Ops Brief — 2025-W33 (2025-08-11 → 2025-08-18)

Editor's Intro

This week, something curious kept happening across conversations that, on the surface, couldn’t be more different—an AI governance workshop in Silicon Valley, a tactical masterclass on co-manufacturing agreements, a reflection on burnout’s ripple effects in high-stakes litigation. From big law to bootstrapped legal ops shops, from ESG supply chain tracing to trust accounting compliance, the same quiet truth kept emerging: legal innovation is hitting the limits of what technology alone can solve.

Sophie Best captured it flatly: “We’ve got so much tech, hardly anyone uses it.” But it wasn’t cynicism—it was diagnosis. The real challenge isn’t fewer tools or better tools. It’s integrating them into workflows real people can and will adopt. The bigger headline? This misalignment is no longer about features. It’s about trust, context, and culture.

Whether it’s Bridgette Carr coaching her students to say “I don’t know, but I know how to figure it out,” or Chris Grant rebuilding law firm pricing from outcomes instead of hours, the message is the same: we have to unlearn more than we have to invent.

The shift this week is from flash to structure. From buzzwords to fluency. From “AI lawyers” to AI-literate lawyering. And it’s not just showing up in forward-looking interviews. It’s embedded in risk conversations: Rio Laine warned that some of the most common malpractice claims—missed deadlines, botched documents—stem from fragmented systems and untrained teams, not rogue attackers or exotic tech failures.

Even in the underlying architecture of law practice management tools, the emphasis is falling on integration, governance, and aligning software with everyday human behavior. Adoption isn’t stalling because tools can’t do the job; it’s stalling because no one bothered to ask what job needed doing—or how a lawyer exhausted from a 12-hour grind might actually engage with yet another system.

Lexlee Overton called out the cost of this directly: “You can’t innovate, connect and lead when you’re chronically depleted.” Her focus on energy regulation—not in some abstract mindfulness sense, but in terms of physiological performance—resonated more deeply this week because so many legal tech failures turn out to be failures of attention. You can’t transform workflows in a system that trains everyone to triage first, reflect never.

And yet, there’s progress. More legal departments are resisting “magic bullet” solutions and demanding governance, clarity, and transparency from vendors. Colin Levy summed it up in an offhand line about CLM sales, but it might as well apply to the whole industry: “We happily tell a prospect, we’re capable of this, we’re not capable of that.” That frankness not only builds trust—it accelerates better-fit adoption.

The connective tissue here isn’t any one technology. It’s a maturing acknowledgment that innovation is social architecture as much as it is software. It’s a renewed attention to interfaces—not just user interfaces, but the human ones: across departments, disciplines, and hierarchies. Expect to see more innovation efforts grounded in behavioral economics, neuroscience, and operations design than in engineering breakthroughs.

What should we be watching? For starters, how firms re-scope the definition of tech competence. It may look less like “learn prompt engineering” and more like “build a feedback loop that survives fatigue and turnover.” It may mean that the next killer app isn’t an app at all, but an internal pattern of relationships, governance, and accountability that makes tools usable and useful—not just purchased.

Because if there’s one message echoing across all ten corners of this week’s legal tech landscape, it’s this: Tools matter—people more.

Deep Dives

Fresh Voices on Legal Tech with Bridgette Carr

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Podcast: Legal Talk Network - Law News and Legal Topics
Aug 8, 2025

One-Sentence Summary: This episode offers valuable insights from Bridget Carr, a clinical professor at the University of Michigan Law School, on how legal professionals, especially new lawyers and those in legal operations, can embrace design thinking, AI, and interdisciplinary collaboration to solve complex problems and redefine modern legal practice.

Why it matters: Carr reframes competence away from tool mastery toward the willingness to say “I don’t know, but I know how to figure it out,” then experiment, fail, and refine. For legal ops, this supports building sandboxes, lightweight pilots, and cross-functional learning loops over big-bang rollouts.

Analysis:
Hosts Dennis Kennedy and Tom Mighell continue their Fresh Voices on Legal Tech series with Bridget Carr, a clinical professor and co-director of the Human Trafficking Clinic and Lab at the University of Michigan Law School. Carr’s portfolio spans hands-on legal service to trafficking survivors, a design-thinking-based course on building a fulfilling legal career, multi-disciplinary problem-solving initiatives, and the upcoming launch of an AI law and policy clinic in January 2026. Her throughline: pairing deeply human lawyering (compassion, empathy, community) with pragmatic innovation and technology to improve outcomes at scale.

Carr frames legal tech adoption as a mindset shift rather than a tools race. Lawyers, she argues, must get comfortable with ambiguity, cultivate curiosity, play and experiment, and normalize failure/reflection—core design thinking behaviors that directly counter long-standing legal cultural norms. Her definition of technology competence is notably simple and powerful: be willing to say “I don’t know, but I know how to figure it out,” and then do the work—ask experts, test, iterate. She extends that human-centered approach to the judiciary through compassion retreats for judges, designed to build self-compassion and resilience so they can bring greater humanity to their work—an antidote to the historical myth of judges as “robotic” arbiters.

On practical innovation, Carr emphasizes cross-functional delivery models and low-friction interfaces. She challenges the profession to reassign certain legal-adjacent work to non-lawyers when that’s where the leverage is—e.g., positioning expungements as a human resources function because HR already manages background checks and has strong incentives to resolve records. She also advocates for high-tech that feels low-tech—like phone-based AI that a rural user can call without realizing they are interacting with advanced systems—so solutions meet people where they are.

Carr’s lab work showcases how AI and OSINT can make opaque systems visible. Her team has demonstrated that U.S. agricultural supply chains can be mapped “from soil to shelf” using social media, logos, maps, and public documents, offering a path to monitor forced labor and other human rights risks without relying on corporate or worker disclosures. The lab is also building multilingual tools to help self-represented parties navigate guardianship filings in ways that simultaneously reduce court friction by producing better, more complete submissions. She closes with career advice rooted in agency and experimentation—bet on yourself, design your own metrics for a good life in the law, and bring students and diverse experts into the innovation process early and often.

Key Takeaways:

Tech competence is a mindset: comfort with ambiguity, curiosity, and iterative learning. — Carr reframes competence away from tool mastery toward the willingness to say “I don’t know, but I know how to figure it out,” then experiment, fail, and refine. For legal ops, this supports building sandboxes, lightweight pilots, and cross-functional learning loops over big-bang rollouts.
Re-center the human differentiators while scaling with AI. — Compassion, empathy, and community are not soft extras; they are the core value lawyers and judges bring that AI cannot. Carr’s compassion retreats for judges show how investing in human skills enhances decision quality and change readiness—critical for legal ops leaders managing transformation and adoption.
Reassign legal-adjacent work to the highest-leverage owners (even outside Legal). — Carr argues expungements could be driven by HR, which already handles background checks and has incentives to resolve records. Legal ops can apply this lens to triage and redesign workflows—moving tasks to HR, Procurement, or shared services where process ownership, data, and motivation align.
Use AI and public data to illuminate supply chains for ESG and human rights compliance. — Her lab maps agricultural supply chains using OSINT and ML without relying on corporate or worker disclosures. Legal ops can partner with compliance and sourcing to pilot similar monitoring for forced labor risk, third-party due diligence, and regulatory reporting.
Design high-tech solutions with low-tech, accessible interfaces. — Phone-based AI and multilingual, court-aligned self-help tools meet users where they are and reduce downstream rework for courts. For legal ops, that translates to omnichannel client intake, clear document automation that produces court-ready outputs, and inclusive design for non-digital-native users.

Key Quotes:

"I don’t know, but I know how to figure it out." (context: Carr’s definition of true technology competence for lawyers—embracing uncertainty, asking for help, and learning by doing.) — Listen to this soundbite (at 7:22)
"Lawyers are the only people who weaponize interviewing." (context: A lesson from her multi-disciplinary problem-solving courses, highlighting how legal interviewing differs from user research in other fields and why collaboration requires redefining shared terms and intentions.) — Listen to this soundbite (at 13:55)
"If you’re not going to bet on yourself, why would anyone else ever do it?" (context: Career advice that guided Carr’s pivotal decision to take a visiting role at Michigan, underscoring agency and risk-taking in building a meaningful legal career.) — Listen to this soundbite (at 33:22)

Here’s the Issue with Making AI Work for Lawyers with Sophie Best

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Podcast: More Than A Lawyer with Holly Cope
Aug 12, 2025 • 38 mins

One-Sentence Summary: This episode offers an insightful look into the challenges of legal tech adoption, highlighting the critical role of people-centric strategies, effective training, and cultural change over simply implementing technology, which is highly relevant for legal operations professionals.

Why it matters: Overpromising and ‘magic button’ narratives erode credibility. Lawyers worry about reputational risk and job security. Trust grows when firms set realistic expectations (AI as copilot, not replacement), clarify accountability, and show how tools reduce drudgery without compromising quality.

Analysis:
The episode centers on a candid conversation with legal tech leader Sophie Best about why AI and legal technology often underdeliver inside law firms. The core thesis: this is not a tech failure—it’s a people, culture, and change management problem. Best recounts repeated stories from CIOs and partners who sit on large stacks of underused tools. She attributes the trust deficit to overpromising vendors, press-release-driven buying, poor rollout strategies, and inadequate, misaligned training. Lawyers are not resisting change out of laziness; they’re protecting reputations and workloads in environments that don’t set them up to succeed.

Best argues that firms must pivot from a “shiny object” mindset to a people-first adoption playbook. That includes involving practitioners early to define problems before selecting tools, running small, safe pilots with credible champions, delivering use-case-based training in bite-sized sessions, and telling persuasive internal stories about outcomes (time saved, risk mitigated, revenue unlocked). Integration is non-negotiable: if tools don’t sync with email, DMS, timekeeping, and practice management, lawyers won’t use them. A portfolio approach beats one-size-fits-all—different use cases warrant different tools, curated and governed by innovation teams to ensure proper application and expectations.

Beyond adoption, Best predicts structural shifts: AI will democratize law firm hierarchies and hasten a move away from the billable hour toward value-based pricing. Clients are becoming more informed, reshaping the outside counsel relationship toward strategic advisory over commodity doc review. Early AI wins often come from adjacent, high-friction tasks—meeting prep, summarization, redlining against playbooks, and information retrieval—freeing lawyers to focus on higher-value judgment work. Real-world examples include innovation-led portfolios at firms like Adleshaw, and an IP monitoring tool that surfaced a major infringement opportunity—illustrating how targeted tech can generate revenue and deepen client relationships when champions help translate capability into business outcomes.

The path forward: build trust through realistic expectations and practical training, integrate tools into real workflows, measure both efficiency and revenue impact, and accept that rollout takes months or years. Firms that get culture, change, and portfolio selection right will thrive; those prioritizing press clippings over adoption risk being left behind.

Key Takeaways:

Adoption is a people and trust problem, not a technology problem. — Overpromising and ‘magic button’ narratives erode credibility. Lawyers worry about reputational risk and job security. Trust grows when firms set realistic expectations (AI as copilot, not replacement), clarify accountability, and show how tools reduce drudgery without compromising quality.
Build a structured, use-case-led change program. — Involve practice leaders and end users early to define real pain points. Pilot with credible champions, create psychological safety to experiment, deliver bite-sized, workflow-specific training, and scale in stages. Peer storytelling drives adoption far better than generic vendor trainings or mass emails.
Prioritize integration and workflow fit to remove friction. — If tools don’t sync with core systems (email, DMS, timekeeping, PMS) and add manual steps, lawyers won’t use them. Design for zero extra data entry and seamless access; measure and eliminate friction points to sustain usage and data quality.
Adopt a portfolio approach—no single tool will do it all. — Different tasks require specialized solutions (e.g., contract review, IP monitoring, e-discovery). Innovation teams should curate and govern tools, aligning them to specific use cases and ensuring proper training and expectations. Avoid press-release buying that leaves licenses idle due to cost and poor rollout.
Prepare for business model shifts toward value and strategy. — AI will democratize elements of hierarchy, de-emphasize low-value doc review, and accelerate movement away from the billable hour toward value-based pricing. Clients are more informed; firms that lean into strategic advisory and AI-enabled business development will deepen relationships and win more complex work.

Key Quotes:

"We’ve got so much tech, hardly anyone uses it." (context: A CIO told Best this, encapsulating the core adoption gap despite significant tool spend.) — Listen to this soundbite (at 0:07)
"It’s not because they’re lazy or they don’t want to embrace change. It’s because it’s not being dealt with in the right way… the biggest gap is training." (context: Best argues firms blame lawyer resistance when the real issue is mismanaged rollout and lack of practical, use-case training.) — Listen to this soundbite (at 0:30)
"I think the billable hour is a little bit dead… we’re going to switch to value-based selling." (context: Best’s view on how AI-driven efficiency will pressure traditional pricing models and reward outcome-focused delivery.) — Listen to this soundbite (at 11:08)

The role of the client in innovation - Chris Grant, Managing Director of Client Value at Goodwin

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Podcast: Cracking Legal Innovation
Aug 7, 2025 • 56 mins

One-Sentence Summary: This episode offers a valuable, candid discussion on client value, effective fee arrangements, and the future of legal services from both in-house and law firm perspectives, providing insights into driving innovation from the client side and within a firm.

Why it matters: Grant reiterates that clients care about speed, risk mitigation, predictability, and business impact—far more than time spent or staffing levels. He advocates for output-based scoping, clear articulation of desired outcomes, and effective fee arrangements (EFAs) that align price with results and predictability instead of hours.

Analysis:
Daniel Porras (Legatics) and co-host speak with Chris Grant, Managing Director of Client Value at Goodwin and former legal ops leader at Barclays and HSBC. Grant lays out a client-value operating model that goes beyond legal excellence to deliver commerciality, predictability, and partnership. Having switched from the in-house “pain-giver” to the law firm side, he brings empathy for how firms actually work while pressing for change that clients have been asking for for years. He stresses that clients define value by outcomes—speed, risk mitigation, certainty of result, and stakeholder impact—not hours or headcount. That view underpins his push for Effective Fee Arrangements (EFAs) and for systematically scoping, pricing, managing, and measuring matters based on outputs.

Grant describes how his team at HSBC moved the needle toward 80% of matters on EFAs by conducting deep dives with firms, confronting scoping weaknesses, and creating accountability through relationship reviews. He emphasizes that not every matter suits an EFA and regional norms (e.g., Asia) can slow adoption, but EFAs are gaining ground. On competitive tenders, he rejects reverse auctions and the race to the bottom, using price disparities to improve scope clarity and align proposals to value. Post-matter, his preferred disciplines include net promoter scores (NPS), KPIs aligned to expectations (pricing predictability, tech usage, matter management), and structured debriefs that ask, “What could we have done better?”—with non-lawyer relationship owners available to handle hard conversations if needed.

On innovation, Grant is candid about “innovation theater” (pitch promises vs. delivery) and the practical barriers to deploying tech with heavily regulated clients. He argues law firms must be held to their commitments (e.g., did you actually deploy the tech you pitched?), but also recognizes that clients—especially global banks—need to “do the work” to clear InfoSec hurdles. He calls for industry-level standardization or mutual recognition among banks so vendors don’t need to pass 20 different, only slightly different security reviews. He notes a shift: firms now push harder to secure client approvals because they need the tools live in matters, not just referenced in decks.

On who pays for innovation and tech, Grant draws a line between the cost of doing business (e.g., email, KM) and client-specific, outcome-driving tech that may merit a price tag or disbursement—especially early in the lifecycle when investment is front-loaded. Over time, as tech becomes embedded and amortized, costs should taper and move into BAU. Whatever the approach, he insists on transparency: no hidden charges. He also argues for outcome-based proposals (team + LPM + tech + expected outcome and price) and fewer conversations about hours; where hours persist, tech pricing questions persist.

Looking forward, Grant envisions law firms as tech-enabled legal service providers that run more like businesses: using data from platforms and matters to manage operations, benchmark, and even predict client issues before they hit. That means deeper client-law firm partnerships, shared ideation space outside live matters, and pricing aligned to value delivered. He expects competition from ALSPs and the Big Four to continue to pressure transformation. He encourages clients to use their leverage more constructively—including banding together—to set standards and demand outcome-based service. Goodwin, he notes, is already leaning in, with partners proactively approaching him to price and deliver differently.

Key Takeaways:

Clients value outcomes over inputs; scope and price to the result, not the hours. — Grant reiterates that clients care about speed, risk mitigation, predictability, and business impact—far more than time spent or staffing levels. He advocates for output-based scoping, clear articulation of desired outcomes, and effective fee arrangements (EFAs) that align price with results and predictability instead of hours.
Operationalize EFAs with accountability: deep dives, better scoping, and measurement. — At HSBC, Grant targeted 80% of new matters on EFAs and used relationship reviews to audit what firms reported vs. what was real. Firms surfaced obstacles (poor scoping, shifting instructions), which were addressed collaboratively. EFAs won’t fit every matter or region, but the overall trend is positive. Rate cards became a fallback, not the default.
Use tenders to enhance value—not to race to the bottom. — Grant eliminated reverse auctions and used tender platforms to see selection patterns. Price disparities helped identify missing or unnecessary scope items. Sometimes a higher bid exposed a better approach, informing either the award or a scope reset across bidders. This converts pricing variance into scoping clarity and value alignment.
Make feedback a discipline: NPS, KPIs, and post-matter debriefs that ask what could be better. — He recommends embedding NPS at matter close and aligning KPIs (pricing predictability, tech usage, management) to the initial expectations. Post-matter debriefs—and using non-lawyer relationship leads when helpful—surface lessons, validate where tech or ALSPs added value, and build a shared definition of ‘value’ by client.
Treat technology pragmatically: avoid theater, standardize approvals, and be transparent about costs. — Firms must deliver the tech they pitch and clients must prioritize InfoSec approvals. Grant calls for industry-level security standardization or mutual recognition to avoid duplicative reviews. On cost-sharing, he distinguishes BAU tools from client-benefiting tech that may merit a fee early in its lifecycle—with full transparency and no hidden charges.
Run firms like businesses and get proactive with data. — Grant’s future state: tech-enabled delivery, outcome pricing, LPM as a standard capability, structured ops metrics, and using matter data to predict client issues. Create space outside live matters for ideation and co-pilots. Clients can amplify change by acting together and by being explicit about what ‘value’ means to them.

Key Quotes:

"We don’t really care how you do the work… did that work actually get us to the right result and get us what we wanted?" (context: Grant on why clients prioritize outputs—speed, risk, predictability, business outcomes—over hours or staffing inputs.)
"Feedback is a gift… If you’re not happy having the conversation, find the right person to have the conversation." (context: His guidance on normalizing post-matter debriefs, using NPS/KPIs, and leveraging non-lawyer relationship leads to handle tough discussions constructively.) — Listen to this soundbite (at 18:54)
"Put the work in, but let’s not put the work in 20 times; let’s put the work in once—with a little flavor and flair 20 times." (context: A call for industry standardization or mutual recognition in InfoSec/tech approvals so firms and vendors can deploy tools across multiple banks without redundant reviews.) — Listen to this soundbite (at 33:30)

Lexlee Overton | Beyond Burnout: Building High-Performing Legal Teams Through Well-Being

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Podcast: The Lawyer's Edge
Aug 12, 2025 • 41 mins

One-Sentence Summary: This episode focuses on lawyer well-being and burnout, offering insights into personal and team resilience, and emphasizing the importance of emotional intelligence for sustainable high performance in legal settings.

Why it matters: Overton explains how emotional states drive heart–brain coherence, opening or closing access to higher‑order thinking. Chronic fight‑or‑flight narrows cognition and creativity, while brief, science‑backed resets (e.g., gratitude, paced breathing) improve clarity, judgment, and advocacy—critical in litigation and client strategy.

Analysis:
Host Elise Holtzman interviews former trial lawyer Lexlee Overton, founder of Mind Over Law, on reversing burnout and building high‑performing legal teams through science‑backed well‑being and leadership practices. Overton shares her own breaking point—severe physical symptoms early in her career—that pushed her to study neuroscience, mindfulness, and the heart–brain connection. Her core argument: in law, chronic fight‑or‑flight is normalized and undermines performance, decision quality, creativity, and health; regulating energy (not just time) unlocks better advocacy, leadership, and team outcomes.

The conversation reframes well‑being as a performance imperative. Overton explains how emotional states rapidly change heart rate variability and brainwave patterns, gating access to higher‑order thinking in the frontal lobe. That’s why lawyers think of the perfect argument hours after a heated exchange—stress narrowed their cognition. She links sustained depletion to increased mistakes and malpractice risk, citing research tying depression and substance abuse to a large share of claims and disciplinary actions, and notes ABA initiatives pushing well‑being CLEs and renewed study of depression/burnout in the profession.

For firms, the business case is clear: one anxious or toxic person can incoherently disrupt a team, driving errors, disengagement, and turnover. Money alone doesn’t retain talent; belonging and care do. Overton’s playbook starts with leader self‑work and awareness, then “show, don’t tell”: use biofeedback to visualize state shifts; conduct anonymous culture surveys and exit interviews; create routine feedback loops in 1:1s; and implement simple, non‑woo practices (brief gratitude or breathing resets, clear boundaries, recovery time). She urges replacing the “hustle as a badge of honor” norm with emotionally intelligent leadership that fosters coherence—teams that are calm, connected, collaborative, and creative. Drawing on research (including Google’s team studies), she emphasizes that high performers can intuit and work with emotional states—of colleagues and clients alike—improving courtroom performance and client experience. The episode closes with a leadership challenge: you can’t build a high‑performing team until you first become the best version of yourself—and that requires boundaries, rest, and recovery by design.

Key Takeaways:

Energy management beats time management for legal performance. — Overton explains how emotional states drive heart–brain coherence, opening or closing access to higher‑order thinking. Chronic fight‑or‑flight narrows cognition and creativity, while brief, science‑backed resets (e.g., gratitude, paced breathing) improve clarity, judgment, and advocacy—critical in litigation and client strategy.
Burnout is normalized, so early warning signs get ignored. — Common signals—anger/irritability, waking with dread, brain fog, resentment toward clients, withdrawal from relationships—are often dismissed as “just part of practice.” Over time, low‑grade, continuous stress correlates with physical symptoms and depleted nervous systems, increasing risk for depression, substance use, mistakes, and malpractice exposure.
Leaders must model well‑being to get high performance and retention. — One dysregulated person can throw off team coherence; anxious leaders create anxious teams. Modeling boundaries and recovery, teaching practical state‑regulation, and investing in people reduce errors and turnover. Talent stays for belonging and care—compensation alone ranks lower as a retention driver.
Start with ‘show, don’t tell’ culture moves that skeptics accept. — Use biofeedback demos to visualize stress/coherence; run anonymous culture surveys and exit interviews to surface issues; add structured feedback prompts in 1:1s; adopt short state‑reset practices; leverage ABA well‑being CLEs. These create visible, low‑friction wins that build buy‑in and readiness for deeper change.
Dismantle the ‘hustle is the only way to win’ norm and address toxic highs. — Grinding as a virtue harms health, judgment, and culture. Emotional intelligence is a competitive advantage: Google’s research on teams shows that sensing and working with emotions, not raw intellect alone, predicts performance. Don’t let toxic rainmakers derail coherence; psychological safety and EQ fuel collaboration, innovation, and client outcomes.

Key Quotes:

"You can’t innovate, connect and lead when you’re chronically depleted." (context: Overton on the hard business cost of always‑on lawyering and why recovery is a performance requirement, not a perk.) — Listen to this soundbite (at 20:46)
"I would change this rule that hustle is the only way to win." (context: Overton’s ‘magic wand’ culture shift for the legal industry—replacing grind‑as‑virtue with sustainable, high‑performance leadership.) — Listen to this soundbite (at 29:15)
"Money is not the reason that people will stay in a place. Matter of fact, it’s like fifth on the list." (context: On talent attraction and retention—belonging and feeling cared for drive engagement more than compensation alone.) — Listen to this soundbite (at 27:51)

#209 - Operations Law 101: Co-Mans & Distribution Deals

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Podcast: The Startup CPG Podcast
Aug 12, 2025 • 1 hr 4 mins

One-Sentence Summary: This podcast episode provides a comprehensive legal overview of critical operational agreements (co-manufacturing, supply, and distribution) for CPG brands, focusing on key clauses, common pitfalls, and negotiation strategies to safeguard business interests and relationships.

Why it matters: The lawyers urge founders not to rush signatures. Use fair, brand-led templates that include mutual confidentiality and indemnification, assignment on change of control, sensible liability allocations (avoid arbitrary caps for co-man mistakes), and clear specs/performance obligations. A poor agreement can trap growth and destroy exit value.

Analysis:
This episode is a practical masterclass on the legal backbone of CPG operations, guided by attorneys Anthony Uzzolino and Ryan Hall of Giannuzzi Lewinden. The conversation covers the full journey from sourcing and co-manufacturing through warehousing and distribution, emphasizing how contracts, not just relationships, protect growth, optionality, and valuation. The lawyers repeatedly stress that clear agreements set expectations, allocate risk, and preserve exit pathways—while warning that a bad contract can be worse than none at all.

On co-manufacturing, they break down the core decision between turnkey and tolling pricing models, how to structure adjustments, and why capacity commitments, forecasts, quality specs, recall protocols, shipping terms, and payment cycles must be explicit. They urge founders to lock in IP with work-made-for-hire language (while carving out a co-man’s proprietary processes), avoid onerous volume commitments and one-sided liability caps, and build redundancy as they scale. Real-world failures—plant fires, bankruptcies, and an eight-figure payment to recover a formulation at exit—underscore the stakes of getting this right early.

For distribution, the team walks through territory/channel scope, exclusivity, carve-outs, performance targets, marketing obligations, and non-compete expectations—plus the tough reality of termination payments. Market benchmarks today often center around 1–2x distributor gross profit (with some players pushing 3x+). They recommend brand-led templates to anchor negotiations, invasion fees to preserve optionality, and contract assignability so an acquirer can assume agreements (recognizing buyers may net termination costs from purchase price). Internationally, pre-register trademarks before talks—Australia was cited as a recurring problem—and keep overseas deals “unsticky” (prepay, terminable on notice, no buyouts).

Warehousing/3PL agreements typically disclaim broad liability, making robust insurance a must across custody handoffs. If you’re already stuck in a bad contract, leverage breaches tied to clear specifications and performance obligations; if terms are loose and exclusive, you may need to ride out the term—another reason to invest in precise drafting from the start. The durable theme for legal and ops leaders: use fair, brand-forward templates, insist on assignability and sensible risk allocation, and build optionality at every step so growth—and exit—remain under your control.

Key Takeaways:

Contracts are the operational backbone—bad paper is worse than no paper. — The lawyers urge founders not to rush signatures. Use fair, brand-led templates that include mutual confidentiality and indemnification, assignment on change of control, sensible liability allocations (avoid arbitrary caps for co-man mistakes), and clear specs/performance obligations. A poor agreement can trap growth and destroy exit value.
Co-manufacturing: choose pricing model by stage and lock down IP, specs, and risk allocation. — Turnkey can leverage a co-man’s purchasing scale early; tolling offers control and direct cost wins later. Whichever you pick, define pricing-adjustment cadence, capacity commitments, forecasts, QC/recall/shipping terms, and payment. Use work-made-for-hire to own formulations (including enhancements), while carving out a co-man’s proprietary processes via license. Avoid aggressive volume commitments and one-sided liability caps.
Preserve optionality in distribution: manage territory, performance, and exit economics. — Clearly define geographic/channel scope and exclusivity, and seek carve-outs (e.g., certain chains or existing accounts) or invasion fees. Set performance/purchase targets so you can exit underperformance. Benchmark termination buyouts at roughly 1–2x distributor gross profit (some push higher). Ensure agreements are assignable to facilitate an acquisition; note acquirers often net termination costs into price.
International deals: protect trademarks first and keep terms non-sticky. — Register trademarks in-country before talks (Australia was flagged for repeated issues). Favor prepayment, easy termination on notice, and no buyouts. Don’t apply sticky DSD-style economics to overseas distributors where enforcement and recovery are harder.
Plan for failure modes: redundancy and insurance are non-negotiable as you scale. — Real failures included a co-man plant fire, a bankruptcy, and a $10M formula buyback at exit. Build multi-source manufacturing over time to avoid single-point failures and keep partners honest. 3PLs commonly disclaim loss; fill gaps with robust insurance covering factory-to-warehouse-to-retailer custody.

Key Quotes:

"Getting an agreement in place is really important... It's the backbone of your company." (context: Anthony Uzzolino emphasizing why written contracts—not just relationships—are essential to define responsibilities and protect the business through growth and exit.) — Listen to this soundbite (at 1:22)
"Co-men are great at producing things except for contracts." (context: Anthony highlighting the variability and frequent brand-unfriendly starting points in co-man templates, underscoring the need for careful legal review and brand-led forms.) — Listen to this soundbite (at 21:58)
"I'd like to see it no more than two years of gross profit." (context: Anthony’s benchmark for a reasonable DSD distributor termination buyout, with Ryan noting market pressure in some cases toward higher multiples.) — Listen to this soundbite (at 48:04)

Mastering Law Practice Management Tools

Podcast: Lifetime Legacy Lawyers
Aug 11, 2025

One-Sentence Summary: This episode provides a comprehensive overview of law practice management tools, detailing essential elements like calendaring, contact management, document storage, email, task management, word processing, billing, and accounting, and then reviews specific platforms like Rocket Matter, MyCase, Leap, Smokeball, and Clio, offering valuable insights for legal operations professionals seeking to optimize their firm's technology infrastructure.

Why it matters: The presenter urges firms to map essential functions (calendar, contacts, DMS, email, tasks/workflows, productivity, billing/trust) and then select tools that match practice philosophy and fee models. LPM suites overlap heavily, but success hinges on alignment with how your team actually works and integrates across your existing ecosystem.

Analysis:
The episode provides a pragmatic blueprint for evaluating and assembling a modern law practice management (LPM) stack. It starts by inventorying the essential operational building blocks—calendaring and docketing, contact management, document/file storage, email, task/workflow management, word processing and spreadsheets/presentations, and billing/accounting with trust compliance—then maps common technology choices for each. The presenter stresses that no single platform is truly one‑size‑fits‑all; instead, firms should align tools to their workflows, security obligations, collaboration needs, and existing ecosystems (Microsoft 365 vs. Google Workspace vs. Apple).

On infrastructure, the episode compares calendars (paper with a digital backup, Outlook/M365, Google Calendar/Workspace, Apple iCloud) and highlights governance basics like deciding a “source of truth” and ensuring shareability/backup. For contacts, it urges clarity on where records live (iCloud, Outlook/Exchange, Google) and policies for separating personal from work data and maintaining legal names for conflict checks and filings. For file storage, it contrasts enterprise options—Box (strong governance/versioning, secure links, compliance tiers), OneDrive (native to M365, improving sharing), Google Drive (collaboration leader), and Dropbox (mature sync/share)—and notes built‑in e‑signature add‑ons and the importance of security/compliance. Email selection is framed as part of a broader suite choice (Workspace vs. M365), with the recommendation to use domain‑based, professionally hosted email; Exchange Online tiering is outlined for firms that only need hosted mail.

Task management coverage spans Google Tasks, Microsoft To Do (with Planner and flagged email integration), and Apple Reminders, with an emphasis on using workflows/Kanban, voice capture, and AI‑assisted cleanup. Office productivity options include Word/Excel/PowerPoint (desktop vs. web co‑authoring), Google Docs/Sheets/Slides (real‑time collaboration strength), and Apple Pages/Numbers/Keynote. Billing/accounting options include QuickBooks Online and time/invoice tools like Harvest (with QuickBooks integrations), underscoring trust accounting as a non‑negotiable capability.

The second half surveys leading LPM suites—Rocket Matter, MyCase, LEAP, Smokeball, and a deeper dive on Clio—through the lens of core features: matter/case management, time/billing/payments, document automation, e‑signature, calendaring/tasks, CRM/lead management, analytics/reporting, integrations, and mobile apps. Differentiators highlighted include Rocket Matter’s legal project management and website/CRM; MyCase’s LawPay integration and reusable workflows; LEAP’s relationships with Lexis (Time Matters’ cloud path) and WealthCounsel; and Smokeball’s smart workflows.

Clio is examined in detail: personal and firm dashboards surfacing tasks, calendar, billing and cash performance against goals; comprehensive calendaring with a firm backup calendar; task workflows with time estimates and relative due dates; Kanban‑style matter stages with aging indicators; structured contacts (people/companies); streamlined time capture from any screen; billing with draft/approval flows, online payments, and payment plans; robust reporting; communication logs (email, phone, text) and a secure client portal; and mobile apps for both firm users and clients. The episode closes with practical selection advice: evaluate practice‑area fit (e.g., contingency vs. hourly), integration with your existing stack (M365/Google, LawPay, e‑signature), security/compliance posture (e.g., HIPAA attestations), e‑signature quotas, analytics depth, and pricing tiers, and treat the talk as a checklist to guide due diligence and change management.

Key Takeaways:

Build a modular stack that fits your workflows—avoid the one-size-fits-all trap. — The presenter urges firms to map essential functions (calendar, contacts, DMS, email, tasks/workflows, productivity, billing/trust) and then select tools that match practice philosophy and fee models. LPM suites overlap heavily, but success hinges on alignment with how your team actually works and integrates across your existing ecosystem.
Prioritize governance, security, and compliance across the stack. — Use domain-based, professionally hosted email; know where contacts and files reside; prefer secure sharing links over attachments; enforce a single source of truth for calendars with reliable backups; and ensure any system supports rigorous trust accounting. Vendors like Box offer compliance tiers (e.g., HIPAA) and e-signature is commonly built-in but may be tier-limited.
Workflow automation and analytics are becoming core operational levers. — Task flows, relative due dates, Kanban matter stages, and AI features (like contact de-duplication) reduce error and speed delivery. Advanced reporting surfaces firm, attorney, and task performance trends. Clio’s dashboards illustrate how daily metrics, overdue tasks, billing pipelines, and goal tracking drive accountability.
Choose infrastructure that matches collaboration needs and your suite strategy. — If real-time co-authoring is central, Google’s Docs/Sheets/Slides and Drive shine; if you’re standardized on M365, Word/Excel web co-authoring and OneDrive/SharePoint may suffice. File platforms differ: Box leads on governance/versioning; Dropbox excels at sync; OneDrive’s sharing has improved; Google’s collaboration is strongest.
Vendor selection should account for practice area, integrations, and tier economics. — Rocket Matter, MyCase (with LawPay), LEAP (Lexis Time Matters/WealthCounsel), Smokeball, and Clio all cover the basics but vary in project management, CRM/lead handling, document automation, and reporting. Scrutinize e-signature caps, payment plan support, trust accounting, and required integrations (M365/Google, accounting) to right-size per-user pricing.

Key Quotes:

"Law practice management tools are often touted as a one size fits all solution. And oftentimes we know that's not the case." (context: Sets the strategic tone: selection should be driven by firm-specific workflows and needs rather than vendor promises of universality.)
"The lifeblood of any practice is clients." (context: Underscores the importance of a disciplined contacts/CRM approach, accurate data, conflict checks, and centralized activity tracking.)
"Any tool that you utilize needs to have capability to do [trust accounting] for you and do that for you consistently well." (context: Highlights compliance and risk management as non-negotiables in evaluating billing/accounting and LPM systems.)

Flexibility and Innovation in Legal Tech

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Podcast: BDO's Legal Tech Talk Podcast
Aug 11, 2025 • 42 mins

One-Sentence Summary: This episode offers valuable insights for legal operations professionals through discussions on career evolution, the human element in legal tech adoption, and the importance of soft skills like vulnerability and curiosity in leadership within the legal field.

Why it matters: Cole stresses that legal tech and AI need auditing, check-ins, and human intervention to be effective. Programs justified primarily on headcount reduction often underperform and miss their objectives. For legal ops, plan governance (owners, workflows, QA), change management, and ongoing enablement into the total cost of ownership.

Analysis:
BDO’s Legal Tech Talk hosts interview Cynthia Cole, partner and global chair of Commercial Technology and Transactions at Baker McKenzie, former CEO and general counsel, and adjunct professor at Northwestern Law. The conversation blends leadership philosophy with practical legal-ops guidance on AI governance, technology adoption, and change management. Cole opens with a story behind her unconventional LinkedIn photo—fronting a charity band despite stage fright—anchored by a drummer’s advice that everyone in the audience is rooting for her. She connects that moment to leadership: explicitly telling teams they’re supported, creating psychological safety, and normalizing vulnerability. Cole’s career arc—Big Law to in-house, CEO during a crisis, then back to Big Law in 2016 to build a Silicon Valley tech transactions/privacy practice—illustrates turning adversity into opportunity and timing the market for emerging needs. A self-described humanist, Cole argues that technology, including legal tech and AI, never runs itself: successful adoption requires human oversight, auditing, continuous check-ins, and relationship-driven implementation. She cautions against budget narratives that treat tools as human replacements—those programs tend to fail their original goals. On AI governance, Cole notes most legal departments know acceptable-use policies are being violated; the real work is delicate, ongoing enablement: benchmarking peers, designing usable rollouts (even visually), creating contracting playbooks that reflect AI-era shifts (indemnities, limits of liability, etc.), and experimenting within controlled parameters. She urges outside counsel to provide a regular cadence of relevant updates so clients can pivot quickly. Cole emphasizes risk triage and the discipline of pausing—even mid-implementation—to revisit first principles: What problem are we solving? What is the biggest risk we must address now? Building credibility to pause starts with relationships (especially with decision-makers), consistent principles, and transparency about uncertainty. For talent development, she supports junior attorneys using AI for mundane tasks but insists they still perform foundational research and writing to build judgment—experience and even mistakes are irreplaceable. The throughline is a culture that fosters curiosity as a form of generosity and active listening, psychological safety, and the general counsel’s role as the conscience of the company—balancing innovation with principled leadership.

Key Takeaways:

Tech doesn’t run itself—budget for human oversight, not replacement. — Cole stresses that legal tech and AI need auditing, check-ins, and human intervention to be effective. Programs justified primarily on headcount reduction often underperform and miss their objectives. For legal ops, plan governance (owners, workflows, QA), change management, and ongoing enablement into the total cost of ownership.
AI governance must move beyond policy PDFs to practical, living enablement. — Most organizations know acceptable-use policies are being ignored. Cole helps clients with benchmarking, user-centered rollout materials, and contract updates that reflect AI risks (e.g., indemnities and limitation of liability). She recommends controlled experimentation and a regular cadence of updates from outside counsel so the program can adapt quickly.
Re-center on problem definition and scalable risk to avoid tool-first decisions. — When pressure mounts to ‘buy the tool,’ Cole advises pausing to ask what problem you’re solving and which two risks matter most. Build credibility to pause by cultivating relationships with decision-makers, setting expectations that you ask hard questions, and ensuring you have full information before committing resources.
Develop talent by pairing AI efficiency with foundational legal work. — Cole and a client GC agree: junior lawyers should still do the research and writing that build judgment; AI can shorthand mundane tasks but shouldn’t replace core learning. For legal ops, set role-based AI guidelines that clarify when to use tools and when to do the work manually to preserve training and quality.
Lead change with authenticity, psychological safety, and consistent principles. — Frequent pivots are inevitable in the AI era. Cole maintains team stability by being transparent about uncertainty, inviting feedback, and staying consistent on values. Her leadership playbook: explicitly tell teams you’re rooting for them, normalize vulnerability, and remember the GC’s role as the conscience of the company.

Key Quotes:

"Everyone in that audience is rooting for you. They want you to kill it." (context: Advice from her band’s drummer before she performed live—her touchstone for how leaders should explicitly communicate support to their teams.) — Listen to this soundbite (at 7:06)
"Any tech, legal tech, any tech, doesn’t run itself." (context: Cole’s core principle for technology adoption: tools require human oversight, auditing, and relationship-driven implementation to succeed.) — Listen to this soundbite (at 16:54)
"The general counsel is the conscience of the company." (context: A reminder that even amid rapid innovation, legal leaders must raise uncomfortable issues and anchor decisions in consistent principles.) — Listen to this soundbite (at 36:42)

Why Corporate Lawyers are Invested in the Legal Services Corporation

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Podcast: Legal Talk Network - Law News and Legal Topics
Aug 12, 2025

One-Sentence Summary: This episode highlights the critical role of corporate legal departments in supporting access to justice through pro bono work and financial advocacy for legal aid organizations, emphasizing the mutual benefits for both communities and corporate attorneys.

Why it matters: Legal aid organizations provide client intake, triage, training, supervision, and quality control—functions corporate departments cannot replicate at scale. Ford emphasized that without LSC-funded groups, even well-structured corporate programs (policies, committees, tracking) stall.

Analysis:
This Talk Justice episode spotlights how major Michigan corporations—Rocket (Rock Family of Companies), Ford Credit, and General Motors—structure, justify, and scale corporate pro bono and access-to-justice efforts in partnership with Legal Services Corporation (LSC)-funded organizations. Moderator Robert Gray frames civil legal aid as a joint venture requiring corporate leadership alongside courts and community stakeholders.

Jared Fleischer (Rock Family of Companies) argues that corporate engagement in civil legal services is fundamentally values-driven, not merely a talent or business ROI play. He calls civil legal aid one of the most effective forms of human services and urges companies to expand beyond case-by-case litigation to help people navigate legal-adjacent bureaucratic processes (e.g., housing counseling, permits, business licensing, Medicaid eligibility). He points to Rocket’s alignment with the Gilbert Family Foundation’s work on heirs’ property and eviction defense in Detroit, carried out through partnerships with LSC grantees such as Lakeshore Legal Aid and Michigan Legal Services. Fleischer also notes a market gap: most corporations don’t directly support LSC, creating a sizable opportunity for broader corporate penetration and support.

Kim Yurchuk (General Motors) focuses on mobilizing in-house attorneys who are eager to contribute but fear stepping outside their subject-matter lanes. GM’s pro bono committee has increased participation by: partnering closely with legal aid organizations and law firm pro bono departments for training and supervision; offering discrete, high-impact matters (expungements, driver’s license restorations, custody stability, nonprofit governance, trademark help); and surveying lawyers to align opportunities with interest and bandwidth. She stresses that pro bono is still practicing law—standards and competence matter—and credits legal aid partners for their patience, structure, and expertise that make corporate participation feasible and ethical.

Kim Ray (Ford Credit) underscores the indispensable role of LSC-funded organizations as the pipeline and training infrastructure that connects corporate lawyers with clients—“nobody’s knocking on Ford’s front door asking for a lawyer.” Ford is a longstanding signatory to LSC’s Congressional funding letters and actively advocates on Capitol Hill (often alongside the State Bar, State Bar Foundation, and firms like Dykema) to tell district-specific impact stories. Ray outlines Ford’s internal scaffolding—policy, committee, tracking system—while emphasizing that without LSC-funded partners, corporate pro bono “falls on its face.” For companies looking to scale, she advises starting by using LSC’s website to find vetted local partners nationwide, reflecting the distributed nature of modern in-house teams.

On scaling, the panel converges on three levers: tone at the top (leaders model participation and spend political capital to support LSC funding), systems and measurement (formal policies, participation tracking, and bite-sized projects that fit modern workloads), and partnerships (LSC grantees and law firm pro bono teams for training, supervision, and client intake). Robert Gray closes with a proven scaling tactic from private practice: a local office reached 100% participation because the leader personally led by example, which was then replicated firmwide to achieve sustained universal pro bono participation. The episode offers a playbook for legal operations leaders: anchor programs in corporate values, reduce fear with training and scoped matters, use LSC’s network for pipeline and quality control, measure participation, and advocate publicly for LSC funding to ensure long-term sustainability.

Key Takeaways:

LSC-funded partners are the essential infrastructure for corporate pro bono. — Legal aid organizations provide client intake, triage, training, supervision, and quality control—functions corporate departments cannot replicate at scale. Ford emphasized that without LSC-funded groups, even well-structured corporate programs (policies, committees, tracking) stall.
Lead with values; the business case is helpful but not necessary. — Rocket’s perspective: civil legal aid is a high-impact human service and a corporate cultural imperative (“do the right thing”), not just a talent or brand strategy. Framing pro bono as values-driven can unlock executive sponsorship and sustained commitment.
Design for participation: offer bite-sized, skills-aligned matters with strong training. — To overcome in-house attorneys’ fear of leaving their lanes, GM curates discrete, high-impact matters (expungements, license restorations, nonprofit governance, trademarks) and relies on legal aid and law firm partners for training and supervision—reinforcing that pro bono still requires full professional competence.
Scale through leadership, systems, and measurement. — Tone at the top drives adoption, but ops mechanics make it stick: formal policies, interest surveys, refreshed opportunity catalogs, participation tracking, and local champions. The 100% participation model shows how leader behavior becomes a norm when paired with expectations and transparency.
Corporate advocacy for LSC funding multiplies impact. — Ford’s direct engagement with Congress—backed by district-level impact stories—demonstrates how corporate voices can protect and grow the funding that sustains the entire pro bono pipeline. Outreach to in-house networks (e.g., ACC) can also help new departments get started.

Key Quotes:

"Nobody's knocking on the front door of Ford Motor Company saying, hey, I want a lawyer... The only way we can get out into the communities... is through our LSC-funded organizations." (context: Kim Ray explaining why LSC grantees are the indispensable conduit connecting corporate legal teams to community clients.) — Listen to this soundbite (at 0:01)
"I push back on the notion that you have to have a business justification. You can do philanthropy and you can do pro bono legal work because you have the ability to do it and it's the right thing to do." (context: Jared Fleischer on anchoring corporate access-to-justice efforts in values rather than purely ROI.) — Listen to this soundbite (at 8:02)
"It's still practicing law when you're pro bono, right?" (context: Kim Yurchuk underscoring the need for proper training, supervision, and standards—delivered by legal aid and law firm partners—to ensure ethical, competent service.) — Listen to this soundbite (at 15:33)

EP 29: Building a Legal Tech Brand with Colin Levy & Innovating the Future of Law

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Podcast: Legal Leaders
Aug 8, 2025 • 39 mins

One-Sentence Summary: This episode features an in-depth interview with Colin Levy, GC of Malbec and a prominent voice in legal tech, discussing his career progression, the importance of technology adoption in law, building a personal brand, and the evolving role of AI in legal practice.

Why it matters: Levy rejects buzzwords like “AI-powered” and “revolutionary,” pushing vendors and buyers to align on what a tool actually does and doesn’t do. He highlights Malbek’s practice of telling prospects precisely where the product fits—and where it doesn’t—which he links to superior customer outcomes and long-term trust.

Analysis:
General Counsel Colin Levy traces a nonlinear path from Boston College Law to leading the legal function at Malbek, a CLM company, while becoming one of legal tech’s most visible educators. Early exposure to e‑discovery in Big Law and a strong preference for transactional work set his direction, but he found law school largely disconnected from the realities of technology and modern practice. After graduating into the tail end of the Great Recession, he built skills through temporary roles before landing in-house at Velcro Group, where he supported sales and finance on contracts, helped with corporate governance for numerous international entities, and even co-developed a rudimentary NDA review tool—his first hands-on experience with product development and legal tech. A mental health break and a short stint at CW Services were followed by a role at Pearson, where he managed contract negotiations with deeper exposure to IP and digital content as the business shifted to software. A mentor GC at Pearson encouraged him to lean into his growing interest in tech and public writing. Consistent content creation and community-building on LinkedIn—paired with solid in-house execution—ultimately opened the door to Malbek. Now a team of one, Levy triages priorities daily, relies on outside counsel only for specialized matters (patents, trademarks, complex corporate actions), and benefits from autonomy aligned to business needs. He is outspoken about the cultural barriers that slow legal tech adoption, arguing that transparency and specificity beat buzzwords. He pushes back on marketing that overpromises (e.g., “AI-powered,” “revolutionary,” or calling tools an “AI lawyer”), and praises Malbek’s culture of telling prospects exactly what the product can and cannot do—an approach he says underpins strong customer outcomes (the show cites 120% retention and 96% CSAT). Looking ahead 1–5 years, Levy believes the key shift for in-house teams will be learning to collaborate with AI rather than compete with it. He urges realistic expectations—AI is imperfect and not a panacea—but notes that “AI is as bad as it’s ever going to be right now,” implying rapid improvement and the need for readiness. He criticizes law schools for lagging in AI and practice skills (though some are improving), and he’s acting as an adjunct at Albany Law to help close that gap. His advice to both sellers and rising lawyers is relationship-first: listen more than you talk, build trust by being candid, and focus on concrete value over hype.

Key Takeaways:

Culture is the biggest bottleneck to legal tech adoption—transparency and specifics build trust. — Levy rejects buzzwords like “AI-powered” and “revolutionary,” pushing vendors and buyers to align on what a tool actually does and doesn’t do. He highlights Malbek’s practice of telling prospects precisely where the product fits—and where it doesn’t—which he links to superior customer outcomes and long-term trust.
Treat AI as an augmentor, not a rival, and calibrate expectations. — Levy argues the near-term challenge is learning to collaborate with AI, not compete with it. AI won’t solve everything and will make mistakes, but it will improve quickly. Legal ops teams should pick use cases where AI’s strengths (speed, patterning) complement human judgment and build governance accordingly.
A team-of-one GC model can scale with rigorous triage and targeted outsourcing. — Levy runs Malbek’s legal function solo, prioritizing daily tasks based on business needs and engaging outside counsel only for specialized work (e.g., patents, trademarks, complex transactions). For lean legal ops, this underscores the value of clear intake, prioritization, and a curated specialist panel.
Personal brand and networks materially influence in-house career mobility and buying influence. — Consistent, authentic content creation and relationship-building helped Levy move across roles and into the GC seat. His networking guidance—approach people to learn, not to ask for jobs; listen more than you talk—also maps to effective vendor relationships and internal stakeholder management.
Law school’s lag on AI and practical skills reshapes talent strategy. — Levy notes most law schools still under-serve tech/AI and often funnel students into narrow buckets. Legal ops leaders should expect to upskill hires, consider candidates from adjacent roles (legal ops, contract admin), and partner with practitioners/adjuncts who bring modern workflows into training.

Key Quotes:

"AI is as bad as it's ever going to be right now." (context: Levy’s counsel to in-house teams to plan for rapid capability gains and shift from fear of AI to pragmatic collaboration.) — Listen to this soundbite (at 34:13)
"we kind of happily tell a prospect, you know, we're capable of this, we're not capable of that." (context: Describing Malbek’s transparent approach to sales and customer alignment, which he ties to trust and strong satisfaction/retention.) — Listen to this soundbite (at 31:09)
"The way to build a relationship is to listen more and talk less." (context: Career and go-to-market advice for lawyers and vendors: prioritize learning, empathy, and specificity over self-promotion and hype.) — Listen to this soundbite (at 38:13)

Risky Business - Managing Technology for Ethical Competence with Rio Laine

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Podcast: Adventures In Legal Tech
Aug 8, 2025 • 29 mins

One-Sentence Summary: This episode offers solid, practical advice for legal operations professionals on building a tech stack, mitigating malpractice risk through technology, and vetting tech vendors, making it highly actionable for improving firm operations and security.

Why it matters: Matter-centric PMS plus calendaring is foundational for tracking deadlines, tasks, documents, time, and communications. These are the highest-risk workflows—get them right first, and look for automation (rules-based docketing, template-driven drafting) to reduce malpractice exposure.

Analysis:
Host Jared Correia and guest Rio Lane (Director of Strategic Partnerships at ALPS Malpractice Insurance) tackle a common problem: how lawyers should build a tech stack when they’re overwhelmed by choices and uncertain how to buy. Lane’s first principle is clarity on essentials versus nice-to-haves. For most firms—especially solos—practice management software and robust, preferably integrated calendaring are non‑negotiable because deadline and drafting errors are among the most frequent sources of malpractice claims. The conversation moves from tools to the operational layer: the biggest risks often stem from fragmented systems that don’t integrate, manual data entry, and the absence of standardized processes and training. Lane urges firms to write simple SOPs, onboard consistently, and look for automation opportunities (especially in calendaring and document generation). Adoption barriers are cultural as much as technical—lawyers’ risk aversion and fear of choosing “wrong” stalls progress. Start with low‑stakes wins (e.g., calendaring), then build momentum. Younger attorneys may be tech‑comfortable but still need coaching on using technology in a business context because law school rarely teaches law firm operations. On procurement and vendor risk, Lane lays out a due‑diligence checklist: require written security/privacy policies; confirm breach-notification procedures; clarify data portability and deletion when you offboard; test integration with your current stack; audit for overlapping features to avoid tool sprawl; favor vendors who understand law firm requirements; and insist on transparent pricing and cancellation terms to avoid sticky subscription costs. Lane also highlights a fast‑rising threat vector—wire fraud and sophisticated social engineering (including deepfakes). Standard cyber policies often exclude losses from social engineering, so firms should pair proper cyber coverage (separate from malpractice) with operational controls like wire-verification tools. ALPS has launched a curated vendor ecosystem to offer insureds discounts on risk‑reducing tools; its first partner, Certified, verifies wire details and provides a fraud recovery hotline that liaises with the Secret Service. On insurance selection, Lane advises shopping about three months before renewal, ensuring the policy fits the practice (e.g., coverage for pro bono, prior acts/tail coverage when moving firms, limits appropriate to matter types), and adding dedicated cyber coverage for events such as email compromises and data breaches (noting that typical cyber does not cover wire fraud). The actionable playbook for legal ops: anchor your stack with PMS and integrated calendaring, map and document workflows, train to consistency, vet vendors rigorously on security and contracts, deploy wire-fraud controls, and close insurance gaps with purpose‑built policies.

Key Takeaways:

Build the stack around practice management and integrated calendaring. — Matter-centric PMS plus calendaring is foundational for tracking deadlines, tasks, documents, time, and communications. These are the highest-risk workflows—get them right first, and look for automation (rules-based docketing, template-driven drafting) to reduce malpractice exposure.
Process and integration reduce malpractice risk more than features do. — The biggest failures come from tools that don’t talk to each other, manual data entry, and inconsistent usage. Create simple SOPs, enforce uniform training, and select systems that integrate cleanly to minimize rekeying and data drift (e.g., a single date entered differently in two systems can create a claim).
Use a vendor due‑diligence checklist focused on security, data, and contracts. — Demand written security/privacy policies and breach‑notification procedures; confirm data export and deletion at offboarding; verify integration with your current stack; test for feature overlap to avoid tool bloat; prefer vendors who understand legal confidentiality; and require transparent pricing and cancellation terms to avoid being locked into underused subscriptions.
Treat wire fraud and social engineering as top-tier risks—and insure and tool accordingly. — Standard cyber policies often exclude social engineering/wire fraud losses. Pair cyber coverage for email compromise/data breaches with operational controls like wire-detail verification and a fraud recovery service. Deepfake-enabled scams are rising; callbacks and verification software are now essential safeguards.
Manage change deliberately: start small, coach for business use, and retire legacy tools. — Lawyers’ risk aversion and time pressure stall adoption. Begin with low-stakes wins (e.g., calendar hygiene), teach younger lawyers how to apply tech in a business context, document workflows, and replace legacy software (e.g., WordPerfect) when it blocks collaboration or integration.

Key Quotes:

"The majority of standard cyber policies, they do not protect lawyers... for losses incurred due to, like, social engineering that results in wire fraud." (context: Lane explains why firms need both cyber coverage and operational controls for wire transfers, and why specialized tools (and recovery services) matter.) — Listen to this soundbite (at 6:17)
"Some of the most common malpractice claims come from calendaring and document drafting." (context: A reminder that everyday workflows, not exotic scenarios, drive most risk—underscoring the need for integrated calendaring and drafting automation with clear SOPs.) — Listen to this soundbite (at 10:42)
"It’s way easier than you would think to make a mistake with your tech." (context: Lane highlights how poor integrations, manual entry, and inconsistent processes create hidden error paths that can lead directly to claims.) — Listen to this soundbite (at 8:21)

Also of Interest

Entrepreneurship Meets Law: Legal Essentials for Wellness & Aesthetic Business Owners: This episode focuses on the legal complexities of operating medical spas, emphasizing the importance of specialized legal counsel, compliance with state-specific regulations, and avoiding common pitfalls to protect licenses and finances.
LegalTechTalk Uncovered 2025 - Anna Balabina - E19: This episode from Legal Tech Talk 2025 provides a high-level overview of discussions around legal efficiency, AI as a tool for lawyers, and the growth of the legal tech industry, and a brief introduction to CasePal.
Policy And Innovation: This episode focuses on a congressional candidate's past work in fostering innovation and entrepreneurship in Houston, particularly around challenges in accessing capital for women and minority entrepreneurs, but offers limited direct insights for legal operations professionals.