Mid-Sized Law Firms Are Balancing Potential and Pitfalls in Charting an Unpredictable Path Forward

How law firm leaders are preparing for 2026—and where they see the greatest opportunity ahead

The legal industry is standing at a crossroads. Mid-sized law firms, in particular, are navigating rapid shifts in technology, talent expectations, competitive pressures, and client demands. According to a new law firm leadership report, developed by Ari Kaplan Advisors in partnership with SurePoint Technologies, iManage, and Affinity Consulting Group, mid-sized firm leaders are moving decisively toward a future defined by both innovation and risk management.

To unpack the findings, Ari Kaplan, host of the Reinventing Professionals podcast, sat down with:

• Olivia Mockel, Chief Brand & Market Strategy Officer at SurePoint,
• Debbie Foster, CEO of Affinity Consulting Group
• Laura Wenzel, Global Marketing & Insights Director at iManage

Their conversation explores how CFOs, COOs, CIOs, and Executive Directors are approaching generative AI, data and financial intelligence, technology modernization, and supporting their attorneys and staff through change.

Listen to the full episode here.

Keep reading for the most compelling themes from both the research and the discussion.

Generative AI is Already Influencing Everyday Decision-Making

More than six in ten firms have formally adopted generative AI tools, and many more are actively piloting use cases across research, drafting, and workflow automation. Leaders emphasized that AI isn’t about replacing legal expertise—it’s about scaling capacity, improving accuracy, and freeing teams to focus on higher-value work.

Yet concerns around reliability, ethics, and risk management remain top of mind. As Mockel notes in the conversation, the firms seeing the greatest early benefits are the ones building “guardrails, governance, and education” into their AI strategy.

Data and Financial Intelligence Are Reshaping Strategic Planning

Midsize firms are becoming more metrics-driven. Leaders are leaning into financial intelligence to guide everything from client strategy to staffing models to long-term growth planning.

A major insight from the report: the firms that feel most confident about the future are the ones using real-time data—not gut instinct—to make decisions.

As Debbie Foster highlights, financial visibility is no longer a “finance-team initiative.” It’s becoming a firmwide competency.

Technology Modernization Is Now a Business Imperative

The report reveals a clear consensus: legacy systems and fragmented technology stacks are slowing firms down. CIOs and operational leaders are prioritizing modernization—cloud migration, integrated solutions, and platforms that support end-to-end workflows.

Laura Wenzel underscored this shift, noting that firms are moving from isolated tools to connected ecosystems that support the entire client lifecycle, from intake to invoice.

Talent Expectations Are Evolving Alongside Innovation

With attorney attrition still elevated across the industry, firms are rethinking how technology, career development, and work experience factor into retention. Leaders emphasized the value of training, communication, and change management, especially when introducing new tools or processes.

The firms that manage change effectively—providing clarity, support, and context—are outperforming those that treat transformation as merely a “technology project.”

Leaders Are Optimistic—but Realistic—About the Road Ahead

Perhaps the most notable takeaway: midsize law firm leaders are striking a balance between embracing potential and acknowledging pitfalls. They recognize the opportunity for growth, innovation, and improved performance—but they also understand the need for thoughtful, deliberate execution.

It’s this balance that defines the next era of legal services.

Hear the Highlights on the Reinventing Professionals Podcast

To dive deeper into what’s shaping the future of midsize law firms—and hear directly from the leaders behind the study—listen to Ari Kaplan’s conversation with Olivia Mockel, Debbie Foster, and Laura Wenzel:

Listen to the podcast episode

For the full research, download the report: https://surepoint.com/law-firm-leadership-2025.