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Lawyer to Leader

Lawyer to Leader

By: Jonathan Cullen
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This show is built around a single question: why do technically brilliant lawyers so rarely break through as strategic leaders? The answer is simpler and more uncomfortable than most lawyers expect: technical excellence is the entry ticket, not the destination. The Lawyer to Leader is the podcast for driven attorneys who have mastered the law and are ready to master the room, the strategy, and the career that follows. I'm Jonathan Cullen, award-winning former General Counsel and certified Leadership & Performance coach. I've spent nearly two decades in legal leadership, and I built this show for the lawyer who wants more. More progress. More influence. More life. Start here: grab your free Lawyer to Leader Assessment at jonathancullencoaching.com and find the one thing holding your career back.Copyright 2026 Jonathan Cullen Career Success Economics Personal Development Personal Success
Episodes
  • The Power of Curiosity: Why the Best Lawyers Ask More & Answer Less ft. Rebecca Hockin

    The Power of Curiosity: Why the Best Lawyers Ask More & Answer Less ft. Rebecca Hockin
    Jun 5 2026
    Episode IntroductionMost lawyers are trained to have the answer. To advise, fix, and move on. Rebecca Hockin spent years doing exactly that. She was good at it. But something kept drawing her in a different direction. In this episode, Jonathan Cullen talks with Rebecca about what happened when she started pulling on that thread, how she built a practice that's part lawyer, part coach, entirely on her own, and why curiosity might be the most underrated skill in the legal profession. If you've ever wondered whether there's a version of your career that's both successful and sustainable, this one's for you.Guest BioRebecca is a commercial lawyer who is also trained as an executive coach. She's based in Vancouver, British Columbia. Rebecca has worked both in private practice at a national firm and in-house on global legal teams. She currently practices law as a fractional in-house counsel, where she brings her legal, leadership, and coaching experience to legal and business teams. She also coaches and mentors other lawyers to help them create rewarding and sustainable law practices.Timestamps[00:00] - Opening[01:01] - Podcast intro and guest introduction[03:00] - Why Rebecca always wanted to be a lawyer[05:00] - Psychology: how it shaped everything[07:00] - Finding work that felt like being part of something[10:00] - How a broad practice prepared her for in-house work[11:00] - The moment that broke her out: burnout, a friend's loss, and three days of vacation[13:00] - What surprised her most about going in-house: the point of the legal work[14:00] - Working directly with the business and what it unlocked[15:00] - The feedback shift: from "firm lawyer" to "commercial and practical"[17:00] - How she actually learned to be commercial: site visits, questions, and proximity[20:00] - The Center for Creative Leadership, and a new pull[21:00] - "I don't know what this is, but I want to do it": finding coaching[24:00] - The decision to leave in-house and give coaching a real shot[25:00] - Discovering she still loved practicing law, just differently[26:00] - How the fractional model came together[27:00] - Five coaching skills that made her a better lawyer[30:00] - Why more lawyers should learn coaching[33:00] - The identity shift from advisor to coach: "I don't have to be a lawyer here"[36:00] - What creativity actually means for lawyers[39:00] - Greenhousing: letting things grow before you cut them[41:00] - Safe but not always comfortable: how coaching creates growth[43:00] - The relationship with time and what lawyers get wrong[45:00] - Protect your life outside of work[46:00] - Sleep, routines, & why constraints make you more effective[50:00] - Rapid fire[53:00] - CloseKey TakeawaysStaying broad isn't a weakness. Rebecca resisted over-specializing in private practice, and it's what made her so effective in-house. Adaptability, pattern recognition, and knowing how to figure things out: those compound over time.The signals don't always announce themselves. Rebecca's move toward coaching wasn't a plan, it was a pull. Psychology in undergrad. A leadership course that made her think, "How can I do this?" It all connected later.Burnout rarely announces itself. But back at the office after the kids went to bed, running on empty, a close friend hit with loss, three days of vacation that cracked it open. That's what it looked like. And it led to the best decision she ever made.Coaching and advising pull in opposite directions. Lawyers are trained to have the answer. Coaching asks you to hold back. Rebecca describes it as taking off one hat and putting on another. The relief she felt, discovering she didn't have to advise, tells you everything about how heavy that hat was.Constraints make you more efficient. Having to leave at a certain time to pick up her kids forced Rebecca to use her time better. The boundary wasn't the problem, it was the solution.Links and MaterialFind Rebecca at recreativecoaching.ca and on LinkedInTomorrow and Tomorrow and Tomorrow by Gabrielle ZevinFour Thousand Weeks by Oliver BurkemanIf this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.comShareable MomentsLines worth pulling for social:"I stayed very broad and did a lot of different things. That's not usually the recommendation, but it worked out really well for me.""What hit me really early on was the point of the legal work. Oh, we're doing this because we have to sell this. This is how we make money.""I had to create it for myself first. I built a coaching practice to help other lawyers, but really I just needed that for myself.""I remember having this realization: I don't have to be a lawyer here.""Safe but not always comfortable. That's what leads to growth.""Foundational things like sleep, hydration, exercise. I have a lot of energy. I have to get it out so I'm not getting it out every time I talk to a client."
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    56 mins
  • Running a Modern Law Practice in the AI Era (ft. Dylan Gibbs)

    Running a Modern Law Practice in the AI Era (ft. Dylan Gibbs)
    May 19 2026
    Episode IntroductionMost lawyers are trained to work alone, grind through problems in silence, and figure out their careers by watching the person above them. Dylan Gibbs saw that model up close, from the Supreme Court of Canada to national litigation firms, and decided there had to be a better way. In this episode, Jonathan Cullen sits down with Dylan, founder of Inn Laws, to talk about why lawyers are so isolated, what happens when you give them a real space to compare notes, and why AI is no longer something you can afford to put off. If you've ever felt like you were guessing at how your career actually works, this episode is for you.Guest BioDylan Gibbs is the founder of Inn Laws, a private community for Canadian lawyers who want to move the profession forward instead of waiting to see where it goes. Members are building modern firms, rethinking client service in the AI era, and taking an intentional approach to growing their practices.Before Inn Laws, Dylan clerked at the Supreme Court of Canada and litigated at national firms. He started Inn Laws after seeing that the next generation of legal leaders didn't have a place to get together, exchange ideas, and learn the things they don't teach in law school.Timestamps[00:00] - Newsletter to business: the bet most lawyers thought was crazy[00:59] - Podcast intro and guest introduction[02:53] - Dylan's origin story: from software developer to Supreme Court clerk[03:55] - What clerkship and big law actually taught him[08:09] - Burnout, perfectionism, and tech frustration: the breaking point[11:47] - Going all in on the newsletter[14:30] - Finding a writing voice that didn't sound like a law firm blog[17:09] - What was missing in the Canadian legal information space[18:46] - How the peer group concept was born[19:36] - What networking looked like pre and post-COVID[20:35] - Building a community lawyers actually want to be part of[21:52] - How membership works day to day[25:26] - How Dylan matches lawyers into peer groups[27:36] - Trust, confidentiality, and the Chatham House rule[30:43] - What transformation actually looks like in the groups[33:16] - Individual vs. firm buy-in: who gets the most out of it[34:47] - AI challenges in law: the turning point that changed everything[41:35] - Where Inn Laws is going: quality over scale[43:39] - Rapid fire questions[44:44] - Leadership and AI: what today's leaders need to understand[46:14] - Closing and call to actionKey TakeawaysThe peer group model works because it's forced in the best way. Everyone has bought in, the agenda is built from real problems, and the confidentiality holds. That's what creates the space for honest conversation.Lawyers consistently hedge before sharing a problem in a group setting: "This might not be relevant" or "Don't worry about this one." It almost always turns out to be the thing everyone else is dealing with too.The newsletter success formula: people think they want to read about work, but what they actually want is entertainment. If it also happens to be educational, even better.Burnout in law often hits the best people hardest. When you're a perfectionist in a profession that rewards thoroughness, the work expands to fill every available hour. Good work earns more work.AI is no longer an admin tool. Since late 2024, lawyers are asking how to use it for substantive work, not just toning down emails. The lawyers who figure this out first are building a real advantage.The 20-hour problem: Dylan's observation that the bulleted notes from an hour of research were often 90% of the final memo, and the remaining 20 hours were just turning it into something deliverable. That's exactly what AI can compress.Buy-in matters more than firm support. The members who get the most out of Inn Laws are the ones who pay for it themselves, or at least feel personally invested. When it's just another employer-funded benefit, the commitment isn't the same.Today's legal leaders need a concrete answer to: how am I using AI, and how am I helping my team use it? That's not optional anymore.LinksInn Laws - Dylan's community for Canadian lawyersDylan on LinkedInFree Lawyer to Leader AssessmentIf this episode is still on your mind, here's where to go next:Take the free assessment. Find the one thing holding your leadership back at jonathancullencoaching.comFollow the show. Apple Podcasts, Spotify, and YouTube. It helps more lawyers find this content.Share this episode. If you know a lawyer who's grinding through their career alone and wondering why it's so hard, send them this one.Shareable MomentsLines worth pulling for social:"Do good work and your reward is more work. That's the trap.""We're not running a webinar. We're getting lawyers in a room to talk about the problems they can't ask about anywhere else.""The lawyers I was working for, I looked at their jobs and thought: if that's the reward, I'm not sure I want it.""When I say lawyer, I think: tired. But you don't have to be.""Today's leaders know ...
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    47 mins
  • Building a Speak-Up Culture for Lawyers (ft. Stephen (Shed) Shedletzky)

    Building a Speak-Up Culture for Lawyers (ft. Stephen (Shed) Shedletzky)
    May 19 2026

    Episode Introduction

    Most lawyers are trained to have the right answer. Stephen (Shed) Shedletzky argues that the most powerful thing a leader can do is ask the right question and then actually listen. In this episode, Jonathan Cullen sits down with leadership expert Shed Shedletzky to unpack why speak-up culture isn't a "nice to have, it's the difference between a team that performs and one that quietly fails. If you've ever wondered why smart people in your organization stay silent, this episode will tell you exactly why, and exactly what to do about it.

    Guest Bio

    Stephen (Shed) Shedletzky is a leadership expert, keynote speaker, host of the Shed Some Light podcast and author of Speak-Up Culture: When Leaders Truly Listen, People Step Up. A former Head of Brand & Communications at Simon Sinek Inc., Shed has spent his career helping leaders build environments where people feel both psychologically safe and genuinely motivated to speak up. He works with organizations worldwide on the connection between culture, trust, and performance.

    Timestamps

    • [00:00] - The pickle jar culture metaphor
    • [00:54] - Podcast intro
    • [01:54] - Meet Shed
    • [04:28] - What does "speak up culture" actually mean?
    • [07:21] - Why silence is killing your team
    • [10:14] - Culture is local - your team is your culture
    • [12:24] - Vulnerability with context
    • [17:27] - Soft skills aren't soft - they're career-defining
    • [23:10] - Why work is not family (and what it should be instead)
    • [26:41] - Designing meetings that include introverts
    • [32:27] - Leading from any seat - without formal authority
    • [38:50] - Curiosity and context in client service
    • [45:49] - Rapid fire wrap-up
    • [49:12] - Outro

    Key Takeaways

    • Culture isn't set at the top of the organization, it's local. Your immediate team is the culture you can actually control and change.
    • The "pickle jar" metaphor: you absorb the environment you're placed in. Leaders set the brine.
    • Speak-up culture requires two conditions: psychological safety and genuine worth. People need to feel safe and believe their voice will matter.
    • Vulnerability without context is just noise. Leaders need to share struggles in ways that inform and build trust, not create anxiety.
    • Soft skills are the hard skills. The technical work gets you hired. The so-called soft skills determine how far you go.
    • Rubber ball vs. glass jar: not all mistakes are equal. Design your learning environments to match the stakes.
    • Inclusive meetings aren't accidental -pre-reads, deliberate silence, and inviting quieter voices are leadership choices.
    • Mandela's lesson: meet in a circle, speak last. Position and posture both signal whether you actually want input.
    • Curiosity is a client service strategy. Lawyers who ask better questions build better relationships.

    Links

    • Speak-Up Culture: When Leaders Truly Listen, People Step Up by Stephen
    • Shed on Substack
    • Free Lawyer to Leader Assessment

    If today's conversation is still rattling around in your head, that's a good sign. Here's where to go next:

    • Take the free assessment. Find the one thing holding your leadership back at jonathancullencoaching.com
    • Follow the show. Apple Podcasts, Spotify, and YouTube. It helps more lawyers find this content.
    • Share this episode. If you know a lawyer who stays quiet in rooms they should be leading, send them this one.

    Shareable Moments

    Lines worth pulling for social:

    • "Soft skills aren't soft. They're the skills that determine how far you go."
    • "Culture isn't set at the top. It's local. Your team is your culture."
    • "People don't speak up when they don't feel safe or when they don't believe it's worth it."
    • "The pickle jar doesn't care what kind of pickle you were before you went in."
    Show More Show Less
    49 mins
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