Community Table: From ClioCon 2025, Navigating a Tech Show

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Announcer:

This is Unbillable Hours Community Table, a monthly virtual round table where lawyers discuss issues their practices are facing and receive feedback from lawyer and law firm management consultant Christopher T Anderson. Join the conversation live every third Thursday at 3:00 PM Eastern. This episode’s content comes from the live q and a that Christopher hosted at the 2025 CLE in October. Highlighted in this episode are questions about feeling overwhelmed at legal tech conferences, the difficulty of hiring attorneys in rural areas and final steps to take before hiring a non-attorney salesperson.

Christopher T. Anderson:

Alright, welcome everybody. This is the Unbillable Hour community table live from Boston, Massachusetts at ClioCon. So this is just going to be tremendous amount of fun. I hope everybody’s brought lots of great questions. And also just remember you can, if you want to, if there’s something that really moves you, you can chime in and help one of our other guests that are asking questions. Really exciting show we’re going to get started. Just remember for everybody, you can catch all the episodes of the Unbillable Hour at Legal Talk Network or on your favorite podcasting channel, including iTunes. And this community table is available at 3:00 PM Eastern every third Thursday of every month from now until the end of time. So you are welcome to join us live. So without further ado, we’ve got now we’ve got a bunch of people waiting in line to join us here. So we’re going to go one online, one live,

Caller #1:

Christopher. I think for those of us mere mortals when we’re at the Clio Con and we hear Jack’s whole big thing, and those of you who are not even here, I think it can get pretty overwhelming pretty quickly. All of the legal tech, that was my predominant feeling. I was excited on the one hand and also overwhelmed and kind of scared with all of the potential and everything that’s coming at us so quickly. And I just wonder if you could speak a little bit to that feeling of overwhelm with AI and computers and all of the things and what to do with it.

Christopher T. Anderson:

That’s a pretty big question. Listen, I think I felt overwhelmed and I’ve never seen them do that at ccle. So just for everybody, Jack Newton is the CEO of Clio. I just saw him, so I don’t want to make sure he’s bright behind me while I’m talking about him, but I’ve never seen him do that. They’ve always been really good about picking a theme and kind of going with it, a product or an enhancement or whatever. And today they just fire hose it. They’ve been investing and spending and acquiring and putting lots of money. So just for everybody’s background, I think to give context to this question, and guys, this is really relevant for each and every one of you on this call. I came with a mission last year and they were very receptive and they said, listen, we are working on this. And my mission was that your guys are becoming irrelevant for firms that are actually successful, right?

Once firms get to a certain size, a lot of your stuff doesn’t work for us anymore. And they seemed very receptive to it and they’d hired a couple of product managers and they were standing up some stuff, and so they listened. I’ve been to industry events, vendor events before where they listened and they say, oh, well yeah, we’re really investing in that. So I didn’t know what to expect. Well, they’ve done it. I mean, they spent this year doing a lot and investing a lot of money. One of the companies they bought, they spent a billion dollars, they just spent one B billion dollars acquiring a company, and it’s just one of the ones that they bought. So they’re getting into it. And what they started announcing that they’re blowing up their product line, they’re adding so many new products, a lot of them to do with ai, some of them do with research, some of them to do with some other aspects of legal practice.

And it was just a fire hose. It was just so much. So my advice and all of you are experiencing this in the world too. If you’re like me, you’re getting hit with AI vendors, you’re getting hit with marketing vendors, you’re getting hit with all sorts of people who have all sorts of new products, all of which sound really cool. Some are legal based, some are not, and it can be overwhelming. And just as you start to go down one path, you learn about something new. And so my advice to that is just to drop back to what do I want to do with my firm and what will help get me there and to digest what it is and realize that we are all finite human beings and we can only do a certain number of things. So which one are we going to pick?

And so I sit in these things, I take lots of notes, and then I digest, I make no buying decisions at an event like this, and I digest it and I say, what’s going to move my firm forward the most right now? Sometimes I also consider what do I need to do? Because if I don’t do it now, I’m going to get my lunch eaten by somebody. And those are the sort of the two criteria. What I do promise to everybody is I’ll do this digestion. And when we come back together two weeks from now for the Ask Me Anything again, we can follow up and I’ll have made some decisions and some recommendations for my firms and I will share them with you because my goal is for all of you to be successful so that I can buy your firms and the path to that and to serving our clients.

Jack said some things that I’ve been thinking for a long time, which is that and the way I’ve built my firms has all been about access to justice. That we are in a revolution where we shouldn’t be afraid of AI as replacing us. We should be attentive to AI as magnifying us and the number of people we’re going to be able to help. And I really do believe that this market is about to be exploded and those who pay attention and are willing to make the changes will thrive. And there’s a lot who won’t. So let the overwhelm wash through you and then capture the golden nuggets and move forward with those and the rest will come. That’s where I am right now.

Caller #1:

And I think for me, when I was there, so I was getting that when I feel overwhelmed and then I feel panicked a little bit and then a little scared, and then everything goes to, oh, no, oh no, and I won’t. And then my whole law firm’s going to fall apart and then, oh no, and then I’m not going to be able to feed my family and oh my God, right? It’s like your brain goes to the worst case scenario. And I guess for me, I’ll just share what I did to work through this in case you’re experiencing it about maybe yours isn’t AI today. If you’re not in Boston, you’re not that worried about that today, but maybe you’re worried about how you’re going to get your client calls done. How are you going to answer the phone that’s ringing? Whatever it is. What I did was number one, I breathed through it.

I forced myself to take some big deep breaths and recenter and come back into my own body and not go in the ether of all the fears and all the swirl and all the worries and all the bad things that could happen. And then I think what I instinctively or intuitively was doing, Christopher was connecting with, okay, wait a minute, who am I? What am I doing? What’s the point? And I’m not going to be, I know myself, I’m not going to be the one to scour every single tech tool that ever existed and go to every single booth and compare all the features and benefit, blah, blah, blah. I’m not doing that. But what I can do is I care a lot about the access to justice and I care a lot about explaining things to people in a way that they can digest.

So it’s like, okay, pick your place and reconnecting with that why and who you are. And to me, then once I got back to that place, I’ve had calm for the rest of the day. I think the overwhelm feeling is one that I am afraid. I think in general, my natural tendency is to be afraid of it, and I think we all are. But I like what you said Christopher about let it wash over you, wash through you, let it come and then experience it and then let it go. That’s what I did. And the thing is, sometimes I think with overwhelm, we want to stay in it. We like that chaotic energy and we like that hustle. And even right now, my arms going back and forth like I’m running, but instead just let it flow on through and then I could be present for the rest of what’s happening here.

Christopher T. Anderson:

And that may be your reaction, I promise you. There’s some people whose reaction was they went back to their hotel room and hid under the covers.

Caller #1:

Oh, I literally had a thought and I thought that multiple times through the day when I’m sitting here is like, I remember this last year being at Clio Con, it was not nearly the same level of drinking from a fire hose feeling obviously AI in one year where we went from asking GPT how to make a hamburger to now it’s going to tell you how to raise the beef or whatever. So throughout the day I’ve thought when I go back to my regular life, I don’t have to worry about all this stuff and I’m going to feel a lot better and I just run away and hide from this. I mean you can I guess for a minute, but just the way you couldn’t hide from computers the way you couldn’t hide before that from fax machines and before that, right? The typewriter and whatever. It’s here and it’s upon us. And I think that tendency to run and put your head be like ostrich, right? Put our head in the sand, but I don’t think we can afford to do that. I think you give yourself five minutes, give yourself the day. But I’m sure a ton of people did. I had moments where I wanted to, I wasn’t going to, but I kind of felt like I wanted to

Christopher T. Anderson:

Absolutely.

Caller #2:

First time attending Clio Khan in person. Nice. My associate got me set up to come and talk with you. I have many questions rattling around in my mind, especially after the keynote this morning. I was not expecting to have my mind so blown. But I am very mind blown right now. And one of my biggest takeaways from that is we have a need for attorneys. We’re in North Dakota and Minnesota and there is the kind of baby boomer generation starting to phase out or has been for a while now, and there’s a shortage of attorneys in some of the outlying areas. Based on what and what you’re seeing in the trends, how could the new platform with Clio work and the Vincent AI and all these things help to bridge the gap and then create opportunity for someone like me who is very much aggressively wanting to grow my firm and my practice and our reach.

Christopher T. Anderson:

What is your practice area?

Caller #2:

We’re in litigation, civil litigation and business. Real estate employment law has been pretty big for us the last few years.

Christopher T. Anderson:

Cool.

Caller #2:

Yeah,

Christopher T. Anderson:

Thanks. Alright. Question. And everybody else online heard it so I don’t need to repeat this one. So great question. And as a country actually we are facing a huge demographic shift that is going to affect many, many of us. For those of us who live in major metros, no big deal. There’s probably going to be plenty of lawyers for a while, but a lot of rural places. Maine is one that I know pretty well and it is suffering big time and it’s going to just get worse. And probably, I don’t know that much about North Dakota, Minnesota, but it’s probably the similar thing where the older attorneys are aging out and young attorneys aren’t moving in. And so one of the things I think that we’ve seen that is a trend that we can believe in is during the pandemic we faced sort of an artificial acceleration of this trend and a big shifting.

So actually a lot of people move to rural areas but away from where they practice and where their businesses were. And so courts suddenly had to become very accommodating to this. And we’ve already started to develop this culture of remote appearances and people being able to do a lot more away from court than they used to. So I mean I think the first answer to your question is to really just be thinking more broadly about where your attorneys are going to come from and how many of them really need to be there. Now you’re in litigation you mentioned, so they’re going to court, but even our litigation cases, going to court doesn’t always mean going to court for the trial maybe yes, but for motions hearings and stuff like that, a lot of this stuff is now being done remotely. But the other part of your question, I think this will be interesting for everybody, was really about recruiting.

And your question was how does some of the Clio stuff, I’m going to broaden that out to how does legal technology writ large, how can that help? How can AI help? How can the tools that we have help? And for me the answer is first of all to change the way you think about recruiting Most people, and maybe you’ve got this already, I don’t know you, but most people don’t think about recruiting the right way. Recruiting is marketing period. It’s just no different whatsoever. You should be thinking about it exactly the same way. So what is marketing? Marketing is letting the general public or a slice of the general public know what it is that you have to offer and giving them enough information to be interested enough to have a conversation with you and learn more, right? That’s marketing. It’s getting people interested enough to have a conversation with you to learn more.

And then we can talk about funnels and how to work them down the funnel and that’s spend all day on it. But we have to think about it that way, except the sell here is a job. You’re selling them on learning enough information to eventually make the decision that they want to work at this place. So when you think about it that way, then you can really go out broader and start to ask questions like what would make someone move to my location? Or what would make someone want to travel here enough for court and start to talk to ’em about that? I have a book that I recommend always about this that I think puts you in the right mindset and it’s called Who the A method for hiring by Jeff Smart, G-E-O-F-F, smart and Aaron, sorry, Randy Street. Randy Street is the other author. Fantastic book. And there’s five stages to that hire and it describes them very deeply, but you’ve got a challenge in front of you, but understand that you’re not the only one. And so I think another thing to be thinking about is be a leader in how the courts are going to deal with this, get involved with them and say, we’re all facing this demographic problem. How are the courts going to respond and help us and make sure that we can serve our clients well?

Caller #1:

The way I think about recruiting is it’s an all the time situation because I think what we’re all guilty of is we get busy, so we stop, start like we are, oh my God, we’re recruiting, puts the job out and hurry, hurry, hurry, try to do something and then as soon as we get the person signed up, we’re like, thank God I’m done. So I think for me it’s about trying to keep it to the forefront of your mind at all times. And one thing that I’m working on trying to do to solve this problem is to grow my own and recruit around my problem. So what I mean is I am taking a bit more of like a grow my own. So what I’m thinking of and you live in this rural place, okay, let me say this. Before I was a lawyer, I had a recruiting business for nurse practitioners and physician assistants and I recruited somebody one time.

I cannot tell you it is the most middle of nowhere town in Texas. It is unbelievable. I actually went there to call on this doctor one time and if I can recruit to there, you can recruit to some of these other places. And I think one thing that everybody might consider doing, and it’s a longer term play, but we’re all going to be around for the long term, new grads getting out of school, need a job. And so can you start a grow your own program where they come in, they’re a summer, they come in, they’re looking for that first job, and you give them some relocation allowance, maybe you pay a little better than anybody in the neighboring states, develop relationships with the on-campus recruiting and then start that way. And yeah, the first year it sucks and it’s hard and you’re not going to make money and it’s a lot of work.

But after you’ve invested that year too, I’m in family law. So a couple years in you’ve got a really great employee who hasn’t learned all these bad habits either. So I think there’s the keeping it forefront in your mind at all times. And I think there’s the, I like to have a workaround solution because when we post a job ad, we’re a little bit at the whim of who’s pushing search that day. So to me, the grow your own is the other half of that equation. I mean it’s a theory still for me. I’m working on it. I don’t have it perfected yet, but that’s part of my solution to do it.

Caller #3:

I’m not sure exactly how to phrase this question. The context is we’re hiring another salesperson. We’ve had the third interview with them, they’re closer obviously, and we’re trying to figure out how to move forward in the interview process. Our thought was we need to give her a little bit of legal training first just so she understands what a divorce entails. And then we were going to put her live on calls with people to be sort of like the last round of interviews. I just came out of the interview with her, so this is a fresh question. I was talking to Srin about bringing this to you to see what can we do to vet this person?

Christopher T. Anderson:

Fantastic. So for the people who are alive, they’re on their third round of interviews with a non-attorney salesperson and he’s wondering what they should do in this third round. And one of the suggestions that Christopher bought, which I’m going to totally reject, is whether they should teach them a little bit about family law and then put them on live calls as part of the interview process. And so I think you already, we haven’t known each other for very long, but you’re beginning to learn. I don’t pull punches. I tell it the way I see it, and that would to me not be the way to go. And I’ll tell you why. For all of us who have failed with non-attorney salespeople and have had great success with non-attorney salespeople, any one of us who’s had great success has failed. So nobody came in and just was successful right off the bat, right?

We make mistakes, we figure it out. One of the great things about this group is you’re getting the history of our mistakes and learning from them faster. The typical time to put somebody onto live calls with real live clients is several weeks. And you want them shadowing your calls, critiquing the calls themselves, doing some mock calling, going to sales floor with the empirical if that’s available to you. And it’s a real process to get them ready to start taking live calls in our firm even we put them on intake for a while before we move them to live calls. Even though we do one touch sale, we have enough calls to come in when everybody’s busy, so we can’t do a one touch. So we have them be sort of that backup and intake. So I think it would be a disservice to your client, your potential clients, but mostly to your candidate because that puts a lot of pressure on someone who’s not had the time to develop the knowledge and the skills and your other premise that you need to teach ’em about family law, quite honestly, there are plenty of people that I would put in the seat on a non-attorney salesperson seat who I could teach what they need to know about family law in about 10 minutes.

It is the least important knowledge because the more they know about family law, the more they’re likely to show off about it. What you want is someone who can listen, who can reflectively listen, who can deal with objections, who can guide you, sat through my presentation, guide the prospects through the five stages. You don’t need to know a damn thing about fate law to say what’s the problem, and then listen to the problem and say, do you want to do something about that? What do you want to do about it? Get that clarity right and I’m going through it again, right then. Are you sure that’s something you want to get done right now? Then teach them the magic words. We can help you with that. No giant big deal. If it is in fact something you can’t help them with, we can fix that much easier.

They don’t need to know a lot about family law, say, we can help you with that. Why do you want to do something about it soon? Get that urgency in. The options are going to be the hardest part, right? Where you have to teach them what your products are and how they can work with you. It depends on what you’re selling to and then get them to a decision. So that’s the training they need. You don’t want to delay your hiring process to get them there. You need to test for their empathy. You need to test for their willingness to deal with objections. You need to deal with their ability to listen. You’re hiring for those characteristics and hopefully they’ve had some sales experience. But the family law piece is really, to me, the least important. I told you my favorite hire is mattress salespeople. I will hire them before they know the first thing about family law because they really know to sell a product and know how to match what the client needs to the products we have available. Does that help you?

Caller #3:

That’s very helpful. In fact, a couple of just quick follow-up things. We did take your advice and we looked specifically for luxury salespeople. This person we’re interviewing sold infrared saunas of all things like it’s not a need to have for most people, infrared saunas in the same price category, five to $15,000. So that was number one. And I really like what you said about putting them on intake for some time. We don’t have a weekend intaker, so it’d be a perfect opportunity to say you’re going to do weekend intake for now. We want to hear how you are on the phone with people as part of the training and then have them shadow and go to sales floor. So all great stuff. Thanks for such a good summary.

Caller #1:

I actually hired one of my team members, my non-attorney salespeople, literally, literally was a hot tub sales guy. And what I was looking for was someone who took a consultative approach to sales, which is a big mouthful of words, but what I mean is who didn’t come in? You don’t feel like you’re being sold, right? You feel like someone’s trying to understand your problem and then figure out whether or not they have solutions that can help you. So for me, Blake in my office, I got a B in my bonnet that I wanted to buy a hot tub in the middle of summer in Austin, Texas, another hot tub place. This gal was trying to give me the Rolls Royce of hot tubs. And I’m like, you don’t understand. I want the Kia Sorento of hot tubs. I did not ask for the Rolls Royce of hot tubs, but versus my experience was he was asking all the questions, trying to understand, and then ultimately recommended a product that got him less commission and was cheaper because it’s what better suited my needs. And that’s been my experience with every single non-attorney salesperson I’ve hired. They didn’t come from a legal background, they weren’t paralegals before or anything like that. They just knew how to listen and really seemed to kind of give a dang about what was happening in the other person’s life. I think that’s something, Christopher, there’s all of that and how can we help? But that component, I’m not sure how much you said about this, but for me this really important. Is this a person who really gives a crap

Christopher T. Anderson:

About

Caller #1:

The other person on the other end of the phone?

Christopher T. Anderson:

Exactly right.

Caller #1:

Or are they just trying to get their money in whatever the way is? So I think that that empathy, compassion, interest component, you’re listening for that in a luxury sales place. You may not get that if they’re selling Louis Vuitton purses, right? And so if I was going to a luxury place, I would still try to make sure that this person can sell to luxury, but has an empathy overwrite for me.

Christopher T. Anderson:

I mean, guys, remember Southwest Airlines hires flight attendants without ever teaching them or testing them on anything having to do with evacuating an airplane or doing the seatbelt demonstration or anything. They test for attitude. And that’s a lot about what goes on here.

Announcer:

Thank you for listening. This has been Unbillable Hours. Community Table on the Legal Talk Network.

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