James Lawler joins Warren Kucker to discuss Why ROI Isn't Always the Right AI Pitch. Key takeaways include ROI alone doesn't close deals in traditional industries; lifestyle benefits resonate more strongly and Privacy concerns outweigh performance skepticism in conservative sectors.
Why ROI Isn't Always the Right AI Pitch
with James Lawler
"I Just Want to Play More Golf"
About This Episode
James Lawler discusses why traditional ROI messaging fails when selling AI to legal professionals. The episode explores selling AI to change-resistant industries, privacy concerns superseding performance skepticism, using Copilot during calls for technical translation, and reframing the same product differently for different buyers.
About the Guest
James Lawler
Managing Director of TriCoStar, an AI-powered time recording and email management platform for law firms. His father founded the company 38 years ago; James now leads founder-led sales in the legal technology sector.
Key Takeaways
- ✓ ROI alone doesn't close deals in traditional industries; lifestyle benefits resonate more strongly
- ✓ Privacy concerns outweigh performance skepticism in conservative sectors
- ✓ Using AI tools live during sales calls helps demystify technical concepts
- ✓ Reframing identical products around different value propositions dramatically impacts buyer interest
- ✓ Founder-led sales require relationship-building strategies beyond templated outreach
Show Notes
The time entry has not changed in fifty years, only the way it gets captured
James Lawler is managing director of Tricostar, a UK legal tech supplier his father founded in the late 1980s and one of the few still independently owned. The business began with time recording, at a point when lawyers were still keeping time with pen and paper. Its first tool ran on a small handheld that looked like a mini laptop: a lawyer could take it into a meeting, hit the spacebar, type notes, then plug the memory card into a central mainframe back at the office to produce an electronic timesheet. Around the turn of the century the company built its first case management system, and it has worked mostly with local and central government legal teams that have strict data governance and security requirements.
Lawler's point is that the output lawyers have to produce has stayed the same for decades. A time entry still records the matter, the client, what was done, how long it took and the activity. What has changed is how much of that work a person has to do by hand.
Passive time recording only works if it can write the narrative too
Lawyers dislike recording time, and Lawler describes three ways it costs them money. They forget what they worked on and try to rebuild it days later. They write too little narrative, so a client challenges the charge and it gets written off. Or they simply undercharge because the entry is not made in the moment. That is the basis for the claim Kucker opens with: capturing 30% more billable time and cutting time-recording admin by up to 90%, to about an hour a week.
Rather than build a new product himself, Lawler found Billables AI, a San Francisco company that had just come out of stealth. Just before Christmas in December 2024 he flew out to meet the team and signed a deal to bring it exclusively to the UK through Tricostar. He explains that passive time recording has existed for years, but older tools took periodic screenshots of a desktop and inferred activity from them. That raised privacy concerns, struggled with constant switching between windows and tabs, and broke when someone moved from a desktop email to their phone on a train.
The newer approach integrates directly with the platforms where the work happens. A lawyer signs in with Office 365 or Gmail, and time is recorded as they open an email or a document in OneDrive, SharePoint or on the desktop. The large language model then reads what they were writing or reviewing, summarises it and drafts the narrative for the client. It also adapts to personal style over time, such as long or short narratives or using initials instead of names. Lawler says the generated data is not stored and is deleted once it has been used.
Selling time back, not just more billable hours
Lawler expected skepticism about generative AI itself, but lawyers already use it to draft and review documents. The pushback he hears is about privacy. If time is captured passively, then checking football scores, booking a holiday or shopping on Amazon gets recorded alongside client work. Tricostar's answer is that each timesheet stays private until the lawyer reviews and releases it at the end of the day.
His bigger lesson concerns the sales message. Legal is a billing-led profession, an exchange of time for money, so it is easy to pitch every efficiency gain as extra hours billed and another one, two or three million in revenue for the firm. He has come to see that this misses the human side of the work.
Actually, sometimes I'm not looking to bill more, I just want to spend more time with my family.
He walks through the maths. A lawyer working eight hours and capturing six might now capture the same six in six and a half hours, getting an hour and a half back. One lawyer told him plainly that he just wanted to play more golf. Kucker builds on this: time tracking is work nobody values and clients are no better off for it, so it should not matter to the seller what a buyer does with the time saved.
Fixed fees still need time data
Kucker suggests that if AI automates much of the junior paralegal work, clients will stop paying hourly rates for it and the value will shift to strategic work, which pushes firms toward fixed fees. Lawler says many firms are already telling him they are moving that way. His reply in sales conversations is to ask how they know the fee is right. Firms point to years of experience doing the work, and he counters that what they really have is years of experience charging for it the way they always have. Time data is what lets them budget and price fixed-fee work properly.
That links to a wider worry about junior roles. If firms decide paralegal and junior work can be fully automated and stop hiring for it, there will be no juniors to become the next seniors. Lawler sees the opposite path as the opportunity.
We shouldn't get rid of our juniors or the amount that we hire. We can just start to skill them much quicker.
Kucker takes the idea further, suggesting entry-level hiring across professions could start to look like apprenticeships, with multi-year contracts where someone is paid to learn and then commits time back to the firm. Lawler compares it to the military, where a fighter pilot commits years of service because they will not be effective for the first 12 to 24 months.
AI as a sales assistant that keeps the process human
As a founder doing his own sales while running the business, Lawler says the fundamentals have not changed: he still needs to know who the technical buyer and budget holders are. What has changed is speed, since buyers want to decide faster and see products implemented quickly. He started with ChatGPT and now uses Copilot internally to plug gaps across many open opportunities.
I've yet to experience a sales process where I have been completely hands off.
During online sales meetings he asks Copilot live questions, such as what a buyer asked five minutes ago, how he answered, or whether he covered a particular point. Afterwards, follow-up actions are produced from the transcript, and he now records and transcribes in-person meetings too. He finds it especially useful for turning a technical answer into plain language. Lawyers usually do not want the technical detail, so he reaches for real-world comparisons, such as all cars having four wheels and going around a racetrack while some are faster, more efficient or go longer without refuelling.
On long sales cycles, he uses an AI assistant to keep up a dialogue that feels considered rather than boilerplate, and to remind him to mirror the buyer: short emails for people who write short emails, more detail for those who give long answers. He would rather prospects not notice the AI at all, because people buy from people and face-to-face conversation still matters in B2B sales.
Looking two to three years ahead, he does not expect time recording to disappear from legal, since firms have talked about fixed fees for years without it happening. In sales, he expects one person to operate like a two or three person team, with virtual assistants handling most of the grunt work. Those assistants will still have to be taught the processes a team already has, while people keep the human touch points.
Full Transcript Show Hide
00:00 Warren Kucker: Hey there and welcome to another episode of Selling AI. Today we're diving into what it's like selling AI into one of the most conservative industries out there, legal. I have James Lawler on the show today and James is the managing director and founder of TriCoStar, an AI powered time recording and email management platform built specifically for law firms. Here's what makes this conversation interesting. James is doing founder led sales, which means he's in the trenches every day selling a product that promises to unlock 30 % more billable time and save 90 % on administrative drag. That's a really bold claim in an industry that's notoriously skeptical of new tech. In today's episodes, James and I talk about how he navigates selling AI to lawyers who are resistant to change. What his own sales process looks like as a founder and the AI tools he's personally using to sell more effectively. And lastly, how his clients are actually starting to engage with his AI features. We'll also get into what he's learned the hard way about selling into traditional industries. All right, let's hop in. Hey James, thank you so much for being here with us today to talk about selling AI into law firms. Welcome to the show.
01:08 James Lawler: Hi Warren, no worries. Happy to be here. I appreciate you setting this up with our respective time differences as well.
01:14 Warren Kucker: Oh great, great, great, great. Cool. Well, first, can you give us a quick background on Trikostar and what problem you've historically been solving in the legal space and how that's shifting over the past year going forward?
01:27 James Lawler: Yeah, So, Trichostyle was actually founded by my father in the late 80s. So, I think we're in our 38th year this year, probably one of still the only independently owned legal tech suppliers in the UK. So, we've been around for a long time and the business started on the basis of time recording. This is when lawyers were probably doing it with pen and paper and we developed this little tool for the Scion. Most people probably won't even know what that is, but it looks like a mini laptop. And it had a big old memory card in it. And we developed this little piece of software that you could take the SIE onto a meeting. You could hit spacebar, record your time, type your notes in, and then bring it back to the office, plug that memory card into a central mainframe, and it would upload all the time. And you'd have an electronic timesheet, or electronically created timesheet. And that really went all the way through the 90s until turn of the century when we developed our first case management system. We've always been predominantly in government, not because we didn't want to go into private sector, it's just a niche we found ourselves in. So we work with lots of local government and central government legal teams, some quite high profile teams as well who have a lot of data governance and data security requirements. And that has naturally evolved. where we are today. And I suppose this is a very short summary of what we've done, but the natural evolution is now into how can we use AI to make that process more efficient. So it's something, you know, I suppose we've been making the process more efficient since we started the business in the late 80s. And I took over as managing director, albeit I've been here for nearly 20 years. I took over as managing director a few years ago. And one of the things I started to look at was like, okay, How do we use AI to make time recording more efficient? Same goes for the email management that you've mentioned as well. So we work with a Canadian based company called Collego who have a really cool add-in for Microsoft Outlook which helps manage all the filing and governance of emails because we all live in our mailboxes and tend to use them as storage repositories. which makes it really easy for us to find things but not for our colleagues, which in legal when a lot of that is considered evidence, it's obviously really important that that is filed away to a place where it can be accessed.
04:01 Warren Kucker: That's awesome. That's really cool. The evolution from, let's say, the first iteration of non-paper time tracking to now, like 40 years later, you're talking about how you can use AI to almost infer billable hours from the work. It's really fascinating. Let's dive in. tell me a little bit more. How are you using AI to solve that problem now?
04:25 James Lawler: Yeah, it was a, I knew it was something we had to look at. in fact, we initially had a look at, okay, do we build this or do we buy it? We developed our previous time recording system. How far advanced is it now? And actually I ended up finding a business which had just come out of stealth based in San Francisco now called Billables AI. and had a look at their product, I was like, this is exactly what I want to do. I didn't actually, we didn't end up developing our own solution for this at all because at the time we were in the midst of actually developing our next gen case management system. So back in December 24 now, just before Christmas, much to my wife's dismay, I jumped on a plane to San Francisco, went and met with the team and did a deal with them to bring this exclusively to the UK through Triacostar. And I suppose the way that people have time recorded since the 70s hasn't really changed, The way that lawyers, or what lawyers need to do is have a time entry which states what the matter is, who the client is, what they were doing, how long they spent doing it, and what the activity is. That actually hasn't changed. But I know it's a process they all loathe. They hate doing it, right? They forget. And so you're trying to figure out what you were doing on certain days or times of the week. You don't put enough of a narrative in there, so it gets written off because a client goes, well, you've given me a charge for this, but there's no explanation as to what it was actually for. Or they just undercharge because it's not necessarily happening in the moment, albeit there are tools available to manually record time. It's a very disciplined task and exercise. You end up missing out on potentially billable hours as well. So I suppose this is where the whole premise that you mentioned at beginning in terms of capturing 30 % more billable hours and reducing the administration of actual time recording by up to 90%, like down to almost an hour a week. That's where it comes from.
06:49 Warren Kucker: That's awesome, yeah. I mean, that's an incredible evolution. Was there something in particular that like LLMs have kind of unlocked that like is able to you, what's the actual function of the LLM in that process?
07:01 James Lawler: Yeah, so I suppose passive time recording, or how we refer to it as passive time recording, i.e. it's hands off, you don't have to actually click any buttons to make it happen. The actual technology itself in terms of passive time recording isn't new. That's been around for a few years now. But the way it's been done is typically through taking, let's say, screenshots of your desktop or your laptop periodically, and then... inferring from those what you were doing and building a picture based on that. Now that generates privacy concerns. I don't know you're like me, but I've got windows and tabs all over the place and I'm switching between them all the time. it creates problems in terms of like, how are you actually spending your time and what on? And it's not cross-device compatible in the sense of I can't move from one... like say writing an email on my desktop to then jumping on a train and carrying on the work that I was doing on my phone without that becoming a new time entry. But it does exist as a technology. So passive time recording, the ability to not kind of have to time record or significantly reduce how much time you spend doing it does already exist. How LLMs have changed that and how technology has changed that is really, I suppose, what billables have been able to achieve. with their solution and that is twofold. One is we now, because of cloud computing, SaaS, et cetera, now we can integrate directly into the platform we actually want to record time from. So to keep that really simple, you you sign in with your Office 365 or Gmail address and as you access your email or as you go to a document in OneDrive or SharePoint or on your desktop, the time is recorded. We can actually... We know you're there and we can record that time. And where we've been able to go one step further is that with LLMs, they can now determine what you were doing whilst you were there, what you were reading or what you were writing or drafting, and take a summary from that on your behalf and then produce a narrative for your customer.
09:15 Warren Kucker: That's That's really cool. Okay, cool. Let's pivot a little bit to sales process.
09:21 James Lawler: Yeah.
09:21 Warren Kucker: As you're kind of like managing a sales process yourself and on top of it kind of like taking a big shift in like product and what you're actually pitching along
09:28 James Lawler: Mm. Mm.
09:31 Warren Kucker: the way, how has your sales process evolved over the past couple years and what is a typical like deal look like for you now?
09:39 James Lawler: Yeah, I mean, I suppose the same sales principles still exist, right? We're still all following the same principles of needing to understand who our technical buyer is, who the budget holders are, all those kind of things. I don't think any of those things have actually really changed for me. I think the speed at which you can get a sale to close has definitely gone up. I also think people expect to make, I think people want to make decisions quicker. You know, they kind of, when they know they want or need something or discover they have a need for a certain technology, they want to see it implemented as quickly as possible as well. So I suppose, you know, it wouldn't be very good of me to be selling products which help make people more efficient through the use of AI without actually implementing it myself.
10:34 Warren Kucker: All right.
10:35 James Lawler: That started very, very basically, I suppose, with the likes of using ChatGPT, know, copilot we use internally now as well, to help us plug gaps, I think. The thing is, is when you're trying to juggle lots of different sales processes across multiple opportunities, it's really easy to miss something, you know, or forget to ask a certain question. And so I would say, and I've always said this about AI anyway, is you should always see them as a... see AI as an assistant, right? can take over what you do, but I've yet to experience a sales process where I have been completely hands off. And I'm a, like you say, I'm a founder-led sales as well. So I've got a business to run at the
11:20 Warren Kucker: Right, right.
11:21 James Lawler: same time. So for me, it's been about using tools that fill in the gaps for me or give me feedback on... on how my sales process is going based on what it can infer from emails that I am sending or receiving, documentation that I provided, demos that I've given and I'll transcribed, know, questions that have been asked by the client in that time, to make sure that, you know, we tick all the boxes we need to, to get to the end. And actually it's made it easier. One thing I love about Co-Pilot, especially when we're doing online sales meetings, is that it's there in the moment. So I can actually, mean, I'm not, the greatest at multitasking, but I've got better at it. In the moment, I can ask copilot questions like, I spoken about this? What question did they ask me five minutes ago and how did I answer it? Did I include an explanation of X, Y or Z? So in the moment, it's been really helpful as well.
12:25 Warren Kucker: Yes.
12:26 James Lawler: And obviously, afterwards, I've not got to. even think about what my follow-up actions are because those things are all being produced for me based on the process that I'm following and what was said and recorded during those meetings. And in fact, I've gone as far as even in-person meetings, recording those now and transcribing them, having
12:45 Warren Kucker: nice.
12:46 James Lawler: them transcribed automatically so that I don't have to think about it too much.
12:50 Warren Kucker: That's awesome. So you're using live transcription when you're having a meeting and talking to copilot about
12:55 James Lawler: Mm.
12:56 Warren Kucker: the meeting as well. Do have like a specific example
12:58 James Lawler: Yeah.
12:58 Warren Kucker: that's come up like recently on a call?
13:01 James Lawler: There will be, especially if I've got someone from technical pre-sales with me, so it's not just me in the room effectively, there'll be questions that asked that they are answering. Sometimes, one thing I've found it really good for actually, Warren, is turning things into plain language, like plain speak, or trying to use a real world example of how to give context. So let's say for example, a client asked a really, really technical question. Because I'm technical, I can sometimes fall into the trap of giving them a technical response. And actually, they're just a lawyer, right? They just want to know, how is this going to make my life easier? Like, what context can you give me? So I'll always use things usually personally interested in mine, unless I've had time to. to spend a bit of time with the person speaking to to find out their personal
14:00 Warren Kucker: Right?
14:01 James Lawler: interests are, I might liken it to how, you know, all cars have four wheels and will go around a racetrack, but certain cars
14:09 Warren Kucker: Okay.
14:09 James Lawler: will do it quicker than other cars. Some cars will do it more efficiently. Some cars will go for longer without having to refuel, you because I'm into motor sports.
14:17 Warren Kucker: All
14:19 James Lawler: So that's where I've found it really helpful actually in those kind of in the moment scenarios that help people
14:24 Warren Kucker: Interesting.
14:25 James Lawler: get the context of what you're actually trying to. help them understand.
14:31 Warren Kucker: That's awesome, man, that's really cool. Cool, cool, Great. In particular, selling into law firms, have you found
14:40 James Lawler: Mm.
14:40 Warren Kucker: that they've been skeptical of generative
14:44 James Lawler: Yeah.
14:45 Warren Kucker: AI technology, receptive, open, seeking, how are those conversations gone, and how have you navigated the sales process that way?
14:52 James Lawler: Yeah, it's a funny one. I suppose they've been using generative AI quite extensively, I would say, kind of drafting and reviewing documentation for quite a while. That's quite normal to them. Obviously, we don't sit on that side of the fence really. We're on the much more on the administrative side of what they do. The bit they really do hate doing. It's not what they trained to do. So It is met with some skepticism. I think skepticism actually leans more towards the privacy side of things instead of, this make my life easier? And what I mean by that is in our instance, when we're capturing time passively on behalf of a lawyer, the whole idea is that they don't need to check the time sheet until the end of the day. They can just come and review what's there. But that does mean that if they went and checked the football scores or were looking to book a holiday or buy something on Amazon, that time's getting recorded. So actually one of the biggest push backs I get is, well, I don't want my private interactions being recorded alongside my work interactions. Obviously we manage that. We make sure that their time sheets are private until they release what's there.
16:14 Warren Kucker: Right.
16:15 James Lawler: But yeah, that's the biggest level of skepticism because I think from from most people, not talking to us unless they are interested in how AI can make their life easier. Right, they all know it can. One really interesting thing I was thinking about actually though was when it comes to using AI, I think in any industry that's specifically legal, one of the things that we've always focused on in our sales messaging, and I came to realize this wasn't necessarily the right. the right approach all the time. And we've already done it in this call, is we've talked about how much time someone can save and therefore how much more time they can bill. But
17:02 Warren Kucker: Right.
17:03 James Lawler: it doesn't always take into consideration the human aspect of work, which is we're all looking for a better work-life balance. Actually, sometimes I'm not looking to bill more, I just want to spend more time with my family. So how
17:15 Warren Kucker: Right?
17:15 James Lawler: do I achieve that? So you take AI time recording as an example. Actually, what I'm helping lawyers to do is capture time they were missing. So before they were working six hours a day, or let's say they're working eight hours a day and capturing six hours of billable time as a result.
17:34 Warren Kucker: Right.
17:35 James Lawler: Now, only have to work six hours a day to capture, well, let's not be unrealistic. Let's say they only have to work six and half hours a day to capture. six hours available time because it was done for them, right? So they get an hour and a half back
17:48 Warren Kucker: Gotcha. Right,
17:51 James Lawler: to go and do the things they like to do. And I've literally had this conversation with a lawyer who was like, yeah, I just want to play more golf. don't want to actually have to
17:58 Warren Kucker: Yeah.
18:00 James Lawler: do more work. I think it's really interesting sometimes that you have to, again, being techies and it also being a very billing led profession, right? That's it. It's an exchange of time for money. It's really easy to fall into the trap of just being like, okay, well, you can bill these extra hours and therefore your firm can do another like million, two million, three million revenue every year. But some people aren't looking for that. They're looking for time back by being more efficient.
18:32 Warren Kucker: Yeah, that's a good call out. It's almost like what you're doing is eliminating work that's not value added for anyone and that no one likes doing, right? So like
18:42 James Lawler: Mm. Yeah.
18:45 Warren Kucker: their clients aren't better off when they track their time, right? Like that's not work that matters, right? So like, it's almost like... what's it for you to say what they're gonna do with that time? Like who cares, right? Like so you're gonna get your time back. You don't like doing this work. And it's not the most expensive solution in the world, right? It's relatively inexpensive to do these things. However you see fit to do that time is great, know, honestly and on top of you're gonna more accurately build. So that's interesting way to look at the sales process there. How are you finding anything specific on the privacy aspect other than like reviewing your timesheet at the end of the day before it's public to the org? Is there any concerns about like the data that like the LLMs or your application to accessing or that you had to get around?
19:38 James Lawler: No, we don't. I mean, we don't store it. we use it. actually the way the LLM uses the data that it generates for the time sheet is that it does inform future narratives. So if I have a certain style of writing, whether I like to like even if I go as far as writing long narratives or short narratives or I don't use people's names, I always use their initials, things like that, it will automatically change over time for me so that it's much more in my style. But we don't store any of that data that we then produce anywhere. It gets deleted. So it's learning
20:19 Warren Kucker: Catch you.
20:20 James Lawler: and it's applying that learning to a model that it then uses for future narrative generation, but it's not then keeping that data or doing anything else with it.
20:30 Warren Kucker: and you found that answer sufficient. People are like, great, that sounds good. They moved that part. Yep.
20:32 James Lawler: Yeah, Most of the... It's like, I think the problem, especially time recording, it's a very big brother type process, right? And it's a necessary evil because most firms are set up to record time, give a breakdown to a client of how their time was spent, what they were doing, and that's how they get paid. And if that's not accurate enough or not detailed enough... they end up writing it off because the client argues with them and it costs them, you know, it's costing them more to go and try and justify the time because they've got no way of justifying what they were doing. Then just saying, okay, don't worry about it. So we're trying to reduce the level of write off as well. And ultimately it just means people can focus on what they train to do, which is become lawyers. There's an interesting conversation going on, I think constantly going on. There's two things actually that come to mind. One is fixed fee work. I think a lot of, to try and stay competitive, firms are really interested in the fixed fee conversation. For this type of work, we charge fixed fee. And that's creating some interesting conversations in sales because a lot of them are going, well, we're moving to fixed fee. And I go, OK, but how do you know that you're charging the right amount?
21:58 Warren Kucker: Right?
21:58 James Lawler: And they, you
21:58 Warren Kucker: Yeah.
21:59 James Lawler: often they'll go, well, we've got years of, we've got years of experience of doing this type of work. And so this is has charge. And I said, well, you've got years of experience of charging the way that you do, but do you know if
22:09 Warren Kucker: Right.
22:09 James Lawler: that's the most efficient way to do it? that's one particular conversation, which I think is really interesting. I think an area where we can also help firms budget better when it comes to,
22:24 Warren Kucker: Right.
22:24 James Lawler: to proposing fixed fee work.
22:27 Warren Kucker: That's awesome. Yeah, I mean, yeah, absolutely. That's a funny narrative around like, actually the technology out there could change fundamentally how an industry is charging, right? Like for example, I think if, let's say the most base level of like junior... paralegal and attorney work is relatively Automatable right then you're doing more valuable strategic work, but you're doing it in a lot less time, right? So like what's the juxtaposition one? Your let's say corporate clients gonna ask for that time like you shouldn't charge me what you used to But in the same token then the value of the strategic work just goes up, right? So like cool So then that moves that to like let's move to fixed fee, right? Like which is which makes sense, right? then like it's a you now have like a completely different meaning as to what time I mean, now time is an efficiency standpoint, right? Like how much does it take? How much should I bill? And then on a particular project, like did I make money or did I really end up losing money? So you're like, now you're tracking time in a more traditional sense of like an optimization problem. Is that how like your
23:32 James Lawler: Yeah. Which is a...
23:35 Warren Kucker: customers are seeing it? Are you having to explain that? Like how's that going?
23:42 James Lawler: Yeah, it depends who you're talking to in the firm. operationally, they kind of get it, but the lawyers just need to record their time and the lawyers understand they just need to record their time to allow them to even arrive at that kind of ability to make those kind of decisions. I think one really interesting point you kind of angle on there and it's a big something I think is a buzzword that won't go away is efficiency. certainly in the UK, you know, in the big city law firms, their rates are very high. I mean, they're skilled people. you
24:14 Warren Kucker: Yeah.
24:14 James Lawler: that we expect it. But, know, for somebody who's, you know, putting their hand in their own back pocket to pay for something, you know, paying £800 for a letter, you know, can seem very, very expensive. And the reason I say this is because if they're efficient, obviously they can charge more and you can see that they're efficient. But it does,
24:37 Warren Kucker: Yeah.
24:37 James Lawler: I think it's going to create a slight problem or it could create a slight problem. You know, this is kind of the things that people are talking about but don't want to admit are happening and that is, will AI take the jobs away from those people? I don't think it's going to take the jobs away from lawyers because lawyers are still needed to do the really heavy lifting. AI just makes them more efficient at what they do. I think where the... where the issue comes is where we believe what a paralegal could do is completely, can be completely automated and therefore do they stop hiring paralegals to do those things? But what happens when that workforce ages, right, where does the new, all the new skill come from or where does the next generation come into that in terms of carrying on that level of skill? So you can see it in one of two ways. You could either say they could shoot themselves in the foot. if they decide to automate what I would call, you know, paralegal low-level assistant junior work, because they won't have any juniors who then become seniors to carry on the work.
25:45 Warren Kucker: Right.
25:47 James Lawler: Or you could take a, you know, you can look at it from a positive perspective and say, well, actually, you know, we shouldn't actually get rid of our paralegals. We shouldn't get rid of our juniors or the amount that we hire. We can just start to skill them much quicker. You know, they can become seniors so much more quickly because All of that menial, automatable work now doesn't need to be done by them. They can use AR
26:11 Warren Kucker: Yep.
26:12 James Lawler: to do it. So I think that's a, I think it's a massive opportunity for lawyers who are charging high fees and using AR to make themselves more efficient, actually to bring juniors up to skill, other than, I suppose, experience in terms of time in court and all those things, much more quickly. Sorry, I've gone slightly off track there, but it's kind of just one of the themes that I...
26:34 Warren Kucker: Yeah, so no, it's not off track at all. It's a common theme, right? Like in some, in these conversations, I'm seeing this come up over and over again. It's actually that the new technology is bubbling up old processes, right? So we talk a lot about how we think AI, we're worried that AI's gonna... tear at the fabric of the human to human relationship, but in a lot of the conversations I've had, it actually shows that like, can like elevate that human-human relationship in a better way? This scenario is a little bit different. This life cycle you talk about there is, let's say we, in a worst case scenario, where it ends up completely eliminating the entry level in a bunch of different professions, right? Like engineering, business development, like entry level roles end up being 80 to 90 percent like automatable and then the 10 percent just goes into the mid level or senior level roles, right? Cool. Well, you still need mid level and senior level people. You end up in almost a scenario where you need to go back to apprenticeship programs, right? And if you do that, right, like if you're going to take on an employee, great, I'm going to bring out hire someone at the entry level of the legal profession in hopes that they become mid level senior. It's a good perspective that one they could do that faster But two then we're gonna have to end up or enter relationship where like great I'm gonna pay you and not get any value for a while right like out of it And then when you I can get value of you, I can't have you leave, right? So you're gonna end up in a scenario where you're gonna have to have like contracts, right? Like five-year programs where like you get paid for three years to learn and then you give me two years at a lower rate And then hopefully my culture is so great that you stay longer. That's how we that's how we used to do manufacturing jobs, right? so It's interesting, right?
28:18 James Lawler: It's how the military do it now. If you want to go into a high level military position, you want to become a fighter pilot, right? You
28:24 Warren Kucker: Yeah.
28:25 James Lawler: commit an amount of years to that role
28:28 Warren Kucker: Yeah.
28:28 James Lawler: because the military know you're not going to be effective as a fighter pilot for the first 12 to 24 months that you're in the role, right? So, yeah, it'd be interesting to see that spill down.
28:33 Warren Kucker: That's a good point, yeah. Yeah. That's how we've always done it. Right? Like it's kind of funny to think that that's you could end up in a scenario for a while Junior-level roles were great because they were inexpensive ways to do work that senior level folks didn't want to do if AI becomes that inexpensive way Then we're gonna have to find ways to bridge that gap which could end up being employment contracts for a while, right? Which is interesting Cool. Let's dive in just a little bit. So on the sales process. Let's let's dump hell back to this. Do you find that like your perspective customers care? like about how the AI is doing it or do they more care about just the result? Could you literally be like... Great, from a sales process standpoint, we wanna do time tracking, we know we spend time on it, we don't wanna spend time on it anymore, and we think there's relatively inexpensive ways to do that. You seem to be one of the best four providers out there that can do this. I like you, let's try it, and if it works, I'll buy it. Or is there still a decent amount of having to explain how you get to the end result when you're selling this time tracking solution?
29:40 James Lawler: I think it's a mix. And it's a mix because it depends on where they are in their understanding and, you know, if they're a discovery stage, then you've got to teach them what these things do. If you come in a bit later into the process, then they might already understand how a tool like yours works, but you're obviously playing catch up from a rapport perspective and a trust perspective. I don't think... They even necessarily need to know that you're using AI to assist the sales process. I mean, I hope I don't make it obvious. try to, I want it to feel human because people buy from people, right? They, having a face-to-face conversation, I think is still incredibly valuable, especially in, you know, when you're doing B2B type sales. So my sales process certainly, from the perspective of AI, is still trying to keep it as human as possible, just using AI to assist me in making sure that I've ticked the boxes I need to tick or I haven't missed anything glaringly obvious. And that could be something nuanced in a conversation that we had that I missed, right? But at least I can use AI to say, have I interpreted this correctly or have I missed something or do I need to be asking more questions? I think one of the biggest problems... that I've always had as a salesperson where sales cycles are a bit longer is keeping some level of dialogue up with that person or that prospect, which doesn't just feel like I'm sending them some boilerplate information that I do to everybody. It feels like I'm thinking about their problems and trying to come up with solutions for it or innovative ways of approaching something. So I've used AI to help me with that. mean, like the topic, you that's really good because you can actually have a conversation with Ada, the assistant, and say, look, I've got this problem or we haven't spoken for this long and this was the last conversation we had and I don't want to just fill their mailbox with something which isn't actually of use to them or feels like I'm just trying to be a name in their mailbox. I want it to be something that I feel like they can action. And it's got to succinct. think this is the other thing is, well, mirroring, you know, when you're actually speaking with somebody or you're selling to them is you've got to mirror their behavior, right? So if they write short emails, you write short emails back. You know, if they give you long-winded answers, you aim to give them as much detail back as you can. So I think, and again, I forget this all the time. You know, I'm telling you these things that I know I should be doing, but I get into the moment that sometimes I forget. So actually having an AI assistant. to help you or bring you back down to earth and not get too excited about things is really helpful. So yeah, think I'd hope they don't know I was there, but I'm using it all the time to try and
32:44 Warren Kucker: awesome.
32:45 James Lawler: improve the way that I saw.
32:47 Warren Kucker: Cool, great. All right, let's say maybe a last question. Looking two to three years ahead, either in the legal profession or how we're selling or anything process-wise, give me a hot take you have about where things might evolve.
33:05 James Lawler: Well, Hot Take on, well, I think in the legal profession, I don't think the time recording will ever go away. They've talked about moving to fixed fees for years and years and it's never really happened. I think we'll make it easier for them to budget what fixed fees should be. But I don't think it'll go away. think Hot Take is one there. we've already discussed is that potentially they could inadvertently do away with paralegals and juniors when actually they should be upskilling them. have contracts. I think in business from a sales perspective. I think we'll be in a position, I we probably already are, it's whether people can change their behavior. We'll be in a position where we probably can operate as a two, three person sales team, but they'll just be one of us. There will be virtual assistants there handling most of the grunt work for us, but they'll have to be taught that based on processes that we already have in place. I don't know if that's particularly hot take, but I know I'd certainly like to feel that way. I'd certainly like to feel like
34:12 Warren Kucker: Right, right, right.
34:13 James Lawler: I'm not trying to run a business and everything that comes with that and also trying to lead a sales team. I'd like to feel like actually
34:20 Warren Kucker: Yeah.
34:21 James Lawler: that there's an assistant there who can do most of the job for me other than the human touch points that need to be there.
34:29 Warren Kucker: That's awesome, man. That's great. Cool. Well, to wrap it up, where could people find you? In particular, if your potential customers wanted to reach out to you, who would they be and how should they reach out? Anything you got to plug there.
34:42 James Lawler: Yeah, well, I mean, we're on LinkedIn. So you'll find us as TricoStar, which is a T-R-I-C-O-S-T-A-R. So you'll find us on LinkedIn as TricoStar. They can drop you an email, [email address removed]. And I'll be more than happy to speak to anybody who's got an interest in what we're doing or just wants some advice on how they can be doing things better from an AI perspective.
35:08 Warren Kucker: Yeah, James, that's great to hear. Obviously, your perspective in this specific area, like legal tech moving from just like time recording at a Scion, which I had never heard of before, and progressing
35:17 James Lawler: Yeah.
35:17 Warren Kucker: through to where we are now is just fascinating and one of the leaders in this space. So really appreciate taking the time with us today.
35:23 James Lawler: Yeah, don't worry. Cheers, Warren. Thanks for having me. I appreciate it. Take care.
35:27 Warren Kucker: care.
About the Host
Selling AI is hosted by Warren Kucker, founder of Topiq. Each week he sits down with revenue leaders, founders, and operators to unpack the strategies, tools, and stories behind selling AI products and using AI to sell smarter.
Warren Kucker
A revenue leader and entrepreneur who founded Basiq.work, focusing on conversational AI for sales teams. Previously served as VP of Sales and CRO at Series B companies, scaling revenue to $2M+ quarterly bookings. His exits include Shelly.ai (ML email automation) and Boxton (digital freight platform). Started his career at Apple managing a $100M shipping efficiency program.
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