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.
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Running a Modern Law Practice in the AI Era (ft. Dylan Gibbs)
Season 1 · Episode 3
Tuesday, May 19, 2026 • Duration 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
[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 action
Key Takeaways
The 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.
Follow 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 Moments
Lines 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 how to use AI. That's not a future skill. It's a now skill."
Building a Speak-Up Culture for Lawyers (ft. Stephen (Shed) Shedletzky)
Season 1 · Episode 2
Tuesday, May 19, 2026 • Duration 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
[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
[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.
From Google to Nonprofit Chef: One Engineer's Search for a Life of Purpose (ft. Chris Ito)
Season 1 · Episode 1
Tuesday, May 19, 2026 • Duration 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
[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
The Power of Curiosity: Why the Best Lawyers Ask More & Answer Less ft. Rebecca Hockin
Season 1 · Episode 4
Friday, June 5, 2026 • Duration 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"
Courage, Entrepreneurship & Boundaries: Building a Law Firm Young (Featuring Sevana Poladian)
Season 1 · Episode 6
Friday, August 7, 2026 • Duration 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
The High Pain Threshold: Why Lawyers Miss Their Own Warning Signs (Featuring Allison Canton)
Season 1 · Episode 5
Tuesday, August 4, 2026 • Duration 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
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Discover shows related to Lawyer to Leader, based on actual content similarities. Explore podcasts with similar topics, themes, and formats, backed by real data.
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."
[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 action
Key Takeaways
Don'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.
Links
Hope's Corner - Where Chris began his non-profit journey
Follow the show. Apple Podcasts, Spotify, and YouTube. It helps more lawyers find this content.
Share this episode. If you know a lawyer who's climbing a ladder leaning against the wrong building, send them this one.
Shareable Moments
Lines worth pulling for social:
"Walk the high wire with no net. If you're thinking about the safety net, you're not fully committing."
"I don't know where I'm going, but I know exactly how to get there."
"If it takes you that long to decide, you already know the answer."
"The body keeps score. It never lies."
"I recovered from a life that wasn't aligned with my values."
"At the beginning of the night we're always strangers. At the end of the night we're always hugging."
[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.
"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."
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."
[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.
