Legally On The Move: The Lawyers Retreat is Back in Ibiza 2026 – Kim Simmonds – E05

You can hear Rob and Kim discussing:

Connect with Kim Simmonds here: 

https://www.linkedin.com/in/kimsimmonds/

Transcript

Welcome to Legally on the Move, The Lawyers Retreat Ibitha 2026, a special legally speaking podcast miniseries sponsored by Cleo. We’re back here in Ibiza as the official media partner for the Lawyers Retreat. And if last year taught me anything, it’s this: when you get the right people in the right environment, good conversations quickly turn into real opportunities.

Across this series, we’ll be bringing you voices, ideas and honest reflections from a retreat built around leadership, well-being, AI, growth, business development and the future of lore. So whether we’re poolside, post-panel, or catching up in between sessions, expect practical insights, fresh thinking, and conversations that go beyond the surface. So let’s get into it.

Welcome to the legally speaking podcast recording live here from Ibetha for the Lawyers Retreat. And I am joined by name, title, and organisation, please. Kim Simmonds. I’m CEO and founder of Law365 and Cloud Contracts365. You absolutely are. It’s been an absolute pleasure getting to know you more over these couple of days here in Ibiza. And with that, what brought you to the Lawyers Retreat this year? So I never heard of the Lawyers Retreat, to be very honest with you. And a friend of mine, Alex, who’s also here.

Said to me, you really must come along. I think you’ll find it really interesting. I’m obviously a law firm owner. Yeah. And sometimes we do move in the dark. We don’t always know what we’re doing. And sometimes it’s really nice to be surrounded by like minded people with some amazing sessions that can sort of push you out of your boundaries and ⁓ your comfort zone. So that’s why I’m here. Yeah, the comfort zone is great, but nothing ever grows there, as we say a lot on the show. So you’ve built businesses around the idea that legal should help.

growth rather than slow it down. So where do you see legal creating friction for ambitious companies? So where ⁓ what I’ve always seen throughout my whole working life, now I worked for a big American law firm in New York as an MA lawyer, all the way through to a regional firm to a small, you know, all kinds of size firms. And the reason why I created Law through 65 in the first place was because the friction for me that I saw was there was a lack of transparency with what the lawyers were doing. So clients were frustrated. They didn’t know if a piece of work

Really took five hours or twenty hours. They had absolutely no understanding. This whole thing with hourly and billable rates and all the rest of it was a real taxing effort on the client side to really get their head around. But also the client success, lawyers were not interested in how customers or clients felt about the work that they were giving the lawyers because you know, a lot of them it’s their business, they’re under time pressure, they want to get that deal done.

The lawyers have got ten things to do. They’re not worried about that particular one client, but that one client’s only concerned about that one piece of work. So it’s really bridging the gap and making lawyers more aware of customer success, which is definitely being more recognised these days, but it wasn’t always the case. Yeah, absolutely. And another big theme of the the lawyers retreat this year has of course been AI. ⁓ can’t get away from that. What are the most practical ways you think AI can improve contract work throws growing businesses right now?

Okay, so I mean I have a really interesting take on this. Maybe a bit of my background might help first frame it. So about five years ago, we set up Cloud Contracts 365, which is a separate business to my law firm Law 365. Cloud Contracts was built very much, it’s an AI legal platform, and it was built for business owners, so where business owners could self-serve. That meant that they could go on the platform and they could build their own contracts, they could review contracts using our own proprietary AI review tool.

And they could manage contracts. Now that dealt with a lot of the startup and SME SME market because those were the price sensitive clients that we had. Yeah. Those were the ones who didn’t understand, they were very green as to how to use lawyers, and they didn’t really understand the value of lawyers. So we really wanted to put them in a place that they were satiated, they had their needs met, it was legally approved, everything was sanctioned and they felt safe and comforted. But the lovely thing about what we’ve done now.

Is that they can push a button in the platform and go to my law firm and to my lawyers when they need more customization, when they need negotiation, when they need high level advisory work. And what I’ve always advocated, and maybe this sort of answers your question, is where law where the legal industry really needs to start going and thinking about is becoming that high-level advisory service industry and allowing AI to take the mundane, to take the routine, the low-hanging fruit work off the lawyers.

And build automation around that so that clients and lawyers are in a happy place. Yeah, and who doesn’t want that? You know, that’s tech for good. Okay, you work very closely with tech businesses, MSPs, Microsoft partners, and so forth. So, what do fast growing companies need from their lawyers today that many traditional legal methods still miss? 100% fast-paced. This is like critical, which is why a the AI race is really important to take stock of.

You know, AI is instant, it’s cheap, ⁓ and it’s getting more accurate. So when you’re taking those three elements against a lawyer’s perhaps ten pieces of work for every single day, ⁓ being in a queue, expensive, maybe not understanding what the clients really need, or not talking in their language, or talking in a simple way, you’re dealing with the biggest issue, which is the fast pace that these clients absolutely need, and they will be driven and hungry for it.

Because they’re now going to get the tools to have it. So actually understanding and and r recognizing what is your proposition to compete with this, but to to showcase to the client that it’s still better to go to the lawyer. That’s the interesting piece. Yeah, absolutely. And I think you made it sound extra interesting. So thank you for for sharing that. And you’ve l built and obviously led very successful, you know, strong teams and cultures. So what have you learned about leadership, especially

When you’re trying to scale and still trying to stay close to that mission? One thing that I and I’m gonna be very honest here, one thing that I have understood deeply with all law firm owners, actually all business owners, is that they’re oft their number one biggest headache is of obviously people management. And I’m I don’t say that lightly. I I understand I’ve been an employee and I’ve been an employer, right? I understand we’ve all been employees and employers. What I say to people with the cultural stuff.

Remember, we are human. And I don’t say that lightly. Every single person has has an issue in their lives of some sort, has family pressures, whatever whether that that’s direct family or indirect family. They have other things going on. They are human and they need things. Okay, so just being empathetic to that, talking to people like they are humans, not trying to be

I I guess assuming a lot of the situation, but having good quality conversations with people regularly. Don’t do it just when there’s a problem. Do it incrementally. Make sure you understand your team, know where their pressures are in their lives as well, if they’re willing to open up to you. And don’t take that for granted. That’s a privilege. That’s a real privilege to have as a leader. And really try to make that secure. Make people feel safe, whether they’re going through something or not, if they feel safe enough to talk about it.

You can address it and everyone it can be a happ happier outcome. Yeah, I I love that. You know, it’s that human to human connection, H to H, isn’t it? And it’s that open transparency and not just sort of, you know, having that constant communication. I think where things always fall down is because there’s gaps in communication. Okay, so if there’s a law firm owner or leader watching this, ⁓ you know, want to become more future ready over the next twelve months, what’s one move they should make first? I think you need to absolutely understand what

Is it that you’re trying to achieve by being a law firm owner? Don’t just do it for the sake of, you know, I’ve been doing it for another practice, I’ve been quite successful at it, therefore let’s just do it on my own. There are very different pressures when you are on your own and you don’t have people around you to support you. And that’s really a start-up life. So make sure you’re doing it for the exact right reason. I would also get some law firm own owners who are who can be mentors to you so that at least they’re stress testing ⁓ your ideas and that

you are really making sure that you’re going into it with the right purpose. And once you do that, believe in yourself. And really take that view of what you can achieve and deliver is something that people want. I love that. And and self accountability. I remember when I set up my first company I wrote BTA, which is like believe to achieve and then someone said that’s great, but you’ve also got to take self accountability. So if it’s meant to be, it’s up to me. Remember that folks. Okay, what’s one idea, one habit, one conversation you’re going to be leaving with following this trip?

It’s there’s so many, honestly, and it’s hard to boil it all down, but I think for me it’s there’s a feeling about it’s not really a conversation. There’s a few things, a few themes. The feeling that we’re all connected. Yeah. All all firm owners are going through the same things. You’re not alone. And ⁓ we’re all s we’re all quite stressed about what the future looks like. We’re all quite in the dark as to what does it mean with with the AI revolution.

What does it mean for the future of our businesses? How do we adopt it? How do we successfully carry on doing what we’re doing? But also being able to transform what we’re doing. And I think really it’s that just ability to take a step back and go and to remember the mission and to remember like where is it that you can achieve what you can achieve, where are you going and what are the tools around you to help you? Love it. Okay. If we want to know more about yourself.

Your businesses, where can they go? Feel free to share any social media handles, any websites, we’ll share them in this episode for too. Yeah, so LinkedIn you can find me Kim Simmonds. You know, feel free to DM me if you ⁓ would like to learn a bit more about my journey. I’m very happy to talk to anyone who’s thinking about going on a AI slash, you know, law firm journey. ⁓ or if you’re an employee right now thinking about how to develop yourself more in a firm. I also love to mentor ⁓ employees who are really looking to take the next step and next ⁓ layer in their careers as well.

Fantastic. Well, it just leads me to say thank you so much for joining me here live in Ibiza for the Legally Speaking Podcast. But from now, from all of us on the show, over and out. Thank you for listening to this week’s episode. If you like the content here, why not check out our world leading content and collaboration pub, the Legally Speaking Club, over on Discord? Go to our website, www.legallyspeakingpodcast.com. There’s a link to join our community there. Over and out.