Nobody has AI figured out yet.

Why they built it

Amanda went looking for the course, the certificate, the college that would teach a firm leader how to manage the AI shift. The answer to every one was none, because nothing is evolving fast enough. So they decided to build it. The job is lonely inside a firm, and everyone turns out to be quietly in the same boat.

FOMO is running the show

The clearest pattern from the first twelve weeks is that nobody has this figured out and most decisions are driven by fear. Not only fear of the wrong call, but fear of a right call that lands badly with one lawyer, who tries it once, decides it does not work, and writes the tool off for good.

Saying no to a loud partner

44% of firms have no formal way to say no to a partner pushing a tool. Another slice does not say no at all. They let it stall in committee, the way a bill dies on Capitol Hill. A resistant partner is not a quiet problem. That person is drag on every initiative, and the more power they carry, the heavier it gets.

The tool you buy today, free tomorrow

One of Rob’s favorite apps emailed mid-week to say it was shutting down, because Claude now does the same thing for less. Amanda takes longer on AI decisions than on anything else, because she is trying to predict what a model will make redundant in two years. Debbie’s counter: there is still real value in the build, because you cannot build anything without finally understanding how the work actually gets done.

Find one thing

Debbie’s answer for anyone stuck: pick one small thing you can actually solve, find a willing lawyer, get a win, and tell everyone about it. That is how you build believers. Do not chase every shiny object. Staying still is the dangerous move. The goal is never to figure it all out, only the next right thing.

Transcript

Wait, are we actually live?

Rob: Hey, we are live. Our first Sidebar Live session is finally here. I can see it right across the top. We are live right now.

Amanda: Are you sure we are actually live?

Debbie: It does say live. Here we are.

Why we built Sidebar

Rob: This is a good place to start. Let us talk about the why. How we came up with the idea, and why we are doing it. Do you want to jump in, Amanda?

Amanda: Happy to. I have spent a lot of time in legal management, and this AI topic has me backpedaling more than any topic that has ever come out. Go all the way back to the cloud. Do we move to the cloud, do we use VoIP, what is the metaverse. This is the first time I have felt completely unprepared to do my job around a specific topic. When I started talking with others who manage law firms, I realized we are all in the same boat. So I said to Rob, I cannot figure this out alone. I asked what education I should get, what certificate, what college. The answer to all of it was none. Nothing is evolving fast enough. We are going to have to build it. In a nutshell, that is the impetus behind Sidebar.

Rob: It is such a lonely profession inside your own organization. You gather with other administrators and it is that is a great idea, that is a great idea, but it is hard to keep up with what is going on. Everything is moving so fast. There is business to go around for everybody. But how, as an industry, do we help everyone level up their firms?

Debbie: A couple of things stand out for me. First, what is everyone else doing. What is the firm across the street doing. The number of times I get asked for benchmarking, they do not always use that word, but that is what it is. I want to make sure I am doing the right thing and not making a big mistake. The second part is that it is not just moving quickly, it is that there are so many unknowns. The unknowns create fear. Fear of the wrong decision, but also fear of a decision you believe is right that does not land well with the lawyers in your firm. They try one thing one time, it does not work, and then the tool, AI in general, is dead to them. Change management and user adoption are what we are all struggling with. Sidebar is a community where people can come together and talk about what is working and what is not.

Rob: We are the first to raise our hand and say we do not have the perfect answer. None of us do. It is going to take all of us to do this together.

Twelve weeks in: nobody has AI figured out

Rob: We are twelve weeks in now. Our goal is to get to 400 firms. If you work inside a firm, go to gosidebar.ai and sign up. So over the first twelve weeks, what have we seen?

Amanda: It is interesting. I write a lot of the questions, so they come from my place. I walk in and think, what did an attorney just ask me. What has been wild is that it is the same questions other attorneys are asking everywhere. We ran a question on AI timekeeping and got a really high response rate, a lot of people telling us what they are doing and thinking. The very next day I saw the same question posted in a different forum, where nobody was answering it. So I responded, I have a report on what other firm administrators are doing, email me. My inbox lit up. Send me the report, send me the report, over and over. People just need that feedback. My number one takeaway is that nobody has this figured out, and we are all operating on fear. FOMO is driving AI adoption in law firms.

Debbie: That social proof idea is real. When we did a session at ALA Annual on keeping up with the Joneses, I sent the report afterward and had ten people come back and say they pulled it up in their management committee meeting or sent it to their managing partner. The same thing happens with the Sidebar synthesis. Here is proof for why we should move in this direction. The other age-old law firm problem is the silo issue. Everybody does not have to do the same thing. Where a practice group or a lawyer is leading and genuinely into exploring how to get work done differently, adoption is naturally higher and resistance is lower, because you have a believer carrying the flag. Then another group says I will not participate in the gutting of the legal profession, and those people are doing exactly nothing, or running their own shadow AI on their phone under the desk. We read those responses and go, yes, all of that is so true.

Saying no to a loud partner

Rob: Some of the results touched on governance. One stat we shared with the community is that 44% of firms have no formal way of saying no to a loud partner. As you look at this by practice area, how do you manage that. You are sometimes telling your boss no.

Amanda: That 44% does not mean the other 56% have a way to say no. What also came out is that some firms use committees to slow-play the no. They are not saying no, they are letting it get stuck in committee, literally the way things work on Capitol Hill. So 44% have no way to say no, and 22% let it stall in committee. We do not all have a way to say no to partners.

Debbie: It is the same on my side. I had a conversation with a client, short version, do not tell me how to practice law. The practice of law is an art, it is my professional responsibility, it is my law license. Nobody is going to tell me I have to use this tool for depo prep if I do not think it is the right way to prep. Every lawyer has that card in their pocket. Someone on our team used to say attorneys who do not act will be subject to the whims of the weather. The truth is, for a person in Amanda’s position, that partner is drag on your initiatives. Depending on their power and where their name sits in the firm, the drag can be really heavy.

Putting AI in: expectations vs. reality

Rob: Amanda, you are putting AI into your firm right now. You just went live with AI time entry, sixteen days in. What does the resistance look like, and how do you manage it?

Amanda: For this tool in particular there was not much resistance. What there is, is expectations that reality will not meet. They think I am putting in a magic wand that will solve why they have not entered time in twenty years. Everybody was excited. Now that it is in, people come and say, well, this is not doing this thing. And I never told you it would do that. It is not going to track your phone calls. You asked that in a meeting and I said no. With other tools the resistance is about cost. But some people are genuinely afraid, especially with generative AI, the citations and the hallucinations hitting the legal industry so hard. That is where it gets fear-driven.

Debbie: For sure. There is an element of how a lawyer has gotten into the habit of processing the facts of a case. AI interrupts that process, because it becomes their thought partner and does some of the processing, and they have to absorb that differently. These are thought partners, helpers. You do not just plop them into how your work gets done. You have to consider how your work changes as you use them. It feels like magic, but magic is often overstated. Every one of us knows deep down that a tool that solves one problem is also going to create nine new ones. Some of those are hard to overcome, because it is about changing how we think.

Rob: AI has become the new API. It used to be you can do that through an API. Now it is AI can handle that. So now more than ever, leading with an outcome, what are you trying to achieve, matters more than what technology do you want to put in.

Amanda: That is one of the biggest things out of our first twelve weeks. The firms being successful are leading with the outcome. Debbie preaches this, and I preach what Debbie says, though I do not always give her credit.

The tool you buy today, free tomorrow

Debbie: Keeping up is hard. Even if you make the right decision today, the right decision for July 16th at 2:17 in the afternoon, tomorrow someone says you did not have to buy that thing, you just click this button now. We have built things for firms that took a week, a month, three months, that later became a single button released in a product. The firm paid us to build the proof of concept, it worked, and then you do not need it anymore because you can do it right there in eleven seconds. That is a real fear, and there is no answer for it. We will never have an answer for that.

Rob: Funny timing. Right before we got on, one of my favorite apps from a year and a half ago, it created agentic workflows, emailed to say they are shutting down, because Claude can do it now for a lot cheaper. So how do you think about those investments?

Amanda: Debbie’s answer is do not sign a contract longer than a year. But the contract is a small part of the investment. The time lost, my time, attorney time, training, staff time, implementation, all of that is gone. I take longer to make these decisions than anything else. I can pick a copier from three contracts in a couple of hours. Deciding whether to add the AI function of a research platform, I am trying to predict the future. What will Claude or ChatGPT do in two years that makes this redundant. That is why we built Sidebar, so we are not all figuring it out alone.

Debbie: We should not lose sight of the value in the build. To build something, you have to understand how the work gets done, make decisions about efficiencies and silos, rein some people in, pick a font, choose your margins. Even when a button later does the same thing, there was tremendous value in going through why do we do this work, how do we do it, how can we do it most efficiently. The black box in many firms is how the work actually gets done. Do not discount the whole project because a faster way showed up. And it broadens horizons. If we built this for one thing, maybe we can build for three others, and use the button for those.

Rob: I love building. I will spend a lot of time on a project and then sometimes kill it, but I go back and take the pieces and the learnings and keep building. It is just continuous.

Debbie: My LinkedIn says I help law firm leaders get unstuck. There is no path from unstuck to figuring it all out. It is from unstuck to the next decision you can make with the information you have. Then the next one. You will get some of it wrong, and somebody will build the one-button version. But staying still is incredibly dangerous. What is the next right thing?

Amanda: Being fast to act also means you make mistakes. I have made recommendations I have sat back on and thought that probably was not the best one, or realized if I had just waited two weeks, this would have come out. That does not help our members, but I am dealing with it too.

How to actually evaluate AI

Rob: Is there a strategy you are taking in evaluating AI for your firm. Are you going to core vendors, or seeing all the frontier products?

Amanda: There is too much to evaluate. I am going to rely heavily on the names that rise to the top from Sidebar. This community has led me to where I am. Using trusted vendors helps too. If you have had a document management company for six years and they roll out something, you have a lot of questions to ask. A stamp of AI does not make it what you hope. I like to use Claude to write the questions I hand the vendor, get their answers back, then upload those and ask what this really is. The best part is I can now speak a language I could not before.

Debbie: The benefit of hindsight cannot be overstated. It is so clear two weeks, two months, two years past the decision. We take that in and it helps the next right decision. It should not get us stuck, because we are going to make mistakes. What if we get 86% of it right. Are we happy with 86%. When we get something wrong, that feeds the 14% we were not going to get right anyway, because not moving is risky.

Come join us

Rob: Can you believe we have four minutes left, on our first session. For anyone watching later, this is our first LinkedIn Live. We honestly did not know if the record button would work. We want to keep using this platform to help law firms navigate these changes, and we want other people’s opinions on here. If you are not one of the firms in the Sidebar community yet, join us at gosidebar.ai.

Amanda: We want to hear what people want on these, whether you get tired of the three of us, which is fine. We would love to hear from a member. Come tell us about an agent you built, a product, the impact it is having, the conversations you are having. If you want show and tell, we will give you the platform. If you have questions you want answered, we will help with that too.

Your Homework

Rob: Debbie, on the spot, two minutes left. If someone is feeling stuck at their firm today, what is one thing they can do to unstick themselves?

Debbie: Find something small you can solve. The list is long and always will be. Find one thing, find a willing participant, a lawyer who says let us figure this out, and focus on that. Do not be distracted by every shiny object. Find one thing, find some successes, and then tell everyone about your success. That is how you build the believers.

Amanda: If I know as much as I can about it, I can lead others through it. The only way to learn this is to do it. I did a presentation recently using Claude, and an administrator said, you showed me great examples, but what if they figure out AI can do all the things I was doing. I said, when was the last time you looked at intake at your firm. At customer service. At your off-site storage. You have a million projects that will never get done. Do not worry about AI taking away the jeans Friday email. Pick something. Doing your own job better with generative AI is an easy place to start. I have a great prompt to use your second brain as a firm administrator. Email me and I will share it.

Rob: Great conversation. We will be back next week. Send us feedback, we want to add value. And while you are at it, join Sidebar. Go apply and join. See you next week.

Debbie: Bye everyone.