Welcome to Season 15, Episode 6 of Notes to My Legal Self, the in-house counsel podcast for lawyers navigating AI, legal technology, leadership, and the future of legal work.

Adam Becker, Director of Legal Operations at Cockroach Labs, returns to the podcast to share his perspective on one of the biggest changes facing legal departments today: the shift from using AI as a tool to working with AI as an advisor.

For in-house lawyers, legal ops professionals, general counsel, and legal leaders, this conversation explores what it takes to move beyond checking the "AI box" and become more fluent in AI-native ways of working.

In this episode, you'll learn:

- Why legal operations is becoming essential to modern legal departments

- The difference between adopting AI and becoming AI-native

- How AI can help legal teams work differently, not just faster

- Why legal ops leaders need to understand how lawyers actually work

- How knowledge management enables better AI outcomes

- How to build trust when introducing AI to legal teams

- Why legal leaders should experiment rather than wait for a mandate

- How to identify practical workflows where AI can make an immediate difference

- Why sharing AI learnings across legal teams matters

Timestamps:

00:00 Introduction

03:00 Legal operations becomes essential

05:00 AI and the second stage of legal ops maturity

08:00 From systems to AI advisors

10:00 The evolution of the Core

1213:00 Knowledge management and AI

15:00 AI adoption vs. AI-native legal teams

19:00 What makes a strong legal ops leader

23:00 Building trust with lawyers

27:00 Taking initiative with AI

31:00 Where legal teams should start

35:00 Mistakes legal departments are making with AI

38:00 One action legal ops leaders should take

Adam's hot take: The biggest opportunity isn't simply saving 10% of your time, it's changing how you work.

What would you eliminate or simplify if you had an AI advisor working alongside you?

Tell us in the comments.

If you enjoy this legal tech podcast and podcast for lawyers, rate and review Notes to My Legal Self on Apple Podcasts or Spotify. It helps more legal professionals discover the conversation.

Want to be a guest on NTMLS or know someone who should be?

Reach out! Self-nominations are acts of courage.

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Explore more episodes at https://www.notestomylegalself.com

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#LegalOperations #LegalOps #AIinLegal #LegalTech #InHouseCounsel #PodcastForLawyers #FutureOfLaw

Welcome to Season 15, Episode 4 of Notes to My (Legal) Self, where Olga V. Mack sits down with Carly Mcallister to explore what it means to move from practicing law to practicing leadership.

Together, they discuss why the best in-house lawyers do more than manage risk, they build trust, empower business partners, and create possibilities.

Carly shares how her transition from litigation to financial services taught her that technical legal excellence is only the beginning of becoming an effective in-house leader.

Drawing from her experience in litigation, judicial work, and financial services, Carly explains why understanding the business, investing in yourself, and developing sound judgment are essential to legal leadership. She also explores why, in an AI-driven world, human judgment, communication, and connection will remain among a lawyer’s greatest competitive advantages.

You'll discover:

• Why moving in-house requires shifting from legal expert to business partner

• How legal teams can create possibilities instead of simply managing risk

• Why great in-house lawyers look for responsible ways to get to “yes”

• How understanding the business builds trust and strategic influence

• Why listening, humility, mentorship, and continuous learning strengthen judgment

• How personal development can make you a better lawyer and leader

• Why collaboration across teams creates better business outcomes

• How legal departments can empower people through thoughtful governance

• Why AI can amplify legal work but cannot replace human judgment

• How lawyers can evolve from risk managers into leaders who create possibilities

Whether you're considering an in-house career, growing as legal counsel, or leading within an organization, this conversation offers practical insights on business partnership, judgment, personal development, and creating value beyond traditional legal advice.

If you've ever wondered how to become a more trusted, strategic, and human-centered legal leader, this episode is for you.

Takeaways:

• Technical legal excellence is the foundation, not the finish line.

• Great in-house lawyers create confidence and possibility.

• Understanding the business is essential to becoming a trusted partner.

• Judgment grows through experience, humility, listening, and continuous learning.

• AI will transform legal work, but leadership and human judgment remain essential.

S U B S C R I B E!

Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage. Engage with us below, like, comment, and subscribe to follow the future of in-house law!

Thank you for watching!

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Subscribe to our channel: @NotesToMyLegalSelf

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#LegalLeadership #InHouseCounsel #Leadership #CareerDevelopment #GeneralCounsel

Welcome to Season 15, Episode 4 of Notes to My (Legal) Self. In this thought-provoking conversation, host Olga Mack sits down with Bradley Bald, In-House Counsel at Lifestyle Communities, to explore how taking a pause can become one of the most powerful leadership tools in a lawyer’s toolkit.

Together, they discuss the realities of burnout, the courage required to take a sabbatical, and why cognitive empathy may be one of the most underrated superpowers for modern legal professionals. Bradley shares his personal journey from private practice to in-house counsel, the lessons learned during a career pause, and how listening, reflection, and emotional intelligence can create stronger relationships, better negotiations, and more impactful leadership.

Bradley Bald serves as In-House Counsel for Lifestyle Communities, a nationwide mixed-use multifamily real estate developer focused on creating wellness-centered communities. With experience spanning private practice, real estate, business development, and in-house leadership, Bradley brings a unique perspective on career growth, resilience, and the evolving role of legal professionals.

Key insights from this episode:

• Why the most enduring regrets often stem from inaction rather than action

• How taking a sabbatical can provide clarity, prevent burnout, and create space for personal growth

• The importance of embracing discomfort during career transitions

• How the “power of the pause” can improve communication, negotiations, and conflict resolution

• Why cognitive empathy helps legal leaders understand others without absorbing their emotions

• How modern in-house counsel can add value beyond legal advice by becoming proactive business partners

• The role of self-awareness, reflection, and emotional intelligence in effective leadership

Whether you're navigating burnout, considering a career transition, building your influence as in-house counsel, or looking to become a more effective communicator, this episode offers practical insights and meaningful perspective for legal professionals at every stage of their careers.

About the Guest:

Bradley Bald is In-House Counsel at Lifestyle Communities, where he supports a vertically integrated real estate development organization spanning development, construction, property management, hospitality, and lifestyle brands. With a background in private practice and over a decade of experience in real estate, Bradley is passionate about leadership, psychology, cognitive empathy, and helping legal professionals build careers that align with both purpose and well-being.

Takeaways:

• Taking a strategic pause can create opportunities for long-term growth.

• Burnout prevention requires intentional reflection and self-awareness.• Cognitive empathy strengthens relationships while preserving objectivity.

• Great legal leaders are valued for influence, not just expertise.

• Listening often creates more impact than speaking.

• Emotional intelligence is becoming a critical leadership skill for modern lawyers.

• Career success is not only about advancement, it is also about alignment.

S U B S C R I B E!

Want to be a guest on NTMLS or know someone who should be?

Reach out! Self-nominations are acts of courage.

Engage with us below, like, comment, and subscribe to follow the future of in-house law!

Thank you for watching!

Like, Comment, Subscribe and hit the bell so you never miss an episode!

Subscribe to our channel: @NotesToMyLegalSelf

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#InHouseCounsel #CognitiveEmpathy #LawyerWellBeing #BurnoutPrevention #CareerGrowth

Welcome to Season 15, Episode 3 of Notes to My (Legal) Self, where Olga V. Mack sits down with Kemi Ijitimehin to explore why the most meaningful careers aren't carefully mapped, they're built through courageous pivots.

Together, they discuss how trusting your instincts, embracing creativity, and investing in relationships can transform not only your legal career but the businesses and people you serve.

Drawing from a career that spans public policy, the federal government, and the technology sector, Kemi shares how every unexpected turn prepared her for the next opportunity. From navigating rejection and career transitions to becoming a trusted business partner, she explains why curiosity, authenticity, and human connection remain every lawyer's greatest competitive advantage in an AI-driven world.

You'll discover:

• Why "pivoting is a vibe" and how trusting yourself can unlock unexpected opportunities
• How family history, resilience, and adaptability shape long-term career success
• Why rejection is often redirection toward a better opportunity
• How creativity is one of the most underrated skills in modern legal practice
• Why product counsel requires lawyers to think beyond legal answers and help build businesses
• The importance of curiosity in learning your business and becoming an indispensable legal partner
• Why relationships and trust matter more than always having the perfect legal answer
• How authenticity helps lawyers build credibility across cross-functional teams
• Why AI can improve efficiency, but judgment, empathy, and human connection remain irreplaceable
• How today's lawyers can evolve from legal advisors into strategic business leaders

Whether you're an aspiring lawyer, an experienced in-house counsel, a legal operations professional, or a business leader navigating constant change, this conversation offers practical insights on career pivots, business partnership, leadership, and the uniquely human skills that define exceptional lawyers.

If you've ever wondered how to embrace uncertainty while building a meaningful legal career, this episode is for you.

Takeaways:

• Career pivots are often driven by purpose, not perfect planning.
• Curiosity is one of the most valuable skills an in-house lawyer can develop.
• Strong relationships create trust, and trust creates better business outcomes.
• Great lawyers don't just solve legal problems—they help build businesses.
• AI will continue to transform legal work, but creativity, empathy, and judgment remain a lawyer's greatest strengths.

S U B S C R I B E!

Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage.

Engage with us below, like, comment, and subscribe to follow the future of in-house law!

Thank you for watching!

Like, Comment, Subscribe, and hit the bell so you never miss an episode!

Subscribe to our channel: @NotesToMyLegalSelf

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#InHouseCounsel #LegalLeadership #CareerGrowth #BusinessPartner #ProductCounsel

Welcome to Season 15, Episode 2 of Notes to My (Legal) Self, where host Olga V. Mack sits down with Elizabeth Colombo, Associate General Counsel at Vendavo.

Together, they explore why great negotiation is about more than contracts. Beth shares practical lessons on empathy, business judgment, communication, and how in-house lawyers can become trusted business partners in an AI-assisted world.

In this episode, you'll learn:

• Why negotiation is about people, not just paper

• How empathy leads to better business outcomes

• Why lawyers must embrace calculated risk

• The difference between being a referee and a decision architect

• How "embedded humanity" creates value AI can't replace

• Practical communication strategies for cross-functional teams

• Why human judgment remains a lawyer's greatest competitive advantage

  
  

Whether you're an in-house lawyer, legal leader, or aspiring counsel, this episode offers actionable insights on leading with trust, business acumen, and humanity in the modern legal profession.

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#InHouseCounsel #LegalLeadership #GeneralCounsel #Negotiation #NotesToMyLegalSelf

Welcome to Season 15, Episode 1 of Notes to My Legal Self, the in-house counsel podcast for lawyers who want to lead. Alexandra Sepulveda, Associate General Counsel at Trust & Will, joins Olga V. Mack to explore how lawyers build legal judgment when AI does more of the thinking.

Alexandra shares her path from patent litigator to in-house counsel at General Mills, Kabam, and fast-growing startups. She explains what junior lawyers miss when AI drafts first, why judgment is different from benchmarking, and the simple habits she uses to keep her own "lawyer gut" sharp.

In this episode, you'll learn:

- What junior lawyers lose when they skip the early reps

- The human-AI-human "Oreo cookie" method for using AI well

- Why the purposeful pause is a negotiation tool AI can't replace

- The difference between legal judgment and knowing what's market

- How to spot and close judgment gaps on your legal team

Timestamps:

00:00 Introduction

03:34 Meet Alexandra and Trust & Will

05:11 From patent litigator to in-house counsel

09:23 The early work that teaches judgment

13:30 The power of the purposeful pause

16:02 How AI is changing legal team capacity

21:48 The human-AI-human method

24:53 Judgment vs. benchmarking

28:26 Why junior lawyers need informal mentors

32:35 Expecting senior judgment without junior reps

36:14 Redesigning law school for AI

39:00 Habits that build legal judgment

44:53 Final takeaway: stay curious

Alexandra's advice: stay curious, because no one is going to replace your gut.

Do you write your own first draft before asking AI, or let AI go first? Share your answer with us in the comments.

If you enjoy this lawyer podcast, rate and review Notes to My Legal Self on Apple Podcasts or Spotify. It helps more in-house counsel find these conversations.

Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage.

Like, comment, and subscribe to @NotesToMyLegalSelf so you never miss an episode.

Explore more episodes at https://www.notestomylegalself.com

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#NotesToMyLegalSelf #InHouseCounsel #LegalJudgment #AIinLaw #LegalLeadership #LawyerPodcast

Welcome to Season 14, Episode 10 of Notes to My (Legal) Self®.

In this thought-provoking conversation, host Olga Mack sits down with Dharshi Harindra, Assistant General Counsel, APAC at FTI Consulting, to explore one of the most important questions facing the legal profession today: When AI starts doing lawyers’ work, what labels still matter?

Together, they examine the evolving role of lawyers in an AI-enabled world and why judgment, not just technical proficiency, may become the profession’s most valuable skill.

Dharshi brings a unique global perspective shaped by nearly two decades of experience spanning the UK, Australia, Dubai, and Singapore.

With a background in technology, media, telecommunications, data privacy, executive coaching, and inclusion leadership, she offers a nuanced view of how AI is transforming legal work while simultaneously revealing the enduring importance of human reasoning, accountability, and ethical decision-making.

Key insights from this episode:

• Why the phrase “AI won’t replace lawyers, lawyers using AI will” may oversimplify the future of legal practice

• How AI acts as a mirror that reflects and amplifies existing human judgment

• Why legal value is shifting from information access and technical precision to decision-making under uncertainty

• The growing importance of accountability, context, and strategic wisdom in legal counsel

• How bias, labels, and assumptions can be reinforced through AI systems, and what lawyers must do about it

• Why asking better questions may become a defining legal skill in the age of AI

• How lawyers can help organizations deploy AI responsibly while preserving human oversight and judgment

Whether you're an in-house lawyer, law firm leader, legal operations professional, legal technologist, or simply curious about the future of the profession, this episode offers practical insights into what legal excellence will look like in an era where information is increasingly abundant but judgment remains scarce.

Takeaways:

• AI can accelerate legal work, but it cannot replace accountability.

• Human judgment remains the critical differentiator in legal decision-making.

• The future lawyer will be valued less for information retrieval and more for wisdom, context, and strategic guidance.

• Bias doesn't disappear with technology, it can be amplified by it.

• Great lawyers will combine technological fluency with strong ethical reasoning and business judgment.

• The ability to navigate ambiguity may become more important than having all the answers.

S U B S C R I B E!

Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage.Engage with us below, like, comment, and subscribe to follow the future of in-house law!

Thank you for watching!

Like, Comment, Subscribe and hit the bell so you never miss an episode!

Subscribe to our channel: @NotesToMyLegalSelf

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#NotesToMyLegalSelf #LegalInnovation #LegalTech #FutureOfLaw #LegalLeadership