Flex Legal Talent and How Lawyers Can Position Themselves to Succeed in 2026

Welcome to Reinventing Professionals, a podcast hosted by industry analyst Ari Kaplan, which shares ideas, guidance, and perspectives from market leaders shaping the next generation of legal and professional services. This is Ari Kaplan and I'm speaking today with Kyle Robish, a partner at Latitude Legal, a provider of flexible legal talent, and he is also the founder of its Tampa office. Hi Kyle, how are you? Great, Ari.

Good to see you. And thanks for having me. I'm looking forward to the conversation. So tell us about your background and your role at Latitude Legal.

I took the classic path, I think outta law school that k JD went to the University of Florida, Vandy Law, federal clerkship. And then I practiced at a big firm, Venable in DC for four years, lateral to Bradley and Tampa, another big firm rose to partner. And then one day, and I say one day, it was really a formative, year or two process. I decided I wanted to.

Get outta litigation and do something different. And that led me to Latitude and this flexible legal talent model and the opportunity for me to be a business owner and business operator as opposed to somebody who fought and argued all day. But what I did before is a big part of what I do now, and I love my time litigating, but I love my time being a business owner even more. How did working with a large law firm and that experience shape your mission at Latitude?

So there's a couple different ways. The most obvious way, the easy answer is a good chunk of our clients here at Latitude are law firms and they're firms of the size and shape that I worked at big law firms, ML 100 law firms. Then there's solo practitioners and everything in between. So all of my 10 years of practice go in every single day into thinking about the kinds of lawyers.

All my clients would want to engage their skillset, their culture fit, their background, their experience. And then obviously I worked with a lot of legal departments representing them in litigation. And that's the other big chunk of our clients. It's legal departments, big Fortune 10, down to single GC solo shops, early stage companies.

So all of that experience I spent practicing goes into what we do now, and that's one of the things I liked about Latitude. Everyone at this company practiced at a high level as either a partner at a big law firm or a boutique law firm, or a senior in-house legal leader at a big company or a small company. And so we all sat in our client's seats and we now serve those same clients just in a different capacity. How do you define flex legal talent and how do law firms and legal departments most often use that service?

It means a lot of different things. When I was, early in my practice days and even before I took this job, if I'm being candid, when I thought of a contract lawyer or an engagement lawyer, I thought of a doc reviewer. And that was I do my own due diligence on Latitude and the whole industry before I even came here. I learned, really over the last five or 10 years, the idea of flex legal talent is you practice in a little bit of a different way, but a lot of the times you've worked at a big law firm, you've worked in house at a major company, even maybe as the GC or as a partner at that law firm, and you've either gotten to a point in your life.

Where you want or need, or there's some mix of those elements to work flexibly to work differently. You don't wanna do doc review, that's fine. But you wanna work at a high level doing sophisticated work. You just need something about it to be a little different, or you want something about it to be different.

So we have lawyers who work six months on a leave coverage for a client, and they'll work 60 to 80 hours a week during that leave. And then they'll take six months off or three months off. And then we've got lawyers who. Practice 20 to 30 hours a week.

And this is a part of what they do. And they've got other things in their lives that they care about and balance and need or want to give time to. And so flex legal talent means a lot of things and it means a lot of things to a lot of different people. But the beauty of it is that means almost everyone can have a role in, in that ecosystem.

Whether it's getting help from a flex lawyer or being a flex lawyer and having that fit into your life or practice at some point in some way. What's the distinction in the role at a law firm versus in a corporate legal department? When a law firm comes to us, we're obviously thinking about putting our law firm hats on, thinking about that background and skillset, making sure giving them the kind of lawyer they want to hire permanently. Just for our fractional or engagement piece.

If you're a litigator or a litigation department at a big law firm. They might have a an MDL or A class action or a mass actions, or they need somebody to come in and help draft briefs or run depositions. We're finding someone who's done that same work at other law firms of similar caliber and plugging them in-house. It's a similar setup in terms of matching the need to the background, but we're looking for folks who've done that work in house before, so they know what it's like to move at the speed of the business to make decisions in that gray area that in-house lawyers have to live in.

And to get to Yes. Again we're matching the specific background experience and skillset of folks to the needs of the clients. The way they set that up might be different, but the end of the day, the result is the same, which is we're tailoring the specific lawyer to the specific need that client has. Is flex legal talent designed to be tactical or strategic?

Both is the answer when I thought of it tactically when I started, bring someone in for a specific need. Believe coverage, backfill support. Step it out. Maybe I'll call you back in six months or six years.

Over time, as I've worked with more legal departments and law firms, I've learned it's actually deployed more effectively. Strategically, the tactical elements fit in. Yes, you have people stepping out for big things and you need to get that filled, leave coverage, backfill, whatever it might be. But then you also have this day to day legal work that.

A lot of times you can get busy, you need some overflow help. Sometimes the law firm's not a great fit for that because of the nature of the business, the in and out side of it, the niche, commercial contracts. Not a lot of law firms focus on commercial contracts. That's all the upshot of all of that are a, is the legal departments and law firms that use, I think us most effectively are using us strategically.

They're plugging tactical goals, and along that while they go, but they're also making it a part of their broader structure. So they can not only get, the big items done, but they can get the day-to-day work done. They have someone on tap that they can use throughout a year or throughout multiple years to provide overflow, prevent burnout, have their teams get the support they need. And it's been fun to see that evolution because I think that's also been pretty recent.

I think most of our clients thought of us tactically for the past five or 10 years, and it's really only been in the last, I'd say, three to five, where a lot more folks are coming to us and saying. Hey, I might have a leave coverage, but actually really interested in thinking about a three year plan and all the different ways we can plug a flex lawyer in. What does that look like? How does it sound?

What are the budgets? And those are fun conversations to have Is your team comprised of lawyers with particular skills in particular practice areas or at particular levels of experience? Yes. We have a bench of folks, I can put 'em in the general buckets.

At the end of the day, they always find a way to elude those buckets. Most of our lawyers have 10 plus years of experience. A good chunk of them have practiced in-house and at law firms. There's also plenty of lawyers though, who have worked three to five years who come to us or have worked 35 or 40 years and come to us.

Some that have only lived at law firms, others who've only lived in house. The skill sets and experience breakdown pretty similarly too. We've got plenty of in-house generalists and plenty of litigation generalists, commercial litigators, but we also have tax lawyers with LLMs from NYU and Georgetown. We've got ERISA attorneys.

We've got healthcare regulatory attorneys. We've got mass tort and environmental litigators. We've got folks who can operate at a high level if that's what you need generally. But then we also have a niche bench.

Obviously the niche bench is a little smaller because when we wanna hold someone out as an expert in tax or ERISA or the Stark Act, we wanna make sure they actually do those things. But just like our clients who, variety of needs, we've got a variety of folks who we can plug into each situation. Why do your lawyers choose a career in flexible legal talent? For some, it's a season of their life.

For maybe six months or two years, or five years, whatever it might be, wanna step out, reset, and figure out things a little differently. And that can be a variety of reasons for that. Then for others, it's just the logical next step of what they're doing. We have folks who've worked with us for 10 plus years.

The common factors in all those buckets are that people come to us either, either out of want or need. Most commonly means something like something has happened in their life and they were practicing at a big law firm or a fancy legal department and somebody got sick in their family, and they're the primary caregiver, or some life event occurred where they needed flexibility. They couldn't get out of their current setup, but they're a really great lawyer and they wanna keep doing high level work.

So they come to us to help get that, give them those opportunities to do that level work while also. Taking care of their family or their life or their personal aspects need to take care of. We've got folks who also come to us out of want. They've gotten to that point in their career, or they've simply made the decision earlier in their career, Hey, I've, cut my teeth.

I've learned some things that I'm ready to bet on myself, and I wanna make latitude part of that, what does that mean? Maybe they have their own practice and they use us to supplement that practice. Maybe they just want to do engagements. Maybe they love the idea, like I mentioned earlier, of.

Going really hard for six or nine months in a year and then going to borrow for three months. Maybe they own a travel business and they operate that at some level, 10 hours a week. For most of the year, and then three months outta the year, they either take their clients abroad or go try out some of the resorts they put their clients into. So they'll take three months off with us and lean heavily into the business and then pop back in and let us know, Hey I'm ready for the next lead coverage or backfill, or whatever it might be, fill me up.

So the. Common thread of all of that. It's all about what people's lives are delivering to them. And now they've got an opportunity through latitudes and companies like us to build their own adventure and build a way of practicing in their life at a high level that works for them and then also works for our clients.

How is AI creating headwinds and tailwinds for flex legal talent? I feel like I have this in this question. A lot in the last three months. Thank you.

Open AI and anthropic. I think the answer's a little bit of both, but I are would argue, and obviously I'm biased, I think we're getting more tailwinds than headwinds. On the headwind side, I think it's undeniable that a lot of. The legal work is being commoditized and even more will be commoditized.

And some of it can be done by ai and some of it can be supercharged by ai and that can lead to less work for lawyers. And that can mean less work for flex lawyers. That's undeniable at some level, but I think the tailwinds are still bigger for our industry and our company. And the reason is I think AI is creating more work and more demand.

How is that, why is that? Time and time again? I spend most of my days talking to general counsels and law firm partners. They tell us AI is creating more work for them, not less, at least right now.

It's implementation, it's outputs that need to be reviewed. It's mistakes that it's generated that they now have to fix. Almost every in-house lawyer has a story of the sales person who plugged a contract into AI, said, I've got it, and now it's worse than before. And now they have to go undo that work, rewind it, and fix it again.

That's more work, not less. It's just as a litigator. When you look back to ESI and e-Discovery, when that dawn, we were talking about wiping out first year associates for a decade. Instead, there's more work than ever.

Why? Because more data created more documents, created more work, and now we have whole discovery teams and practice groups that, law firms that practice just in that space. I think this is going to be similar, so I think AI is gonna create more work and I think it's gonna create more tailwinds, but. At the same time, we're also gonna be dealing with some headwinds over here, so we can figure out how to navigate that.

How can lawyers best position themselves to succeed in 2026 and beyond? Being open to career pivots and saying yes to opportunities. 2026 is the best time to practice law. I bet if you ask me in 2027, Ari, I'm gonna say 2027 is the best time to practice law.

I firmly believe that, but I also feel like that's the opposite of what I read in the media and allah.com. I hate seeing that because I, having lived both the traditional model, if you will, being a big law attorney, rising a partner, and then now where the law is going and where it is that Wayne Gretzky get to where the puck is going, quote, I feel like people have more options than ever and I think leaning into those options and that optionality is really important. Some of the most successful partners at law firms and general counsels.

Have done work adjacent to the law and have done work outside the law and come all the way back into the law. And they'll tell you that made them a better lawyer because they sat in the sales seat for a little while, made them a better GC because they've worked in finance or accounting and they've lived what the budget crunches mean. So when they're advising on those same things and those issues. There's a camaraderie and experience you can't get unless you've literally earned it.

People should be unafraid of leaning into pivots and opportunities that might seem a little bit off the beaten path. You can always go back onto the path. It's a great path. It's where I came from and I might go back to one day but in 2026 you can practice law however you want on whatever terms that work for you.

And I think that's pretty awesome and I think we should be leaning into that. This is Ari Kaplan speaking with Kyle Robish, a partner at Latitude Legal, a provider of flexible legal talent. Kyle is also the founder of Latitude Legal's Tampa office. Kyle, thanks so very much.

My pleasure. Thanks for having me, Ari. I. Thank you for listening to the Reinventing Professionals Podcast.

Visit reinventing professionals.com or ari kaplan advisors.com to learn more.