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Sidebar Advisors

Sidebar Advisors

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A podcast exploring the careers, choices and strategies shaping today’s legal landscape.


Hosted by Niraj Chhabra, each episode explores the intersection of law, career growth, and financial decision-making. Through conversations on leadership, professional development and business building, we unpack the moments that define success.


For those thinking about what’s next or looking to grow and feel more fulfilled in their current role, these conversations offer a thoughtful look at building a meaningful and successful career in and around the legal world.

© 2026 Sidebar Advisors
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Épisodes
  • Bruce MacEwen: The Future of Law Firms Isn’t What You Think
    Apr 22 2026

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    What actually separates durable law firms from those that won’t make it through the next decade?

    In this week's episode, Niraj Chhabra, CFP, MBA, CLTC, CRPC sits down with Bruce MacEwen, founder of Adam Smith, Esq., LLC, to unpack how law firm economics and structures are being reshaped in real time.

    They discuss why the traditional business model is breaking down, how the industry is shifting toward a smaller group of elite firms, and what makes those firms fundamentally different.

    A major theme throughout the conversation is AI — not as a distant threat, but as something that could quickly challenge the billable hour and reduce the need for large associate classes.

    Bruce also shares:

    • why many firms aren’t prepared for what’s coming
    • how career paths for lawyers could change dramatically
    • what happens when firms are forced to shrink
    • and why the most valuable skill going forward may not be legal expertise

    It’s a candid, forward-looking conversation for anyone thinking about the future of the legal industry.

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    1 h et 6 min
  • Jill Cruz: How Attorneys Can Advocate for Their Value More Effectively
    Apr 15 2026

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    Negotiation, compensation, and advancement shape a lawyer’s career — but most attorneys are left to navigate those decisions without much transparency.

    In this episode of the Sidebar Advisors Podcast, Niraj Chhabra sits down with Jill Cruz, executive coach, career strategist, and founder of JLC Consulting.

    Before launching her practice, Jill spent years in senior HR and talent leadership roles inside law firms, advising on hiring, promotion, and compensation decisions. Today, she helps attorneys better understand their value, navigate career inflection points, and advocate for themselves more effectively.

    They discuss what Jill learned from seeing these systems from the inside, why so many attorneys underestimate their leverage, how negotiation really starts long before an offer is made, and why mindset plays such a big role in whether people step into bigger opportunities.

    They also talk about the structural and cultural barriers that continue to affect women and attorneys of color, and how Jill’s research has shaped the way she coaches today.

    To learn more or connect with Jill:

    Website: www.jlc.consulting
    Email: jcruz@jlc.consulting

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    43 min
  • Michelle Calcote King: How Law Firms Actually Build Visibility, Credibility, and Demand
    Apr 8 2026

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    Michelle Calcote King, Principal & President of Reputation Ink, joins the podcast to break down how professional services firms — especially law firms — can turn their expertise into real visibility, credibility, and growth.

    At Reputation Ink, Michelle works with law and other B2B firms to help them become known authorities, earn meaningful media coverage, and build reputations that drive business development.

    In this episode, we talk about why marketing should look different depending on firm size, how owned, earned, and paid media actually work together, and what clients are paying attention to today.

    We also get into what separates firms that consistently generate opportunities from those that struggle to stand out — and how to build a strategy that creates long-term visibility, not just short-term activity.

    If you’re thinking about how your firm shows up in the market, or why it’s not translating into growth, this is a practical conversation worth listening to.

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    57 min
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