Watch on YouTube HERE. AI is everywhere—but are enterprises actually using it effectively?

In this episode of Contractually Speaking, Matt sits down with Shashi Bellamkonda, Principal Research Director at Info-Tech Research Group and a 2026 Thinkers360 Top AI Thought Leader, for a candid conversation about what enterprise AI adoption looks like beyond the hype.

Shashi explains why organizations need to stop thinking of AI as synonymous with ChatGPT and instead focus on where AI's analytical and predictive capabilities can deliver measurable business value. The key isn't simply having access to a more powerful model—it's having clean data, asking precise questions, and choosing the right technology for the task.

Matt and Shashi explore what that means for contracting and procurement. From compliance and missed obligations to revenue, renewals, supplier performance, and customer experience, contract intelligence is creating opportunities that go far beyond simply saving employees time.

They also tackle the human side of adoption. As AI agents become increasingly capable of communicating and acting on our behalf, how do organizations make sure AI continues to support people rather than speak for them?

🔑 Key Takeaways:

• Separating enterprise AI hype from practical business value
• How AI can unlock insights across thousands of contracts
• The connection between contract intelligence, compliance, revenue, and customer experience
• Why human validation still matters
• "Chat fishing" and the risk of letting AI speak for us
• How procurement and contracting teams can approach AI more strategically

Shashi will continue the conversation at Malbek Envision 2026 in Austin, October 12–14, where he'll speak about his research into enterprise AI adoption and how procurement and contracting teams can make the most of AI.

🚀 Register to see Shashi and other industry leaders live at Malbek Envision 2026: https://envision.malbek.io/

👉 Subscribe and listen to Contractually Speaking on the platform of your choice: https://podcast.malbek.io

🎙️ Interested in being a guest or sponsoring the show? We’d love to hear from you—email us at [email protected]

💡 Learn more about Malbek: https://malbek.io

Watch on YouTube HERE. In this episode of Contractually Speaking, Matt sits down with Malbek General Counsel, legal technology advocate, professor, and author Colin Levy to discuss his new book, Code Switched: A Lawyer’s Guide to the Era of AI.

For legal teams, the biggest questions now are how to use AI responsibly, how to govern it across the enterprise, and how to manage risks that are evolving almost as quickly as the technology itself.

Colin explains why he wrote the book to help legal professionals cut through both the hype and anxiety surrounding artificial intelligence, and develop a more practical understanding of what AI can—and cannot—do.

The conversation explores how legal teams are moving from individual AI use cases toward enterprise-wide governance, why lawyers need a voice in corporate AI strategy, and how data privacy, confidentiality, security, and ethical obligations are shaping adoption not only for today’s technology, but for what may come next.

🔑 Key Takeaways:

• How lawyers can separate useful AI applications from hype
• Confidentiality, security, ethics, and responsible AI use
• Why legal teams should help shape company-wide AI policies
• Future-proofing agreements as AI models, pricing, and capabilities evolve
• The risks of autonomous and agentic AI
• How lawyers can balance innovation with risk rather than simply avoiding it

📘 Pre-order Colin’s new book, Code Switched: A Lawyer’s Guide to the Era of AI (20% off with promo code SWITCHED20)

👉 Subscribe and listen to Contractually Speaking on the platform of your choice at podcast.malbek.io

🎙️ Interested in being a guest or sponsoring the show? We’d love to hear from you—email us at [email protected]

💡 Learn more about Malbek

Watch on YouTube HERE. Season 2 of Contractually Speaking launches with an out-of-this-world conversation between our host Matt Patel and former NASA astronaut Mike Massimino. What does it take to stay calm when you're hundreds of miles above Earth, something goes wrong, and the success of the mission depends on your next move? Mike takes us inside the unique experiences of seeing Earth from orbit, becoming the first person to tweet from space, and even appearing as himself on The Big Bang Theory.

Mike shares lessons that apply far beyond NASA: how great teams prepare for the unexpected, why asking for help is a strength, how setbacks can lead to better opportunities, and why understanding what you're agreeing to—including the contracts you sign—matters.

Across a decades-spanning career, Mike shares stories from his two Space Shuttle missions servicing the Hubble Space Telescope. He reflects on the training, teamwork, perseverance, and trust required to operate in an environment where mistakes can have extraordinary consequences.

🔑 Key Takeaways:

• How Mike went from being rejected by NASA to becoming an astronaut
• What launching into space and seeing Earth from orbit actually feels like
• What The Big Bang Theory got right about astronaut life
• Why Mike has learned to appreciate the lawyers who help him understand his contracts
• The Hubble repair that seemed impossible—and the teamwork that saved the mission

🚀 Join us at Malbek Envision 2026, Oct. 12-14 in Austin, TX to see Mike’s keynote live: Register Now

📘 Get Mike’s book, Moonshot: A NASA Astronaut's Guide to Achieving the Impossible

👉 Subscribe and listen to Contractually Speaking on the platform of your choice at podcast.malbek.io

🎙️ Interested in being a guest or sponsoring the show? We’d love to hear from you—email us at [email protected]

💡 Learn more about Malbek

Watch on YouTube HERE. In the Season One finale of Contractually Speaking, Matt Patel shares two conversations recorded recently on-location in Chicago during the CLAS and CLOC events, with Gabriel Saunders and Jonathan Perkel.

Gabriel explores a challenge every legal technology provider faces: how to prioritize customer requests, feature enhancements and product innovation at scale. He shares how his team uses AI agents to automatically analyze customer conversations, identify patterns and generate actionable product insights — helping product teams reduce duplication, accelerate prioritization and improve responsiveness.

Jonathan focuses on the buyer perspective, reflecting on his organization’s CLM evaluation journey, and breaking down the real-world tradeoffs legal departments face when choosing enterprise legal technology. From integrations and AI capabilities to total cost of ownership, configurability and long-term scalability, he and Matt highlight the

Together, these conversations provide both the vendor and customer perspective on how AI is reshaping legal tech product development, evaluation and adoption.

🔑 Key Topics Covered:

• Using AI agents to manage product requests and feature prioritization
• Balancing innovation with usability and product stability
• Evaluating CLM platforms based on business needs and budget
• The importance of integrations with Salesforce and AI tools
• Configurable vs custom-coded enterprise platforms
• AI-powered contract intelligence and repository analysis

👉 Subscribe and listen to Contractually Speaking on the platform of your choice at podcast.malbek.io

🎙️ Interested in being a guest or sponsoring the show? We’d love to hear from you—email us at [email protected]

💡 Learn more about Malbek

Watch on YouTube HERE. In this episode of Contractually Speaking, Matt sits down with Steph Corey and Sumi Trombley from UpLevelOps to discuss how legal operations teams can navigate the fast-moving world of AI, point solutions and enterprise legal technology.

With new AI tools emerging constantly, legal teams are under pressure to evaluate sandboxes, run pilots, compare vendors and determine what actually solves the business problem. Steph and Sumi explain why the best starting point is still the basics: understanding requirements, defining use cases and identifying the real pain points before chasing the newest AI tool.

The conversation explores when a point solution may be enough, when a broader legal technology platform is needed and why AI adoption requires more than enthusiasm. From governance and ethical use to cross-functional ownership and ROI measurement, this episode highlights the growing role of legal ops as the function that brings structure, accountability and clarity to legal AI evaluation.

Whether your team is testing multiple AI tools, debating Copilot versus other LLMs or trying to decide between a point solution and a full CLM platform, this episode offers practical guidance for making smarter, more sustainable legal tech decisions.

🔑 Key Topics Covered

• AI point solutions versus enterprise legal tech platforms
• Why legal teams need clear use cases before evaluating tools
• The role of legal ops in AI governance and adoption
• How to manage multiple AI pilots, sandboxes and POCs
• Comparing vendors with scorecards, requirements and ROI
• Why base LLMs and legal-specific tools serve different needs
• Total cost of ownership, tuning and long-term maintenance
• Cross-functional ownership of AI across legal, IT, sales and marketing

👉 Subscribe and listen to Contractually Speaking on the platform of your choice at podcast.malbek.io

🎙️ Interested in being a guest or sponsoring the show? We’d love to hear from you—email us at [email protected]

💡 Learn more about Malbek

Watch on YouTube HERE. It’s a Matt-fest on this episode of Contractually Speaking, as Matt Patel is joined by Matt Linder from Harbor to break down what a CLM deployment really means — and why it’s about far more than just implementing technology.

Drawing from real-world experience implementing CLM for large global organizations, Matt Linder shares how successful deployments focus first on solving contract chaos — from slow cycle times and lack of visibility to inconsistent language and missed business value.

The episode tackles one of the biggest topics in legal tech today: AI. From pre-signature contract review to post-signature intelligence across large contract repositories, the discussion outlines what it really takes to make AI effective — including structured data, strong templates, clear processes, and well-crafted prompts.

Whether you’re implementing CLM for the first time or modernizing an existing system, this episode offers practical, experience-driven insights to help you build a scalable, high-impact contract management strategy.

🔑 Key Topics Covered:

• Solving contract chaos: speed, visibility, and consistency
• Why workflow design should come before repository and AI
• Repository strategy: from storage to business intelligence
• Integrating CLM with CRM, finance, and other business systems
• AI across the lifecycle: pre-signature and post-signature use cases
• The importance of structured data, templates, and clause libraries

👉 Subscribe and listen to Contractually Speaking on the platform of your choice at podcast.malbek.io

🎙️ Interested in being a guest or sponsoring the show? We’d love to hear from you—email us at [email protected]

💡 Learn more about Malbek

Watch on YouTube: HERE. In this episode of Contractually Speaking, Matt Patel sits down again with Devon Misterman from Epiq to tackle one of the most challenging — and often underestimated — parts of any CLM implementation: data migration.

Whether transitioning from a legacy CLM or starting fresh with thousands of contracts stored across systems and PDFs, migration is more than just moving files. It’s about structuring, extracting, and validating critical contract data so it becomes searchable, reportable, and actionable.

Matt and Devon break down why organizations should avoid trying to “boil the ocean” and instead take a phased approach — focusing first on high-value contract types and active agreements. The conversation also highlights the reality that, despite advances in AI, human oversight remains essential for ensuring accuracy, handling edge cases, and properly mapping contract relationships like amendments, SOWs, and master agreements.

From understanding your current data landscape to setting realistic expectations around time, cost, and effort, this episode offers a practical guide to getting migration right — and setting your CLM implementation up for long-term success.

🔑 Key Topics Covered

• Why data migration is the hardest part of CLM implementation
• The role of human validation alongside AI extraction
• Challenges with contract structure, hierarchy, and relationships
• Extracting key metadata (renewals, terms, clauses) for reporting
• Setting realistic expectations for cost, effort, and timelines
• Using migration as a way to understand past contracting practices

👉 Subscribe and listen to Contractually Speaking on the platform of your choice at podcast.malbek.io

🎙️ Interested in being a guest or sponsoring the show? We’d love to hear from you—email us at [email protected]

💡 Learn more about Malbek

Watch on YouTube HERE. In this episode of Contractually Speaking, Matt sits down with Malbek’s General Counsel, Colin Levy, to break down a foundational — yet rapidly evolving — concept in legal operations: the contract playbook.

While playbooks have existed for decades, the rise of AI is fundamentally changing how they are designed, structured, and used. Colin shares how legal teams must rethink traditional playbooks — moving away from long, narrative documents and toward structured, clause-based systems that AI can interpret and apply at scale.

The conversation explores what it takes to build an AI-ready playbook, including consistent terminology, clause libraries, agreement-specific variations, and simplified, accessible language. Matt and Colin also discuss why teams should start small — focusing on a handful of high-risk clauses — before expanding into more complex playbook strategies.

From embedding negotiation rationale into redlines to introducing risk scoring for faster contract triage, this episode provides a practical framework for legal teams looking to modernize their contract review process in the age of AI.

🔑 Key Topics Covered:

• What makes a playbook “AI-ready”
• Moving from documents to structured clause libraries
• The importance of consistent terminology and categorization
• Why playbooks should vary by agreement type and context
• Starting small: focusing on high-risk, high-value clauses
• Embedding negotiation rationale into playbook-driven redlines
• Designing AI-friendly templates and formatting
• Using risk scoring to prioritize contract review

👉 Subscribe and listen to Contractually Speaking on the platform of your choice at podcast.malbek.io

🎙️ Interested in being a guest or sponsoring the show? We’d love to hear from you—email us at [email protected]

💡 Learn more about Malbek

Watch on YouTube HERE. In this episode of Contractually Speaking, Matt sits down with Ellen Kranz from Lighthouse for a candid conversation recorded live at the true Austin speakeasy Here Nor There. The setting may be hidden — but the topic is all about uncovering what’s hidden inside your contracts.

Ellen shares how Lighthouse has matured its vendor-side CLM program by integrating legal, procurement, compliance, and accounting into unified workflows. Instead of siloed contract reviews and reactive payments, the team is now taking a strategic approach to renewals, budgeting, and vendor oversight.

The discussion dives into one of the biggest shifts happening in 2026: AI at scale. It’s no longer about reviewing a single contract — it’s about analyzing thousands at once to surface renewal terms, price caps, discounts, termination clauses, and cost-saving opportunities.

From budget forecasting to identifying overlapping vendors and missed discounts, this episode explores how organizations can move beyond storing contracts and start unlocking real business intelligence from them.

🔑 Key Topics Covered

• Integrating procurement, legal, compliance, and accounting
• Moving from siloed contract reviews to strategic oversight
• Tracking renewal terms and budgeting proactively
• Identifying hidden discounts and pricing caps
• AI at scale: analyzing thousands of contracts at once
• Using contract data to inform 2026 planning and beyond

👉 Subscribe and listen to Contractually Speaking on the platform of your choice at podcast.malbek.io

🎙️ Interested in being a guest or sponsoring the show? We’d love to hear from you—email us at [email protected]

💡 Learn more about Malbek

Watch on YouTube HERE. In this episode of Contractually Speaking, Matt sits down with legal operations leader Deisha Vazquez for a conversation that goes beyond CLM and technology — and straight to the core of performance, mindset, and self-care.

With over 25 years in the legal industry, Deisha has rebuilt legal teams through chaos, bankruptcy, private equity transitions, and pandemic disruption. But today’s discussion focuses on something even more fundamental: you are your most valuable asset.

From speaking affirmations over yourself to reframing “I’m sorry” into “thank you for your patience,” Deisha shares practical ways to shift workplace culture through language, energy, and boundaries.

This episode is a powerful reminder that productivity, culture, and performance start with how we treat ourselves first.

If you lead a team — or aspire to — this conversation offers actionable mindset shifts that can immediately improve both your professional impact and personal well-being.

🔑 Key Topics Covered

• Affirmations and self-leadership
• Language shifts
• Email and response-time boundaries
• Lunch breaks and calendar protection
• Modeling work habits as a leader
• Mental health in high-meeting environments
• Physical wellness: movement, posture, screen habits
• Reducing burnout through energy regulation

👉 Subscribe and listen to Contractually Speaking on the platform of your choice at podcast.malbek.io

🎙️ Interested in being a guest or sponsoring the show? We’d love to hear from you—email us at [email protected]

💡 Learn more about Malbek