Notes to My Legal Self®

Welcome to Season 15, Episode 7 of Notes to My Legal Self, the in-house counsel podcast for lawyers navigating AI, legal technology, leadership, and the future of legal work.Whitney Stefko joins host Olga V. Mack to explore one of the biggest challenges facing legal departments today: how to turn AI experimentation and technological innovation into meaningful, lasting organizational change.Working at the intersection of law, AI, and organizational transformation, Whitney shares why successful legal transformation starts with people, not technology. From responsible AI adoption to influencing stakeholders without formal authority, this conversation offers practical insights for in-house counsel, legal operations professionals, general counsel, and legal leaders navigating the changing legal landscape.In this episode, you'll learn:
Why technology alone isn't enough to drive successful legal transformation
How to move from AI experimentation to responsible, meaningful adoption
Why understanding real workflows is essential to implementing legal technology
How psychological safety helps legal teams adapt to change
Why AI fluency doesn't necessarily mean competence or accuracy
How to influence stakeholders without formal authority
Why understanding people's incentives can improve collaboration
How legal operations leaders can bridge the gap between legal, technology, and business teams
Why in-house counsel should build relationships with business partners before legal issues arise
How to identify practical opportunities to improve repetitive legal workflows
Timestamps:00:00 Introduction to Notes to My Legal Self00:43 Whitney Stefko on law, AI, and organizational transformation01:37 Whitney's career journey: From litigation to legal operations04:16 Why technology initiatives fail to create change06:17 The human side of change management09:28 Diagnosing why transformation efforts stall11:30 What organizations misunderstand about technology adoption13:26 Moving from AI experimentation to meaningful adoption16:25 What it means to be an AI realist17:31 AI fluency vs. accuracy and competence20:34 Influencing people without formal authority22:21 Understanding incentives and motivating stakeholders23:41 Building influence through communication and connection28:33 Aligning legal, technology, and business stakeholders33:11 The role of in-house counsel in business strategy35:26 Where in-house lawyers should begin37:08 Whitney's key takeaway: People are the strategyWhitney's hot take: Technology is not your strategy. Your people are your strategy.AI can transform legal work, but lasting progress requires more than new tools. It takes strong leadership, continuous learning, human connection, and a clear understanding of how people actually work.How can legal leaders make AI adoption more effective while keeping people at the center of transformation?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 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.Explore more episodes at https://www.notestomylegalself.comINTERSECTION OF LAW AND FUN®#InHouseCounsel #PodcastForLawyers #LegalAI #LegalOperations #LegalTech #ChangeManagement #FutureOfLaw

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.
Like, comment, and subscribe to @NotesToMyLegalSelf.

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

INTERSECTION OF LAW AND FUN®

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

Welcome to Season 15, Episode 5 of Notes to My Legal Self, the in-house counsel podcast on legal judgment, leadership, and getting to yes. Carly McAllister, Associate General Counsel in financial services, joins Olga V. Mack to discuss the move from litigator to trusted business partner.

Made for in-house lawyers and general counsel, this conversation explores how legal teams can create confidence and possibility for the business, instead of only managing risk.

In this episode, you'll learn:
- How to transition from litigation to an in-house legal career
- Why in-house lawyers must think like business partners
- How to find responsible ways to get to "yes"
- How to develop legal judgment, and why there is no cap on it
- Why AI can amplify legal work but not replace judgment

Timestamps:
00:00 Introduction
04:33 Leaving litigation to go in-house
07:10 Becoming a business partner in financial services
12:41 Why technical excellence is not enough
16:35 Creating confidence with executives
20:13 How legal departments create possibility
27:24 Legal judgment in the age of AI
32:15 How to build good judgment
38:00 Final advice for future in-house lawyers

Carly's advice: technical legal skill is the foundation, not the finish line.

When was the last time your "no" came with a path to "yes"? 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

INTERSECTION OF LAW AND FUN®

#NotesToMyLegalSelf #InHouseCounsel #GeneralCounsel #LegalLeadership #LegalJudgment #LawyerPodcast

Welcome to Season 15, Episode 4 of Notes to My Legal Self, the in-house counsel podcast for lawyers who want to lead. Bradley Bald, In-House Counsel at Lifestyle Communities, joins Olga V. Mack to talk about burnout, taking a sabbatical, and why the power of the pause is an underrated legal leadership skill.

Bradley shares his path from private practice to in-house counsel at a vertically integrated real estate developer. He opens up about what a career pause really feels like, how to answer interview questions about a resume gap, and how cognitive empathy helps lawyers resolve conflict without absorbing other people's emotions.

In this episode, you'll learn:
- How to know when a sabbatical is the right move for your legal career
- Why most lasting regret comes from inaction, not action
- How to handle interview questions about a resume gap
- How the power of the pause improves negotiations and conflict resolution
- What cognitive empathy is and how it differs from sympathy
- How in-house lawyers add value beyond contracts as proactive business partners

Timestamps:
0:00 Introduction
0:35 Meet Bradley and Lifestyle Communities
2:10 From real estate to in-house counsel
3:53 Taking a sabbatical to prevent burnout
6:43 Returning to work after a career gap
11:12 The ""gray place"" during a career pause
13:09 Building visibility as an in-house lawyer
15:54 Handling interview questions about a resume gap
19:25 The power of the pause
25:51 Cognitive empathy vs sympathy
28:01 What executives expect from legal leaders
31:50 The decision that shaped his legal career
33:47 Final takeaway: life is long

Key takeaways:
- Career success comes in stages. Life is long, not short.
- A strategic pause can prevent burnout and create clarity.
- Listening and cognitive empathy often create more impact than a quick, witty answer.

Enjoyed this episode? Rate and review Notes to My Legal Self on Apple Podcasts or Spotify. It helps more in-house lawyers find the show.

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

Like, comment, subscribe, and hit the bell so you never miss an episode.
Subscribe: @NotesToMyLegalSelf

INTERSECTION OF LAW AND FUN®

#InHouseCounsel #LawyerPodcast #LegalLeadership #LawyerWellBeing #BurnoutPrevention

Welcome to Season 15, Episode 3 of Notes to My Legal Self, the in-house counsel podcast for lawyers who want to lead. Kemi Ijitimehin, an Atlanta-based advertising and ad tech attorney, joins Olga V. Mack to talk about the power of the pivot, building trust as product counsel, and growing from first-gen lawyer to trusted business partner.

Kemi shares her path from public policy in Washington, D.C., to the federal government during COVID, to in-house work at a tech company. She explains how her family's history shaped her comfort with change, how to turn rejection into redirection, and why authenticity is what turns lawyers into trusted strategic advisors.

In this episode, you'll learn:
- How to know when it's time to pivot your legal career
- How to turn rejection into redirection
- Why product counsel work is one of the most creative roles in law
- The difference between advising a business and helping build one
- What ""learning the business"" really means for in-house lawyers
- How authenticity builds trust and buy-in with stakeholders
- The first step to take after a layoff or career transition

Timestamps:
0:00 Introduction
1:03 Becoming an advertising and ad tech lawyer
3:08 Family roots and the power of the pivot
7:16 How to know when it's time to pivot
10:51 Can lawyers trust their gut?
12:03 Turning rejection into redirection
13:55 Creativity in product counsel work
15:43 What surprised her most about going in-house
17:33 Advising a business vs helping build one
20:26 How to build trust and buy-in
22:42 AI and the human side of lawyering
24:19 Thinking like a business leader
26:44 What ""learning the business"" really means
29:17 Becoming a trusted strategic advisor
31:34 First steps after a layoff or career transition
33:06 Final takeaway: be brave

Key takeaways:
- Pivoting starts with a feeling, but your ""why"" decides the right move.
- Relationships and authenticity matter as much as knowing the law.
- Learn the business by sitting in on engineering, product, and marketing meetings.

Enjoyed this episode? Rate and review Notes to My Legal Self on Apple Podcasts or Spotify. It helps more in-house lawyers find the show.

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

Like, comment, subscribe, and hit the bell so you never miss an episode.
Subscribe: @NotesToMyLegalSelf

INTERSECTION OF LAW AND FUN®

#InHouseCounsel #ProductCounsel #LawyerPodcast #LegalCareers #LegalLeadership