Careers and the Business of Law

Hosted by David Cowen | Careers and the Business of Law David Cowen sits down with Bobby Malhotra, litigation partner and chair of Winston's eDiscovery and Information Governance practice, member of the firm's AI strategy group, and founding member of Legal Data Intelligence. Bobby sits at the intersection of eDiscovery, digital forensics, cross-border data, privacy, cybersecurity, information governance, and AI governance, bringing a rare combination of legal judgment, technical fluency, and hands-on curiosity. This conversation covers why AI governance has arrived, why information governance is making a comeback, and why the next generation of legal professionals will need to become tech-and-data lawyers. WHY THIS MATTERS? AI governance is no longer a future issue. It is already here. Companies are dealing with employee use of public AI tools, data exposure, privacy risk, cybersecurity concerns, regulatory pressure, AI policies, privilege questions, AI transcription, and AI-related incidents. For lawyers and legal professionals, this is one of the clearest career white spaces in the market. KEY TAKEAWAYS AI governance has arrived. It is already one of the hottest and busiest areas in the legal industry. AI governance is about vision, guardrails, policies, ethical obligations, legal obligations, regulatory compliance, and business risk. Information governance is the backbone of AI governance. You cannot govern AI if you do not know where your data lives. Data governance sits inside AI governance, and may be the most important part of the whole program. The legal role is expanding, not shrinking. AI governance and data governance are creating new career lanes across law firms, corporate legal departments, privacy, cybersecurity, eDiscovery, and legal operations. You do not need 20 years of AI governance experience. No one really has that. Curiosity, teachability, issue-spotting, and legal judgment matter more. The best professionals in this space combine legal thinking with technical literacy. It is not just about knowing the tools. It is about applying the law to the facts, the technology, and the risk. AI governance is not just about models anymore. It now includes privilege protection, AI transcription, employee AI usage, public AI tools, data exposure, and AI-related breach scenarios. Outside counsel and in-house teams both have a role. Some companies rely heavily on outside counsel, while others use outside counsel for strategy, policy review, sanity checks, regulatory guidance, and high-risk questions. If you want to build a career in this space, get comfortable being uncomfortable. Follow the law. Follow the technology. Find mentors. Set up news alerts. Stay close to communities like LDI and IAPP. PEOPLE MENTIONED David Cowen - Host Bobby Malhotra - Litigation Partner; Chair of eDiscovery and Information Governance; AI Strategy Group Member; Founding Member of Legal Data Intelligence Melanie Prevost - Referenced in connection with career creation and emerging opportunities Malcolm Gladwell - Referenced in connection with the 10,000-hour rule COMPANIES & ORGANIZATIONS MENTIONED Winston - Bobby's firm Legal Data Intelligence / LDI - Community and framework for legal data professionals IAPP - AI governance and privacy education resource CLOC, ILTA, SOLID - Legal operations, innovation, and business of law communities M365, SharePoint, cloud platforms, data lakes, and metadata - Referenced as examples of where organizational data lives Colorado, Connecticut, Illinois, California, and Texas - Referenced in connection with emerging AI legislation EU AI Act - Referenced in connection with AI regulatory obligations NAIC - Referenced in connection with AI guidance in the insurance industry New York DFS - Referenced in connection with regulated financial institutions 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

Hosted by David Cowen | Careers and the Business of Law Fresh off four days at McCormick Place in Chicago, David Cowen sits down with Oyango Snell, President & CEO of CLOC, for a post-CGI debrief. The energy on the floor was unmistakable: this is not the same industry it was twelve months ago. From Second City opening every morning to standing-room-only sessions on AI maturity, CGI 2026 signaled that the legal ops community has moved from anxiety to confident curiosity. WHY THIS MATTERS The legal industry is no longer asking if AI matters. It's asking how to measure it. With budgets flat and demand rising, legal ops professionals are being forced to get strategic. This conversation captures the mood of the market and where the next five years are headed. KEY TAKEAWAYS Attendees came with hands-on experience and real questions. Anxiety is out, confident curiosity is in. Legal ops has moved from chaos to at least ad hoc, if not operational, on the maturity arc. "Do more with less" is hogwash. Flat budgets plus rising demand requires strategy, not just effort. AI won't replace jobs. People who leverage AI will replace those who don't. A growing economy means more demand for legal services. The doomsday narrative doesn't hold up. Education is the new currency. CLOC Academy is hitting the road to reach those who can't make it to CGI. Legal ops sits at the intersection of law and technology. That's the superpower. Own it. CGI 2027 is back at the Aria in Las Vegas. Pro tip from David: Thank the speakers. Easiest networking move there is. Pro tip from Oyango: Own your professional stake. Relationships are built through follow-up, not just introductions. PEOPLE MENTIONED David Cowen, Host Oyango Snell, President & CEO, CLOC Kevin Clem, Harbor; co-author of the State of the Industry Report Zach Kass, CGI 2026 Keynote Speaker Mary O'Connell, Market leader, referenced Connie Brenton, Founder and CEO, LegalOps.com COMPANIES & ORGANIZATIONS MENTIONED CLOC, Corporate Legal Operations Consortium; host of CGI and legal ops community anchor Harbor, Co-produced the 2026 State of the Industry Report with CLOC Second City, Opened each day of CGI 2026 and set the tone for the conference Anthropic, Ivo, OpenAI, Among the vendors actively hiring legal tech talent SOLID, Legal career and education community; Solid New York on October 1st CLOC Academy, Educational arm of CLOC, now going on the road beyond CGI 📅 Mark your calendar: SOLID New York, October 1st in New York City 📊 Get the 2026 State of the Industry Report at the CLOC website or Harbor's website. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next. 💡 To learn more about the future of legal innovation, visit: https://solid.legal/podcasts/ Never eat alone!

Hosted by David Cowen | Careers and the Business of Law Everyone's talking about Harvey, Legora, Spellbook, and Ivo. Nobody's talking about what they ride on top of. Tom Baldwin - founder and CEO of Entegrata, former CIO at Foley, Sheppard Mullin, Reed Smith, and Cadwalader - argues the real story is data infrastructure. Without a single source of truth, every AI tool in your firm is working from a partial picture. WHY THIS MATTERS? If your firm is buying AI tools without auditing the data underneath them, this is your warning shot. Tom's framing: toaster ovens need an electrical grid. KEY TAKEAWAYS AI tools work on narrow tasks, not whole-firm intelligence. 50 asset purchase agreements? Great. 200 million documents? No. Pulling documents out of your DMS strips away the metadata that makes them valuable - judge, opposing counsel, area of law, industry. That context is what AI actually needs. Business-of-law use cases (lateral prediction, cross-sell, client attrition, FP&A) are wide open. Practice of law got all the attention. A data lakehouse unifies data across 20-40 systems. Snowflake popularized it; Azure/Databricks/Fabric are the modern stacks. Cost is roughly the same at 200 lawyers or 2,000 - six figures, ongoing. Compute and storage are cheap; talent is the investment. Firms move from "nice to have" to "must have" after a near-miss. Tom's example: a firm almost fired an associate because their FTE calc didn't account for maternity leave. The chief data officer is becoming a real C-suite role. Sidley's among the early movers. Watch the forward-deployed legal engineer trend. Harvey is hiring practitioners for these roles. PEOPLE MENTIONED David Cowen - Host Tom Baldwin - Entegrata founder & CEO Andrew Sieja- Founder of kCura/Relativity; Entegrata's first angel investor Renee Morris, Katrina Dittmer, Glenn LaForce - Data leaders Tom mentioned COMPANIES AND TOOLS MENTIONED Entegrata - Turnkey data lakehouse in Azure Snowflake, Azure, Databricks, Microsoft Fabric - Data platform stacks Harvey, Legora, Spellbook, Ivo - Practice-of-law AI tools Sidley Austin - Early adopter of the chief data officer role 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

Kim Wolfe is one of the few non-lawyer executives running operations at the top of corporate legal. With a Wharton MBA and a quantitative background, she leads legal administration at State Street. David Cowen sits down with Kim to unpack what executive-level legal ops looks like inside one of the world's most regulated industries, and the career advice that changed everything. Key Topics Covered: The non-lawyer operator archetype: How business operators in legal leadership are reshaping the function Banking's slower AI path: Why regulation means Kim is two steps behind Intel and HP, and okay with that Lawyer-to-lawyer training: Why pairing power users with hesitant adopters moves the needle Who owns training: Why 67 percent of legal ops says it belongs to them The career lesson: As long as I see you here, I cannot give you more The 5:30 AM discipline: Why two hours of solo thinking is Kim's most important investment Simulation training: Why flight-simulator-style learning may fix inconsistent mentorship 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

Carl Morrison is the legal operations ambassador to Las Vegas, a CLOC board member, and one of the people who built the legal operations function on the Las Vegas Strip. David Cowen sits down with Carl to trace the evolution of legal ops from his first CLOC at the Bellagio a decade ago to today's McCormick Place, and to unpack the central question of this moment: are we using AI as a tool, or are we becoming enslaved to it? Key Topics Covered: The CLOC origin story: Building the first legal ops function in Las Vegas gaming and hospitality The CLOC 101 Academy: Why the entry-level program now serves over 150 attendees Slavery vs. freedom: Carl's framing of the choice every legal team faces with AI Personal agency as the answer: Why the automation question is fundamentally about who you want to be The Claude conversation: Why model preference shifts month to month and why the relationship matters more than the tool Fearlessness as career strategy: Why curiosity matters more than credentials 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

Joe Stephens just helped close a 49-million-dollar raise at steno. He also became a sommelier on the side. David Cowen sits down with Joe, director of legal solutions, law school professor, and one of the most thoughtful voices in litigation technology, to ask the question that defines this moment: what would you not automate? The answer pulls in John Cage, Unreasonable Hospitality, and why curiosity may be the only truly un-automatable skill left. Key Topics Covered: Service vs. hospitality: The distinction that powers steno's brand and why feel beats commodity What Joe would not automate: Physical connection, hugging his kids, walking the dog John Cage's 4'33": Why four and a half minutes of silence is the hardest piece of music ever composed The sommelier hobby: How Joe spends part of his AI dividend on deep human pursuits Listening and curiosity: The two skills Joe tells his students matter more than any technical knowledge Voice to text vs. pen and paper: Why composing a prompt forces slow thinking Unreasonable hospitality: Why delivering experience — not service — is the central differentiator in legal tech 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

David Cowen and Ari Kaplan have known each other for twenty years - this is their first podcast together. It is one of the most candid conversations in the series. Ari shares the philosophy that has carried him through two decades at the highest levels of corporate legal, why the US mindset about reclaimed time is a problem worth confronting, and why the most important question of the next decade may be the one Zach Kass asked from the keynote stage. Key Topics Covered: The validation tax: Ari's framework for the time you spend verifying AI output The AI dividend, US edition: Why Americans fill saved time with more work and Europeans leave earlier Permission to stop: David's confession of guilt around saved time and how to reframe it The mentorship moat: Why a Stanford-style simulation program might out-train a senior partner What AI cannot touch: Why high-stakes corporate work still requires human judgment and network Legal as R&D center: Why legal departments are becoming the experimentation hubs of the modern enterprise The renaissance of legal: Why the energy on the CLOC floor in 2026 feels fundamentally different 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

The pace of change in legal tech is no longer linear - it is exponential. David Cowen sits down with Colin Levy, one of legal tech's most prolific voices, to unpack why we are still at the frontier, why human appetite is failing to keep up with capability, and why daily discipline is the unsung superpower of every leader in this space. Key Topics Covered: Still at the frontier: Why the next five months will deliver more change than all of last year Appetite vs. capability: The widening gap between what AI can do and what humans can absorb The 5:30 AM discipline: Colin's daily writing practice and why a blank page is his most valuable tool Curiosity as a multiplier: Why the people winning right now read the technical guts of AI, not just the headlines The tipping point ahead: Colin's prediction that something big is coming — not a black swan, but a development beyond what anyone is imagining 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!

In a market flooded with AI tools, the smartest legal teams aren't chasing technology first - they're slowing down to ask better questions. In this episode of Careers and the Business of Law, David Cowen sits down with Stacy Lettie, James Vinson, and Scott Milner to unpack why design thinking is making a comeback in the AI era. Special shoutout to Nitant Narang for jumping into the conversation and raising one of the most important questions of the episode: when does asking "why" become too much? The conversation cuts through the hype around legal AI and focuses on something far more valuable: defining the right problem before rushing toward a solution. From practical frameworks to real-world failures, the panel explores how legal professionals can think more strategically, collaborate more effectively, and avoid wasting time and money on "shiny software" that doesn't solve the actual issue. Key Topics Covered: Why most legal teams are moving too fast into AI adoption without defining the underlying business problem first The real meaning of design thinking - minus the consultant jargon and buzzwords How asking "Why?" repeatedly uncovers the actual issue hiding beneath the surface The shift from "technology first" back to "people, process, then technology" Why communities like Legal Data Intelligence help legal professionals solve problems faster and avoid reinventing the wheel The importance of prototyping, failing early, and learning through experimentation instead of chasing perfection Why the future value of legal professionals will come from asking the right questions - not just delivering answers 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!