Beyond the Legal Job Title: Lessons Relearned in Law on Career Choices, Discomfort and Executive Thinking

In this episode of Lessons Relearned in Law, Scott looks back across the Lessons I Learned in Law archive to explore what happens when in-house legal careers move beyond the traditional boundaries of the legal role.This recap episode brings together clips from previous guests, each offering a different perspective on how lawyers can build careers that go beyond legal advice alone. The common thread is that none of these career moves were presented as superhuman or perfectly planned. Instead, they came from deliberate choices, uncomfortable opportunities and a willingness to think more broadly about what lawyers can contribute.Scott reflects on James’s point that meaningful career change often starts with one honest question: are you in your current role because you chose it, or because it was simply the next thing available? From there, the episode turns to Pola’s lesson on choosing discomfort, and why messy, challenging work can teach lawyers more in a few months than years of routine business-as-usual activity.Finally, Jim Reid shares why senior lawyers need to step away from being the expert in every detail and start thinking like the person who runs the room. For aspiring legal leaders, the message is practical: choose deliberately, pick discomfort, and watch how your CEO operates — then try it for yourself.Resources & Links Mentioned in This EpisodeRegister your interest in joining The Lodge In-house Legal Community: https://bit.ly/TheLodgebyHBHeriot Brown: https://heriotbrown.com/Wordsmith AI: https://www.wordsmith.ai/Legal Engineering Project Application form: https://wordsmith.fillout.com/legalengprojectListen to the PodcastSpotify: [LINK]Apple Podcasts: [LINK]YouTube: [LINK]Connect with Heriot Brownhttps://heriotbrown.com/About Heriot Brown:At Heriot Brown, we help lawyers find fulfilment in their careers. Beyond recruitment, we foster a thriving community of in-house legal professionals who share insights, experiences, and growth opportunities.Enjoyed this episode? Subscribe to Lessons I Learned in Law, leave a review, and share it with someone thinking about what their legal career could become next.

Christie McCluskey is Chief Legal and People Officer at Ooni, the pizza oven and cooking products company, having joined in 2022 as its first in-house lawyer. Before Ooni, she spent almost six years at William Grant & Sons, home to brands including Glenfiddich and Balvenie whisky and Hendrick's Gin, after training and qualifying in Scotland.In this episode of Lessons I Learned in Law, Christie talks through building a legal function from scratch at a fast-growing, founder-led business, and the shift in mindset that came with moving from a 130-year-old institution to a younger, more agile one.Her three lessons: first, that legal is only one lens — good in-house lawyers give firm advice while recognising there are other legitimate factors at play, and that the job is to navigate risk rather than eliminate it entirely. Second, that it's okay to say "I don't know yet" — slowing a decision down to get it right is different from blocking it, and confidence and self-doubt can coexist productively. Third, to find your passion within the role — for Christie, that's the relationship-building that comes from sitting across every part of the business — because a sustainable legal career needs more than just the technical work.She also reflects on Ooni's growth from Scotland to Austin, Texas, and the value of building a strong network within Scotland's legal community.This episode is brought to you in partnership with Wordsmith AI — the legal AI platform built specifically for in-house teams.Resources & Links Mentioned in This EpisodeRegister your interest in joining The Lodge In-house Legal Community: https://bit.ly/TheLodgebyHBHeriot Brown: https://heriotbrown.com/Wordsmith AI: https://www.wordsmith.ai/Legal Engineering Project Application form: https://wordsmith.fillout.com/legalengprojectListen to the PodcastSpotify: https://open.spotify.com/episode/4H4tBzknDSCejrvIqKxKyiApple Podcasts: https://podcasts.apple.com/us/podcast/lessons-i-learned-in-law/id1563397804YouTube: http://www.youtube.com/@HeriotBrownInHouseRecruitmentConnect with Heriot Brownhttps://heriotbrown.com/

Umar Aziz, Partner, Chief Operating Officer and General Counsel at DG Partners, joins Scott Brown to share lessons from a career that nearly took him into shipping brokerage before a major life event brought him back to law.In this episode of Lessons I Learned in Law, Umar reflects on how personal circumstances shaped the start of his legal career, including his decision to return to Clifford Chance after initially turning down his training contract. His first lesson is that there is more to life than work. Drawing on his own experiences of loss, family responsibility and high-pressure legal environments, he discusses the importance of building a full life outside the job — and why excellence matters across work, family, friendships and personal pursuits.His second lesson comes from advice he received early in his career: learn from the best bits of the lawyers around you. Umar explains why every lawyer you work with has something worth copying — and something worth leaving behind.His final lesson challenges the idea that lawyers should always try to “win” every point. Whether negotiating with clients, managing internal teams or building long-term business relationships, Umar argues that sustainable success comes from fairness, trust and mutual respect — not squeezing every last drop out of the other side.Along the way, Umar discusses moving from litigation into funds, the transition from private practice into DG Partners, his COO and GC role, and why full-contact karate helps him stay disciplined, present and switched off from work. This episode is brought to you in partnership with Wordsmith AI — the legal AI platform built specifically for in-house teams.Guest RecommendationsSport: Full-contact karate Sauce of choice: Buffalo or curry sauce Resources & Links Mentioned in This EpisodeRegister your interest in joining The Lodge In-house Legal Community: https://bit.ly/TheLodgebyHB Heriot Brown: https://heriotbrown.com/ Wordsmith AI: https://www.wordsmith.ai/ Legal Engineering Project Application form: https://wordsmith.fillout.com/legalengproject Listen to the PodcastSpotify: https://open.spotify.com/ Apple Podcast: https://podcasts.apple.com/4 YouTube: http://www.youtube.com/Connect with Heriot Brownhttps://heriotbrown.com/ About Heriot Brown: At Heriot Brown, we help lawyers find fulfilment in their careers. Beyond recruitment, we foster a thriving community of in-house legal professionals who share insights, experiences, and growth opportunities.Enjoyed this episode? Subscribe to Lessons I Learned in Law, leave a review, and share it with someone building their career in legal leadership.Chapters: 00:00 Intro – Umar Aziz & DG Partners   03:40 Turning down Clifford Chance twice   09:28 From private practice to GC & COO   16:12 Lesson 1 – There’s more to life than work   24:03 Karate, resilience & switching off   30:08 Lesson 2 – Learn from great lawyers   34:22 Lesson 3 – Winning isn’t everything   39:55 Building long-term relationships   44:31 GC, COO & wearing multiple hats   56:42 Hot or Not, AI & closing thoughts   

Selene Brett, Chief Legal, Risk and Compliance Officer at PPRO, joins Scott Brown to share thoughtful lessons on legal leadership, humility, and how lawyers can add real value without hiding behind the mystique of the profession.In this episode of Lessons I Learned in Law, Selene reflects on her role at PPRO, a payments platform helping merchants and payment service providers connect to local payment methods around the world. With a broad remit spanning legal, risk, compliance, outsourcing and internal audit, she discusses what drew her to a business where those functions are seen as strategic enablers rather than the “business prevention unit”.Her first lesson is that lawyers are special, but not that special. Selene challenges the idea that legal teams should sit above the business as guardians of all good judgement. Instead, she argues lawyers earn their seat at the table by being approachable, constructive and genuinely useful.Her second lesson is to make it count. Senior legal roles come with influence, access and privilege — and Selene believes that creates a responsibility to use that position well, whether through difficult conversations, mentoring, or helping others find routes into the profession.Finally, she talks about gathering the nuggets: taking something meaningful from every role, every relationship and every experience, even the difficult ones. From rural Norfolk to Harvard, New York and senior in-house leadership, Selene’s story is a reminder that careers rarely move in straight lines — and that empathy, trust and agency matter just as much as technical skill. This episode is brought to you in partnership with Wordsmith AI — the legal AI platform built specifically for in-house teams.Guest RecommendationsSauce of choice for chicken nuggets: Blue cheese Event recommendation: Heriot Brown’s Charity Burns Night Resources & Links Mentioned in This EpisodeRegister your interest in joining The Lodge In-house Legal Community: https://bit.ly/TheLodgebyHB Heriot Brown: https://heriotbrown.com/ Wordsmith AI: https://www.wordsmith.ai/ Legal Engineering Project Application form: https://wordsmith.fillout.com/legalengproject Listen to the PodcastSpotify: https://open.spotify.com/ Apple Podcast: https://podcasts.apple.com/4 YouTube: http://www.youtube.com/Connect with Heriot Brownhttps://heriotbrown.com/ About Heriot Brown: At Heriot Brown, we help lawyers find fulfilment in their careers. Beyond recruitment, we foster a thriving community of in-house legal professionals who share insights, experiences, and growth opportunities.Enjoyed this episode? Subscribe to Lessons I Learned in Law, leave a review, and share it with someone building their career in legal leadership.

Jim Shaughnessy, Chief Legal Officer at DocuSign, joins Scott Brown to share lessons from more than 20 years operating at the top of global legal teams.In this episode of Lessons I Learned in Law, Jim reflects on his role leading legal at DocuSign, a business best known for e-signature and now expanding into intelligent agreement management. He explains how DocuSign is helping businesses move beyond signing documents into managing agreements more intelligently, using AI, automation and better contract visibility.Jim’s first lesson is that an in-house legal career is not always about the law. For senior lawyers, influence is everything: being in the room when important decisions are made, being sought out when the issue is broader than pure legal advice, and helping the business get important things done.His second lesson is a reminder that influence only works if it is underpinned by technical excellence. Lawyers may contribute to strategy, policy and commercial decision-making, but when the issue is legal, they need to be precise, trusted and properly prepared.Finally, Jim discusses the importance of professional identity. At every stage of a legal career, lawyers need to understand what success looks like in their role, which relationships matter most, and how to build credibility for the next step. He also shares his perspective on AI, why legal teams should embrace change, and how junior lawyers can create real impact by experimenting with new tools.This episode is brought to you in partnership with Wordsmith AI — the legal AI platform built specifically for in-house teams.Guest RecommendationsSong: Talk of the Town – The Pretenders Resources & Links Mentioned in This EpisodeRegister your interest in joining The Lodge In-house Legal Community: https://bit.ly/TheLodgebyHB Heriot Brown: https://heriotbrown.com/ Wordsmith AI: https://www.wordsmith.ai/ Legal Engineering Project Application form: https://wordsmith.fillout.com/legalengproject Listen to the Podcast Spotify: https://open.spotify.com/ Apple Podcast: https://podcasts.apple.com/4 YouTube: http://www.youtube.com/Connect with Heriot Brownhttps://heriotbrown.com/ About Heriot Brown: At Heriot Brown, we help lawyers find fulfilment in their careers. Beyond recruitment, we foster a thriving community of in-house legal professionals who share insights, experiences, and growth opportunities.Enjoyed this episode? Subscribe to Lessons I Learned in Law, leave a review, and share it with someone building their career in legal leadership.Chapters:00:00 Intro – Jim Shaughnessy & DocuSign 03:12 Beyond e-signature – DocuSign IAM 10:52 Lesson 1 – Influence matters most 18:06 Building influence as a junior lawyer 24:38 AI leadership & visibility in legal teams 29:28 Using influence at the right time 36:58 Lesson 2 – Be an excellent lawyer first 44:54 One-way vs two-way door decisions 48:43 Lesson 3 – Professional identity matters 01:01:44 Hot or Not, AI & closing thoughts  

James Ryan, Chief Legal Officer and Chief Business Officer at BioNTech, joins Scott Brown to discuss the lessons he’s learned leading through one of the most transformative periods in the biotech industry.In this episode of Lessons I Learned in Law, James reflects on his journey from scientist to lawyer, before eventually stepping into one of the most influential legal leadership roles in biotech. Joining BioNTech before it became globally recognised, he shares what it was like helping scale a fast-growing research-focused company into a world-leading biotechnology business, while navigating the intensity and pressure that came with rapid global growth and strategic partnerships, including BioNTech’s landmark collaboration with Pfizer.James’ first lesson focuses on the importance of curiosity. From scientific research to complex legal negotiations, he explains why asking better questions, understanding the client’s objectives, and genuinely engaging with the business leads to stronger advice and deeper trust.His second lesson is about objectivity. James discusses the challenge lawyers face when businesses want a particular answer — and why legal leaders must remain calm, analytical, and willing to give the advice that needs to be heard, not simply the advice others want.Finally, he talks about remembering that everyone is human. Reflecting on periods of extreme pressure and workload, James explains why approachable legal teams build stronger businesses, why mistakes need to be surfaced early rather than hidden, and why lawyers need downtime and perspective to perform at their best.Along the way, James also shares insights into:Transitioning from Chief Legal Officer into a broader Chief Business Officer role How legal teams earn influence inside high-growth businesses Why biotech companies think differently about risk The importance of relationships, curiosity, and trust in leadership How climbing helps him switch off and solve problems more effectively This episode is brought to you in partnership with Wordsmith AI — the legal AI platform built specifically for in-house teams.Guest RecommendationsFilm: Free Solo Hobby: Climbing Resources & Links Mentioned in This EpisodeRegister your interest in joining The Lodge In-house Legal Community: https://bit.ly/TheLodgebyHB ECA: https://www.cpduk.co.uk/courses/heriot-brown-executive-counsel-accelerator-eca-courseWordsmith AI: https://www.wordsmith.ai/ Listen to the PodcastSpotify: https://open.spotify.com/ Apple Podcast: https://podcasts.apple.com/4 YouTube: http://www.youtube.com/Connect with Heriot Brownhttps://heriotbrown.com/ About Heriot Brown: At Heriot Brown, we help lawyers find fulfilment in their careers. Beyond recruitment, we foster a thriving community of in-house legal professionals who share insights, experiences, and growth opportunities.Enjoyed this episode? Subscribe to Lessons I Learned in Law, leave a review, and share it with someone building their career in legal leadership.Chapters:00:00 Intro – James Ryan & BioNTech 03:22 CLO to Chief Business Officer 05:42 BioNTech before COVID 07:21 From s

Lucy Tyrrell, General Counsel at Wordsmith AI, joins Scott Brown to explore how in-house lawyers can evolve by combining legal expertise with technology, process design, and commercial thinking.In this episode of Lessons I Learned in Law, Lucy shares her journey from private practice into high-growth tech environments, culminating in her role at a fast-scaling legal AI startup backed by Index Ventures and General Catalyst. Sitting at the intersection of law and product, she offers a unique perspective on what it means to be an “AI-native” legal function—where lawyers don’t just advise the business, but actively shape how legal work is delivered.Her first lesson centres on thinking like the business. Lucy explains why legal advice cannot exist in isolation and how understanding commercial drivers—often expressed through metrics—allows lawyers to prioritise effectively and deliver more impactful guidance.Her second lesson highlights the power of networks, both internally and externally. Whether navigating uncertainty, making career decisions, or solving unfamiliar problems, she emphasises the importance of knowing who to turn to and building relationships before you need them.Finally, she focuses on curiosity—encouraging lawyers to embrace new technology, experiment with AI tools, and develop “legal engineering” skills. Rather than waiting for perfection, she advocates for a mindset of testing, learning, and iterating—mirroring how modern tech teams operate.This episode is brought to you in partnership with Wordsmith AI — the legal AI platform built specifically for in-house teams.Guest RecommendationsSong: The Chain – Fleetwood Mac Resources & Links Mentioned in This EpisodeRegister your interest in joining The Lodge In-house Legal Community: https://bit.ly/TheLodgebyHB Legal Engineering Project (Slack Community for in-house lawyers): [APPLICATION FORM LINK] Wordsmith AI: https://www.wordsmith.ai/ Listen to the PodcastSpotify: https://open.spotify.com/ Apple Podcast: https://podcasts.apple.com/4 YouTube: http://www.youtube.com/Connect with Heriot Brownhttps://heriotbrown.com/ About Heriot Brown: At Heriot Brown, we help lawyers find fulfilment in their careers. Beyond recruitment, we foster a thriving community of in-house legal professionals who share insights, experiences, and growth opportunities.Enjoyed this episode? Subscribe to Lessons I Learned in Law, leave a review, and share it with someone building their career in legal leadership.Chapters:00:00 Opening insight – Metrics, AI & modern legal roles 00:48 Scott introduces Lucy Tyrrell, GC at Wordsmith AI 03:39 Inside a legal tech business & AI-native legal teams 09:23 Lesson 1 – Think like the business 16:06 From private practice to in-house & startup life 20:48 Lesson 2 – Your network is everything 29:50 Career opportunities driven by relationships 31:31 Lesson 3 – Stay curious & embrace change 40:53 Hot or Not – KPIs, AI & legal team performance 47:21 Walk-on song, legal engineering & closing reflections 

Jonathan Wiseman, General Counsel and Chief People Officer at Ocado Retail, joins Scott Brown to share practical lessons on influence, adaptability, and building a truly commercial legal career.In this episode of Lessons I Learned in Law, Jonathan reflects on his dual role leading both legal and people functions within a fast-growing retail joint venture between Ocado and Marks & Spencer. He shares why the most effective in-house lawyers don’t stay confined to their “legal lane,” but instead operate confidently in the grey areas between legal risk, commercial decision-making, and broader business strategy.Jonathan’s second lesson centres on career progression—encouraging lawyers to take opportunities when they arise, even when they don’t perfectly align with a pre-defined plan. He candidly discusses his initial hesitation in stepping into a Chief People Officer role and how that decision ultimately expanded his leadership capability and perspective.His final insight focuses on commercial judgement. Rather than trying to “win” every legal point, he explains why the best long-term outcomes come from building sustainable relationships and balancing legal precision with business reality. It’s a reminder that success in-house is as much about collaboration and trust as it is about technical expertise.Listeners also get a glimpse into Jonathan’s personal side, from navigating music choices on family car journeys to his reflections on how AI is already reshaping both legal and HR functions.This episode is brought to you in partnership with Wordsmith AI — the legal AI platform built specifically for in-house teams.Wordsmith Legal AIGuest RecommendationsSong: Waterloo Sunset – The Kinks Resources & Links Mentioned in This EpisodeRegister your interest in joining The Lodge In-house Legal Community: https://bit.ly/TheLodgebyHB Listen to the PodcastSpotify: https://open.spotify.com/ Apple Podcast: https://podcasts.apple.com/4 YouTube: http://www.youtube.com/Connect with Heriot Brownhttps://heriotbrown.com/ About Heriot Brown: At Heriot Brown, we help lawyers find fulfilment in their careers. Beyond recruitment, we foster a thriving community of in-house legal professionals who share insights, experiences, and growth opportunities.Enjoyed this episode? Subscribe to Lessons I Learned in Law, leave a review, and share it with someone building their career in legal leadership.Chapters00:00 Opening insight – AI, judgment & modern legal roles 00:56 Scott introduces Jonathan Wiseman, GC & CPO Ocado Retail 03:13 The dual role – Legal, HR & executive leadership 07:04 Lesson 1 – Don’t stay in your swim lane 12:57 Developing commercial thinking in lawyers 19:09 Lesson 2 – Take opportunities (even if they don’t fit the plan) 24:22 Leading people, culture & HR at exec level 34:54 Lesson 3 – The best deal isn’t always the right deal 40:32 Hot or Not – AI, legal value & the role of GC 47:24 Walk-on song, music & closing reflections  

Episode 100: Perspective, Candour, and Strategic Leadership — Rachel Canham, Rentokil Initial In the 100th episode of Lessons I Learned in Law, Rachel Canham, Group General Counsel and Company Secretary at Rentokil Initial, reflects on what it actually takes to operate as a strategic leader at executive level — across a legal function of around 70 lawyers spanning 90 countries. Rachel stepped into her first "top seat" role after a career that took her from private practice through senior in-house roles, and the shift required more than technical excellence. It required a change in mindset and responsibility that she's still refining. Three lessons shape the conversation:Perspective. Shaped by personal adversity, Rachel explains why the best lawyers in a crisis aren't the ones who panic, but the ones who can zoom out and make balanced decisions when the stakes are highest. Calm, objective, clear-headed — and aware that most things are less catastrophic than they first appear.Candour. Rachel makes the case that candour is one of the most underrated qualities at senior leadership level — but only works if you've done the groundwork. Building trust, credibility, and human connection first is what earns you the right to be honest later, even when the message isn't well received.Strategic leadership. Rachel pushes back on the familiar "business partner" framing for in-house lawyers. Her view: lawyers shouldn't be partnering from the sidelines. They should be embedded in decision-making, contributing beyond legal advice, and taking an active role in delivering strategy.Rachel was recorded the same day she addressed the haggis at our Charity General Counsel Burns Supper — in a style I'm unlikely to forget. Genuinely grateful she agreed to be the 100th guest.About the guest Rachel Canham is Group General Counsel and Company Secretary at Rentokil Initial, the FTSE-listed pest control and hygiene services business. She leads a global legal function of around 70 lawyers across 90 countries and sits on the company's executive team.Guest recommendation Song: Belter — Gerry CinnamonResources mentioned Register your interest in The Lodge, Heriot Brown's in-house legal community: https://bit.ly/TheLodgebyHBGive us a Follow! Spotify: https://open.spotify.com/ Apple Podcast: https://podcasts.apple.com/4 YouTube: http://www.youtube.com/About the show Lessons I Learned in Law is the podcast from Heriot Brown, the specialist in-house legal recruitment firm. Host Scott Brown sits down with senior in-house lawyers to hear how they got where they are, what they wish they'd known, and what they're still trying to figure out. This episode is produced in partnership with Wordsmith — the legal AI platform built for in-house teams. Find more at heriotbrown.com.00:00 Opening insight – The courage to be candid 01:13 Scott introduces Rachel Canham, GC Rentokil Initial 04:48 Stepping into the GC role & executive leadership 10:06 Lesson 1 – Perspective shapes better judgment 17:07 Lesson 2 – The power of candour in leadership 24:50 Lesson 3 – From business partner to strategic leader 30:18 Building commercial thinking & executive presence 33:38 Hot or Not – AI, legal leadership & career positioning 43:36 Personal brand, visibility & standing out as a lawyer 44:54 Walk-on so

Dean Nash, Global Chief Operating Officer for Legal at Banco Santander, joins Scott Brown to share practical leadership lessons from operating at scale within one of the world’s largest legal functions.In this episode of Lessons I Learned in Law, Dean reflects on his move away from the traditional General Counsel path into a newly created global operations role focused on transforming a 1,700-lawyer legal organisation. His first lesson centres on identifying and leaning into your unique strengths. Rather than obsessing over weaknesses, he explains how recognising what genuinely gives you energy can unlock unexpected career opportunities and shape more fulfilling leadership paths.Dean’s second lesson is grounded in execution: learning to create momentum and “get things done” in environments that often reward over-analysis. Drawing on experiences in early-stage fintech and global banking, he explores how in-house lawyers can think more commercially by treating legal support as a product that helps businesses grow while managing risk.His final reflection highlights the importance of maintaining interests beyond the day job. By building perspective and protecting personal identity from becoming too tied to professional roles, he argues that lawyers can remain clearer-headed advisers and more resilient leaders.Guest Recommendations:Book: Good to Great by Jim Collins Podcast: The Tim Ferriss Show Resources & Links Mentioned in This EpisodeExecutive Counsel Accelerator (ECA): https://www.cpduk.co.uk/courses/heriot-brown-executive-counsel-accelerator-eca-course The Lodge In-house Legal Community: https://forms.office.com/e/Pq7Uyv8xnS The Lodge In-house Legal Community: https://bit.ly/TheLodgebyHB Connect with Heriot Brownhttps://heriotbrown.com/ Give us a follow·       Spotify: https://lnkd.in/er928hqJ·       Apple Podcast: https://lnkd.in/ea6Y4JYy·       YouTube: https://lnkd.in/eAeMvrgzAbout Heriot Brown: At Heriot Brown, we help lawyers find fulfilment in their careers. Beyond recruitment, we foster a thriving community of in-house legal professionals who share insights, experiences, and growth opportunities.Enjoyed this episode? Subscribe to Lessons I Learned in Law, leave a review, and share it with colleagues growing their careers in legal leadership.Episode Chapters:00:00 Opening insight – Creating momentum in business 00:56 Scott introduces Dean Nash, COO Legal at Santander 03:00 Global legal operations role & transformation remit 08:37 Lesson 1 – Lean into your unique selling point 18:14 Lesson 2 – Get shit done & create commercial momentum 21:03 Helping the business make money faster – in-house mindset 25:52 Lesson 3 – Don’t let your identity become your job title 30:18 Did I Say This? – leadership quotes & light-hearted debate 32:29 AI governance, advisory roles & future of legal leadership 35:52 Book, podcast & walk-on song reflections