Explore every episode of the podcast Lawyer to Leader
| Title | Pub. Date | Duration | |
|---|---|---|---|
| Running a Modern Law Practice in the AI Era (ft. Dylan Gibbs) | 19 May 2026 | 00:47:01 | |
Episode Introduction Most 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 Bio Dylan 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
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| Building a Speak-Up Culture for Lawyers (ft. Stephen (Shed) Shedletzky) | 19 May 2026 | 00:49:26 | |
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
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| From Google to Nonprofit Chef: One Engineer's Search for a Life of Purpose (ft. Chris Ito) | 19 May 2026 | 01:18:10 | |
Episode Introduction Most 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 Bio Chris 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
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| The Power of Curiosity: Why the Best Lawyers Ask More & Answer Less ft. Rebecca Hockin | 05 Jun 2026 | 00:55:45 | |
Episode Introduction Most 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 Bio Rebecca 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] - Close Key Takeaways Staying 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 Material Find Rebecca at recreativecoaching.ca and on LinkedIn Tomorrow and Tomorrow and Tomorrow by Gabrielle Zevin Four Thousand Weeks by Oliver Burkeman If this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.com Shareable Moments Lines 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." | |||
| Courage, Entrepreneurship & Boundaries: Building a Law Firm Young (Featuring Sevana Poladian) | 07 Aug 2026 | 00:37:28 | |
Most lawyers build a career to check boxes: prestigious firm, litigation wins, a steady climb. Sevana Poladian checked those boxes too, then built something of her own. In this episode, Jonathan Cullen talks with the Montreal litigator about launching a solo practice in the middle of COVID, why she chose to partner up years later instead of staying independent, and how she's learned to say no to the wrong clients. This is a story about building a practice on her own terms, one boundary at a time. If you've ever wondered whether going out on your own is worth the risk, this episode is for you. Guest Bio Sevana Poladian built the kind of legal career most young lawyers dream about. She started at smaller firms then, moved into a larger litigation firm before eventually going out on her own. Today she's co-founder of Rastani Poladian Légal, a Montreal firm she launched with Camaylia Tavakol Rastani, pairing her civil and commercial litigation expertise with Camaylia's criminal law practice to serve clients across Quebec. She's also co-chair of the Armenian Bar Association's Québec chapter, where she supports Armenian lawyers and students. Timestamps 00:00 Show intro 00:55 Meet Sevana 02:41 Starting out in litigation 04:07 How litigation builds confidence under pressure 06:44 The leap to solo practice during COVID 08:01 The entrepreneurial skills law school never teaches 10:52 Wearing every hat in a solo practice 13:33 Should young lawyers start their own firm early? 15:51 Why she decided to partner up 17:45 Building Rastani Poladian Légal 19:57 Two practices, one culture 21:02 Spotting client red flags 25:21 Her ideal client today 25:49 Leading the Armenian Bar Association 27:31 Boundaries and balance 30:49 Defining success on her own terms 31:42 Rapid fire 33:46 Closing thanks and where to find Sevana 35:19 Outro and takeaways Key Takeaways Litigation is training for entrepreneurship. Years of thinking on her feet and staying calm under pressure in court gave Sevana the exact muscles she needed to run a business. The leap doesn't need perfect timing. Sevana launched her solo practice in the middle of COVID, after a personal awakening, not once things felt "ready." Running a firm takes a different skill set than practicing law. Resilience, risk tolerance, empathy, and leadership matter as much as legal knowledge, and none of it gets taught in law school. Wearing every hat is a phase, not a permanent job description. The growth comes from learning to delegate and finding mentors who've done it before you. Partnering up can cure the loneliest part of solo practice. Joining forces with Camaylia in 2026 wasn't about needing legal help. It was about growth, and no longer building alone. Selectivity is a skill you build over time. Sevana has learned to spot client red flags early and has gotten comfortable turning down work that isn't the right fit. Success isn't a title or a verdict. For Sevana, it's inner peace. Links Sevana on LinkedIn: https://www.linkedin.com/in/sevana-poladian-b70b2b128/ Rastani Poladian Légal: info@rplegal.ca Recommended show: The Good Wife If this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.com Shareable Moments "I don't consider age as a factor anymore. A case can be won solely on the strength of the case, not the person handling it." "I'd already proved to myself I could do it alone. So why not do it with someone else?" "Nobody knows everything in this world, including lawyers." "There must be a point where you draw a line, build a wall between yourself and your clients." "Success to me looks like inner peace. There's a constant inner peace knowing that whatever decisions you make are the right ones." "Nothing is guaranteed in life, not even the judge you get. About 95% of cases settle amicably." "One word young lawyers need more of? Patience. Not just young lawyers, everybody, especially in litigation." | |||
| The High Pain Threshold: Why Lawyers Miss Their Own Warning Signs (Featuring Allison Canton) | 04 Aug 2026 | 00:49:38 | |
Episode Introduction In this episode, Jonathan Cullen talks with Allison Canton about what it actually looked like to unravel while succeeding, why lawyers have such a high tolerance for their own misery, and how she rebuilt her life through small experiments instead of one dramatic exit. They also get into sleep, boundaries, and why "don't overthink it" might be the most useful advice a lawyer can hear. Guest Bio Allison Canton spent years checking every box on the traditional success list. Harvard Law. BigLaw. General Counsel at high-growth startups, where she scaled legal teams through hypergrowth and a multi-billion-dollar acquisition. Then came the uncomfortable realization: the work she excelled at was also making her miserable. She didn't leave the law. She rebuilt her relationship with it. Today, Allison is a Senior Advisor at Markups.ai, where she helps legal teams use AI to move from contract processors to strategic partners. And through her new project Fit to Practice, she teaches entertaining, practical and data-backed CLE programs to help high-achieving lawyers protect their most valuable asset: their wellbeing. She also writes and podcasts about ambition, meaning, and life after chasing gold stars on her Substack, Practically on Purpose. Timestamps [00:00] - Dream job misery [00:45] - The sleep deprivation trap [01:39] - Podcast intro [02:20] - Allison's story, and how she almost became a sociology PhD instead [04:37] - 1L anxiety and not sleeping for days at a time [07:58] - How a sleep meditation search became a 15-year practice [09:24] - BigLaw reality check: they're buying 100% of your time [12:08] - The leap to Flatiron Health as employee number two [16:02] - Hypergrowth and the breaking point [19:29] - Leaving to heal, and getting pregnant three weeks later [22:16] - Rediscovering the self she'd cut off to fit the mold [24:30] - The identity box: why her lawyer friend won't publish her books under her own name [25:20] - The small experiments mindset [26:02] - Testing meditation teaching in her own backyard before building anything bigger [30:01] - The alarm bells lawyers miss: impatience, dread, a tight throat [33:05] - Rebuilding a legal life: advising, investing, and stepping back from GC-level weight [38:39] - Making wellness data-backed for a skeptical audience [43:30] - Redefining success [46:10] - Rapid fire [48:31] - Where to follow Allison Key Takeaways Lawyers have a dangerously high pain threshold. Allison didn't notice she was unraveling until she was snapping at her three-year-old and journaling "I hate this" at 3am. The signs were there long before she acted on them. You don't need 100% of your fulfillment from your job. Allison's advice: find one small thing outside of work, a ceramics class, a walk, whatever it is, before you try to overhaul your whole career. Small experiments beat big plans. Instead of quitting to become a meditation teacher, she offered one free session in her backyard and asked for feedback. Lawyers tend to over-engineer the thing before they even know if they want it. Sleep is non-negotiable, not a nice-to-have. Being chronically underslept is functionally like being drunk, and most lawyers would never practice law drunk. Allison holds a hard boundary now: in bed by 9 or 10, no exceptions. Don't overthink the decision. Lawyers are trained to argue both sides, which means they can talk themselves into staying in something that's making them miserable. Trust your gut first, then use the analytical skills to execute. Links Allison on LinkedIn: linkedin.com/in/allisoncanton Fit to Practice CLE: fittopractice.law Practically on Purpose Substack: Allisonalliecanton.substack.com Recommended book: Designing Your Life by Bill Burnett and Dave Evans If this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.com Shareable Moments "I don't want to do this." "We're really good at coming up with plans and following plans." "Don't let analytical reason run rampant." "That's the thing I always compromised on." "This life, even as a lawyer, can be a playground." | |||