Episode Notes

Zack talks with CARET Legal’s Chief Product & Experience Officer, Jennifer Sherman, about technology expectations in a law firm. They dig into how a lack of technology could cost your firm clients, time, and even valuable team members. The infrastructure table-stakes are changing from well-appointed office space and libraries to client-centered processes and efficient technology.  

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About Caret 

CARET Legal is the leading solution for legal professionals to manage their practice and create space for what matters, including delighting clients and maximizing billable time. From client intake, to matter management, to back-office reporting, CARET Legal helps you save time, increase team collaboration, increase accuracy, scale your business, and collect revenue faster than ever before. 

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? Check out our coaching community to see if it's right for you.

  • 6:08. The Impact of Automation on Attorney Workload
  • 11:37. The expectation gap
  • 24:00. Getting Paid Faster and More Efficiently with Technology


Announcer (00:04): 

Welcome to the Lawyerist Podcast, a series of discussions with entrepreneurs and innovators about building a successful law practice. In today’s challenging and constantly changing legal market, Lawyerist supports attorneys building client-centered and future-oriented small law firms through community content and coaching, both online and through the Lawyerist lab. And now from the team that brought you the small firm roadmap and your podcast hosts. 


Jennifer Sherman (00:35): 

I’m Jennifer Sherman, and I am the chief Product and experience officer for Caret. We’re a legal technology provider and I am accountable for our product management and where we’re taking our products as well as our support and our professional services and client success functions, which means that I’m accountable for both your human and your digital experiences with the company. And I’m at Caret because my why in life and the thing that wakes me up every day is I want work to suck less for people. I want to work on technology that makes someone’s job better, smarter, faster, and I want to give my team a better chapter of their career. And I was attracted to legal technology because lawyers enter their profession because they want to help people. And if I can help the people who help people, I can have an outsized impact on work on this planet. 


Zack Glaser (01:26): 

Love that. Love that. Yes. Kind of an impact in an order of magnitude. That’s fantastic. Well, Jennifer, thanks for being with us on the podcast. I really appreciate it. And it sounds like you are well positioned to field the questions and talk about the things we’re talking about today, which is the need, and I say need capital letters, the need for law firms to deliver technology internally. We’re seeing that it’s not just a wowing the people that work for us or just making it a little bit better for the people that work for us to use appropriate technology, but it’s driving who’s working for us, whether they’re going to stay with us, how well they do things. So what are you seeing from your perspective of building some of this technology for people? 


Jennifer Sherman (02:18): 

Yeah, absolutely. Recently one of our clients said to us, the way that you established legitimacy as a law firm 10, 20 years ago was you had a big fancy office and it was your big fancy front door that told people you were legit. And no one goes into those big fancy offices anymore. And so your front door has become your technology and what your clients expect because frankly, our digital expectations are set by the last great digital experience we had, whether that was a bank or an eCommerce site. And so client expectations are high. We’re not saying, ah, they’re a law firm. I don’t expect them to have a portal to have email to be textable. And so part of Affirm’s ability to show up and show up in a way that their clients expect is their digital footprint and the way in which they communicate. 



So it’s important for our clients to see that we have that level of sophistication. No one wants to feel like they are working with someone who is drowning in paper and confused and lost. We want to work with people who know that they have the information that they need at their fingertips. So it just creates a better client experience. But I think to your point earlier about employee retention and employee satisfaction, we were reading recently that one in five attorneys left their job last year and 58% say they are likely to seek new opportunities in this coming year. That’s a massive amount of turnover. 


Zack Glaser (03:43): 



Jennifer Sherman (03:43): 

Like the great resignation hit legal a little late, but it’s here, 


Zack Glaser (03:46): 

Right? And that’s expensive for law firms and many, many, many ways to have to deal with that. 


Jennifer Sherman (03:55): 

It means that we all have to think about both the cost of retention and what we can do to keep people, but also what can we do to make onboarding new team members as fast as possible? And I think technology is a big unlock for both of those. And I think we also have to think about back to my heart of let’s make work that suck less for people. If attorneys get into this field because they want to help people, whether it is just help them through the minutia and administrative work of everyday life or help them through an event in their life that’s been really traumatic. And if those attorneys are spending more than their fair share of time on administrivia, on admin, on non-billable work, they’re going to get frustrated because that work doesn’t feed their soul. There are studies that have found like 23% of an attorney’s workload can be automated, and 80% of small firms are saying that they are struggling to deal with their administrative tasks. 



And it is keeping 65% of attorneys who say that they’re non-billable work. It is keeping them from doing the work that they want to do and achieving their goals. And so I think what technology does is drive automation. And what automation does is allow us to do the work we love and do less of the work that doesn’t fill us. And so not only does that mean that technology can be a big unlock in terms of the firm’s productivity, in terms of their ability to deliver value for their clients, it’s a huge unlock in terms of employee satisfaction, which will ultimately lead to employee retention. 


Zack Glaser (05:26): 

Right. And when you’re talking about that, when we’re talking about automating things that a lawyer does, a lot of times lawyers have this knee jerk reaction to, you can’t automate me. You can’t make a robot lawyer, you can’t can automate the things I do. But it sounds like we’re not talking about automating the things that the lawyer has in their mind is the fantasy of the things they do. We’re talking about automating, I don’t want to say the crap, but the things that can be automated, there’s stuff that can be automated in your day. I don’t care who you are. 


Jennifer Sherman (05:58): 

Right. It’s funny, my partner is actually a paralegal and he refuses to talk to me about AI because in his mind it’s coming for his job and it is coming for the things that he loves to do. He loves to read, he loves to research, he loves to write. And I would argue that if that’s what you’re using AI for, you’re probably missing the mark because all of these automation technologies are not about taking away the decision making. They’re about taking away the things that you don’t like to do. It’s about timekeepers and automating time card entries. It’s about automating the fill in of forms and documents that we have to do again and again and again and fill in names and addresses and dates. That stuff is fairly rudimentary. Technology doesn’t exist yet that can replace the lawyer. No technology doesn’t exist yet that can replace the paralegal that is deep expertise that cannot be replicated even by the best AI engine in the world. But what it can do is get them started faster. It can write their first draft, which will be a very rudimentary first draft. It can automate the creation of their time entry. It can automate the sending of their invoices, it can automate their collections. And that’s not something anyone wants to do. 


Zack Glaser (07:11): 

No, I mean, it’s not something that I want to do. I can tell you that I’ve learned working at Lawyerist to realize that some people do want to do the things that I don’t like, but yeah, those are not necessarily the things that I want to do as an attorney. I’d rather be doing research, but I’d rather be doing, honestly, even when we get into some of the AI assisted research, I don’t want to do the stuff that the AI portion of the research does, which is go weed through all this information. I want to want somebody to feed me the guts of this argument and then I make a decision or I make an argument based on that. Even Alpha Go, which is the AI product that Google had created in order to win the game, go and it did, but it was very, very specific at what it did. And it also didn’t intuit things. Artificial intelligence can win or assist in winning chess because it’s a ton of different potential outcomes, not because it can really think, not because it can intuit and the lawyers that I know they like sitting around thinking and intuiting and strategizing, and it’s not going to take that away from you. It’s certainly not anytime soon. 


Jennifer Sherman (08:28): 

No, it’s really not. And I think it’s that advancement, it’s that can you get me to the page where these sorts of concepts are talked about? And then let me interpret from there what those concepts are. I a hundred percent agree it’s not going to replace us. It’s going to make us better. It’s going to make us more efficient. It’s going to fast forward us to where we want to be. And I think what’s important about that and whether your technology is AI or not, I know a lot of firms are still in a place of, we’ve seen enough mistakes, we’re not using it. That’s fine. A lot are in a place of what kind of tasks is this appropriate for and where is it just still a little too experimental? I think what really matters in any of those conversations is where can we use it to do the work that doesn’t add the value? Where can we use it to automate, to accelerate us to the things that we love, which is helping customers? 


Zack Glaser (09:20): 

Right? Well, so kind of down that path of getting to where that’s more common. And that’s the question people are asking, is having this technology in your office a thing that the lawyer or the paralegal or the assistant or anybody is expecting because now that we have things that can do these more mundane tasks for us, well, I don’t want to do the mundane tasks, and if my law office doesn’t have the technology to take care of this automation, then maybe I don’t like my desk as much anymore. 


Jennifer Sherman (09:53): 

Maybe I’m going to find another firm. I mean, I think we recently read a study that said that 83% of attorneys say that working for a technology savvy firm is either extremely or very important to them, but meanwhile, only 32% believe that their firm is prepared to make the right strategic investments in technology. So you’ve got this huge expectation versus capacity gap in the law firm. And I think that’s worse in the small to mid-size firms because going to law school to learn about technology is not something that happens, right? I said no attorney ever. And so we expect these firms to be technologically savvy and they just aren’t there yet. And the lawyers, I think our attorney community understands the potential, understands the impact it could have, and yet don’t have a clear path to making the right decisions. I think that’s where you just got to have the right partners in place. 



Whether those are those strategic advisory firms or just the technology partners that you are using today, are you thinking of them as vendors or are you thinking of them as partners? It can help you chart a path to a more automated future. And I think the gap between expectation and reality, it sort of also sits in a work-life balance conversation as well. So going back to the 20% of attorneys turned over last year, we also found that 58% of attorneys put work-life balance on top of their priority list. But again, only 34% say that their firms can deliver that. The key to delivering balance is delivering the tools that take the work off of our plate that we don’t want to be doing. So I think firms are going to be in a lot of trouble where they’re not managing that gap appropriately. 


Zack Glaser (11:38): 

Well, I think one of the things that is interesting about this generation of attorneys and this generation of tech being built, because since the printing press, we’ve been having newer and newer legal technology, so we’re always going to have newer legal technology, but this time, or at least currently, there’s not as much of a infrastructure issue. There’s not as much cost with getting this infrastructure. When I as a firm had to own all the legal books, I had to have a library, and there was a lot of cost associated with having your office in the right place, a library, the right associates, the right people that could create the automation. And people are, you have to pay people, you should have to pay people, but you have to pay people a lot more than you have to pay technology. But now as a lawyer, I can say, I can do this better. I’m going to pop out and I’m going to go get my own technology. I’m going to work from home. And so those 20% of people that are dissatisfied, or I think it was 30 something percent that are dissatisfied now have a much higher opportunity to leave. And so there’s much more need, I think for the established firms, the people that are employing people to make them happier, they can leave. 


Jennifer Sherman (13:02): 

I think you’re not wrong about calling it out as a potentially generational issue. Managing partners are managing partners because they have been around for a long time, which means they’ve probably learned to make do with an older set of technologies, with a library, with an on-premise desktop application that it wasn’t connected to anything and couldn’t pull information from a variety of sources. And so it’s hard to see the need to invest in a world that is different because you have learned to build systems around the old, and then the generation coming up does not accept that. And it doesn’t take that. It doesn’t take that no for an answer. And I think the saving grace is that you’re right, these technologies are becoming more accessible. The cloud means that I can adopt them much more readily and much more quickly. I think true SaaS. So cloud means I can work from anywhere and you can be not true SaaS and deliver that capability. 



We can host anywhere and I can work from the beach. I think the other advantage that SaaS offers to this world of new technology is particularly if it is extensible, the promise that you’ll also always be on the latest and greatest. You’ll never have to go through another software upgrade and you will still get innovation even if you extend the system, even if you integrate with X, Y and Z, even if you change the workflow because you do things a certain way, you’ll still be able to continue to innovate. And so if you choose the right partner, your firm will evolve without really much effort from you because that technology will evolve under you and you don’t need to keep up with it the way you did when most managing partners were coming up and having to manage technology. So I think it’s gotten a lot easier and a lot more palatable. 



Unfortunately. Also, the choices are huge. We’re just coming off of legal tech conference season and my goodness, you walk down the halls of those shows and there are so many options and there are so many things you could do and they all look really cool and they all look really great. And so I think every firm has to start with what is most important, what hurts the most? Now, what can we automate or what can we do to deliver better client value and client experiences and prioritize that list very carefully and then think about their roadmap to achieving it 


Zack Glaser (15:16): 

Well, so that list is interesting to me. And one of the things I like to think about, if we’re trying to think about making our office kind of sticky for people to stay, for people to want to stay, and they go, well, I don’t have that infrastructure, and previously the infrastructure again is the tall building and the name and the website and all that. Well, I can go rent a place, I can get a website, I can spin up a law firm pretty quickly. But one of the things I can’t do quickly is create processes for doing the things in my office, document the processes for doing the things in my office. And then I think this is where we kind of get to that, that’s where you find the automations, that’s where you find the efficiencies when you start to look at those things and you get the technology to make those efficiencies in those processes. Well, now I’m a lawyer sitting there and we’ve got great processes, we’ve got great technology that is managing these processes well, now I look outside and I think, well, I can’t build that. Yes, I can go buy technology quickly, but I can’t go build that quickly. And so having that, the automations, the efficiency, and building it from those processes, I think that’s where we get our sticky infrastructure. 


Jennifer Sherman (16:35): 

Yes, that is the competitive moat. Once your team finds it and they’re in a groove and they can do what they love and not do what they don’t love, who needs to go anywhere else, and your clients will be that much happier if they can communicate with you on text. If they can upload their documents in a portal, why would I go anywhere else? Why would I go back to someone who’s got a bunch of yellow pads and there’s always looking through their notes. I think it creates stickiness all around and it’s that kind of synergy where everyone is in flow and everyone is working on their process. That also frees us up. It creates space for us to innovate whatever innovation looks like for your practice area, for your firm, for your clients, once you have that room, sky’s the limit in terms of what you can accomplish as a firm. 


Zack Glaser (17:20): 

Well, and if you think you were talking about work-life balance being an important thing for this generation, and it’s very weird for me to not feel like the generation that is the new generation of attorneys now, but I mean, I’m 41, so I’m not them anymore, but the work-life balance is important for my generation as well. But if we’re automating things, if we’re creating processes, I remember in my office when we were managing our assistants and paralegals and everything, you don’t manage by just going out and looking to see who’s not on Facebook. You manage by checking your KPIs, making sure people are getting the processes done, making sure people are getting the stuff done. And if you start to automate those things, well now people do have a little bit more time. You’re getting the same stuff done, but people have a little bit more time and now maybe they can take a half day off on Friday or work from home two days a week because you’re managing differently and the technology is allowing you to manage differently. And so work-life balance from the owner standpoint is not a dirty word. It’s not something that makes people less efficient or less effective. It might be something that makes people more efficient. Frankly, I go for runs during the day and I come back and I’ve got 16 different ideas on how to program this different thing, and it’s effective. It’s helpful. 


Jennifer Sherman (18:46): 

Yeah, a hundred percent. I mean, we used to manage just by assuming buts in seats and time in the seat was a function of the productivity you’re going to get out of that. And it’s very interesting to watch this return to office movement to argue against that, which is really kind of a ridiculous notion. I a hundred percent agree with you. If we manage to the metrics, then it does not actually matter how many hours a person put in to get those metrics. And if you give them the room to do the work they want to do in whatever time they want, you’ll get so much more out of that person. It’s interesting was during the pandemic, so my favorite podcast is the Lawyerist one, obviously my second favorite is Adam Grant’s work life podcast. And he did an episode on burnout. And what he concluded in his studies was that the solution to burnout wasn’t to go away and take a vacation and sit on the beach for a while, but actually do more work but do work that feeds your soul. 



That is if you’re a teacher and you’re burning out, go tutor. If you’re a lawyer and you’re burning out, do more law. Now that could be pro bono, but it could actually be more work for the clients that you’ve got today. And what that says, I think, is that burnout isn’t caused by just doing too much work by doing work you don’t love, which goes back to our conversation about let’s eliminate that. And if you eliminate that, who knows what your people are going to return to you and it’ll likely be work that benefits the firm. 


Zack Glaser (20:08): 

Right, right. Yeah. Okay, so we’re kind of on the end of our time. Let’s talk about one of the big things that technology really can do for your firm, and again, it’s got a couple of edges to it, and that’s like getting paid more quickly with technology, more efficiently, more effectively, all of that. Yeah. Let’s dive into that a little bit. 


Jennifer Sherman (20:32): 

The easy one for a managing partner to care about, am I getting paid faster? We’ve seen studies that say those who deal with check will take up to 72 days to get paid. The check is in the mail. I think a lot of folks have gone through that phase in their lives, in their career and their financial development where they’ve lived on the check is in the mail for a few weeks and you needed that float. We actually, we were just talking to a client who turned on credit card processing for the first time, and she was doing her first billing run of the month, and she said she got paid before she was finished sending out all the bills. And to her, they’re like, oh my God, I got within an hour someone paid me. 


Zack Glaser (21:11): 



Jennifer Sherman (21:11): 

Yeah. Well, yeah, because you took a credit card, they probably paid you from their phone and just click the Apple Pay button, make it easier, and you’ll get paid. And sadly, 53% of attorneys will tell you that getting paid by their client is either a moderate or significant challenge. Oh yeah. So it’s not a non-trivial thing. It’s not about getting paid just a little bit faster. It is actually painful for our attorneys in this country to get paid what they’re worth. And if we can shorten that gap, then we’ve done a great thing for lawyers. And this is not easy work. This is highly specialized work that we went to a lot of school to get prepared to do, and we deserve to paid accordingly. 


Zack Glaser (21:52): 

So I remember when I was working with my father, I remember telling him, Hey dad, we’re going to take credit cards. It’s like, can we even do that? And I had done the research and had figured it out, and this was before really any of the specific legal credit card providers were out there. So this was difficult. This is not difficult to do anymore. It is not difficult to spin up and get paid like this. But remember going through the merchant account and everything, and there was a 3.5% fee and the 19 cents for every transaction. And he asked, he was like, are we going to pay that or are we going to pass it on? I said, I don’t care. I really don’t care. I will eat that. And he was just appalled at this saying, do you know how much faster and how much more we’re going to get paid? I mean, it is light years how much faster you get paid. And again, I have been in my office sitting there and all of a sudden you get paid and you’re like, I really needed that $500. It’s the 14th and we’re about to pay some people tomorrow, and I can’t pay people with an IOU from my client. I can’t pay people with a, yeah, yeah, I’ll come by your office and give you cash tomorrow. I mean, I love cash. Tell 


Jennifer Sherman (23:02): 

Them the check’s in the mail, right? Yes. Can’t pay your people. The check is in the mail. 


Zack Glaser (23:06): 

And that happens, but not only is it faster for me, but what I found, and I think that this is what most people find, it’s more convenient for my client and nobody sits there. I’ve never had a client send me an email that said, why did you send me a button that said pay invoice here? Nobody’s ever been offended by that and they don’t want to pay it. Fine. They can still send you a check. 



This is really a good example of a lot of technology that attorneys don’t think about using or put their head in the sand about not using is, well, nobody’s told me they actively want that. None of my clients have told me they actively want that, so I’m not going to do it. None of my clients have told me they actively want a client portal. Yeah, but A, have you asked, and B, have you shown them what that can be? Do I want a client portal? Well, I don’t know. Do you want to be able to check on your case on your phone from your daughter’s soccer game, from the sideline of your daughter’s soccer game? Oh yeah, I want to do that. Okay. Do you want to be able to pay your bill from there? Yes, 


Jennifer Sherman (24:12): 

A hundred percent. And it’s another generational conversation. How many of Gen Zs have a checkbook? Even if your firm is older, your clients are not going to be older or at least not for much longer. And check is just a technology that outside of, I think small businesses is dying. You’re using an obsolete payment method. 


Zack Glaser (24:33): 

And I say that as somebody who just got back from living in South Dakota for two years and rural South Dakota for two years. We did do checks a lot there, but my clients didn’t. I still didn’t, and I didn’t like paying with the check when I was there. It was inconvenient for me. I don’t know where my checkbook is right now. 


Jennifer Sherman (24:50): 

I haven’t ordered new checks in over a decade. I think I’m down to the last few. I’m very stingy about who gets a check because I don’t remember how to get anymore. 


Zack Glaser (24:59): 

No, no, absolutely. And so I think that’s definitely something to think about. So yeah, we’re kind of getting to the end of the time we have for the episode, but one of the things I want to bring up is that obviously we’re talking about holistic technology here across the board for your law firm. The reason we’re talking about that with you and with Caret is because Caret is a holistic soup to nuts intake to billing sort of platform that can get most everything that you need. It is a comprehensive platform here for law practice management for small, medium, large law firms. We’re talking about this from a large law firm perspective as well, but you can use this Caret from a smaller firm. You can automate documents. I mean, just the level of stuff that one can automate in something like Caret is huge. So where can people find out more about Caret and learn more about what you guys have? 


Jennifer Sherman (25:59): 

Absolutely. They can go to get Caret.com or Caret legal.com. Caret legal.com will describe our practice management solution. As you said, soup to nuts, everything from your intake and your CRM functions through your matter management calendar, email timecards, all of the workflows that you need to go through to get through all work by practice area, as well as back office, invoicing, accounting, payables, you name it. We also have assets, as you mentioned in the document automation space. I don’t know if folks know this, but Caret owns Hot Docs, which is probably the premier document automation solution that’s also integrated into Kara Legal, so you can automate generation of contracts for your clients. So all of that and more is available@getCaret.com. We look forward to seeing you there. 


Zack Glaser (26:44): 

Awesome. Awesome. Well, thank you. And I’ve got my Caret legal socks from last time we were at a tech show on for this episode, so 


Jennifer Sherman (26:55): 

Awesome. We won’t pull our feet up on camera, but 


Zack Glaser (26:57): 

Right. Yeah, we’ll do that. But Lawyerist shirt, Caret legal socks on today. Well, Jennifer, I really appreciate your time and your expertise in this. Thank you very much. 


Jennifer Sherman (27:09): 

Thank you, Zach. It’s good being here. 


Speaker 1 (27:13): 

The Lawyerist podcast is edited by Brittany Felix, are you ready to implement the ideas we discuss here into your practice? Wondering what to do next? Here are your first two steps. First, if you haven’t read the Small Firm Roadmap yet, grab the first chapter for free at Lawyerist dot com slash book, looking for help beyond the book. Let’s chat about whether our coaching communities are right for you. Head to Lawyerist dot com slash community slash to schedule a 10 minute call with our team to learn more. The views expressed by the participants are their own and are not endorsed by Legal Talk Network. Nothing said in this podcast is legal advice for you. 

Your Hosts

Zack Glaser

is the Legal Tech Advisor at Lawyerist, where he assists the Lawyerist community in understanding and selecting appropriate technologies for their practices. He also writes product reviews and develops legal technology content helpful to lawyers and law firms. Zack is focused on helping Modern Lawyers find and create solutions to help assist their clients more effectively.

Featured Guests

Jennifer Sherman

Chief Product and Experience Officer of Caret.

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Last updated March 26th, 2024