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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
  • Financial Planning for Lawyers: Why High Income Doesn't Mean Wealth (Featuring Dalia Feldberg)
    Sep 16 2026
    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 BioDalia 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.Timestamps00:00 Financial planning for lawyers: the gap nobody talks about00:02 Why being a great lawyer isn't the whole story00:03 Meet Dalia Feldberg, financial advisor for lawyers00:07 How she got into financial planning for lawyers00:13 Why lawyers are financially underserved00:20 Financial advisor vs. lawyer: the same confidence problem00:23 The real gap between lawyer income and lawyer wealth00:25 Lawyers working into their 60s with no retirement plan00:26 The one habit that builds long-term wealth00:29 Wealth building for women in law: why the focus00:34 Managing money from articling student to associate00:38 Disability insurance and income protection for lawyers00:42 Financial planning for law firm partners00:44 The biggest investing mistake lawyers make00:47 What a financial planning meeting actually looks like00:57 Planning a career change as a lawyer01:00 One financial move every lawyer should make this week01:02 The book that changed how she thinks about moneyKey TakeawaysFinancial 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.LinksDalia on LinkedIn (booking link in her bio)Desjardins Financial Security Independent Network OttawaThe Happiness Advantage by Shawn AchorThe Psychology of Money by Morgan HouselIf this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.comShareable 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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    1 hr and 9 mins
  • AI For Lawyers: Why Your Judgment Matters More Than Ever (featuring Colin Levy)
    Sep 9 2026
    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 BioColin 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. Timestamps0:00 Intro: AI for Lawyers with Colin Levy1:00 Code Switched: What the Book Title Means3:00 Writing an AI Book That Stays Relevant6:00 Global AI Regulation for Legal Teams8:00 Why Bjarne Tellmann Wrote the Foreword9:00 Best Chapter for AI Skeptics11:00 ChatGPT Mistake: A Real Legal Example12:00 How to Prompt AI Like a Lawyer13:00 Why AI Hallucinates: Tokens Explained15:00 AI as a Thought Partner, Not a Chatbot16:00 AI for Lawyers: Judgment Over Replacement19:00 The Chainsaw Analogy: AI and Legal Judgment20:00 Stop Saying Please to Your AI Tool23:00 Why AI Tools Are People Pleasers25:00 AI and the Billable Hour Model27:00 Legal AI Adoption: We're in Chapter One28:00 AI for In-House Legal Teams29:00 Week One of Responsible AI Adoption31:00 Why AI Rollouts Fail Without Training34:00 AI Hallucinations: Feature, Not a Bug37:00 Lateral Thinking and AI Creativity39:00 The #1 Mistake Lawyers Make With AI41:00 AI for Solo and Legal Aid Lawyers42:00 AI Ethics for Lawyers: The Real Question44:00 AI Fails in Law: Real Examples46:00 Disclosing AI Use to Legal Clients47:00 AI Agents Explained for Lawyers49:00 Fruit of the Poisonous Tree: AI Agents51:00 Legal AI in 5 Years: Read the Book or Not52:00 What Writing Code Switched Taught Colin53:00 Rapid Fire: AI Advice for Lawyers55:00 Where to Find Colin Levy and Code Switched LinksColin's website: colinslevy.comColin on LinkedIn: linkedin.com/in/colinslevyColin on Twitter/X: x.com/Clevy_LawColin on Instagram: instagram.com/clevy_lawCode 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/B0CKCZTLWWIf this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.comKey TakeawaysCode 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 ...
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    59 mins
  • Courage, Entrepreneurship & Boundaries: Building a Law Firm Young (Featuring Sevana Poladian)
    Aug 7 2026

    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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    37 mins
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