Why nobody wants to admit they used AI.

Should you be embarrassed to say you used AI?

Amanda, Debbie, and guest Stephanie Everett take on the Sidebar question of the week: is AI coming up in lateral hiring conversations. It rarely does, because firms and attorneys alike would rather stay quiet about how far behind, or how far along, they actually are.

Debbie’s six-minute memo

Debbie turned a call transcript into a full framework for a client in about six minutes using Claude, then sat on it overnight because sending it that fast would have looked like she had not done the work. The tension: the profession rewards effort, not efficiency, so speed itself starts to feel like something to hide.

Billing by the hour when AI does the job in an hour

Stephanie’s clients still pay for her time, so a faster draft cuts against her own incentive to use the tools well. Her example: a managing partner who spotted a broken state law, called the legislature, and got it fixed in under an hour. What is that worth to a client? Not an hourly rate.

Why firms hide how far behind they are

20% of firms admit to staying deliberately vague about their AI position in hiring conversations, to conceal how far behind they are. Debbie’s read: ask any room and everyone looks around relieved to hear they are not the only one still figuring it out.

Prepping for an interview with Claude

One candidate fed Claude the hiring partners’ bios, the job description, and her own resume, then had it grade her rehearsed answers before the interview. She never mentioned any of it afterward, even though it was the most impressive part of her prep.

A lawyer’s value is judgment, not just the draft

The panel lands on why the discomfort is real: a lawyer’s value proposition has always been what is in their head, so admitting AI helped can feel like admitting a deficit. Their answer is that judgment, counsel, and knowing what to do with a draft are the harder, richer part of the job AI cannot replace.

Transcript

Dressed like a grandma, and welcoming guest Stephanie

Amanda: Y’all want to know something about this pearl necklace? Hello, everybody, we’re live. I’m gonna tell a funny side story before we go live with actual things. Yesterday my daughter was at band camp and had to dress up for dress-like-a-grandparent day. So I’m in my bedroom getting dressed, and she comes out of my closet wearing a shirt I wear to work on a regular basis.

Debbie: Yeah.

Amanda: And a pair of shorts I was wearing this weekend, and this pearl necklace. And she’s like, look, I’m dressed like a grandma. I’m like, this is not acceptable. She’s sixteen. I’m not even fifty.

Stephanie: Not.

Debbie: That’s funny. That’s funny.

Amanda: All right, so thank you all for indulging us in our side story. You may notice that Rob is not with us today. He had another assignment, but we’re very lucky, because instead we get to have Stephanie Everett. Stephanie is a practicing, well, non-practicing attorney who also works for Affinity with Debbie. And I think some of what we’re going to talk about today is a little bit about attorneys’ interaction with AI, so we thought let’s bring an expert on and get your thoughts too. Debbie, what else did I miss?

Debbie: I just want to say, about your grandma from the closet, I think that’s a rite of passage that also happened to me when my daughter was a teenager, with those silly school theme days. I’ve loved seeing the memes about it, like, on the first day of school, can you just tell me everything that’s going to happen, every theme day, everything, so I can be prepared. So I remember that same feeling, like, you just came out of my closet and now you think you’re dressed like a grandma. All good, all good.

Amanda: I mean, there’s a ton of different themes, and some of them make no sense. Today is dress-like-your-culture day, and she came in and said, we’re from Texas, do you have a cowboy hat? I’m like, I don’t know that a cowboy hat is culture, but she’s wearing a Whataburger t-shirt and a cowboy hat.

Stephanie: Yeah. Okay.

Debbie: All right, good.

Stephanie: Mine was singing nineties songs with me last night, and that’s equally weird, when you’re like, this is a song I grew up to, and she’s singing it just as loud and proud as me. So it was fun.

Debbie: All old things are new again. I wonder if we’ll say that about AI in ten years. Like, remember that announcement about ChatGPT that set the world on fire in November of twenty twenty three?

Stephanie: Exactly.

Amanda: Yeah. All these Zoomers, it’s gonna be their Y2K, because there’s gonna be a world before AI and after AI. Or nine eleven, maybe not nine eleven, but same concept. It’s gonna be a defining moment, having lived or gone to college without AI and then started your career with it, and how different that is.

Debbie: Right. Yeah. So our topic today.

Amanda: Alright, so what’s on the topic today? What is our topic today?

This week’s topic: are you embarrassed to admit you used AI?

Debbie: We’re talking about whether you should be embarrassed or hesitant to say, I used AI for this.

Amanda: Yeah. ’Cause our sidebar question this week was, is AI coming up in your hiring and lateral conversations. If you’re interviewing an attorney, how does AI come up? And what Stephanie and Debbie and I found really interesting is that it either isn’t coming up, or it’s not coming up as much as you’d think, and we found two reasons: firms don’t want to admit they’re behind on AI, and attorneys don’t want to admit they’re using it, unless they’re proficient, they don’t want to admit it. So where do you think that’s coming from?

Stephanie: Yeah. I sometimes catch myself wondering, is this a woman thing, where it feels like we’re cheating? It’s a little too easy, right? So you think, wait, isn’t this work supposed to be hard? This is simple and fun. Does it feel like I’m cheating by using it?

Debbie’s six-minute memo, and why she waited a day to send it

Debbie: Listen, today I was on a call with a lawyer about succession planning. We had a really great call, and I said, why don’t I just send you some framework in an email of how I’d think about this? Our meeting ended five minutes early, I grabbed the transcript, put it into Claude Enterprise, paid, not training the models, for all the people who need to know that, and then I turned on the microphone and talked for four minutes about what I thought.

Amanda: Yeah.

Debbie: And it created something for me. I read it, and I thought, I would never say those words, that’s not how I talk. And then I thought, well, I’m not sending this to him until tomorrow, because it can’t look like I was able to do this in six minutes. So I’m not sending it until tomorrow.

Amanda: It’s crazy. The other thing we talked about is how we work for an industry that rewards effort, not efficiency, quite the opposite. So why are we so ashamed to admit this came from AI?

Reframing it: “I’ve mastered the tool”

Stephanie: Instead, because I’ve seen your AI output, Debbie, you could frame it as, I understand this tool and I’ve used it so well that I know exactly what to give it, how to alter it. I’ve actually mastered it, to the extent you can. I put my prompts up against other people’s prompts all the time. So instead of coming at it like, wow, this was too fast, this feels like cheating, it’s actually, I’m really good, I know how to leverage the tools, and I’m gonna give you something that’s gonna impress you in six minutes. But we’re not there yet. How do we flip that switch and tell people that?

Debbie: And what about lawyers, though? All of the questions that come after a lawyer leans into AI, and maybe is doing the same work all three of us have done, really pouring into it so what it gives us is usable.

Amanda: Yeah.

Billing by the hour when AI does the job in an hour

Stephanie: I had this conversation this morning with a lawyer, and he said, Stephanie, this is getting really good, the stuff I’m getting from it is amazing. Of course I’m reviewing everything, human in the loop, I get it, but now how do I charge for my work? Which is where I thought he was going, because part of the tension is, it’s not only that it feels a little like cheating, it’s also, if I do it too fast and I’m still billing by the hour, what’s my incentive to actually get this work done faster? I’m gonna charge the client less, and it doesn’t make sense. The example I gave him was a firm we work with, Debbie, you know this firm, where the managing partner picked up the phone, called their state legislature, and said, this law is broken, you need to fix it. They entered a bill, passed a bill, and fixed it. He probably spent less than an hour on that. What was that worth to a client? Was that worth an hour, for them to change a broken law? How do you put a price tag on that? Because that’s not our value.

Amanda: Well, yeah, I mean, I’d argue it’s two different things, right? Either you can take on more work with the time you saved, or you’re seeing a higher realization rate because clients aren’t questioning how much time something took you to do. Those are the two things we’re pushing on. We had a comment in the chat I thought was really interesting, from a firm administrator who says, I wonder if shareholders will give calculations and recommendations the full weight if I admit I used Claude. So maybe they’ll trust it more if they admit they’re using Claude. I’ve had this same conversation, not with lawyers, but with a group of people who said, well, I as a firm administrator don’t want to admit I use Claude, because then what are they gonna need me for? I said, girl, there are a million problems at your firm.

Debbie: Mm.

Amanda: That you can solve. Just because you’re the one who always puts together the cash report, and now the firm can put the cash report together with Claude in five minutes, when’s the last time somebody looked at intake at your firm, or customer service, or response times, or how long it’s been since you did the client engagement survey? But it is a good point, about whether they’re more likely to trust recommendations or calculations if it came out of AI.

Stephanie: It’s interesting they went that way, that it increases their trust factor, because we saw this on our team, with some folks who said, hey, I actually don’t trust the output, I’ve heard it hallucinates, I’ve heard it makes mistakes, I’ve seen it make mistakes, so I’m hesitant to use it, or I don’t want to admit to using it if there’s a problem with it. What do you do with those folks?

Debbie: I think, and I’ve heard this not just internally at Affinity but from our clients too, pick something less volatile, less risky. Let AI help you manage your day before you let it help you with a legal document. If you’re really worried about that, find something you do over and over again, something lower risk. Have you watch what human in the loop actually means, the idea that you can feed something to AI, it gives you something, and then you give it to someone else, no one ever intended for that to be the whole process. There’s that quote, the AI’s confidence has no relationship to its accuracy. We’re trained to believe confidence is the equivalent of fact and truth, but that’s not actually true. So we just say, yep, you’re right, it doesn’t always get it right, that’s why you exist, that’s your job, to look at it in detail and walk through what it created. And you can also ask it, tell me how you got there. It’ll tell you. That’s a lot harder to do with a human.

Amanda: Right. Cite your sources. Yeah.

Hiring: the 20% of firms staying deliberately vague

Amanda: So I think the other interesting thing, and I kind of glossed over this, is talking to candidates, because that was the point of this question, when you’re hiring attorneys, why is a firm hesitant to admit they might be behind on AI? We found that over twenty percent of firms admitted to being deliberately vague about their AI position, to conceal how far behind they are. Have either of you encountered that?

Debbie: I think everyone thinks they’re behind. But then when we ask the room, they all look around and go, yep, right, we’re all struggling, we’re all figuring it out.

Stephanie: I’m not as surprised by that, because isn’t that the case with everything? If you have high turnover at your law firm, you’re probably also gonna be a little cagey about that in your recruiting process, right? You’re not gonna say, yeah, nobody really sticks around who works with that guy.

Amanda: Ha. What happened to his last legal assistant? I think she took another job out of state. What about the one before that? I think her grandma died.

Debbie: Won the lottery. Right.

Prepping for an interview with Claude, without overdoing it

Amanda: Sorry, Stephanie, I digress, but that’s a good point, it’s a little bit of the, why are you hiding things in an interview. I have a friend, not a lawyer, who had an interview and used Claude to prepare for the whole thing, everything from dumping the hiring partners’ bios in, help me prepare for this interview, here’s who I’m meeting with, dumping the job description in, dumping her resume in, and, help me prepare. And now Claude has that feature, the talk-back feature, and she said, help me prepare for this interview, ask me questions, let me respond, judge my responses, be harsh in judging my responses. She said she went into the interview feeling really good about it, and wasn’t afraid when they asked, how did you prep for this interview today? She didn’t mention any of it, and I told her, that seems like something you’d really want to say, they’d be really impressed by that level of prep.

Stephanie: Yeah, I would have been. I thought you were gonna go a different direction, because I’m pretty public, I have a podcast, and the last time we did interviews, somebody clearly used AI to prepare, but it was almost a little stalker-ish, because they were pulling out facts about me I was like, wait, how do you know that? You forget what you’ve said on the podcast, and then when you meet people in real life, you have to remember, yeah, I did share that detail. Someone’s gonna come up to you about the grandma-closet story in six months and you’ll need to remember it.

Amanda: Yeah. Well, actually, the only reason I shared that is because Rob isn’t on here today. I’m really hoping he doesn’t listen to this again, because he’ll never let me live it down. But I don’t think he’s listening, I think he’s doing something else.

Stephanie: Yeah.

Debbie: We are in his ear right now, you know that.

The limbo years before “of course you used AI”

Debbie: So do you guys think we’re in a little limbo spot right now, and that a year from now, two years, three years, people will just boldly admit they used it? I remember, and I won’t name drop, an executive of a cloud product who one day said, we’re never going to call this a cloud product again, because it just is, you don’t have to differentiate that way anymore. Do you think we’re in that weird limbo now, and that soon it’ll be, of course you used AI, why wouldn’t you?

Amanda: Right, right, right. And if you didn’t, that’s more concerning than the other. Yeah, yeah.

Stephanie: Yes. I don’t know when that point’s gonna hit, but it’ll come. It’s still crazy to me, I was with a firm recently and someone said, hey, I was just at a conference, and you should hear about all the firms using AI, it’s not just a West Coast thing anymore. And I don’t know why that made me laugh so much, because I was like, no, it’s beyond Seattle.

Debbie: It never was just a West Coast thing. What is that?

Amanda: People in California are real special. Just kidding, for all you California people listening.

Stephanie: But it’s those little nuggets that make me think, Debbie, but there are still firms that are scared of the cloud. And as much as we’re out here saying, yeah, this is gonna be our new normal, of course you used it, there are still firms, and this firm was very against it, very scared of it, they said, we don’t trust it, we don’t want to use it. And I politely reminded them that their team members probably already are, so they should probably figure that out.

If you didn’t use it, you’ll be the less-prepared one

Amanda: Well, the interview thing, Debbie, is actually interesting, because you’re right, in a couple of years, if you didn’t use it, you’re also gonna be a lot less prepared in interviews. Right now, if you’re using it, your candidates should know all that information, it shouldn’t be a surprise to them that the managing partner also practices in tax and estate planning. You should have a whole persona written out. So in a couple of years, when at the end of the interview you say, do you have any questions, and they don’t have any, that’s gonna be a real tell that they didn’t use AI, because you can very easily have it prepare questions to ask at the end of an interview.

The candidate who read the managing partner’s book

Debbie: Well, it’s interesting we’re talking about interviews. I’ve done five interviews this week for one of our clients, for a director of technology position, and I’m one of many people interviewing. One of them jumped on the call and said, hey, congratulations on your book. Four of them did not. And it makes you think, it used to be the low-hanging fruit was, have you visited our website, have you looked to see who we are, but this one person went a little deeper, went to LinkedIn. It’s pretty easy to find, you didn’t even have to work that hard to get there, but the fact that they did is actually impressive to me, that they took a minute to ask, who are these people I’m talking to today? So the new version of that in the hiring process is, if I’m a lawyer interviewing at a firm, what are all the things I can learn? What’s my prompt to throw into Claude or ChatGPT and say, I want to learn everything there is to know, check their LinkedIn. What’s the prompt you go in with? How do you absorb that information, and how do you show up not looking like a creeper, but looking informed, what is the professional version of, I prepared for this interview in the age of AI?

Amanda: In my mind it’s something like, I saw you were the primary dealmaker on an M&A deal, I did something similar in my role before this. AI can find that by looking at your resume, if M&A was the example, putting your deal sheet in and looking at the website and saying, here’s a comparable deal to what you’ve done, to what we’ve done, and let me show you how something on your website, I have direct experience in a matter similar to that.

Stephanie: Yeah, definitely give it the context that you’re going in for an interview, because that will help it understand what you need to know. And coming back to the firms that are nervous to admit they think they’re behind, maybe here’s permission to speak honestly and say, you know what, we’re exploring it, we’re curious how you’ve used it, we’d love to leverage your knowledge if you come work here, we’re trying to bring in people who understand it and can help us. It’s the same way we’d deal with a retention issue, you can’t hide behind it completely, sometimes you have to address it and say, yeah, we know it’s a problem, and here’s what we’ve done to put it in place. So I’d encourage firms, if you don’t know how to say that, go ask Claude, here’s what we’re struggling with, help me with my interview message, how can I talk to candidates and give them a fair but rosier picture of where we’re trying to go, because you should want to be recruiting the people who are going to help you get there, if you need that help.

Screening for change management, not Claude experience

Amanda: One of the things we uncovered a few weeks ago on Sidebar was that people aren’t screening for AI experience, but they are screening for change management, now more than ever, as a skill set. So an interview question you might ask an attorney, rather than what’s your experience with Claude or rolling out AI, is, what’s a time you were part of a large firm project that changed the way you practice, or changed the structure of your practice? You’re looking for somebody who’s been part of a project or a change, who’s open to something new.

Debbie: I think that’s a really great point, and I loved reading about that in Sidebar this week, people thinking about how they get continuous improvement, how they get just a little bit better. I think people trying to air-quote figure out AI for their firm, who think there’s just a thing to figure out, are always going to feel overwhelmed, because there isn’t a thing to figure out, there’s only the next thing to figure out, because there’s going to be a next thing after that, and a next thing after that. This is our new lot in life, until the next thing gets invented that we can’t even imagine, whatever that is, when the robots come to work. I don’t know what the next thing is, but this idea of continuous improvement, today is the slowest day of change you’re ever going to experience in your whole life. So we should be screening for that, talking about that, asking for examples of it, so that when people come into our firms, they’re prepared for what we’re going to ask them to do next.

A lawyer’s value is judgment, not just the draft

Amanda: Can I take us back a little bit to the stigma we talked about, and about admitting something about themselves? One of the things that came out is that our profession sells judgment, and the judgment is supposed to be yours. Someone said, a lawyer’s value proposition is what’s in their head, and when the tool does part of the thinking, disclosing it feels like disclosing a deficit. No other profession has quite this problem, except maybe medical, except a surgeon using a robot becomes a better surgeon. So in some minds, a lawyer using AI is a lesser lawyer. Why is that gut reaction there, and what’s wrong with it?

Debbie: I don’t know that I have a great answer for this. It makes me think about that article I recently read, about the law firm that created thirty or fifty digital twins of their partners. They take a partner and say, tell AI everything you know, now that’s your digital twin.

Amanda: Yes. Her digital associates.

Debbie: There are actually companies out there that help you create these. Can you imagine two Amanda Koploses? No.

Amanda: This world is barely big enough for one of us, okay?

Debbie: But the digital twin idea is exactly what you just talked about. Now the associates don’t have to come ask Debbie Foster how to handle a case, they’ll go ask my digital twin, how would Debbie Foster have handled this? That’s a thing that’s coming soon to a theater near you, and I think it’s related to your question.

Stephanie: I think the question drives at the heart of what it means to be a lawyer. As a lawyer, I remember people saying, I love watching this TV show, I want to be a lawyer because they think it’s going into court and making arguments. I used to tell them, being a lawyer is a lot more writing, being a great writer, than standing up and arguing. As a litigator, most of my day was drafting. Now AI is completely cutting into that, that’s how I used to tell people what I did for a living, I really wrote. So now you say, well, actually what I do is leverage AI tools to write, it’s the next iteration. So I think your question gets at what value am I actually bringing, and what we’re hearing from industry leaders, and I think it’s right, is your value is in your judgment, your counsel, tying that knowledge and draft and experience together, and there’s so much more to it, it’s richer and more complex. Maybe we know that to be the case, but maybe it’s also scary, because that’s also the hard stuff, it’s the good stuff everybody wants to do, but it’s also kind of hard, if I’m being honest.

Amanda: Yeah. You know, there’s never been a TV show about somebody managing a law firm, because it would be a horror movie, okay?

Debbie: Well, was Suits about Donna or about Harvey? I don’t know, right?

Why join Sidebar this week

Amanda: I don’t know. Alright, so we’ve dropped a link in the chat to join Sidebar. If you’re not familiar with Sidebar, we’re a think tank designed to help law firm administrators find their peer group, because we’re all dealing with AI, somebody came into my office yesterday with a brand new product I’d never heard of, and now I have to go figure out what that product does and whether it fits our tech stack and our strategy. We’ve got a question every week, we have one out now if you want to join, the link is up there. Also, the question we have this week, which I think is really exciting, is just tell us something you individually have done or built with AI lately, whether it’s preparing interview questions, a standard operating something, whatever you’ve done, just tell us. We’re hoping, no promises, that we’ll have somebody come on Sidebar Live and share it with us, we’d love to have somebody tell us what they’re doing, because we’re only better together. So as usual, Debbie, it’s good to see you, I hope nobody missed Rob too much, but hopefully he’ll be back next week. Stephanie, thank you for joining us today, we really appreciate it, we’ll be calling on you again in the future, I’m sure. Does anybody have any questions?

Stephanie: Thanks for having me.

Debbie: Thanks, Amanda.