LEGALLY BINDING
Podcast: 5 key legal tech insights from Jonathan Crook

In the third episode of the Legally Binding podcast, recorded live at the CLOC conference in Las Vegas, Jeroen Thierens is joined by Jonathan Crook, a seasoned lawyer and legal tech innovator. With over a decade of experience in the legal industry, Jonathan has witnessed the transformative impact of technology on the legal profession firsthand. His journey led him to create Blue Pencil Box – a tool designed to simplify contract review and help legal professionals navigate state-specific regulations – reflecting his passion for using technology to improve law practice. As Jonathan puts it, “I built the tool I wanted, and now I have it.”
Now a partner at Fisher Phillips and an ongoing force in the legal tech space, Jonathan shares a broader perspective on the evolving role of technology in the legal profession. From efficiency-driven tools to the exciting potential of generative AI, his expertise offers valuable lessons for firms looking to remain competitive and innovative in a rapidly changing industry.
Our top 5 takeaways from the podcast:
1. The need for technology to drive efficiency
Jonathan highlights technology’s critical role in driving efficiency within legal practices. He asserts, “We owe it to our clients and ourselves to be as efficient as possible.” This mindset reflects a broader shift in the industry, where technology is being used not only to reduce costs, but also to provide better service. By leveraging tools that automate routine tasks or streamline internal processes, law firms can improve their workflow, reduce manual errors, and ultimately focus more on delivering high-value work to clients. This approach helps firms stay competitive in an evolving legal landscape where time is often of the essence.
2. The hybrid approach to knowledge management and automation
When discussing knowledge management (KM) and automation, Jonathan stresses the importance of balancing both human oversight and technology. As he points out, “You can’t have one without the other. If you automate something that’s of poor quality, then the automation isn’t very valuable. You need both.” This philosophy underscores that human effort is essential to ensure that the data is accurate and of high quality before automation can add value. Effective KM requires a solid foundation of accurate, well-organized information that can then be enhanced with automation tools. These tools are only as good as the content they process; and without reliable data, the value of automation is greatly diminished.
3. Generative AI as a complementary tool
Jonathan sees generative AI as an invaluable asset for legal professionals, but he sees it as part of a broader toolkit. According to him, “Generative AI is fantastic for researching fringe issues…for the 10% where you didn’t anticipate the questions.” Rather than replacing traditional methods, AI fills gaps by helping professionals tackle niche or unexpected problems. For example, while traditional automation tools can answer frequently asked questions with predetermined data, generative AI can help when questions fall outside these boundaries. This synergy between AI and more traditional systems enables firms to be more agile and responsive to client needs.
4. Overcoming skepticism around efficiency and profitability
A significant challenge in adopting legal technology is overcoming skepticism that it will undermine the billable hour model. Jonathan emphasizes that technology doesn’t have to threaten lawyers’ income; in fact, it can enhance their practice. He asserts, “Lawyers who find ways to make themselves better at what they do with technology will prevail in the long run over lawyers who don’t.” Law firms that successfully embrace technology can improve the quality of their work, gain deeper insights, and reduce inefficiencies. This ultimately leads to better service for clients, which can translate into stronger client relationships and potentially more lucrative engagements, regardless of the billing model used.
5. The future of legal tech: focus on quality and specialization
As the legal tech space continues to grow, Jonathan predicts a shift toward more specialized and high-quality offerings. He observes, “I think there’s going to be a real focus on differentiation and providing the highest quality version of what you do.” While the rush to develop new technologies in recent years was driven by the need to get to market quickly, in the next phase we’ll see companies and vendors focus on specific problems and refine their solutions. This evolution will push companies to innovate in ways that deliver clear, measurable value to their users. As more legal professionals become familiar with available technologies, they will increasingly seek tools that meet their precise needs, rather than settling for broad, generalized solutions.
Why you should tune in
As Jonathan says, “It’s a cool time to be alive,” emphasizing the exciting possibilities technology brings to the legal profession.
This episode is a must-listen for anyone interested in the intersection of law and technology. Jonathan shares valuable insights from his experience as both a lawyer and legal tech innovator. From enhancing efficiency with tech to the evolving role of generative AI, his expertise offers a roadmap for firms to stay ahead of the curve.