If you’ve ever tried to implement legal tech in-house and felt like you were dragging your company uphill, through demos, budget asks, endless alignment meetings, and skeptical side-eyes, you’re not alone. You’re probably not doing it wrong, but you might be talking about it the wrong way.
In a recent episode of “Notes to My (Legal) Self,” former general counsel and legal operations coach Chad Aboud explains why legal tech adoption often stalls and what actually moves the needle. His advice is not about choosing the perfect CLM or mastering integrations. It’s about shifting your mindset from solving legal problems to enabling the business.
Watch the full episode here:
The Legal Tech Trap: Thinking It’s About Legal
One of the biggest mistakes in-house lawyers make is framing legal tech as something that solves legal problems. You might be thinking about faster contract review, fewer redlines, or better clause playbooks.
But as Aboud points out, nobody outside legal cares about those things. Sales is not losing sleep over how long your redlines take. Finance is not waiting on a better indemnity fallback. What they want is to close deals, collect revenue, and hit targets.
That is the mindset shift. Legal tech, when it works, improves how the business operates. If you want adoption, budget, and support, speak in terms the business already values: revenue, speed, and data.
Don’t Automate Chaos
Aboud cautions against rushing into software before fixing broken workflows. When he stepped into a portfolio of fast-growing companies, he didn’t start with tools. He started by observing where manual work created drag.
His first “automation” wasn’t software at all. It was a locked Word document for NDAs with fillable fields, stored in a folder that the business could access directly. This eliminated hundreds of repetitive legal requests without adding cost or complexity.
The result? Legal stopped being a bottleneck. The business moved faster. Trust was built.
Speak Their Language
When Aboud did move forward with a CLM, he didn’t pitch it as legal tech. He presented it as a solution to business problems.
Sales wanted faster deal turnaround and fewer blockers. Account management needed accurate contract data for client reporting. Finance wanted contract terms that matched billing workflows.
Each conversation focused on the outcome each team cared about most. For sales, it was deal velocity. For account managers, it was data consistency. For finance, it was billing accuracy and cash collection. Legal was not the focus of the conversation. It was the facilitator.
Agree On The Win First
Many legal tech projects stall because they try to solve every edge case from day one. Aboud recommends the opposite approach. Align early on one or two key wins. Tackle the 70 percent use case. Deliver it well. Let the rest wait.
Don’t get bogged down in every “what if.” Move quickly on what matters most. Then, use the success of version one to build support for versions two and three.
This keeps stakeholders engaged and momentum strong. It also shows that legal can drive outcomes without overcomplicating the process.
Legal Tech Is A Partnership
Aboud’s most powerful message is that legal tech isn’t a tool you buy. It’s a partnership you build. And it starts with curiosity.
Ask your colleagues what they like about working with legal. Ask what frustrates them. Ask what slows them down in their own work. These conversations surface the problems worth solving. More importantly, they build trust.
The problem isn’t the tools. It’s the framing. If you are not seeing traction with legal tech, try changing the conversation. Talk about business outcomes. Translate features into wins. Show how automation drives revenue and saves time.
And above all, lead with empathy. When your stakeholders believe you understand their goals, they become champions instead of blockers.
Olga V. Mack is the CEO of TermScout, an AI-powered contract certification platform that accelerates revenue and eliminates friction by certifying contracts as fair, balanced, and market-ready. A serial CEO and legal tech executive, she previously led a company through a successful acquisition by LexisNexis. Olga is also a Fellow at CodeX, The Stanford Center for Legal Informatics, and the Generative AI Editor at law.MIT. She is a visionary executive reshaping how we law—how legal systems are built, experienced, and trusted. Olga teaches at Berkeley Law, lectures widely, and advises companies of all sizes, as well as boards and institutions. An award-winning general counsel turned builder, she also leads early-stage ventures including Virtual Gabby (Better Parenting Plan), Product Law Hub, ESI Flow, and Notes to My (Legal) Self, each rethinking the practice and business of law through technology, data, and human-centered design. She has authored The Rise of Product Lawyers, Legal Operations in the Age of AI and Data, Blockchain Value, and Get on Board, with Visual IQ for Lawyers (ABA) forthcoming. Olga is a 6x TEDx speaker and has been recognized as a Silicon Valley Woman of Influence and an ABA Woman in Legal Tech. Her work reimagines people’s relationship with law—making it more accessible, inclusive, data-driven, and aligned with how the world actually works. She is also the host of the Notes to My (Legal) Self podcast (streaming on Spotify, Apple Podcasts, and YouTube), and her insights regularly appear in Forbes, Bloomberg Law, Newsweek, VentureBeat, ACC Docket, and Above the Law. She earned her B.A. and J.D. from UC Berkeley. Follow her on LinkedIn and X @olgavmack.
The post You’re Selling Legal Tech All Wrong: Chad Aboud’s Playbook For Getting Buy-In appeared first on Above the Law.