Legally On The Move: The Lawyers Retreat is Back in Ibiza 2026 – Gretchen Lennon – E04

You can hear Rob and Gretchen discussing:

Connect with Gretchen Lennon here: 

https://www.linkedin.com/in/gretchen-lennon-55455664/

Transcript

Welcome to Legally on the Move, the Lawyers Retreat Ibiza 2026, a special legally speaking podcast mini series sponsored by Clio. 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, wellbeing, AI, growth, business development and the future of law. 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 Ibiza for the Lawyers’ Retreat. And I’m joined by name, title and organisation, Gretchen Lennon, founder of Lennon Legal. Absolutely. And it’s an absolute pleasure to be hosting you live here in Ibiza. So let’s get into it. What brought you to the Lawyers’ Retreat?

So I’ve been working with ⁓ Suzanne, my marketing consultant, for the last five or six months and she was here last year and she’s here again this year and basically couldn’t speak highly enough of it and likewise another one of my colleagues, Nikki, her think friend on the, like another school mum, had also been on the Lawyers Retreat last year, Aurelia, and again big recommendation through ⁓ that channel as well, so yeah. Good stuff. say no.

Yeah, and had to be here and you’ve been loving it ever since. Love it. so you’ve worked both in-house and on a consultancy basis. How has that shaped the way you support founders and businesses grow today? So having some in-house experience means that you really get to see the inner workings of businesses and how different teams work together and, you know, the kind of commercial realities of running small businesses. But then also working on a consultancy basis means I’ve gotten to work with a huge variety of founders.

with a huge variety of founders over quite a long period of time. So you see a lot of variations of the same kinds of issues coming up time and time again. And so that just gives you lots of experience on how to help deal with it and what works and what doesn’t. Love it. OK, let’s talk about startups and scale-ups because they want pace, but they also need protection. So how do you help clients strike that balance without over-complicating things? Yeah, great question. And yeah, definitely for startups and scale-ups, early stage businesses.

you their requirements when it comes to legal services are very different to make bigger corporates they want yet honestly think they’ve got a higher appetite for risk because they just want to get things done and particularly when it comes to like funding lines for example we do a lot of that they just want to get the deal over the line they want the money and i want to move on to the next thing so we try to work with me we pride ourselves on taking a very commercial and pragmatic approach to the advice that we gave you know you spot the legal issues you sort of highlight the sort of

the degree of risk for the client and then you help them make a of risk-based decision and sometimes it can be well we know what the risk is but we’re just going to go for it anyway. It’s important to kind of get to that point with the client in a quick way and definitely without the sort of know the 10 page advice memo that maybe you might have got from a large law firm. Very true, keep it simple as best you can. Simple and quick. exactly. Okay so this year’s retreat also touches on difficult conversations and difficult decisions. Had some good sessions on that. So from your perspective

What are some of the people or employment issues businesses need to tackle earlier rather than later? ⁓ That’s a good question. think when it comes to difficult decisions in terms of the employment context, if you’re working with a team member and it’s not really working out, you have to kind of tackle that conversation head on as early as you can because honestly these kinds of problems, if it’s performance or discipline or just employee relations, know, like interrelations between team members.

These issues don’t go away on their own and if you as a sort leader, founder or team manager kind of tried to turn a blind eye, it will fester. And also particularly with employment law and employment rights, the longer you let it go on, potentially the higher the value of the claim. If you’ve got a tricky employee and you can sort of see the writings on the wall, it’s a tough thing to do but sometimes you have to kind of cut your losses and perhaps terminate the employment relationship sooner rather than later.

Yeah, no, well said. OK, so in a tougher market, everyone wants value. Of course they do. What does genuinely cost effective legal support look like in 2026, in your opinion? ⁓ That’s a great question. ⁓ I think genuinely cost effective legal support is where the advice absolutely speaks to the of the crux of the client issue as kind of succinctly and efficiently as possible.

no generic answers, no sort of just roll off the template agreement or whatever it is, without really encompassing where the client has come from. Again, kind of going back to same point, what is their risk appetite, what are their commercial realities? ⁓ And I think also…

being a kind of, a sort of an extension of their team, a trusted partner, know, a source of like, reliable advice ⁓ and a kind of a relationship that, you know, they feel that they can pick up the phone or ping you a quick WhatsApp and ask you a question and you’re not gonna charge them a fortune for it. You know, none of this sort of billing in six minute increments, founders in particular, and I think actually a lot of business owners nowadays, not just founders, they’re kind of fed up with how lawyers typically bill, so we need to be more.

We need to be bringing more value for money. Absolutely, and I know you’re doing a great job of that with what you’re building. what is one piece of advice you would give to founders who want stronger legal foundations but without building unnecessary drag within the business? Ooh, I would say…

Identify the right legal partner early on in your company journey. mean, maybe it’s Lenin Legal. It is Lenin Legal. It’s Lenin Legal. Or maybe it’s someone else, or maybe you’ve already got a great legal advisor. But either way, work with a lawyer and get a great set of foundational documents in place, whether that’s your shareholders agreement, your standard client terms, your employment contracts, whatever it may be. And when any kind of legal issues rear their heads.

don’t try and DIY it. mean it’s very tempting to sort of ask TechieBT or try and Google the answer but honestly your time and your resources are better spent elsewhere and again if you’ve got a good relationship with your legal partner you should be able to just pick up the phone to them and say this is the problem how can we fix it and they should be able to give you hopefully a sort of quick and value for money solution.

And save you the headache as well. Yeah, and that’s partnership, it? To your partner, know, trusting them and being responsive, building that relationship and everything else. OK, before let you go, what’s one idea, habit or conversation you’re leaving Ibiza with? I think that the main takeaway for me, and it was one of the sessions yesterday, is just how these very small changes can really combine and incrementally can have a massive shift on, you know, your business, your mindset, whatever it may be.

And so yeah, I’ve of, I’ve come up with a list of small changes I need to make for myself and day on day, I’m hoping I’m going to make them. Absolutely. And it compounds, doesn’t it, over time? And you know, that momentum builds and builds and builds. Well, it’s been an absolute pleasure hosting you on the LVC podcast here in Ibiza. If people want to know more about you or indeed Lennon Legal, where should they go? Feel free to share any social medias or websites and we’ll share them with you too. LennonLegal.com is our website. Follow us on Instagram, Lennon underscore legal, and likewise, find us on LinkedIn, Lennon Legal. There we go. So from all of us here in Ibiza, over and out.

Over and out. 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.