Pola Karolczyk, General Counsel and Chief People Officer at Cowboy, joins Scott to share her dynamic legal journey: from competition law in Poland and US law firms, to regulatory work at Apple, and now building the legal and people functions at a fast-moving e-bike scaleup.

Pola reflects on three powerful lessons, beginning with the need to ditch legal jargon and speak human. She learned early on that most people, especially in business, aren’t interested in the mechanics of the law, just the outcome. This mindset has shaped her ability to communicate clearly, deliver pragmatic advice, and influence senior stakeholders across borders.

She also highlights the importance of developing leadership and commercial skills outside the comfort zone of technical legal work, drawing on her experiences in Big Law, Apple, and now Cowboy. Pola’s final lesson is one for ambitious lawyers: if you want to lead, don’t wait for calm conditions. Join a scaleup, stretch yourself, and learn on the edge.

Now wearing dual hats in legal and HR, Pola offers rare insight into what it means to shape culture and governance in parallel, and why reporting directly to the CEO matters.

Guest Recommendation:
• Podcast: Impact Theory with Tom Bilyeu - Practical strategies for personal and professional growth

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, or share it with someone navigating the leap into leadership.

🎧 Enjoyed this episode? Subscribe to Lessons I Learned in Law, leave a review, or share it with someone navigating the leap into leadership.

Tara Haig, General Counsel at Multiverse, joins Scott to reflect on a legal career driven by curiosity, courage, and instinct. From saying yes to opening a New York office two years post-qualification to leading legal, privacy, and governance for one of the UK’s most prominent edtech scale-ups, Tara’s story is all about leaning into discomfort, and figuring it out along the way.

Now part of the exec team at Multiverse, a $1.7B AI-powered apprenticeship platform, Tara shares her take on three big lessons: embracing stretch opportunities (even when terrifying), understanding the commercial engine behind your business, and showing up with authenticity. Whether it’s tackling GDPR in lockdown, raising a SPAC, or managing legal complexity across Series A to D growth, she’s built a legal career that’s anything but linear.

This episode is a must-listen for anyone navigating scale-up chaos, growing their team, or trying to stay grounded while building something big. Tara also shares candid reflections on working from Kenya, raising twins, and why perspective, and permission to say no, is as important as saying yes.

Guest Recommendations:
• Book: Invisible Women by Caroline Criado Perez
• Podcast: Pivot with Kara Swisher & Scott Galloway
• Podcast: The Rest is Politics

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 us a review, or share it with a lawyer navigating the scale-up world.

Shelley McKinley, Chief Legal Officer at GitHub and Vice President at Microsoft, joins Scott to share career-defining lessons from two decades at the sharp edge of tech, innovation, and regulation.

Now leading GitHub’s global legal, policy, and trust teams, Shelley offers a behind-the-scenes look at the early days of GitHub Copilot, launched before ChatGPT put generative AI on the map, and shares what it really means to advise on emerging technology when the law hasn’t caught up yet. She talks candidly about navigating ambiguity, making smart bets in fast-moving industries, and how the best legal advice can’t be given in a vacuum.

Shelley’s lessons cover how to lead in-house teams with the right mix of legal and non-legal expertise, how to focus on high-impact work in a sea of meetings, and why building strong internal networks is a non-negotiable skill for modern legal leaders. Her reflections are sharp, grounded, and refreshingly honest, touching on everything from grunge music to paralegal strategy, Microsoft’s legal transformation, and the FUD-to-FOMO evolution of AI.

Guest Recommendations:
• Podcast: Acquired — Particularly the Spotify and Microsoft episodes
• Book: The Meditating Mother by Laura Kopchick — A quirky short story collection written by Shelley’s college friend (https://www.amazon.com/Meditating-Mother-Laura-Kopchick/dp/1962148157)

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, or share it with someone curious about leading in tech, AI, or global legal teams.