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Lawyer to Leader

Lawyer to Leader

Von: 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
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  • 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 Min.
  • 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."
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    49 Min.
  • From Google to Nonprofit Chef: One Engineer's Search for a Life of Purpose (ft. Chris Ito)

    From Google to Nonprofit Chef: One Engineer's Search for a Life of Purpose (ft. Chris Ito)
    May 19 2026
    Episode IntroductionMost lawyers are taught to stay on the path. Build the credentials, climb the ladder, collect the titles. But there’s another way, and sometimes it’s good to look outside the professional for a model. Chris Ito did all of that, and then walked away from every bit of it. In this episode, Jonathan Cullen sits down with his oldest friend, a Stanford and Google engineer turned chef and nonprofit leader, to talk about what it actually feels like to leave a life that looks great on paper but doesn't fit who you are. This isn't a story about quitting. It's a story about listening, about the signals your life keeps sending you, and what happens when you finally decide to follow them. If you've ever looked at the person above you and thought "I'm not sure I want that job," this episode is for you.Guest BioChris Ito is a former software engineer, Stanford graduate, and PhD in electrical and computer engineering who spent years at Google and Facebook in Silicon Valley before following a completely different calling. In 2021, he enrolled at the Culinary Institute of America in Napa, left tech, and became a chef. He also served as president of Hope's Corner, a nonprofit providing free meals and services to those in need in Mountain View, California. In 2024, Chris returned to Canada and became a food recovery chef at A Better Life Foundation in Vancouver, where the team recovers unwanted food from grocery stores and produces around 300 meals a day for people in need on the Downtown Eastside. Chris lives in North Vancouver with his wife and their two kids.Timestamps[00:00] - Opening: walking a high wire with no net[01:01] - Podcast intro and guest introduction[03:55] - A prescribed plan: medicine, engineering, & a rejection that opened it all[07:00] - Escaping the rails: how Chris navigated pressure to follow a prestigious track[09:55] - Stanford, Silicon Valley, and pulling on threads[13:20] - How to balance curiosity with focus[15:30] - Life in Silicon Valley: Google, satellites, and the moment Elon Musk walked in[20:45] - The Starlink decision: why Chris said no[23:30] - Google Home, factories in Vietnam, and a growing sense of misalignment[25:00] - "Be the hero of your own life": the David Copperfield moment[26:30] - From Google to Facebook's social impact team: moving toward the feeling[29:00] - Hope's Corner: volunteering with his son and planting a new seed[32:00] - The Culinary Institute of America: an Uber ride & a "why not now?"[36:00] - Going back to school at 44, surrounded by 24-year-olds[37:00] - Terror in a Michelin Star kitchen: the "show up today" post-it note[39:00] - "I don't know where I'm going, but I know exactly how to get there"[40:00] - The Elon Mansion to the Airstream trailer: moments of doubt[43:00] - When it takes too long to decide, you already know the answer[45:00] - Moving back to Canada: a glass of wine, a question, & a 9:34 PM phone call[52:30] - Finding A Better Life Foundation: the dinner that felt like a lightning bolt[57:30] - From dinner guest to volunteer to chef: how it all came together[1:01:00] - Service, mastery, and where real meaning lives[1:02:00] - For people who feel stuck: you don't have to make a dramatic change[1:08:00] - Showing your kids you can reinvent yourself[1:13:00] - Rapid fire questions[1:17:00] - Closing and call to actionKey TakeawaysDon't think about the safety net. Chris's philosophy is to walk the high wire without one. When you keep a fallback in mind, you're not fully committing, and you're not giving yourself the best shot.Signals are everywhere if you listen. What you read voluntarily, who you admire, how you feel when someone asks what you do. These aren't random. They're pointing somewhere.The path analogy: walk it as far as it goes, and when it ends or forks, turn. Time on one path is never wasted. You bring everything with you.If a decision is taking you weeks to make, you probably already know the answer. Your head is just trying to talk you out of what your heart already knows.You don't have to make a dramatic change. Dip a toe in. Volunteer. Take a class. Move toward the feeling in small steps. The universe tends to open up once you start moving.The body keeps score. It never lies. If something is out of alignment, your body will tell you before your mind catches up. Listen to the whisper before it becomes a pile of bricks.Showing your kids you can reinvent yourself is one of the most powerful things you can do as a parent. Chris's move, and Jonathan's own career shift, both landed with their kids without a single objection.The overlap of service and mastery is where real meaning lives. When you're giving your best skills to something that genuinely matters to you, that's where the magic is.LinksA Better Life Foundation - Chris's current home base in VancouverThe Lion Tracker's Guide to Life by Boyd Varty - Chris's top book recommendationFree Lawyer to Leader AssessmentIf this episode stuck with you, here's where ...
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    1 Std. und 18 Min.
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