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

0:00Gretchen Lennon:Welcome to Legally on the Move, the Lawyers Retreat Ibiza 2026, a special Legally Speaking podcast miniseries 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, well-being, 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.

0:45Gretchen Lennon: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, please. 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 um another one of my colleagues nikki her i think friend on the like another school mum had also been on the lawyers retreat last year um aurelia and again big recommendation through um through that channel as well so yeah good stuff couldn't say no yeah and you had to be here and you've been loving it ever since love it okay 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 like running small businesses but then also working on a consultancy basis means I've gotten to work with a huge variety of founder 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 okay 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 know their requirements when it comes to legal services are very different to bigger corporates.

2:41Honestly, I think they've got a higher appetite for risk because they just want to get things done. And particularly when it comes to funding lines, for example, we do a lot of that. They just want to get the deal over the line. They want the money in and they want to move on to the next thing. So we pride ourselves on taking a very commercial and pragmatic approach to the advice that we give. You spot the legal issues, you highlight the degree of risk for the client, and then you help them make a kind 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.

3:13It's important to kind of get to that point with the client in a quick way, and definitely without the 10-page advice memo that maybe you might have got from a large law firm.

3:23Gretchen Lennon:Very true. Keep it simple as best you can. Yeah, simple and quick. Yeah, exactly. Okay, so this year's retreat also touches on difficult conversations and difficult decisions. We've 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. I 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 you know like interrelations between team members these issues don't go away on their own and you know if you as a sort of leader or founder or team manager kind of try to turn a blind eye it will fester and also particularly with um like employment law and employment rights the longer you let it go on potentially the higher the value of the claim you know 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 okay 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 um i think genuinely cost-effective legal support is where the advice absolutely speaks to the crux of the client issue as succinctly and efficiently as possible.

4:55No 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, going back to the same point, what is their risk appetite? What are their commercial realities? And I think also being a kind of sort of an extension of their team, a trusted partner, a source of like um reliable advice um 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 going to charge them a fortune for it you know none of this sort of billing in six minute increments like yeah yeah 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

5:39Gretchen Lennon: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 so what is one piece of advice you would give to founders who want stronger legal foundations but without building unnecessary drag within the business oh i would say identify the right legal partner early on in your company journey i mean maybe it's lennon legal it is lennon legal 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 kind of foundational documents in place whether that's your shareholder's agreement, your standard client terms, your employment contracts, whatever it may be.

6:19And when any kind of legal issues rear their heads, don't try and DIY it. I mean, it's very tempting to sort of, you know, ask ChatGPT 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 um solution and and use the word you the headache as well yeah and that's

6:49Gretchen Lennon:partnership isn't it to your partner you know trusting them and be able to being responsive building that relationship and everything else okay before i let you go what's one idea habit or conversation you're leaving ibiza with oh i think that the me and take away from me and it that came out of one of the sessions yesterday, is just how these very small changes can really compound and incrementally kind of have a massive shift on your business, your mindset, whatever it may be. And so, yeah, 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.

7:21Gretchen Lennon:Absolutely. And it compounds, doesn't it, over time? And that momentum builds and builds and builds. Well, it's been an absolute pleasure hosting you on the Levy Seed Podcast here at NIV. 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, for now, over and out. Thank you for listening to this week's episode.

7:47Gretchen Lennon:If you like the content here, why not check out our world leading content and collaboration of 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.