Practical Copilot Workflows Lawyers Can Use Today (Full Transcript)

Ben Schorr shares actionable Microsoft 365 Copilot use cases for lawyers—drafting, summarizing, brainstorming, and inbox triage—plus safety and limits.
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[00:00:00] Speaker 1: I'm Zach. And I'm Chad, and this is episode 598 of the Lawyerist Podcast, part of the Legal Talk Network. Today, Zach is interviewing Ben Shor about how you can use Copilot in your law firm today.

[00:00:13] Speaker 2: Yeah, Chad, I've interviewed Ben a couple times now about his experience with AI, how you can use AI well, but this one's gonna be fun. This is very specific on like literally what can you do today in your office, because I think a lot of times we're just told like, go use AI and good luck. So anyway. Yeah, Ben's great. Yeah, yeah, yeah, he's fantastic. We haven't done a podcast intro in a while. I haven't seen you in a while. IRL, in real life, as the kids say. But I've seen you on Strava recently. Ooh. And I've been- Strava stalking me. Yeah, I mean, definitely. I mean, Strava's stalking you. I know where you live now and- You know the trails I run.

[00:01:04] Speaker 1: I know your routes.

[00:01:06] Speaker 2: Yeah, all of that.

[00:01:08] Speaker 1: Yeah, what's- You know which trees to hide behind now.

[00:01:12] Speaker 2: I'm always concerned about that. I actually tell my athletes every year to go onto my Strava, because my Strava's public. Go onto my Strava and see if they can figure out like where I live. And I do that to show them how easy it is to figure, like, that out, so they won't do their public Strava. Like, I don't want my high school kids making their Strava public, you know? So now I'm gonna have to go, like, make mine private. I never even thought about that. Right? I start my runs from pretty much the same place every single day, so like, what do you think that means? You know?

[00:01:49] Speaker 1: That's probably at your house.

[00:01:50] Speaker 2: I mean, it's somebody's house. I'm gonna start, yeah.

[00:01:54] Speaker 1: I have two different paths. I'll either drive out to a trail, or I'll, if I'm pressed for time, like in the mornings when I run during the week, I run here in the neighborhood. But yeah, same thing. I start in front of my house.

[00:02:07] Speaker 3: Yeah, yeah, yeah.

[00:02:08] Speaker 2: I mean, for all you out there, I don't start in front of my house. That's somebody I don't know. It is, I go to a completely undisclosed location every time. But, so as much as Strava and things like that are, can be creepy, it's also helpful because I wake up sometimes, and I'm like, oh, Chad gave me kudos. Chad saw me running. You know, and so it's just like virtual community of people that are like, hey, man, good job. Because it's not always easy to get up in the morning and put on your running shoes or your biking shoes or your workout pants or whatever it is and do it. So how do you do it? How do you get up in the morning? How do you get up in the morning?

[00:02:53] Speaker 1: I have to, I need leverage. So I'm planning to do these Spartan races this year. Gonna do three this year. What are Spartan races? So it's like the obstacle course races where there's distance, either a 3K, a 10K, or a 21K with obstacles, and it's off-road, trails, mud, cow pasture oftentimes here in Florida.

[00:03:18] Speaker 2: Oh, like what you think cross-country should be.

[00:03:21] Speaker 1: Yeah, yeah, much more mushy.

[00:03:24] Speaker 2: Okay, cross-country in the United States is like you're running on a golf course. It's really like well-defined and everything. Cross-country in Europe, they like intentionally make things wet and like intentionally put stuff out to jump over. So we want that, and we just won't do it in our cross-country. So we're like, hey, let's make Spartan races and all that, which I think is super cool. Like how awesome is that if you're running as like an 11-year-old, that's what you wanna do. I wanna like dive over fences and stuff. Yeah, right, so much more fun. So what do you mean by leverage? What do you mean by you need leverage to get up?

[00:04:01] Speaker 1: So I committed. I signed up for three. I'm gonna do at least three this year, the Sprint, the Super, and the Beast. Oh. And so now we got the dates on the calendar, and it's real. You either get ready, or it's gonna suck when you get out there. So those are kind of the choices. Because it's happening one way or the other. It's one way or another gonna be there. Yeah, that's fair. So this morning, it was 45, 46 degrees when I stepped out from my run, and definitely didn't feel like it. Oh, man. But had to do it. Yeah.

[00:04:32] Speaker 2: Okay, so.

[00:04:33] Speaker 1: And I did not start from my house.

[00:04:35] Speaker 2: Yes, yeah.

[00:04:35] Speaker 1: For anybody listening.

[00:04:36] Speaker 2: Right, right, yeah, did not start from there.

[00:04:40] Speaker 1: Walked to an undisclosed location, and then started Strava.

[00:04:45] Speaker 2: I flew to a different city, and then, yeah, it's not even close to there. So leverage sounds like something that you could do in your business, too, right?

[00:04:55] Speaker 1: Mm-hmm, yeah.

[00:04:56] Speaker 2: Yeah.

[00:04:57] Speaker 1: Yeah, leverage helps. And one of the first things we do in lab is we have them identify what's important to them and set some personal goals. And oftentimes, that is the leverage that will keep people going, right? Why are you doing this? What kind of life do you wanna live? How can you build a business that serves you, not the other way around?

[00:05:23] Speaker 3: Yeah.

[00:05:23] Speaker 1: Right, and that's the leverage, if we get it right. And we usually try to do that. I mean, we always do that in the beginning of the lab journey with our labsters coming in.

[00:05:33] Speaker 2: Yeah, well, I remember when I was running my firm, I would often have days that I thought, like, what do I wanna do? What do I wanna be? How do I wanna make it work? And a lot of times, the answer's where I wanna make more money, or I wanna work less hours, or whatever. But the thing I like about this leverage that you have here, and the thing I think that works, is that you have a date certain, you know? You have an impending thing that is gonna happen. There's an idea of like, oh, I guess the difference between I want to make more money in my office, or I wanna take more time off, and an actual thing that is leverage is kind of like me being like, well, I wanna be faster.

[00:06:14] Speaker 1: Yeah.

[00:06:15] Speaker 2: I wanna be, quote-unquote, healthier. Okay, well, I mean, you can do that. Yeah, but why? But why? And, you know, the Spartan races, yes, they're important, they're fun, they're interesting. But at the end of the day, I don't think you're a professional Spartan racer. And so, I don't imagine that it, in and of itself, has much effect on your life any more than any other race that would've been there. And so, it's really just there to motivate you.

[00:06:48] Speaker 1: Yeah, that's not, being a professional Spartan racer is not my aspiration. But I do wanna do much better than I did when I ran the races two years ago. So, I did the three races two years ago, and I wanna do better. I wanna be able to do all the hanging obstacles, because those are the ones that killed me last time, is the ones where you have to, like, monkey bar across stuff, and anything where you have to hold on and go across, like, those were the tough, tough on me. I just couldn't hold on.

[00:07:21] Speaker 2: Yeah, that's not talent we learn in cross-country. That's not what I learned running track in college. Yeah.

[00:07:28] Speaker 1: So, that's my goal on this round, is to be able to do all the obstacles. Because if you fail on one, you have to do 30 burpees. Oh. Before you can move on. Oh, yeah. And 30 burpees, just doing 30 burpees once.

[00:07:42] Speaker 2: Just doing them right. Yeah.

[00:07:44] Speaker 1: Yeah, if you're doing them correctly. But just having to do that set of 30 the first time is brutal, imagine having to do it six times throughout the race. So, yeah, that's the goal.

[00:07:55] Speaker 2: Yeah, well, good. Well, I wanna hear more about your races each time you do it. So, I'm looking forward to hearing more about that.

[00:08:03] Speaker 1: I mean, you wanna sign up? Come do one with me.

[00:08:06] Speaker 2: You're gonna put me on the spot here.

[00:08:08] Speaker 1: Listen, I mentioned it to Stephanie. I had her thinking about it. Oh, man, you got me.

[00:08:12] Speaker 2: I'm gonna tell you, you got me thinking about it. It sounds very, very cool. Sounds very, very cool. I'll have to look into it. Another thing that sounds very, very cool is Ben talking about CoPilot. And I don't say that in jest. It is always fun listening to him talk about CoPilot. So, here's my conversation with Ben.

[00:08:37] Speaker 4: Hi, I'm Ben Shore. I'm an innovation strategist at Affinity Consulting Group, and I help people be more successful with Microsoft 365 and AI.

[00:08:52] Speaker 2: I love that. I help people be more successful with Microsoft 365 and AI. And I know that you do. I mean, I'm a customer. I'm a customer. I know that you do, but I'm also a partner with Microsoft 365 and AI. So, you know, I have a little bit of a team that helps people with Microsoft 365 and AI. I know that you do. I want to dig a little bit further. For some people, and I think a lot of people on The Lawyer's Podcast, you actually need no introduction, but I wanna give you a little bit deeper introduction for those that haven't been fully introduced or haven't seen you at tech show or haven't seen a CLE that you've put on. Before you were with Affinity Consulting, you were with Microsoft. Ta-da. For nine years. Nine years. What was it you did there?

[00:09:30] Speaker 4: Yeah, so I worked in a group called Customer Success Engineering, and my team created and managed all the content that you find at support.microsoft.com, on learn.microsoft.com. We also did quite a bit of the in-app content that you would see, whether it's help and training, little tips, things you would find that would show up inside the apps. Sometimes we would do what we call UX design, where a product team is adding a new button or a new feature, and they want some text that helps to explain what that feature does, and so we would do some of that. And so that's basically what we did, is we created and maintained content that helped customers be successful with Microsoft 365 and ProPilot.

[00:10:15] Speaker 2: That's exactly what I wanted to get to, was that even before you were here with Affinity, you were not only in the CoPilot environment, you were in the how do I use CoPilot environment. And so I wanted to make sure that we brought that up, because my question for you is, how do I use CoPilot, Ben? That's obviously a big question, but for this conversation, I wanna get into some practical stuff of how attorneys can be using CoPilot in their office today, and just a couple weeks from now, not way out. But before we do that, I wanna talk about, I wanna differentiate CoPilot from this big, broad term of AI. Talk to me about what CoPilot is specifically in this environment.

[00:11:08] Speaker 4: CoPilot is Microsoft's productivity AI, and it's built on the OpenAI platform. And so the same platform, basically, that ChatGPT is built on, right? And so it's a large language model. I know Microsoft adds a lot of its own little magic on top of what OpenAI creates. But under the hood, it's basically OpenAI's model. Now, recently, Microsoft has started adding some other models like Anthropic to CoPilot that you can choose to use in certain circumstances. But yeah, for the most part, that's what it is. It's Microsoft's productivity AI. And one of the things that makes it different from the other ones, and a little bit special for lawyers, the vast majority of lawyers are Microsoft 365 customers. We know there's a small percentage that are Google Workspace, but for the vast majority of them, they're Microsoft 365 customers. And that's where CoPilot thrives, right? CoPilot is built in Microsoft 365. And so CoPilot can see all of your Microsoft 365 stuff that you have access to. And so it can see your email, your calendar, your Teams chats, your documents, the documents that are in SharePoint and OneDrive. And so all those things that are inside your Microsoft 365, CoPilot has access to. If you have access to it, CoPilot has access to it. I should emphasize that, because that's a question I get all the time from attorneys is, you know, are all of my documents suddenly exposed to CoPilot? And the answer is no, CoPilot has the same permissions that you do, so you only see what... Your CoPilot can only see what you can see. But that's a big part of it, right? Is that CoPilot's built into Microsoft 365, so all that stuff is there already. Is there a way that, you know, ChatGPT that you could add a connector and see OneDrive with ChatGPT? Yeah, you can, but it's not built in, right? It's something you have to add on and configure. And then the other part can make...

[00:12:56] Speaker 2: But I can see SharePoint.

[00:12:58] Speaker 1: Yeah.

[00:12:59] Speaker 4: Okay, okay. Yeah, definitely, you can see SharePoint, OneDrive, all of that with CoPilot. And, you know, there is a way to make that work with ChatGPT, it's just not native.

[00:13:06] Speaker 2: Sorry, I was getting into what we're trying to avoid right now. I conflated right there, ChatGPT and CoPilot. What you were saying is that, yes, you could connect ChatGPT to your OneDrive or your SharePoint, but it's not native. It has to do something else, whereas CoPilot, that's what it does. CoPilot natively accesses all of that, yeah.

[00:13:27] Speaker 4: Okay. Yeah, and then the other part of it with CoPilot that makes it special is that because CoPilot's inside your Microsoft 365, everything you do with CoPilot stays inside your Microsoft 365. So from a security and privacy standpoint, you know, if you have a client document, you absolutely should not be uploading that to free ChatGPT, right? Right. Because that's a huge privacy nightmare. You absolutely should not be updating that to free, you know, Grok or Claude or whatever, right? And not free CoPilot either, by the way. I wouldn't upload that to the free version of CoPilot either. Right. But with Microsoft 365 CoPilot, you're signed in with your Microsoft 365 credentials. There, anything you upload to it, anything you ask it, anything you have CoPilot draft for you, all of that stays inside your Microsoft 365 tenant. So it inherits all the same privacy and security that your Microsoft 365 does. That's a big deal, especially for attorneys.

[00:14:22] Speaker 2: Yes, because to me, then that is, if you were comfortable with your documents being on SharePoint, then you should be comfortable essentially with using CoPilot within, logged in within that Microsoft 365 environment on those documents. Absolutely. And I think that's huge.

[00:14:41] Speaker 4: To be fair, if you have a ChatGPT enterprise license, then you also get very good privacy and security, but not very many firms do have that enterprise license. Right. And, you know, that's a separate license you have to have there.

[00:14:56] Speaker 2: And that's, you know, one of the things I, one of the reasons I wanted to talk about CoPilot specifically is because not only is that a separate thing that you have to do, it is also a separate hill you have to kind of like climb inside your firm to get that enterprise license. You have to go to your IT department, or I mean, you may be your IT department if you're a small firm, but you still have to go through all these hoops. Whereas the first one, it is much more likely that you as an attorney have access to CoPilot than, you know, the appropriate CoPilot mechanism. As opposed to the appropriate ChatGPT that you can put client files into. I mean, you can do marketing, you know, on pretty much anything, but we're talking about like helping you in your day-to-day being a lawyer.

[00:15:48] Speaker 1: Yeah.

[00:15:49] Speaker 4: And in fact, these days, if you have a Microsoft 365 license, you get a limited version of CoPilot that already is going to be secured by your enterprise data protection. And so just having a Microsoft 365 license gets you a little taste of CoPilot. Then if you can also get the Microsoft 365 CoPilot license on top of that, then you get the whole party.

[00:16:10] Speaker 2: Okay. That's how they get you. They get you a little taste, and then you want the rest of it, you know. They're just dealing artificial intelligence to everybody. So, okay. So CoPilot lives in that Microsoft 365 environment. Most attorneys are on CoPilot. Let's talk about how to use it then in a law office. I know there are a lot of ways that people can come up with, and I use chat GPT in a lot of different ways. But again, we're talking about this like internal AI. How can lawyers be using that right now?

[00:16:47] Speaker 4: So there's a few different sort of big buckets I kind of think about when I think about how people and attorneys can use it. So one of them would be in the create and edit mode, right? That's the one that people think of a lot of times as a generative AI. You tell it to draft something and it does. And so you could, for example, in Word, ask it to draft a letter, a document, a brief, a memo. The more specific you can be with the instruction, the better the results you're gonna get. It is really important to remember that it's not in most cases creating finished product for you. What CoPilot's doing is it's getting you from a blank page to a plausible first draft in seconds, right? I have many times done demos for attorneys where I've asked them, tell me a kind of document you've created recently, right? And I'll say, oh, a motion for dissolution of a thing, right? Or an employment agreement for a tech executive or whatever the document happens to be. And I'll open CoPilot in Word and I'll give it a relatively simple prompt and have it create that document, right? Obviously it doesn't have any details because I haven't gone that deep just for the demo, but it'll create the document and it creates three, four, five, eight, however many pages. Then I'll go through with the attorney and we'll scroll through it quickly. We don't read it carefully, but we'll scroll through it quickly. And I'll ask the attorney what they think. And invariably, the answer I get is that's a pretty good start, right? And that is what you got, right? It's a blank page to a plausible first draft in seconds, right? Are you gonna file that? No. Are you gonna send it to your client? No. But you've got a document now, you can edit, you can add your own document, your own info too. You can revise it. It gets you a good part of the way there.

[00:18:26] Speaker 2: That's what I was gonna ask, man, was can I send something that comes directly out of one of these AI products directly to my client or directly to the court without reviewing it?

[00:18:36] Speaker 5: Funny you should ask. There is actually a rule that has somehow come to be named for me.

[00:18:45] Speaker 4: Shor's Law, I think they're calling it. Yes. Which you were leading up to, of course, which says never ever show the output of an AI to a client or the court without reviewing it first. We've heard way too many horror stories about people getting sanctioned for filing fake citations. And that's just another example of, please, please, please review the output before you send it to the client or the court.

[00:19:07] Speaker 2: Right. And I think that, I like that, obviously, because it's very helpful, but too, because it leads into kind of what you're saying here, of you're getting a good first draft on these things. Specifically in Word though, and I like to get very practical with this, specifically in Word, when you say open up Copilot in Word, is that, because I can find Copilot when I go into Microsoft 365 and I can find this like a little button that says Copilot. You're talking about the button, the Copilot button on that upper ribbon inside of Word, and then it opens up like a text box in a sense off to, there's a technical term for that box that opens up, isn't there? It's a side panel. Okay, okay, so it opens up a side panel.

[00:19:52] Speaker 4: So you can do it that way. The other way you could do is when you first open Word, if you have a Copilot license, when you open Word to a blank document, you'll get a little Copilot prompt box at the top of the screen, where it'll ask you what do you want to create, right? And you can tell it from there. That's another way you can do it. So yes, that is definitely a way to do it. Now, of course, we all know that attorneys rarely start from a blank page. Right. A lot of times they're reusing existing documents and that's fine too. And Copilot can be helpful there too, because the other element of this is the edit part of it, right? So you can go through an existing document, for example, and you can ask Copilot to help you edit or revise. And so one of the ways I've done that was a couple of ways. One thing I do is I'll write an article and then I'll ask Copilot, look at this article and carefully fact check it to make sure that I'm being technically accurate. And then Copilot will go through the article, because most of what I write is technical content, of course. And so it'll look through there and it'll find anything it thinks I've made a mistake on or been too vague about. And most of the time, thankfully, it comes back and says, it looks pretty good. But occasionally it says, hey, on page two, you said this, and that might be a little vague, you might wanna clarify, or hey, you said this, but actually that product got renamed last month. And so now that product's actually called this. So sometimes it catches little things like that. And that can be a really handy way to use it in your editing process as kind of a check. I've also occasionally had it look over something I've written and said, act as an attorney who wants to learn more about this topic. Is there anything in this article I've overlooked or been unclear about? And so then Copilot will go through it, it'll look at it and it'll come back and say, yeah, in this section you use this term, it's not really clear what you mean by that term, a lay person might not understand it. So it just kind of prompts me, okay, I should go clarify that. Or yes, you mentioned A, B, and C, but you might also wanna mention D, because that could be relevant. And so it gives me some feedback and suggestions. I don't always take it suggestions, but it can be a very helpful sort of co-author in that regard.

[00:21:55] Speaker 2: Yeah, it's a nice little co-author, to use your word, that's like sitting there right with you, and it's not annoyed that you're making it wait. Definitely. And that you're like, no.

[00:22:06] Speaker 4: The other way I've seen it used, I've seen attorneys use it, is they've written something, and I've never written anything where I loved every paragraph I wrote. There's always some part of it where I'm like, yeah, I like this article, but I'm just not feeling it in this part for some reason. And so you can kind of see the same thing with attorneys. They've drafted something and they like all of this part, but man, this part, I don't know about this part. What I've seen attorneys do is they'll ask co-pilot, hey, suggest ways to make this section more persuasive. Suggest ways to make it clearer. Suggest ways to make it more concise. Whatever it is that their adjective is. And then co-pilot will go through and he'll give them suggestions of here's how you could rewrite this to be more whatever you asked for, persuasive, concise, professional, whatever. And so that's another way that co-pilot can help you in the editing process on an existing document. This could be a document you've used many times and you're just looking to improve it. I had an attorney one time who said, I don't want AI to do the writing for me because I love the writing. That's part of the job I like. And I said, okay, well, here's a way that co-pilot could still have value for you. You write the document. Then you ask co-pilot to write its version of the document and then compare the two. Are you gonna like co-pilot's version better than yours? Probably not. But you might be looking at co-pilot's version and go, oh, I like what it did here in section two. That's kind of nice. I like that. Let me pull that over. And oh, I didn't even think about that thing on page five. Let me grab that too. That's good, okay. So you might find little things, little bits of the co-pilot version that you could steal to make your version better. That's another way that co-pilot can be useful in a writing scenario. Even if you want to do your own writing, that's fine. Co-pilot can be a helpful co-author. I call that parallel authoring where you and co-pilot both write versions and then you steal the best bits of co-pilot's version to improve your own.

[00:23:49] Speaker 2: I like that, I like that. Okay, so we've got create with caveats and then we've got edit as well. What else can we do?

[00:23:57] Speaker 4: So another one that's really big for attorneys these days is ask and summarize. So somebody has just sent you a document, right? You can ask it to summarize the document for you. Now that doesn't necessarily absolve you from reading the document. You still might have to read it. But at least by getting a summary upfront, you kind of get primed as to, okay, what is it that I'm gonna see here? But the other part of that that you can do is you can ask questions about the document. So where I've seen attorneys use this pretty often is they've got some sort of long agreement document. And so what they can do is they can say to co-pilot, create a table of all the dates and deadlines mentioned in this document, right? And then it'll very quickly create a very quick, easy table you can read that shows, okay, this thing that's gonna happen, here's the date. This thing's gonna happen, here's the date, right? It gives you that nice handy table you can reference. Here's the dates and deadlines that are mentioned. It can be amounts, it can be jurisdiction. Any fact that's mentioned in the document, you can ask it, you know, create a table or tell me about this. What jurisdiction is specified? You know, is there an arbitration clause, right? I mean, you can ask any kind of questions like that. The co-pilot will go through the document and very quickly pull that out. And importantly, give you a link to where in the document that is so you can verify it for yourself because we trust but verify, right? Don't assume the AI is the absolute unwavering truth. So that's another great use of AI in the ask and summarize thing. And not only with documents, but I see that done with Teams chats and Teams meetings. Frequently, if the meeting's been recorded or transcribed, you can use co-pilot to ask questions about the meeting. Same kind of questions, like what kind of dates and what dates and deadlines were there? Another one that I love at the end of a meeting or as a meeting is wrapping up, is to ask co-pilot what questions were left unanswered. Ooh. Because then co-pilot will say, oh, okay, well, you know, at minute 30, you know, Alice said something about this and it was never really resolved. So that tells me, that can flag for me things that we should close the loop on before we end this meeting because they're still hanging out there. Or after the meeting, oh, we need to, we still need to finish figuring that out. So whether it's an email or another meeting, I don't know, but it can basically help you get a little bit more out of the meeting because it helps flag those questions that didn't quite get resolved.

[00:26:07] Speaker 2: Well, and I imagine I can ground that kind of flagging in a document. So let's say I create an intake playbook for my intake and I record the meeting that my associate has or that I have or whatever with the new client. And I can say, did I miss anything? Yeah, 100%. Hell, I could probably do that in real time. Have I missed anything? Yeah, yeah, you probably could. Against that playbook because again, even when we're in Word, we're not limited to just that document, right? We're not in the four corners of that specific document. We could go query into anything that we have in SharePoint. So we could say, I'm making a lease and I want to add this type of provision. Could you go find multiple different types of provisions that I've already written and show me the options that I have?

[00:27:06] Speaker 4: 100%, you could do that. You could also say, look at this lease I just created, compare it to these leases in this folder. What in this new lease have I overlooked or what doesn't seem consistent to the way I usually do it? Or, I mean, you could basically ask Copilot to compare that lease to other leases you have as reference material. Yeah. Or if you have a playbook, you could say compare this, looking at our playbook, look at this document, what have we overlooked?

[00:27:34] Speaker 2: So now data, the data that I have in my SharePoint area, not only becomes valuable, but the curation of that data becomes valuable, knowing where I want to point Copilot at in order to have it do something.

[00:27:53] Speaker 1: Yeah.

[00:27:53] Speaker 2: I like that.

[00:27:54] Speaker 4: And by the way, you can also, this kind of circles back to the create and edit mode. You can tell it when you're creating a new document, whatever, and it'll try to match the structure and layout and content of that previous document because it already knows. You've got a contract or whatever it is that you really like the way it's structured. You can ask Copilot, use that as a model when you create your new one so that it'll try to adopt the same structure. Now, is it a perfect replica? No, but it'll often do a pretty good job of trying to match the way you had that previous document structured in the new document. So yeah, you can absolutely have Copilot look at playbooks, at previous examples of documents, and try to adopt the same voice and tone or the same structure, same kind of language and verbiage. Yeah, absolutely.

[00:28:42] Speaker 2: Okay, well, are there other things that you generally tell people that Copilot can be used for today?

[00:28:49] Speaker 4: Yeah. So another one is brainstorming. Brainstorming is another really handy thing you can do. You can ask it for suggestions of things. So for example, I've seen it used, you're writing a blog post for your blog and you've written the post, but you're maybe stumped on a good title, right? You could say, you could tell Copilot, look at this draft of a blog post and suggest 10 possible titles for this, right? And then you can give it a little bit more guidance. Yeah. Yeah, so you could say, make them catchy and fun, but not silly, right? Things like that. And so, or make them very professional or very concise or only three words long or whatever it is you wanna give it. But you can give it some guidance that sort of points it in a certain direction. And then it'll come back with 10 suggestions and you're not gonna love all 10 suggestions, but hopefully there's a couple in there that you think, oh, I kind of like that one. And then you can also riff on that. So like I've occasionally done something like that where it came back with 10 suggestions and seven of them were trash. I didn't want those, but the other three, okay, that's kind of nice. And then I would say, hey, looking at numbers four, six and eight that you suggested there, let's try a few more variations on that. And lean into the seafaring theme or whatever, right? And then Copilot will give you another set of suggestions based on that. And you can go back and forth and have a conversation with Copilot. And then it'll get you hopefully to a title you like or at least to an idea that's useful for you. So that kind of brainstorming is helpful. The other way we see lawyers using brainstorming quite a bit these days increasingly is with personas. And so let's say you're creating a lease agreement. You're representing the owner. You could say, you know, act as an experienced commercial lessee looking at this lease agreement, what possible concerns or objections might you have, right? And then it'll come back and it'll give you a list of what concerns it thinks an experienced commercial lessee might have with the document you're preparing to send over to them. Now, you know, in most cases, what that does is that gives you, it basically prepares you for what might come back. Yeah. It lets you pre-think, okay, they might not like the, you know, the deposit or they may not like the whatever part in here. We just need to be prepared to address that. Or you could be proactive about it because you might look at it and go, oh, actually that is a reasonable objection. We should, let's address that before we send it over. But it gives you that perspective. Now it's important to remember the map is not the territory, right? It's not, the AI is not really an experienced lessee. It's just an AI simulation of an AI, of an experienced lessee. And so when you ask it questions, it's helpful, but you also shouldn't think it's, you know, gospel.

[00:31:25] Speaker 2: Well, I like that kind of flip on it, on the, where it's acting like an attorney. I don't want it to act like me when I'm being the attorney. I don't want it to actively like say what something should be ultimately. But being a, being the other side, I like the idea of it acting as an attorney on the other side, because it doesn't have to be right. Because I'm gonna nitpick it, you know, me as the attorney is gonna nitpick its argument. And so, great, I'm comfortable with it, you know, with having it saying like, be a quote unquote, you know, I'm doing air quotes here, be a quote unquote, you know, experienced lessee attorney. Yeah, I like that.

[00:32:10] Speaker 4: I was working with an attorney who used it for almost exactly that. He was preparing some litigation and he basically said, he basically gave it, act as the attorney for the other side and he gave it some details about who the other side was. You know, what would be your counter to this theory? This is my theory of the case. What would be your counter arguments, right? And it came back and it gave him eight or nine fairly detailed counter arguments to what his position was. And he looked at that and he went, yeah, no, no, that's not right. No, that, oh, yeah, that one, maybe, this one, no. You know, he went down the list and he eliminated about half of them. And there were a couple that he'd already thought of, but there was one or two that he was like, okay, that's interesting, it's good to know. And it took seconds, right? In the matter of seconds, he got that perspective of what the other side might throw back at him. And he found that to be pretty helpful just as a priming exercise.

[00:33:01] Speaker 2: I think that's a really good point, which you brought up there is the ROI on some of this. Like the investment is so low on a lot of this stuff. Now, you don't wanna get into the weeds. You don't wanna just create AI slop that's gonna make you go through and read a ton of stuff. But if we're talking about just like, give me the high level, what are the arguments here? Check my work, you know, let's get a sniff test. Let's have something else do a sniff test on this thing. Yeah, I like that.

[00:33:30] Speaker 4: And then I guess the fourth area other than brainstorming that I see attorneys using it for, there's a lot of sort of business of law things that they're doing, things like triage my inbox. I see attorneys a lot of times, you know, they come in on Monday and they'll say, you know, look at my inbox, which five emails seem to need my attention most urgently? Because they've got 200 messages that came in since Friday, right? And so they wanna get that, you know, just pull out the highlights, which ones seem to need my attention right now? And so they can start there, they know where to start. So I see that kind of thing getting used, you know, looking at my calendar, what's, you know, which meetings stand out as needing, you know, the most prep time, things like that. And even with a specific meeting, I often use it for this myself is I'll say, help me prepare for my Wednesday meeting with Alice, right? And it'll look at the meeting invite, it'll look at any materials that it can find that seem related, and it can help, you know, help you prepare basically for that meeting. So there's a lot of that sort of day-to-day productivity stuff that Copaio can help with also.

[00:34:34] Speaker 2: A lot of that stuff, and I love all those things because I really like the kind of the structure that you put to that, the create, the edit, the brainstorm, the business of law stuff. But a lot of that is kind of like that LLM, sort of like I'm asking a question, it's giving me an answer, I'm getting it to brainstorm. It's Copilot also has the ability to do agentic stuff. Can you talk to me about that a little bit?

[00:35:04] Speaker 4: Use the A word. Yes. Yeah, agentic is a word that gets tossed around a lot. A lot of the things that we see referred to as agentic, really that agentic, just to sort of clarify, when I think of agentic AI, I'm thinking of AI that does things either autonomously or semi-autonomously. Not just you type in a prompt and then it gives you a response, it's the AI is actively. So maybe you've got an AI agent, for example, that's looking for email that comes in from prospective clients and then take some action. Or it's looking for a new document that gets created in a particular folder and then it takes some series of actions based on that intelligently. And so those would be examples of agentic AIs. You could also trigger an agentic AI. So for example, you need to book a trip to go to Chicago for a meeting. Theoretically, you could have an agentic AI that you could say, book my trip to Chicago based on my calendar, whatever. And it'll look at your calendar. You're supposed to go April 9th. And so it'll go ahead and book the travel, it'll book the hotel, et cetera. That's the promise of agentic AI. I don't see a lot of agentic agents that are actually doing that yet. And I think there's a couple of things that we need to consider with agentic AI. One is how autonomous do you want them to be? Especially in law. We just talked about never show the output of an AI to a client or the court without reviewing it first. You probably wouldn't want an AI to draft a document and send it to your client without you looking at that document first. Because who knows what crazy stuff could have ended up in that document. And so you'd want to catch that. So there needs to be some human checkpoints along the way in the agentic process. A big objection I hear, or concern I hear with agentic AI, especially anything that has to do with money. The book my trip to Chicago sounds like a good idea, but if I'm giving it my credit card and now it's on American Airlines website and next thing I know, I've got 43 trips to Chicago booked because it didn't recognize that I didn't want to fly there and back over and over again the same day.

[00:37:15] Speaker 2: It got all the good ones. Or I'm going to Manhattan, Kansas. Yeah, that's right. I wind up in Manhattan, Kansas. And yeah, that's not where I wanted to go. Well, then what, I know like the agentic stuff is a little bit newer to people and I kind of think of the agentic stuff as like Power Automate on steroids. You know, it's Power Automate with a little bit of thought. Yeah. But I also, I don't think people even use Power Automate very well or can like envision what they want Power Automate to do. What would you use agentic for in a law office, do you think?

[00:37:57] Speaker 4: Yeah, I could see, there's a few things I could see it being used for. If you can identify any workflow really where the set of steps are fairly repetitive, they might need a little bit of intelligence to discern A from B, but for the most part, they're pretty repetitive. Now in the past, you're right, we would have used something like Power Automate or Zapier or something like that and create a script, right? But then you have to delineate every step, right? If this word is in there, then it's A. If this word's in there, then it's B. If this word's in there, then it's C, right? And you had to create these sort of elaborate, carefully scripted workflows. And even then some outliers showed up where they didn't use word A, but they had an A scenario and it didn't work.

[00:38:38] Speaker 2: There's always a rip cord that has to be pulled. There's always that, yeah.

[00:38:40] Speaker 4: And so with the agentic AI, in theory, the AI is a little bit more flexible, a little bit more intelligent to be able to look at the email or the whatever it is, whatever the trigger is and correctly identify, this is an A, this is a B, this is a C, take the right actions in theory. And so I think anything you can identify a workflow, for example, a prospective client has emailed your firm about a new wills and trust case, for example, right? You could have an agentic AI that takes that email that then launches off the start of an intake process, maybe it does a cursory conflict check if it needs to, that shouldn't be the final. I mean, you still wanna double check that because that's an important step. But at least could identify, their name does not appear in our practice management system currently. So that's a good starting point. And so it then could kick off, well, here's an initial questionnaire that goes back to this prospective client, for example. So some of those early steps are something that an agentic AI might be able to do a good job with, and especially because intaking a wills and trust case could be very different from intaking an immigration case, from intaking business litigation, from intaking different practice areas. And so if your firm handles multiple practice areas, an agentic AI might be pretty good at identifying a prospective client, what area of law they're probably talking about, and then initiating at least the first steps of an intake process or an evaluation process.

[00:40:05] Speaker 2: Okay, yeah, and as you're talking, I think there's a place that you could put a human in the loop there. Oh, yeah. Where it's like, okay, I see that this person came in, I'm gonna create a certain, I'm gonna use a certain file structure to potentially create this client file folder area, and then I will draft an email response and put it in your inbox, but you gotta send it. But I will have drafted it for your review, and now me as the attorney or as the person that does intake, I don't have to go through some of those drudgery steps.

[00:40:44] Speaker 4: Yeah, 100%. At Microsoft, they had created a thing, their CILO, which is their internal attorneys, corporate counsel, they would get these requests via email all the time, which were, it's something to do with intellectual property, I don't know the details, but they were pretty routine, and they actually created the workflow that when one of those emails would come in, Copilot would take that, would draft the Word document with the requested release, I guess it was, all filled out with everything in it. That would then go to one of the Microsoft attorneys who would review it very quickly and either approve it or decline it, and if they approved it, then it went back to the requester, job done. In the past, when it was being done manually, when it was all having to get routed to humans and humans were having to draft the documents and et cetera, that process could take three or four days from start to finish. Once they got Copilot involved, that process took two or three hours, and the biggest bottleneck was the last step where it went to the human attorney who then had to just look it over, make sure everything was okay, and send it out. Sometimes that attorney was at lunch, sometimes that attorney was in a meeting, so really, in a perfect situation where that attorney just happens to be sitting at their desk just checking their email and not doing anything else important, that request, that fully finished document, or fully finished, I'll put in air quotes, that finished document comes in for review, theoretically, it could cut that time down to 10 minutes, because the document got created automatically in seconds or minutes, and then the attorney could review it, it looks good to me, approve, send. Right? But that was a good example of a somewhat agentic workflow that was able to identify the request that came in, create the document automatically, but then you had the human in the loop, because it got routed to a human attorney who could then look at it and go, yeah, that looks good, or no, no, no, no, no, we're not doing that.

[00:42:34] Speaker 2: I like that one, I like that one. And the mind reels with ideas, you know, I think, but I also think that a lot of people don't have the ideas of like what I could do. And I think some of this goes back to processes, some of this goes back to, you know, kind of I don't know what I don't know sort of thing. So as we wrap up here, I kind of want to do a call to action to the people listening here. I would love for people to, in the comment sections, in on our LinkedIn pages, wherever you run across us, if you've got a cool way that you use Copilot in your office, we'd love to hear about it. We'd love to hear about it, love to hear people share about it. And Ben's got a bunch of them, a bunch of ideas, and a bunch of people that he's run across, but you know, we're just scratching the surface on a lot of this stuff too, and it's really about structure. It's about thinking differently. But before we go, Ben, I want to kind of, not necessarily put you on the spot, but we've been talking about how people can use Copilot. I want to quickly ask, how are you seeing people, what is the way to not use Copilot, I guess? You know, like what is something that people think that we can do with this stuff? And it's either not quite there, or it's just, moo, you're asking the wrong question. You're thinking about the wrong thing.

[00:44:06] Speaker 4: I guess the obvious one, I guess, is don't tell it to draft a brief and then just file that with the court. Yes, yeah, that would be it. That would be it. Yeah, so a couple things. So first of all, one of the great things about AI is that, you know, AI is, you don't have to be monogamous with your AI, and I think I've used that line before with you, but the AI doesn't care if you use other AIs. And it's good to use the right tool for the job. Copilot is not tuned for legal specific work. And so like, for example, could you use Copilot for legal research? Yes, should you? Probably not. Because Copilot doesn't have access to Lexis. It doesn't have access to Westlaw. It doesn't have access to VLex. It doesn't have access to all those proprietary databases with the really high value legal research and legal content in them. Copilot doesn't have access to that stuff. It's got access to your content in your Microsoft 365, and it's got access to things that are in the public web and things that are in its training set, which are not tuned for legal tasks. Though, can you do legal stuff with it? Yeah, but you could probably, if you're doing legal research, that's a good example of where you probably should use a tool other than Copilot, something like VLex or Lexis Plus or Harvey Paxton, whatever, a tool that's tuned for that that has access to that kind of research. So that's one example of a bad place to use Copilot. Yeah. In terms of tasks that Copilot still doesn't do very well, one thing that's a big glaring miss for me right now is scheduling meetings. So I can ask Copilot, hey, schedule a meeting with Zach for next Thursday, and Copilot will get me part of the way there, but it doesn't get me very far, right? It basically will end up creating a blank meeting invite for the right day and time, but it doesn't put Zach in there. It doesn't put the topic in there. I've gone to all the trouble to say, schedule a meeting with Zach so we can talk about A, B, and C next week, right? It'll find a time next week when you and I could meet, but then it still makes me do a whole bunch of other stuff.

[00:46:06] Speaker 3: Okay.

[00:46:07] Speaker 4: So that's an example of where Copilot still isn't quite what it should be, is on meeting scheduling. It can do other things with your calendar that are useful, but that's not one of them. Okay. I'm trying to think of other examples there. Oh, so Copilot, this is one that trips people up sometimes when working with email, for example. If you ask Copilot a question about something that's in your email, it's pretty good about being able to find it, right? I used it just earlier today. I had a specific question about an upcoming conference I'm speaking at, right? And I said, looking at my email, what's this answer, right? And it went through all the email I'd received about that conference. In fact, it went through all my email and found the emails related to that conference. And then it was able to answer my question about the conference based on the email. If I had asked it, give me a list of all of the emails I have received about that conference, that probably wouldn't work very well. Copilot's not great at indexing and giving like, here's a full list of all the emails about that conference. If I'm asking a specific question about the conference, that it can probably do, and it does pretty well. But it's not really intended as a search engine per se, in that it's not gonna give you a comprehensive list of things generally.

[00:47:17] Speaker 2: I like that one. And honestly, I like that one as one to end on because what I think happens a lot of times when people go and use Copilot, and I want this to be encouraging. Go use Copilot, provided you're using it in the right place and for the right things. People will use it for something that they usually would use Google for or a search engine or a search bar or something like that. And then when it doesn't do it well, they go, well, this is a stupid thing and it's never gonna work for anything. So I like that as an example, as a really specific example of it doesn't think like that. That's just not the way that you use it. But all the other things that we've outlined here today, those are great uses of Copilot.

[00:48:05] Speaker 4: I've seen that one trip people up too, because I've seen, I had somebody said, I wanted a list of all the emails that I'd received from Bob in 2015 or 2025. So I asked it to give me that list and it gave me a list, but I could see there were a bunch that weren't there. It's like, yeah, well, it's not great at that comprehensive, here's your search results. There are other tools that can do search results. Copilot's not really a search results tool.

[00:48:29] Speaker 2: Yeah, and I've had that frustration myself and I've cursed its name many times. And so, yeah, I think that's a really good one to say. It's just not its jam. It's good at a lot of things and that's not its thing. Well, Ben, I really appreciate you taking the time to talk with me about this. Yeah, and we have talked before about some of the fundamentals related to security of Copilot and what Copilot can see and what it's grounded in and things like that. On a previous episode, I don't have the number in my brain right now, but we will put it into the show notes. So if you wanna hear more from Ben, you can catch him on that. And you can also catch him on our sister channel for Affinity Thought Hub on YouTube. We're doing a AI Calibration Weekly video that Ben is a very, very, as you can imagine, regular guest on. So Ben, thank you again for talking to me about AI and specifically Copilot. My pleasure. I always enjoy talking with you, Jack.

ai AI Insights
Arow Summary
In this Lawyerist Podcast episode, hosts Zach and Chad segue from a light discussion about Strava privacy and motivation (“leverage” via committing to races) into an interview where Zach speaks with Ben Schorr, innovation strategist at Affinity Consulting Group and former Microsoft Customer Success Engineering leader. Ben explains what Microsoft Copilot is (Microsoft’s productivity AI built largely on OpenAI models) and why it matters for lawyers: it is natively integrated into Microsoft 365, respects existing user permissions, and keeps prompts and outputs within the firm’s M365 tenant (unlike consumer/free AI tools). Ben outlines practical, near-term Copilot uses in law firms: (1) create and edit in Word to generate first drafts and improve sections; (2) summarize and ask questions of documents, emails, Teams chats, and meeting transcripts—e.g., extract dates/deadlines, identify clauses, and surface unanswered meeting questions; (3) brainstorm, including persona-based “other side” objections and counterarguments; and (4) business-of-law productivity, such as inbox triage and meeting preparation. He cautions against sending AI output to clients/courts without review (“Schorr’s Law”), warns Copilot is not tuned for legal research because it lacks access to proprietary databases, and notes current limitations like meeting scheduling and comprehensive email listing/search behavior.
Arow Title
How Lawyers Can Use Microsoft Copilot Today (Safely)
Arow Keywords
Lawyerist Podcast Remove
Microsoft Copilot Remove
Microsoft 365 Remove
legal AI Remove
productivity AI Remove
SharePoint Remove
OneDrive Remove
Teams Remove
Word Remove
document drafting Remove
document summarization Remove
deadline extraction Remove
meeting transcripts Remove
brainstorming Remove
persona prompting Remove
inbox triage Remove
agentic AI Remove
Power Automate Remove
privacy and security Remove
permissions model Remove
legal research limitations Remove
human-in-the-loop Remove
Arow Key Takeaways
  • Copilot is Microsoft’s productivity AI integrated into Microsoft 365 and largely built on OpenAI models.
  • Copilot can access what you can access in M365 (email, calendar, Teams, SharePoint/OneDrive) and respects existing permissions.
  • Using Microsoft 365 Copilot keeps prompts and outputs inside your M365 tenant, improving privacy/security versus consumer AI tools.
  • Best near-term wins: draft first versions in Word, then edit/revise—Copilot gets you from blank page to a workable starting draft fast.
  • Use Copilot to summarize and interrogate documents/threads: extract dates and deadlines, locate clauses, create tables, and provide citations/links for verification.
  • Teams meeting transcription + Copilot enables summaries, action items, and even identifying unanswered questions before closing a meeting.
  • Brainstorming and persona prompts help anticipate opposing arguments or client objections and improve writing clarity/persuasiveness.
  • Business-of-law use cases include inbox triage, identifying urgent emails, and prepping for meetings based on context.
  • ‘Schorr’s Law’: never send AI output to clients or courts without careful human review.
  • Copilot is not ideal for legal research because it lacks access to proprietary legal databases; use dedicated legal research AI/tools instead.
  • Agentic AI promises semi-autonomous workflows (e.g., intake automation) but should include human checkpoints, especially for legal work and spending money.
  • Current Copilot limitations include weak meeting scheduling and incomplete ‘list all emails’ style retrieval—better for answering specific questions than comprehensive search.
Arow Sentiments
Positive: The tone is upbeat and practical, emphasizing actionable ways Copilot can help lawyers today while maintaining careful, responsible cautions about review, security, and tool limitations.
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