percent, but it's that twenty percent it gets wrong that could really leave you in a bind. That's where you need the professional experience.

Michael Carr

Yeah — they're sycophants, right?

Collin McKee

Let me ask a couple of questions before we close. For any solo attorneys or small firms who are AI-curious but haven't really started — and there are areas of the country that are ahead of the curve, and others where they may not have heard of ChatGPT at all — what's one thing you'd recommend they do this week?

Michael Carr

I think it largely depends on your own technological comfort level, and your ability to adapt and improvise as you bring in this new technology. I'd advise starting small. If you haven't gotten a free ChatGPT or Claude package, I'd certainly start there — and just play with it in your personal life, not professionally. Kick the tires, look under the hood, see what the capabilities are, and then decide at what level of your practice you're going to start integrating. I don't want this to turn into a commercial for Clio, because it's not, but one thing that appealed to us was that it was more or less turnkey. It seamlessly integrated with our existing platform and procedures — it's got a Gmail plugin, a Microsoft Word plugin, things that make it easy to at least start. My overarching advice would be to go ahead and start, because I don't think we can put the genie back in the bottle at this point. A couple of years ago, the worry was that using AI would be tantamount to malpractice. I think a couple of years from now, not using AI will be considered malpractice.

Collin McKee

If you could talk to the earlier you, as a solo attorney, and advise him to use one AI tool that would have helped at that phase — it may not have existed, but imagine it did — what would it be?

Michael Carr

The tool I'm really enjoying and using the most now is document review. I can remember not terribly long ago getting a thirty-page contract and sitting there toiling over every word. The AI is able to digest that and create any number of things — a table of authorities, a table of contents — in literally seconds. You can find every clause, every contradiction; you can create your own redline copies. So document review, at least for me, looking back over fifteen years of practice — there's no telling how many thousands of man-hours it can save.

Collin McKee

Exactly. Michael, this has been exactly the kind of conversation I wanted — honest and practical, from someone who's actually lived it, from solo into a small firm and the AI the firm is using. I think you're going about it the right way. How can our audience find you and your firm?

Michael Carr

My firm is Johnson, Paseur, & Medley. We're located in Florence, Alabama. You can find us at johnsonpaseur.com — P-A-S-E-U-R. My email is michael.carr@johnsonpaseur.com. If anybody wants to reach out, I'd love to connect and I'll be happy to help any way I can.

Collin McKee

For anyone listening, if you found this useful, please share it with someone in a small firm who's asking the same questions. And if you're an attorney or a business owner wondering whether your own operation is ready for AI — whether you've got gaps, feel exposed, or just want to know where to start — that's what Endeavors AI is here for. You can reach out at endeavorsai.com or find me on LinkedIn. I'm Collin McKee, this is the Endeavors AI Podcast, and we'll see you next time.