They might just use it like a typewriter.

Attorneys are in the room earlier now

Rob’s opening read from the vendor side: two or three years ago a mid-size firm’s big purchase ran through the administrator first and the attorneys arrived late, and if the administrator was happy the firm was happy. That is shifting. Debbie had not clocked it until he said it, then counted how many recent calls have had only lawyers on them. Which works fine for some purchases and falls apart the moment the subject is billing and accounting.

Fear buying, then the fear of buying

Firms still buying out of fear of being left behind rather than from a named problem look for different things and run a different process. Debbie’s version of the pattern: urgency spikes, a solution gets found, the lawyer goes back to their desk, another fire starts, and months later the same person calls back needing it immediately. She traces it to Dr. Larry Richard’s work on the lawyer brain and the resilience factor, how long a lawyer can hold something as urgent.

Spend the thirty minutes on what matters to them

Debbie’s advice for demoing to a lawyer: with that much undivided attention, whoever is running the demo has to know what matters to the person in the room, not to the paralegal or the intake person or the billing clerk. Being a lawyer is one piece of information. Which lawyer, a real estate associate or the practice chair or an executive committee member or the managing partner, and whether they are buying the tool or using it, are two more, and they change the conversation entirely.

The woman who needed a typewriter

A lawyer leaving a big firm to start her own sent Debbie a list of everything she needed, and item number ten was a typewriter. She still kept paper files, the tab on each one needed a sticker with the client name and matter number, and she could not imagine another way to get the words onto the label. Debbie has reused that line ever since. Give a lawyer a powerful AI tool and they may use it like a typewriter, because nobody has shown them what better looks like.

Activation, not training

Training is something you deliver: a session, click here, do that, here is what you get. Activation is the slower work of a tool becoming part of how a practice group or an individual lawyer gets through the day, and it happens over weeks rather than in an hour. Rob’s parallel from his own side of the table: people ask for a microwave, and you cannot always just hand them one, because what they needed was the best heating element and they had no way to ask for that.

The managing partner’s moment

The session the two of them are building came straight out of the comments on an earlier broadcast, where enough people asked to bring their managing partner that they made it real. Debbie’s pitch is aimed at the partner who told her his firm has no AI strategy and refuses to participate in the gutting of the profession, and had every argument ready. Her answer was not a rebuttal. Everybody gets their own opinion, but what if you could be part of shaping what comes next?

Big valuations, and the access to justice gap

Debbie built her ILTA recap by reading what the industry’s regular writers filed, and found the same themes repeating, most of them about booth sizes. The one that stuck was money pouring into legal AI against no real movement for the people who need a lawyer and do not get one. Rob’s read on the valuations: at those numbers investors are not betting on a vendor’s ability to sell to law firms, they are betting on legal services themselves.

Commodity work goes, judgment work stays

Debbie’s marker for where the work actually goes: when KPMG got its license under Arizona’s sandbox rules, the press release said technology enabled legal services, while a law firm delivers human enabled legal services, and the human one costs more to deliver. Commodity work leaves first. Then both hosts describe doing the same thing that same week, asking Claude first and calling a lawyer anyway, because the judgment was the part they were paying for.

Transcript

A rotating team, but we keep showing up

Rob: All right, Debbie, we’re live. Welcome everybody to Sidebar Live. Debbie, I’m really glad there are three of us that do this, because if I look back over the last six or seven weeks that we’ve done it, it seems like we’re a rotating team, but we’re committed to it and we’re going to keep showing up.

Debbie: We are going to keep showing up. I mean, I don’t know what we’ll do if there’s only one of us and it isn’t you, because none of us know how to. Amanda and I tried and we didn’t do very good at that.

How law firms are buying differently

Rob: Well, everybody’s gotta have value, right? I can push the buttons, so I love it. So this week, let’s just jump in. There’s so many different things I’d love to talk about. I know one that’s really resonating with me, and I think we can talk about things from a slightly different approach today, just because of the business that you and I are in. But one of the things that’s really top of mind is how law firms are buying differently. I spoke to somebody that you and I both work with at a larger company, who runs the revenue team, and it’s the same thing. If you went back two or three years, historically the firm administrator, when they’re making a big purchase decision, especially around some of the bigger products they have, is very involved out of the gates. The attorneys, and I’m generalizing, this isn’t the same for everybody, but at mid-sized firms generally the attorneys come in later, and if the administrator’s happy, they’re happy. That’s changing. Are you seeing that?

Lately it has been only lawyers on the call

Debbie: It has not been noticeable until you just said that. But I’m thinking, I’ve been on a few calls lately where it’s only been lawyers on the call. Now, it depends what they’re buying, right? If I’m talking to someone about billing and accounting and only the lawyers are on the call, I’m like, guys, this is not going to work, we’re going to need to bring some other people in, unless the lawyers happen to also be doing the billing. But it kind of depends what they’re buying, right?

A lot of firms are still buying on fear

Rob: Yeah, that’s fair. When I read between the lines on that, it continues to go into the AI conversation. A lot of it, when we look at our Sidebar members, a lot of firms are still buying on fear, fear of being left behind. And so instead of going about the purchasing process like they always have and looking for the key things that they always have, the conversation’s kind of changed.

Debbie: Yeah, I think there is definitely still the fear purchasing, for sure. We’re seeing that. And I think there is fear purchasing, and then when it comes right down to signing, there is the fear of purchasing, right? So you probably see it too. We get these people on calls and they’re like, I’ve got to have this, I need it tomorrow. And then you’re like, knock knock. Hello. Is anyone home?

The lawyer brain and the resilience factor

Debbie: And sometimes I think, I have been talking a lot and thinking a lot about the work that Dr. Larry Richard has done around the lawyer brain. And I think that this is, if this buying trend is true, depending on what you’re buying, and we’re going to talk to more lawyers, one thing that we have seen on repeat for a very long time when we’re talking to lawyers about purchases is the resilience factor. How long can they keep something urgent? Something happens, they’re like, pick up the phone, I’ve got to talk to somebody right now. You’ve got a solution for them. They’re like, okay, this is going to be great, can’t wait for the next thing. They go back to their desk. The urgency dies down a little bit. Some other thing gets on fire. Their attention goes somewhere else. And then you’re like, but remember how you really wanted to solve this problem? And then we’re chasing them. And then we chase, and then we wait. And then when they call you back, they’re like, okay, now I really need it right now. And you’re like, that was three months ago, right?

Rob: I know. Yeah, I know. I always laugh, sales leadership coming into this industry from other industries, it’s always a learning curve, because legal is so different. Those traditional buying patterns that you see in other industries just don’t happen in legal, just because of the way firms are structured.

Advice for the administrator running a purchase

Rob: You know, Debbie, thinking about that and thinking about the buying process, obviously Affinity Consulting, you all, and by the way, let me plug this real quick, you said the lawyer brain, Larry Richard’s research, by the way, phenomenal, look it up if you haven’t read it. There’s some free content on there that’s worth reading and I think it’s evergreen. It doesn’t really change, it doesn’t go away, it’s the same stuff. But going back to what you were saying, Affinity Consulting, you guys handle everything from those first conversations through the whole use of the product, right? You guys stay around for a long time. But focusing on that acquisition, when they’re looking for new products, knowing the attorneys are getting more involved, is there any kind of advice to share with firms, or anything to think about that would make that process smoother as we see this change in the overall industry? If there’s a firm administrator coming to you, is there anything you’d say differently today than you’d say before?

Use their thirty minutes on what matters to them

Debbie: Well, I think we have to use our time wisely with every kind of buyer, right? It’s why, and you and I have talked about this before, about tailoring demos, whatever it is, to whoever your audience is. Because if you’re going to have a lawyer, or it doesn’t even matter who it is, but let’s stick with lawyers for now, if you’re going to have thirty minutes of their undivided attention, as much as you can get of that, we’ve got to focus on things that really matter to them. That means the person doing the demo needs to intimately understand what is important to them, and not what is important to a paralegal or the intake person or the billing person, right? We can’t get caught up in those things, because with that captive audience we have to figure out how we communicate how the features and functionality are going to help the person who is in the room do their job more efficiently, serve their client better, faster delivery of services to the client, whatever their goal is.

Debbie: And so I think we should look at it as an opportunity, and it might actually make all of us change how we think about a sales cycle, right? It’s one thing when you get a firm administrator or COO on the phone and you’re talking about who else is going to be involved in this. It’s a whole nother thing when you have a lawyer on the phone, and quite frankly, which lawyer do you have? Do you have a lawyer that is in the real estate department, or do you have the real estate practice chair, or do you have an executive committee member, do you have an equity partner, do you have a managing partner? Being a lawyer is one piece of information that you need, but you actually need additional information to know who you’re talking to. If you’re talking about selling to that person, and then if you’re talking about meeting their needs, that’s two different jobs. It might be held by the same lawyer, making a purchasing decision and delivering legal services to a client. But if you’re only talking to someone whose responsibility is finding a tool to help deliver legal services better, your demo and your conversation is different than if you’re talking to the person who’s looking for the tool and they’re the decision maker, right?

Which lawyer do you actually have?

Rob: New variables.

Debbie: Yeah, very much so.

Make the vendor make you the hero

Rob: And I think, for any firm administrators watching, or people that are championing, championing, I really struggle with that word, a new product purchase, I’d almost put some more onus on the administrators these days to go to the attorneys, really understand what they’re looking for and those pain points more than ever before, and communicate that to a vendor. So they are making you look good, making you look like the hero, and showing the things that matter to your team. We’ve seen over the years that if a firm administrator doesn’t run the process right, or whoever’s leading doesn’t run that process right, if it goes over a certain number of days, it tends to die, right? It dies because, to your point, another fire happens, something else has got their attention and they put this on the back burner. So running that type of process, making sure you’re doing some of that work up front and understanding what’s changing with AI and how people are approaching things, is super important for any firm going through the process.

From the ILTA breakfast: training is not the thing

Debbie: For sure. And it reminds me, when we were at ILTA a couple of weeks ago, we had that breakfast session, and one of the things that I talked about was how important it is to not be so focused on AI training. Training is something that you deliver. It’s a session, it’s click here, it’s do that, this is what it looks like, this is what you’re going to get. But when you think about what someone needs from an AI tool, the work that you do there is with a practice group or with a lawyer, but it is over time, until that tool becomes part of how they get their work done.

Rob: Yes.

Debbie: And I think what you said before is, a firm administrator, a COO, another business leader in a law firm buying a tool, before the call about the tool you’ve got to understand the friction and the pain points and what better looks like.

The woman who needed a typewriter

Debbie: I promise I will make a five minute story into a one minute story, but there’s this woman who was leaving a big firm and she wanted to start her own firm. And she sent me a list of everything she needed to do it. And item number ten on her list was a typewriter. I mean, this was like ten years ago. It was hilarious ten years ago. She said typewriter. And then she said, stop laughing. I know you probably think I’m crazy, but I still use paper files. And paper files have that little tab on the top. And on the tab on the top, I have a sticker. And on the sticker, I have the client name and the matter name and the matter number. And then she said, I can’t imagine any other way to get that information on the label unless I have a typewriter. So I think I need a typewriter. But if you have another way, I’m open.

Activation, not training

Debbie: And I have used her “I can’t imagine any other way” so many times. And I think it applies here. You give a lawyer a powerful AI tool, they might just use it like a typewriter, because they can’t imagine any other way. And so if we’re not really invested in activation, that’s what we’re calling it. It’s not just, you need training on an AI tool. It’s activation. How do you think about making it a part of someone’s normal life? And if you leave them to their own devices, it’s not painting with a brush stroke that it is true for all of them, but it’s true for a lot of people, that they can’t even imagine what amazing looks like.

You cannot always deliver a microwave

Rob: It’s funny, I have that conversation internally all the time. People don’t always, you can’t always deliver a microwave when people ask for a microwave. What’s the best heating element, right? And sometimes, to your point, they don’t even know what that is. So it makes a lot of sense to me as well.

Planning season or the managing partner?

Rob: There’s a few different directions I could take this in, Debbie, and maybe you can choose, because you’re always being interviewed, you’re always having these conversations. I know you can take anything I throw at you. But last week when we met and we were talking, we’re getting into planning season, or at least we’re getting into planning season and budgeting season, we can go in that direction. Another topic I’d love to talk about is the managing partner conversation we have coming up as well. What sounds more exciting? We truly wing this, guys.

Debbie: I think we should talk about the managing thing, because I am so excited about that event.

The event that came out of the comments

Rob: Okay, so to give people context, you just posted about it, right? Centerbase just posted about it too. I’ll repeat my comment on there. I’m excited about it because it was organic, right? It was organic in the sense that you and I were literally speaking and I was watching the comments, and they were like, I’d love to bring my managing partner to this, right? And so after enough people said yeah, yeah, yeah, and liked it, you’re like, done, we’ll do it. Why are you so excited about it?

The managing partner’s moment

Debbie: You know, I commented back on my post, because I was like, you know what, you’re right, it was so organic. It just naturally happened. But the thing that I think is, for any managing partner that has the law firm kind of in their care for this period of time, we specifically titled it the managing partner’s moment, your role in the transformation of an industry.

Rob: I love that.

We refuse to participate in the gutting of the profession

Debbie: Not that long ago, I was on a call and I said to a group of lawyers, tell me about your AI strategy. And one of them immediately jumped in and said, we don’t have one. We’re not going to use it. We refuse to participate in the gutting of the profession. And I was like, whoa, tell me more about that. I mean, he had his answer at the ready. He listed off all the things. He listed off water. He listed off data centers. He listed off the environment. He listed off, how will we train young lawyers. It’s going to make us stupid. All the things that we’ve heard. And I just said, I hear you. Everybody gets to have their own opinion, but what if you could be a part of shaping what’s next? And I think that’s what this is. You are a managing partner. You are holding the law firm in your hands. What a time to be alive.

Is it scary, too?

Rob: Is it scary, too?

Debbie: Yeah, of course it is. I mean, if you are paying attention to the news, you saw the post from yesterday or the day before, where the Anthropic guy left and was like, the robots are going to kill us in the next ten years. And listen, last night, I’m not going to lie, I was sitting there with my three year old grandson, whose arm is in a cast, reading him a book and thinking, in the next decade, this kid is three, right? We have to be thinking about this from a professional responsibility perspective. But the opportunity here is, what a time to be alive. What an opportunity we have to think about what is next. And so I’m excited about putting together a thirty minute session that makes a managing partner think about the opportunity that is in their hot little hands right now.

Nothing like it since Y2K

Rob: I’m sitting here taking notes, because it’s such a good way to think about it. The glass half full, the opportunity. From a vendor perspective, somebody I talked to said they hadn’t seen an opportunity like this since Y2K, right? And I would even say, Y2K, this is a once in a lifetime thing.

Debbie: I know.

Rob: I was sitting there with my kids last night, my twins are eight, having the same conversation, and my son says, I don’t want to die in ten years. I’m like, you’re going to be okay, don’t worry about it. But it truly is an opportunity. And when you were speaking, I’d almost look at it through the lens too of the opportunity there. It might change, but does this open up the ability for more people to get legal services? Does it make it more efficient and effective? And are we able to serve the community better that’s looking for that service?

The ILTA recap: big money, and access to justice

Debbie: So interesting that you said that. Yesterday we did a What’s New in Legal, and I did an ILTA recap. And how I did my ILTA recap is, I went and read all of our favorite people. Bob Ambrogi, Steve Embry, Nikki Black, the Legal Tech Hub people. I just went and read a bunch of things. Which, by the way, one of the Legal Tech Hub people, Caitlin I think, hers was an ILTA recap all about Dolly Parton. Fantastic. It was so good. I’m going to post it on LinkedIn later. But anyway, I went and read through all of those. There was a lot of recurring themes. Most of them were about the booth sizes. But one of the things that many of them brought up is, boy, we’re spending a lot of money, but are we closing the gap on access to justice? And the general consensus is, we’re really not. We’re chasing big things. We’re chasing shiny things.

Debbie: I mean, did you see yesterday, five hundred and fifty million dollars on a fifteen and a half billion dollar valuation for Harvey? What I didn’t connect the dots on is, earlier this year they raised two hundred million at an eleven billion dollar valuation, earlier in 2026. We have crazy money flying around here, and some large percentage of people who need a lawyer, need legal services, aren’t getting it. So I think that is an interesting problem to think about how to solve.

What the investors are actually betting on

Rob: Yeah. And I think, I’m not naming any specific vendor, but we are seeing a lot of high numbers out there. And obviously these people investing aren’t just investing for the goodwill of investing and helping, right? There’s a return they’re looking for on that investment. And you start to think about the legal market as a whole and law firms as a whole, and some of these valuations are bigger than that. And so it makes you think, the investors are not betting on vendor X’s ability to service law firms. They’re betting on legal services, right? They’re going even deeper and further than that. Which, to your point, comes back to, shape what’s next, right? Be a part of that. It’s the moment.

Debbie: It is the moment.

Technology enabled versus human enabled

Debbie: And you know, if you think about, I mean, I am certainly not a futurist, and I always feel guilty when I start talking about this, because I think of some of my futurist friends in this industry who might listen to what I say and be like, she’s like a kindergartner in all of this. But when I think about legal services, the big umbrella of legal services, there’s a lot of commodity work that happens that, you know, the machines are going to do it. Years ago, when KPMG got their license to practice under the sandbox rules in Arizona, their press release specifically said technology enabled legal services. A law firm delivers human enabled legal services. Which one do you think is more expensive to deliver? It’s the human one, of course, right?

Debbie: So for the people who are inside of a law firm and worried about the kind of work that goes away, the first kind of work that goes away, and maybe the only kind, at least for our foreseeable future, is the commodity work. The judgment work, the reason why I picked up my literal cell phone yesterday and called my attorney and said, I really need to talk to you. I did ask Claude my question first, and I said, no, I need to talk to my lawyer about this, right? Human judgment, a trusted advisor, someone who knows me, knows my situation. That’s the money shot. We need more of that and less of the rote commoditized work.

Rob takes his own agreement to a lawyer

Rob: It’s funny, I did the same thing yesterday. I had built an agreement and I sat on it for a few weeks, because it’s an important document. And I was like, do I trust this, and do I trust myself? And I ended up bringing it to an attorney. I actually said, rip it up if you want to. I did use Claude to do this, and we know how attorneys feel about that, and they love it. But there is still that opportunity, like the way you’re doing work changes.

A two hour walk with Claude

Rob: Your organization, and so did mine at Centerbase, we took Friday off, right, just an extended holiday. I love the concept of it. If you don’t do it at your firm, consider it. Labor Day, Memorial Day, take the Friday off. Four days is so much better than three. And I went on a walk and had a two hour conversation with Claude. People were probably staring at me, wondering what I was doing, but I was working differently, right? I don’t do the busy work anymore. I’m doing a lot of this more meaningful strategic judgment work that AI can’t put a pattern around.

Debbie: But it can certainly help you think about that strategic work, right? And so you show up with the context and everything, your judgment, and you now have a thought partner that you can spar with about that. Why am I right? Why am I wrong? What am I missing? There’s huge value in that, even for a strategist or a trusted advisor, to have that thought partner that’s not going to get sick of us asking it questions.

Rob: One hundred percent. Debbie, we have five minutes left. It’s like when you and I get on the phone, forty five minutes later, we’d miss part of a meeting.

What the focus groups told us

Rob: We’ve been doing work with Amanda lately to understand what the market’s looking for. We put together some focus groups to understand the gap, that the administrators still feel like they don’t feel empowered and have the right information to make the right decisions, right? There’s a lot of fear there still. And what’s come out of that is Sidebar 2.0, that we’re working on some.

A new Saturday email for mid-size firms

Rob: But in the meantime, we did do something exciting this weekend, which was, we had an internal newsletter that you, Amanda, and I received every Saturday. Essentially, you’re talking about all the experts in the space, and we’re the first to tell you we’re not the, we really think everything’s moving so fast that you have to rely on your peers, you have to rely on other information to make these judgments just to keep up. And so we’ve created another newsletter that’s going out, but it’s really focused on mid-sized firms. So it’s pulling five, six, seven of the top themes that we’re seeing from these thought leaders, from other content providers, and putting it together in a simple way for a mid-size law firm to digest. So if you sign up for Sidebar, you’ll get another email from us every Saturday morning, when you’re drinking your coffee, or tea if you’re like me, that just breaks it down and makes it easily digestible. So that’s our first step, but more to come.

Debbie: More to come. And the whole goal, and this is, you and Amanda and I have talked a lot about how we want to be that resource, and we want to be able to provide answers to the questions that people have, because many people have the same questions. And so I think there’s a really great next step, with more to come.

Join Sidebar

Rob: Yes. And we’re funding this ourselves, guys. We’re being transparent and open. We really want to help, and we really want to help solve this problem. So join if you need to join. Go to Sidebar, G O sidebar dot A I. I’m going to try to multitask here real quick, and I’m actually going to drop a link. So right below me, there’s a link, join Sidebar, and make sure you show up, because every week there’s a different question, and there’s going to be a lot of exciting things coming. And if you’re not there, you’re not going to be a part of shaping what happens in the, I’m kidding. But really, we’re going to try to help. Thank you guys.

Debbie: Not at least on this team, right?

Rob: Yeah, exactly. But thank you guys for joining in. We’re at time. We’ll see you next week for another live episode of Sidebar Live. Thanks.

Debbie: Thanks, Rob.