Lawyer to Leader

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.

Lawyer to Leader is a business podcast hosted by Unknown Host, with 8 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts Lawyer to Leader, a business show with 8 episodes published.

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  Episode #8

  Financial Planning for Lawyers: Why High Income Doesn't Mean Wealth (Featuring Dalia Feldberg)

  Sep 16, 20261h 9mS1

  Most lawyers spend years mastering the law and almost no time learning how to protect or grow the income it earns them. In this episode of the Lawyer to Leader podcast, financial advisor Dalia Feldberg breaks down financial planning for lawyers: why a high salary doesn't automatically create wealth, what changes financially the moment you make partner, and the accounts most lawyers are using wrong. Dalia also talks about why she's built her practice specifically around wealth building for women in law, and why covering your downside (wills, disability insurance, income protection) has to come before you chase any upside. If you've never had a real conversation about money as a lawyer, this episode is where to start. Guest Bio Dalia Feldberg is a financial advisor with Desjardins based in Ottawa specializing in financial planning for lawyers, with a particular focus on wealth building for women in law. She holds a First Class Honours degree from McGill University and a Master's in Sustainable Business and Innovation from EADA Business School in Barcelona, and is currently working toward her CFP® designation. Dalia works with lawyers navigating student debt, rising income, and partnership decisions, building financial plans around their actual goals instead of just selling products. Timestamps 00:00 Financial planning for lawyers: the gap nobody talks about 00:02 Why being a great lawyer isn't the whole story 00:03 Meet Dalia Feldberg, financial advisor for lawyers 00:07 How she got into financial planning for lawyers 00:13 Why lawyers are financially underserved 00:20 Financial advisor vs. lawyer: the same confidence problem 00:23 The real gap between lawyer income and lawyer wealth 00:25 Lawyers working into their 60s with no retirement plan 00:26 The one habit that builds long-term wealth 00:29 Wealth building for women in law: why the focus 00:34 Managing money from articling student to associate 00:38 Disability insurance and income protection for lawyers 00:42 Financial planning for law firm partners 00:44 The biggest investing mistake lawyers make 00:47 What a financial planning meeting actually looks like 00:57 Planning a career change as a lawyer 01:00 One financial move every lawyer should make this week 01:02 The book that changed how she thinks about money Key Takeaways Financial planning for lawyers isn't optional, it's overdue. Income and wealth are different things, and most lawyers never get taught the difference. The habit matters more than the amount. Financial planning for young lawyers can start at $10 or $100 a month. Once you've started, there's something to build a plan around. Disability insurance and income protection are the financial planning basics lawyers skip. Wills, disability insurance, and income protection are the pieces lawyers treat as a "later" problem. How accounts are used are the most common financial planning error. Most lawyers don't have a pension, so if they're not building retirement savings themselves, nobody is. Every career transition resets your financial plan. Articling to associate, associate to partner, employee to business owner, each one changes your income, your tax exposure, and often your team. Wealth building for women in law is a growing, underserved niche. Financial planning for lawyers is a gap; that gap runs deeper for women in law, where there's often no one in the room having the conversation with them. Links Dalia on LinkedIn (booking link in her bio) Desjardins Financial Security Independent Network Ottawa The Happiness Advantage by Shawn Achor The Psychology of Money by Morgan Housel If this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.com Shareable Moments "If I don't wake up every day and talk to people about death, I'm doing my clients a major disservice. We all die. That's the one reality." "It doesn't matter how much you're putting away. If you can put something away, we can work with that. Until then, there's not much to work with." "You just went to school for seven years. Surely you'd want to protect your ability to earn that income." "If you were there right now, you wouldn't enjoy the journey as much. The journey is where you see the fruits of your effort." "I can speak their language. We resonate with one another."

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  Episode #7

  AI For Lawyers: Why Your Judgment Matters More Than Ever (featuring Colin Levy)

  Sep 9, 202659 minS1

  Colin Levy has read more legal AI hype than almost anyone, and he thinks most of it is useless. In this episode, Jonathan Cullen sits down with the General Counsel of Malbek and author of the new book Code Switched: A Lawyer's Guide to the Era of AI to cut through the noise around AI for lawyers. Colin explains why he thinks lawyers should stop saying please to ChatGPT, why AI hallucinations are a feature not a bug, and why the real risk in legal AI adoption isn't the technology replacing your judgment, it's you forgetting to use it. They get into tokens, AI agents, the billable hour, and why Colin believes we're only in "chapter one" of what artificial intelligence will do to the legal profession. If you've been putting off learning how AI works in legal practice because you're not sure where to start, this episode is your starting point. Guest Bio Colin Levy is General Counsel at Malbek, and one of the most respected voices in legal technology and AI for lawyers, with a large following on LinkedIn and through his newsletter. He's an adjunct professor at Albany Law School, author of The Legal Tech Ecosystem , and editor of the Handbook of Legal Tech . His new book, Code Switched: A Lawyer's Guide to the Era of AI , is on presale now and releases October 6, 2026. Timestamps 0:00 Intro: AI for Lawyers with Colin Levy 1:00 Code Switched: What the Book Title Means 3:00 Writing an AI Book That Stays Relevant 6:00 Global AI Regulation for Legal Teams 8:00 Why Bjarne Tellmann Wrote the Foreword 9:00 Best Chapter for AI Skeptics 11:00 ChatGPT Mistake: A Real Legal Example 12:00 How to Prompt AI Like a Lawyer 13:00 Why AI Hallucinates: Tokens Explained 15:00 AI as a Thought Partner, Not a Chatbot 16:00 AI for Lawyers: Judgment Over Replacement 19:00 The Chainsaw Analogy: AI and Legal Judgment 20:00 Stop Saying Please to Your AI Tool 23:00 Why AI Tools Are People Pleasers 25:00 AI and the Billable Hour Model 27:00 Legal AI Adoption: We're in Chapter One 28:00 AI for In-House Legal Teams 29:00 Week One of Responsible AI Adoption 31:00 Why AI Rollouts Fail Without Training 34:00 AI Hallucinations: Feature, Not a Bug 37:00 Lateral Thinking and AI Creativity 39:00 The #1 Mistake Lawyers Make With AI 41:00 AI for Solo and Legal Aid Lawyers 42:00 AI Ethics for Lawyers: The Real Question 44:00 AI Fails in Law: Real Examples 46:00 Disclosing AI Use to Legal Clients 47:00 AI Agents Explained for Lawyers 49:00 Fruit of the Poisonous Tree: AI Agents 51:00 Legal AI in 5 Years: Read the Book or Not 52:00 What Writing Code Switched Taught Colin 53:00 Rapid Fire: AI Advice for Lawyers 55:00 Where to Find Colin Levy and Code Switched Links Colin's website: colinslevy.com Colin on LinkedIn: linkedin.com/in/colinslevy Colin on Twitter/X: x.com/Clevy_Law Colin on Instagram: instagram.com/clevy_law Code Switched: A Lawyer's Guide to the Era of AI (releases October 6, on presale now): On Amazon and here: https://amplifypublishinggroup.com/product/nonfiction/industries/technology/code-switched/ The Legal Tech Ecosystem (Colin's first book): amazon.com/Legal-Tech-Ecosystem-Innovation-Advancement/dp/B0CKCZTLWW If this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.com Key Takeaways Code Switched is about the shift from AI helping lawyers finish work to AI helping lawyers build things, a bigger adaptation than any previous legal tech shift. AI for lawyers means AI amplifies judgment, it doesn't replace it. The more powerful the tool, the more skill you need to wield it. Colin's line: a hammer makes it easier to build a wall, but you still need to know where the nail goes. AI hallucinations are a feature, not a bug. Large language models are predictive, token-based systems. They match patterns, they don't understand your question. That means wrong answers aren't a glitch to patch, they're baked into how the technology works. Stop humanizing AI tools. Don't say please, don't treat "I" and "me" as anything but a marketing choice. AI models are built to be people pleasers, which means the lawyer has to be the skeptic in the room, every time. Responsible AI adoption in legal practice starts small and low-risk. Week one should mean one repetitive, low-stakes task done in a controlled way, not a firm-wide rollout with no training behind it. The real AI ethics question for lawyers isn't "should I use AI." It's "how am I using it." Client confidentiality, data hygiene, and transparency matter more than the yes-or-no debate most people are stuck on. Shareable Moments "Assume it knows nothing, and assume you need to give it a seemingly absurd level of context." "These tools don't understand the way humans understand." "AI doesn't power anything." "We're kind of in chapter one. We finished the prologue." "Hallucinations... are a feature, not a bug." "You shouldn't be worrying about hurting its feelings. It has no feelings." "That old saying, it seems too good to be true, can often be the case." "The number one mistake most lawyers make when using one of these tools is assuming it's just gonna be right."

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  Episode #6

  Courage, Entrepreneurship & Boundaries: Building a Law Firm Young (Featuring Sevana Poladian)

  Aug 7, 202637 minS1

  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."

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  Episode #5

  The High Pain Threshold: Why Lawyers Miss Their Own Warning Signs (Featuring Allison Canton)

  Aug 4, 202650 minS1

  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."

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  Episode #4

  The Power of Curiosity: Why the Best Lawyers Ask More & Answer Less ft. Rebecca Hockin

  Jun 5, 202656 minS1

  <p>Episode Introduction</p><p>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...

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