Why did this partner redline my document?

Will AI replace associates?

Debbie ran a professional development workshop for about twelve associates on taking control of their careers. When one asked whether AI will replace their jobs, she asked him back which parts of his job AI could replace. That led to the routine, rote work a computer does faster and often more accurately, and then to using AI for their own training.

Feed the redline back into Claude

Partners often redline an associate’s draft and either send it back, fix it themselves, or send it to the client without ever explaining. Debbie’s suggestion: every time a redline comes back, give it to Claude and ask why the partner changed it, and how much of it is style. Rob connects it to Amanda’s idea of analyzing how someone writes time entries, and to Claude as a learning system for associates who will be hired and used differently, not replaced.

The human side AI does not replace

Debbie asks lawyers to describe their work one level deeper: an M&A lawyer is not just helping rich people get richer, they are keeping hundreds of people employed. She tells the story of a partner who chose a mediator because his client needed to feel heard, even though the client was writing a check. Knowing your clients and the mediators that well is the part AI does not replace.

Why associates resist AI

A Sidebar data point from a month or two earlier found associates more resistant to AI than partners. Debbie offers three reasons: experienced people can spot when AI is wrong and new lawyers cannot, many younger people have environmental concerns, and firms buy tools without giving people the context for where to use them. Rob says next year should be about training and a growth mindset, not buying every tool, and Debbie notes that law firms no longer hire lifers.

Training on a tool is not reimagining the practice

From a Managing Partners session on leading through transformation, Debbie argues that knowing how to use a tool does not help a lawyer reimagine how they deliver legal services. A lawyer, associate, paralegal, and legal assistant already divide work in a rhythm, and adding AI is like adding another person to that mix. Rob says it comes down to building AI into the workflow.

Artifacts change how teams work

Rob is most intrigued by how Claude artifacts can be shared, exported, annotated, and redlined on a team plan, and suggests administrators ask for a mock-up even if they do not build. He also sees partners interested in a virtual chief AI officer. Debbie’s leadership team decided this week to stop passing documents and versions back and forth, while Rob notes his CMO still pushes doing some things by hand because AI output is starting to sound the same.

Start with the business of law

Debbie saw a firm announce it would not use AI for anything client related, and calls that a smart, risk-aware start: marketing, collections, and even facilities are good places to begin, and usually cheaper. She lists HR and people operations, onboarding, standardizing a process done thirteen different ways, financial reporting, data analysis, and IT strategy.

A coach, an idea bank, and a second brain

Both use AI to help leaders lead. Debbie suggests talking a problem through, asking AI to interview you, and role playing a tough conversation with instructions to push hard. Rob keeps a Claude project with his DISC assessment and Enneagram as an executive coach. Debbie proposes a big ideas project that captures thoughts without solving them, Rob describes a Legal Week project he used to track follow-ups, and they tease next week’s topic: building a second brain.

Transcript

Fall in Dallas, winter in New York

Rob: Hello, everybody. Welcome to Sidebar Live on October 15th. It’s still crazy to say October 15th, but the holidays are here, or almost here, I guess. The Christmas stuff is out, Debbie.

Debbie: It is. It is out everywhere. I’m in New York City today, and I’ve only seen one Christmas-like thing. A giant snowflake was up on a, well, that’s not even really Christmas, that’s more like winter. But the mums are out in full force here, like the fall-colored mums. Those are everywhere.

Rob: We’re going to get into the 40s this weekend down here in Dallas as a low, but still, somewhat exciting. I’m ready for it, because it’s been hot in Dallas. It’s been really hot. And I get cranky toward the end of a hot season. I don’t want to be outside anymore. So, champagne problems.

No complaining on the yacht

Debbie: I’ve got to tell you one thing really quick, since you said champagne problems. I just told this story the other day, and I did go verify that it’s true, but now I can’t remember which country artist it was. Some country artist was talking to Keith Urban and complaining about something, and he said, I wish I had learned this earlier in my career: no complaining on the yacht. Similar kind of thing, right?

Rob: No complaining. Very much so. I totally agree with that.

What everyone is asking Debbie

Rob: We’re talking about fall here, going into the winter. I always like to get a pulse. You’re like a celebrity when you walk into a room. Everybody comes up and asks questions. What are they asking you about right now?

Debbie: I mean, I just think the overarching question is still, what should I do? And it almost doesn’t even matter what it’s about. What should I do?

A workshop with twelve associates

Debbie: You know, I was thinking about two things I wanted to talk about today. One is not exactly connected to what you just asked me, but sort of is. I did a workshop with a group of associates yesterday, or the day before, I don’t know. There were about twelve of them. It was meant to be a professional development workshop, helping them understand how they could have some influence and take some control over where they’re going in their career, right?

Debbie: A lot of times we hear partners talking about, do these associates even care? What do they want out of life?

Rob: We heard it for a year on the road.

Debbie: Yes. Right, right. So my objective was to sit down and say, we get that you need more, but we need more too. How do we think about this? How do we think about you coming into your career as a lawyer? What do you want to do? Who do you want to be? What do you want people to say about you when you’re not in the room? When people are thinking about who they should assign this case to, what would make them say, I’m going to assign it to Joe or Bob instead of Tim or Tom or Suzy, or whatever it looks like, right?

Will AI replace our jobs?

Debbie: And when we were talking about that concept of agency, of taking the reins, one of the associates said, do you think AI is going to replace our jobs? And I said, I’m going to answer your question with a question. Do you think AI is going to replace your job? And he said, well, that’s really not fair, I asked you that question. And I said, I know, but let’s just play this out a little bit. Why would AI replace your job? What parts of your job could AI replace?

Feed the partner’s redline into Claude

Debbie: And it led us into this really great conversation about those routine, rote things that a computer can just do faster than a human, and oftentimes more accurately. But it also led us to how these associates could think about using AI for training. One of the examples, which I loved, and I had really never thought of it before until it just came to my mind: we were talking about how often partners ask an associate to draft something, they get the draft back, and sometimes they redline it and send it back to the associate and ask them to fix it. Other times they redline it, send it to the associate, but then fix it themselves and send it to the client, and there’s never really a conversation. Other times they fix it and send it, and they don’t even communicate back to the associate.

Debbie: So I was saying to the associates, what if every time you get a redline back, you feed it into Claude and you say, why do you think this partner redlined my document in this way? And you ask it to tell you how much of it is style, because your style might not be as developed as theirs, or it might not be. Well, these associates loved that idea. That was just one example. We went through a few different things, but that was one example of how you use AI to see something you might not see, right?

Claude as a learning system

Rob: It’s a great example. Not nearly the exact same, but Amanda was talking about taking a bunch of time entries, throwing them into a system, and understanding how somebody writes those time entries. It’s very similar: getting that feedback, and almost using Claude as an LMS to keep upleveling.

Lateral hires and fewer first-years

Rob: I’ve been diving a lot into hiring within firms right now and what’s going on. A lot of lateral hires. It looks like not as many first-year associate hires are coming into firms. Firms are growing, it seems, by increasing rates and technology, and just putting a new person in the seat. There’s a lot of replacement going on. But it’s a really, really interesting way for them to continue to learn. I don’t think AI is going to replace attorneys. They’re just going to be used differently.

Attorneys will be used differently

Debbie: They’re going to be used differently. And relationships, connection with your client, connecting to the human side of legal work: we spent so much time talking about that yesterday. It’s so easy in your regular job to just feel like, I’ve got to file another motion, I’ve got to draft another document, I’ve got to put in another time entry.

More than helping rich people get richer

Debbie: I’ve heard this a bunch of times when I say, describe your legal work. People will say things like, I help rich people get richer, right? If you’re an M&A attorney or you’re doing business work, that might be what it feels like. But go one step down from that. You’re making sure that those 427 people who work for that rich person have a job, right? There is a trickle effect. So while at face value it may be true that that is what you spend some of your time doing, you’re also doing something bigger, and connecting actual legal work back to human experience.

Choosing a mediator so the client feels heard

Debbie: One other thing that came up a few weeks ago: I was working with another firm, and a partner was telling a story. We were talking about the human side of legal work, and he said they were involved in this litigation and he needed to find a mediator. He said, the most important thing for me was that my client really needed to feel like his story was heard, his side was heard, and I chose the mediator based on that. I knew my client was writing a check, but I also knew they really needed to be heard, and that is why we picked this one mediator.

Debbie: Well, guess what? AI doesn’t replace that. AI doesn’t replace the fact that you know your clients so well, and you know those mediators so well, that you could connect the dots there. And even though your client had to write a check, you checked a box that may have otherwise not gotten checked. So there’s so much still. It’s going to replace some of the work, but the human part, the relationship part? I don’t think so. Not anytime soon.

Why associates resist AI

Rob: Yeah. Okay, that’s really interesting. One of the other data points, and I’d be interested to know if you felt this way: a data point that came out probably a month or two ago in Sidebar was that associates were actually more resistant to AI than some of the partners, which surprised me. There might be a reason tied to what you just said. They’re nervous it’s going to replace them, so they don’t want to lean into it. Did you feel that at all in the conversation you had?

Knowing when Claude is wrong

Debbie: Maybe a little. And I’d be curious what you think about this, too. For me, I know so much about how a law firm runs, how to run a law firm efficiently. So when I talk to Claude and it comes back with some bogus thing, I’m like, no, that is literally never, ever going to happen. But think about a new lawyer. They don’t have that. They don’t know it’s literally never going to happen. So I think that’s some of it.

The environmental concern

Debbie: I also think, and I don’t think we’ve talked about this very much on Sidebar Live, there’s an environmental concern that younger people have. I don’t want to paint with a broad brushstroke, but I’ve heard it over and over again. What about the environment? How come no one’s talking about the environmental effects of AI?

The tool without the context

Debbie: I think another part of it is that it’s not always that the law firm hasn’t bought the tools, but the tool and the context for the tool don’t both exist. I’ve heard people say, I have Harvey, oops, we’re not supposed to say names, but pick a thing, Legora, whatever it is. I have it, but I don’t feel confident in its use cases, where it can really help me, and where I should use my brain instead.

Next year is about training

Rob: Right. Yeah. A lot of interesting points. You could go in multiple different directions, but I’ll grab on to the last thing you said. I think a lot of next year, Debbie, is around training. Stop buying every single tool under the sun, really figure out what you’re trying to achieve, and spend time training and learning. And going back to the associate point about replacing associates: have a growth mindset. I’ve been at Centerbase now twelve years. I’ve reinvented myself about four or five times over that period, right? So there’s opportunity. You just have to see it. You have to lean in. You have to have a growth mindset. And sometimes there are things on the other side of the door that are more exciting than drafting a motion, if you’re willing to really look at it that way.

Law firms do not hire lifers anymore

Debbie: Yeah. And you’ve reinvented yourself four or five times within the same company, but there are a lot of people who would tell the story that they’ve reinvented themselves four or five times in different companies. Which is connected to this: law firms don’t really hire lifers anymore. Hiring an associate doesn’t mean that person, I mean, I don’t know what the statistics are, I don’t know how we would ever even figure it out. But if you were hiring an associate in the year 2000, what percentage of them became equity partners, versus hiring an associate in 2020? What percentage of them are on track to be equity partners? I have no idea what the numbers are, but I’d bet a long string of paychecks it’s way higher in the 2020 numbers than in the 2000 numbers.

Rob: I was about to say.

Debbie: Sorry, flip that. Flip that.

Leaving the traditional profession

Rob: Well, and you see so many people, to your point, leaving the traditional legal profession, too. It’s created, again, growth mindset, a lot of opportunities, and some, honestly, that are higher paying than what they might be making as an attorney, if they really look around. It’s wild times, Debbie. It’s hard to keep up.

Training is not reimagining the practice

Debbie: Yeah, it is. It is hard to keep up. But let’s go back to what you said about 2027. This came up in the session we did at the Managing Partners moment, on leading an industry through transformation. One of the things we talked about in that session was that training someone on a tool does not translate into helping them reimagine their practice, reimagine how they think about delivering legal services. So I don’t disagree with you. They have got to know how to use the tool. But in addition to that, I think the other part of it is that oftentimes you have a lawyer and an associate and a paralegal and a legal assistant, or a lawyer and a paralegal and a legal assistant, or a lawyer and a legal assistant, who kind of get work done in this synergistic way. I do this, you do this, I do this, you do this. Then you throw AI in there, and it’s not a whole lot different than throwing another human into the mix. You’ve got to figure out who’s doing what jobs. It’s just a big thing to insert into the middle of how you get your work done.

Rob: Yeah. I mean, it goes back into building it into your workflow, right? You really have to spend the time and the thought to build AI into that workflow.

What Claude artifacts can do now

Rob: Let me tell you, one of the things I’m most intrigued by lately is how far Claude is going with artifacts. Your ability on a team plan to share artifacts, to export them in the different ways you want, to collaborate, to add notes, to create checklists, to redline them and work on them. Stacy and I were just working on an artifact, and she said, do you see at the top where I just typed testing one, two, three? And every week it’s new, right? It’s crazy. I’m creating new product and building little things and sending them to somebody and saying, does this work for you, does this help? Administrators, this is something you could do even if you don’t want to build it yourself. You can say, hey, we need something like this, and just regular old Claude, build me a mock-up.

The virtual chief AI officer

Rob: And one trend we’re seeing a lot of, as we start to interview a lot of our partners, is this virtual chief AI officer. They don’t necessarily have the context of what you’re doing, but you might not have the skill that they have. Is there some way for you to lean into AI that way? Have them take it across the finish line for you, help you build these things in. But again, artifacts make it so easy to do and share.

Stop sharing documents

Debbie: Yes. I have not even fully dug into all of the latest new stuff, but we discovered this just a couple of days ago, and on our leadership team call on Tuesday we were like, we as a leadership team need a whole different way to work together. What we’ve been doing makes no sense anymore. We have got to stop sharing documents. We have got to stop creating versions. We have to quit saying, here’s what I created, and then you go create something else, and then I take what you send me and put it back into my Claude and say, what’s different?

Rob: Oh my gosh, that’s a lot of work.

Debbie: Yeah, it’s a lot of work.

Why the CMO still does some things by hand

Rob: And there’s still something to be said. So Trish, our CMO, really pushes on doing things by hand. And I’m seeing a lot of CMOs pushing on that as well, just because it’s all coming out the same. It’s all coming out the same, and that human context you’re talking about is still very important.

No AI for client work

Debbie: Well, I saw a post on LinkedIn yesterday or the day before from a lawyer that said, our firm has made a decision to not use AI for anything client related. We will use it to improve our business. We will use it for marketing. But we will not use it for anything client related. There were like 700 comments on it. I haven’t gone through and read the comments, but my reply would be, smart. Somebody making that decision has probably made it because they’re being risk averse about something they don’t know about. So making the decision to go away from the legal work: smart. There is so much you could do around the business of law. Marketing, collections, facilities even. Using AI there is a good starting place.

Rob: Also, it’s typically cheaper, right? We see a lot of these firms buying up big licenses, or a bunch of users, and then never using them. So, one thing I wanted to talk about, Debbie: if somebody were listening today and saying, hey, we want to bring AI in on the business side, what are the opportunities?

Where AI helps on the business side

Debbie: I think AI can help tremendously with how you think about transforming human resources and people operations. The basics of how we review people, but also how we onboard people, and how we set people up for success. I think it can help with standardization. We need to do this one thing; here are the thirteen different ways we’ve done it in the past; can you help me figure out how we do it one way? I think it can help with financial reporting. I think it can help with analyzing data. Certainly, from an IT perspective, it can help with thinking about IT strategy, how you use your tech stack, the applications. There are a million things. Marketing. It’s really interesting.

Using AI to help leaders lead

Rob: Right when you started talking, I thought right away, oh, Debbie, how are you using it to help leaders lead? Because inside a law firm, a lot of the time it’s a lonely, lonely job for the administrator or director. How are you using it there?

Debbie: Leading people is one of the big ones. We talk about this all the time. Of course, the caveat is you need to be using an enterprise grade tool, blah, blah, blah. Don’t be using the free stuff. But when you’re struggling with an issue, click that little microphone button and say, here’s my challenge. Here are the three ways I’ve tried to solve this problem. It hasn’t worked yet, and I’m really struggling with what my next steps are. Give me five creative options for how I might tackle this. Or you might say, I have a really big challenge with a relationship with an equity partner. Can you interview me? Ask me questions about why I’m struggling to get past this one issue, or whatever it looks like, and do a back and forth with it to really try to get to the bottom of how to solve something.

Debbie: People leadership, I think, and using it for SOPs. How do we get things done around here? Documentation, the thing that’s been on your to-do list for a hundred years. Great, easy place to start.

Claude as an executive coach

Rob: I can’t remember now if it was you who first told me about this a long, long time ago, but I have a Debbie project in Claude, and I think I created it because you talked to me about this. It has my DISC assessment. It has my Enneagram. It has so much context from conversations I’ve had. And it’s almost like my executive coach. Tell me why this conversation went off the rails. Or, here’s a transcript of something; I know I could have handled that better. How could I have handled it better?

Role play the tough conversation

Debbie: Yeah, I would take it even a step further. If you’re going to have a tough conversation, role play it. Literally push the mic button and have a conversation back and forth, and tell the AI ahead of time, whatever you’re using, be really hard on me. Push me, right? You can test a lot of these things, or try a lot of them, ahead of time.

Speak your ideas into your phone

Rob: To your point about SOPs: I am a divergent thinker. I have a hard time taking all these ideas and putting them in order, and I have a ton of ideas. So what I tend to do is, as I’m watering the plants or doing something else, I speak my ideas into my phone. I might not get to all the different ideas, but I write them down and say, what would a plan look like if I wanted to implement this? And I just put that together and set it aside, and sometimes I come back. But it helps me, to your point, really start to think about things in a linear fashion.

Debbie: Yeah, I love that. I love that idea. I tend to send myself Teams messages. And I’m not always sure I want Claude to answer my question just yet. I have a thought; do nothing with this thought. That’s a really interesting way.

A big ideas project

Debbie: And I’m thinking out loud here: you could create a project called My Big Ideas, and start a new chat every time you have one. And your project instructions could say, many of these chats are just going to start with me giving you an idea, and I don’t need you to solve the problem. I just need you to capture the idea. When I’m ready to work on it, I’ll tell you I’m ready to work on it. And now all of a sudden you have your whole idea bank right there, and you can build on it whenever you’re ready.

Four Claude accounts

Rob: That’s brilliant. Sometimes I’ll mull over things for a few days, or a few weeks. The other thing I’ve done with it: I was actually cleaning out one of my Claude accounts, because I have four of them now.

Debbie: I know, we need a whole separate session on that. Maybe even just me, because I have two.

A Legal Week project for follow-ups

Rob: I’m dying. I know it’s an addiction. I’ll admit it, I have a problem. But I digress. What I found earlier this year, when I was going to Legal Week and some of these trade shows, where everybody wants a follow-up, everybody wants to talk, and you learn different things: I made a Legal Week project, or a chat, and I just fed it everything I learned as I was walking from thing to thing. Hey, I need to follow up with this person. Hey, research this a little more because I’m interested in it. Then I came back and said, okay, dump on me everything I need to look at. What did I learn? And I just worked off that as my project management tool for follow-ups from Legal Week.

Debbie: So smart.

Rob: There are a lot of cool things you can do, and you don’t even have to spend much. Twenty dollars a month.

Next week: your second brain

Debbie: So maybe this should be the topic of next week’s Sidebar, but I want to just drop this right here as an initial thought, and maybe we can make it our topic: the concept of your second brain.

Rob: Yeah, I’m doing a lot of work on that.

Debbie: Okay. Well, I want to talk about that. All right, we’re just going to leave that here. That’s going to be our teaser for next week’s episode. Amanda, if you’re listening, get ready for second brain next week. We need to dig more into that, because I really do think that idea, that there is a mind map of all the things you’re working on that can be accessible to you. Anyway, okay. More on that to come.

Join Sidebar

Rob: Okay. I will talk about that all day long. But guys, join Sidebar: gosidebar.ai. We actually had a lot of attorneys join this week. We’ve traditionally seen administrators, but now we’re seeing managing partners, and partners at firms who care about AI initiatives, who care about moving their firm forward and want to know what others are doing.

Rob: I was standing in line at my kids’ elementary school for one of their events, one of these events where they say it’s a family event but really it’s just another way to get money. Anyway, she said, I’m so busy just putting all these tools together. I said, well, what are you trying to achieve? She said, I don’t know, I’m just trying to keep up, right? And that’s the mindset a lot of these people are in. So join Sidebar. We’re going to help you keep up, with all that fun information on how you can continue to push your business forward. But you’ve got to be part of the conversation. So go to gosidebar.ai, and we will see you next week.