Notes to My Legal Self®

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 4 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

Welcome to Season 15, Episode 2 of Notes to My Legal Self, the in-house counsel podcast for lawyers who want to lead. Elizabeth Colombo, Associate General Counsel at Vendavo, returns to talk with Olga V. Mack about red lines, relationships, and real leadership.

Elizabeth shares how 14 years in-house taught her the psychology of contract negotiation, how to get comfortable with acceptable risk, and why embedded humanity makes in-house lawyers indispensable.

In this episode, you'll learn:

- Why negotiation is about people, not just the paper

- How to separate material risk from theoretical risk

- How to make the business want legal involved early

- How to resolve stakeholder conflict without being the bad guy

- The soft skills lawyers most often underestimate

Timestamps:

00:00 Introduction

03:04 Negotiation lessons: people, psychology, and risk

07:05 How to make the business want legal involved

10:59 Why in-house lawyers should assume they belong

14:32 What ""embedded humanity"" means

20:23 Handling stakeholder conflict

23:41 From referee to decision architect

29:07 Soft skills lawyers underestimate

34:37 Final takeaway: be human

Elizabeth's advice: in the age of AI, your human judgment is what sets you apart.

Is your legal team seen as the referee or the partner who helps make the call? 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 #ContractNegotiation #LawyerPodcast

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

INTERSECTION OF LAW AND FUN®

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

Welcome to Season 14, Episode 10 of Notes to My (Legal) Self®, the in-house counsel podcast exploring AI, legal judgment, and the future of the legal profession.

Host Olga V. Mack talks with Dharshi Harindra, Assistant General Counsel for APAC at FTI Consulting, live from Singapore. Drawing on 20 years across big law, TMT, and data privacy in the UK, Australia, Dubai, and Singapore, Dari challenges the popular claim that ""AI won't replace lawyers, but lawyers who use AI will."" Her view: AI is a mirror, and without strong human judgment it only produces confident but risky answers faster.

This general counsel podcast conversation is for in-house lawyers, legal leaders, and anyone navigating legal tech and AI adoption.

In this episode, you'll learn:

- Why human judgment, not technical fluency, will set lawyers apart

- Which traditional lawyer labels are weakening and what is replacing them

- How AI can amplify bias, and why lawyers are positioned to correct it

- A practical framework for legal judgment: what matters, what doesn't, what happens next, and who owns the consequences

- How early-career lawyers can build judgment without years of ""learning by osmosis""

- Why legal tech needs subject matter experts at the table

Timestamps:

00:00 Introduction

01:06 Meet Dharshi: a global legal career from London to Singapore

03:48 Is ""lawyers who use AI will replace lawyers"" the right framing?

07:10 The lawyer labels that are weakening

11:35 How AI mirrors and amplifies bias

15:21 What legal judgment looks like in practice

21:29 Technically right vs. strategically wise

25:17 Why lawyers should document how they think

31:24 Skills early-career lawyers need now

35:13 Pairing legal tech with subject matter expertise

39:25 Redefining the exceptional lawyer

41:33 The profession five years from now

44:35 Final takeaway

If you enjoy this lawyer podcast, follow the show and leave a rating. It helps more in-house counsel and legal leaders find these conversations.

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

INTERSECTION OF LAW AND FUN®

#NotesToMyLegalSelf #LegalInnovation #LegalTech #FutureOfLaw #LegalLeadership

Welcome to Season 14, Episode 9 of Notes to My Legal Self, the in-house counsel podcast on AI, contracting, and the future of legal work.

Host Olga V. Mack talks with Cherryn-Paige Bissett, Internal Commercial Counsel at LegalSifter, about what to automate in contracting and what still needs a lawyer's judgment. With over 20 years as a commercial attorney, Cherryn shares her ""automate 80%, own 20%"" approach: use AI and playbooks to cut through contract noise, then focus your time on the risks that matter.

This legal tech and legal operations conversation is for in-house lawyers, corporate counsel, and anyone who wants to close deals faster without taking on unnecessary risk.

In this episode, you'll learn:

- How AI contract playbooks build consistency and reduce contract noise

- What separates a useful playbook from one that becomes rigid or ignored

- When to step outside the playbook, including new AI provisions in NDAs

- Which contracting decisions still require human judgment

- How to weigh possibility vs. probability when deciding which risks to push back on

- How a one-page contract primer can speed up negotiations

Timestamps:

00:00 Introduction

00:44 Meet Cherryn Bissett

01:33 From LegalSifter customer to in-house counsel

02:29 Automate 80%, own 20%

03:50 Cutting through contract noise

05:28 Building playbooks that scale across teams

07:35 When to step outside the playbook

09:46 AI provisions showing up in NDAs

10:31 When playbooks slow the business down

12:07 Where AI creates real value in contracting

14:51 Decisions that still need human judgment

18:02 How to be fast and accurate under pressure

20:12 Safest legal answer vs. best business decision

22:32 Skills that will set in-house lawyers apart

24:17 Final takeaway

If you enjoy this lawyer podcast, follow the show and leave a rating. It helps more in-house counsel and legal ops professionals find these conversations.

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

#NotesToMyLegalSelf #LegalInnovation #ContractManagement #CommercialLaw #LegalOperations

Welcome to Season 14, Episode 9 of Notes to My Legal Self, the in-house counsel podcast on AI, contracting, and the future of legal work.

Host Olga V. Mack talks with Cherryn-Paige Bissett, Internal Commercial Counsel at LegalSifter, about what to automate in contracting and what still needs a lawyer's judgment. With over 20 years as a commercial attorney, Cherryn shares her ""automate 80%, own 20%"" approach: use AI and playbooks to cut through contract noise, then focus your time on the risks that matter.

This legal tech and legal operations conversation is for in-house lawyers, corporate counsel, and anyone who wants to close deals faster without taking on unnecessary risk.

In this episode, you'll learn:

- How AI contract playbooks build consistency and reduce contract noise

- What separates a useful playbook from one that becomes rigid or ignored

- When to step outside the playbook, including new AI provisions in NDAs

- Which contracting decisions still require human judgment

- How to weigh possibility vs. probability when deciding which risks to push back on

- How a one-page contract primer can speed up negotiations

About the guest:

Cherryn-Paige Bissett is Internal Commercial Counsel at LegalSifter, which offers AI contract review and a CLM platform. She has practiced commercial law for over 20 years, including at a London-based law firm, and joined LegalSifter after starting as a customer.

Timestamps:

00:00 Introduction

00:44 Meet Sharon Bissett

01:33 From LegalSifter customer to in-house counsel

02:29 Automate 80%, own 20%

03:50 Cutting through contract noise

05:28 Building playbooks that scale across teams

07:35 When to step outside the playbook

09:46 AI provisions showing up in NDAs

10:31 When playbooks slow the business down

12:07 Where AI creates real value in contracting

14:51 Decisions that still need human judgment

18:02 How to be fast and accurate under pressure

20:12 Safest legal answer vs. best business decision

22:32 Skills that will set in-house lawyers apart

24:17 Final takeaway

If you enjoy this lawyer podcast, follow the show and leave a rating. It helps more in-house counsel and legal ops professionals find these conversations.

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

#NotesToMyLegalSelf #LegalInnovation #ContractManagement #CommercialLaw #LegalOperations

Welcome to Season 14, Episode 7 of Notes to My Legal Self, the in-house counsel podcast on legal design, legal operations, and serving clients better.

Host Olga V. Mack talks with Marco Imperiale, founder of Better Hub and author of Practicing Legal Design, about a basic question lawyers often skip: do we actually know our clients? Marco explains why legal design is much more than icons and colors. It is a new way to build contracts, policies, and legal processes around the people who use them.

This legal tech and legal innovation conversation is for in-house lawyers, legal ops professionals, and anyone who wants legal work that people can actually understand and use.

In this episode, you'll learn:

- What legal design is, and what it is not

- Why clearer contracts and policies can save money, not just improve the experience

- The biggest sources of resistance to clearer legal communication

- How to run a "listening dinner" and truly hear your clients

- How to balance clarity and accessibility with legal precision

- Why visuals, white space, and typography matter more than lawyers think

- Why curiosity matters more than specialized knowledge in the age of AI

About the guest:

Marco Imperiale is a former copyright and entertainment lawyer, the first head of innovation at a law firm in Italy, and founder of Better Hub, a benefit corporation focused on legal operations, legal innovation, and AI. He has taught legal design at Harvard Graduate School of Design and is the author of Practicing Legal Design (Globe Law and Business).

Timestamps:

00:00 Introduction

00:41 Meet Marco Imperiale

01:25 His book, Practicing Legal Design

02:03 Why he wrote a practical guide to legal design

03:57 Why legal design matters

07:36 Lawyers, visuals, and "just send the picture"

09:23 Why legal design matters right now

13:30 Where the resistance comes from

18:38 Common misconceptions about legal design

21:20 How to really listen to your clients

24:02 Balancing clarity with legal precision

26:34 Testing and validating your assumptions

29:41 The role of visuals and typography

32:31 Why curiosity beats specialization in the age of AI

36:40 Where curious but skeptical lawyers should start

38:45 Final takeaway: less ego, more humility

When was the last time you asked a client how they actually experience your work? Share your answer with us in the comments.

If you enjoy this lawyer podcast, follow the show and leave a rating. It helps more in-house counsel and legal ops professionals 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

#NotesToMyLegalSelf #InHouseCounsel #LegalDesign #LegalOps #LegalInnovation #LegalTech