AI Archives - The Alexander Group

The days of questioning the importance of Artificial Intelligence are over. Staying competitive and ahead of the curve means delving into AI from both leadership and technological perspectives, and knowing where to start is crucial. From boutique law firms to AmLaw legacies, AI is transforming how leadership approaches all aspects of law firm operations.

Rethinking Leadership Roles

Larger firms such as Cooley and Milbank are AI pioneers, establishing internal workflows and protocols, while also serving their clients’ AI needs. Smaller and regional firms are also adapting, incorporating AI into their practice and adding leaders to the executive roster to implement and execute AI. And while technology is intrinsically tied to AI, staying competitive requires executive talent with a broader, more adaptive skill set – prompting firm leadership to ask the following:

Who should lead this transformation?

Should that person have a JD?
Where in the org chart do they belong—IT, strategy, operations?

Managing Director John Mann has his finger on the pulse of the fast-changing needs of boutique and regional firms, finding that AI leaders may not be who you think.

“What’s particularly interesting is that, more often than not, the person leading the AI function within a law firm comes from a legal background,” Mann said. “In my research and conversations, the consistent feedback is that it’s critical for AI leadership to have a legal background, typically a JD, or experience at another law firm. This isn’t about a Chief Information Officer simply implementing off-the-shelf AI tools. Law firms recognize that to remain competitive, especially midsized firms, they must strategically harness AI, because the larger firms are already doing so.”

Survey Says Yes to AI—But With Caution

A 2025 survey of more than 2,800 legal professionals by the Federal Bar Association tracked the changes in AI adoption by lawyers in firms of various sizes.

Respondents from firms with 51 or more lawyers reported a significant 39% adoption rate of generative AI. By contrast, firms with 50 or fewer lawyers had adoption rates at half that level, with approximately 20% indicating the implementation of legal-specific AI within their practices.

In the survey, respondents indicated that the bulk of AI usage falls into business operations, with 54% of legal professionals using AI to draft correspondence, 14% using it to analyze firm data and matters, and 47% expressing interest in AI tools that assist in obtaining insights from a firm’s financial data.

Thomson Reuters surveyed more than 2,200 legal professionals and C-level corporate executives regarding their acceptance and usage of AI and compiled the results in the 2024 Future of Professionals Report. Respondents have warmed to the technology, raising expectations for its use.

77% of respondents believe AI will have a high or transformational impact on their work by the next five years. That’s an increase of 10 percentage points over the 2023 report’s responses.
72% of legal professionals surveyed in the report view AI as a force for good in their profession.
Half of law firm respondents cite exploring and implementing AI as their highest priority. In addition, they believe AI can help address other priorities, such as enhancing customer satisfaction and improving operational efficiency.

Despite the growing AI implementation, Mann finds law firm leadership is staying vigilant and intentional with AI use, especially when attorney-client confidentiality is concerned.

“The AI landscape is still the Wild West,” Mann said. “I recently had a conversation with a managing partner of a 50-attorney firm, and he said they have restricted the use of AI tools for client matters because of the potential breach of attorney-client privilege. Bottom line? They implemented a policy restricting the use of AI in any client matters.”

New Technology, New Strategies

Firms are looking beyond the IT department for the strategic role, prioritizing an executive’s legal experience and deep understanding of technology to drive efficiency, reduce billing bottlenecks, and enhance client outcomes.

Whether a firm labels the role Chief Innovation Officer, Chief Data and AI Officer, or Director of Innovation, there are consistent requirements for each, including 10 or more years of experience in legal operations, professional services innovation, or technology consulting and a proven ability to lead cross-functional innovation or technology initiatives in a law firm or professional services environment.

Ultimately, AI and its presence within law firm structure and leadership are making their own rules, challenging norms and definitions at every turn.

“AI is coming up as its own function and is not tethered to any one functional area,” Mann said. “There’s the tech piece of course, but there’s also strategy and a need for understanding and expertise in the practice of law. The question many firms are asking is, ‘How can we operate more efficiently to drive greater revenue and profitability?’ And for most, the answer increasingly points to leveraging AI to get there.”

Not-for-profit leaders are accustomed to doing more with less. Still, waves of economic uncertainty, coupled with the rapidly evolving AI landscape, are forcing even the most seasoned leaders to reevaluate and redefine past methodologies and strategies.

Today’s leaders recognize that the decisions they make will have a lasting impact on their organizations’ mission, funding, and strategy. Maximizing the relationship between a Chief Executive Officer and their board, implementing AI literacy, and sharpening fundraising focus are essential for the sustainability and growth of an organization.

Benefits of a Strong Board

The partnership between a CEO and their board is one of shared commitments and a well-crafted strategy. A CEO should be able to lean on their board and, at times, be prepared to hear difficult truths. Board members bear a responsibility to engage with the organization, its executive team, and other key stakeholders.

Organizations that invest in building effective boards often see more stable funding, stronger staff retention and morale, greater influence in their sector, and more substantial donor confidence.

Modern board governance is evolving as the demand for more strategic, diverse, and accountable board members increases. In practice, this translates to broader board representation in terms of age, experience, and diversity. Clearly defining board roles and term limits lays the foundation for continued growth.

“Nonprofits transform their trajectory when boards adopt some of the discipline and accountability models of the corporate world. When CEOs and boards align on clear roles and a shared strategy, they drive greater impact and long-term growth,” said John Mann, Managing Director, The Alexander Group.

Engaged Boards Elevate Fundraising

The top line for fundraising and development activities is always at the forefront of not-for-profit organizations. Cultivating a more engaged board is an effective way for nonprofits to enhance their fundraising efforts, and that starts with empowerment and clear expectations.

Start by setting clear expectations, providing training, and fostering a culture of accountability. A well-informed, mission-driven board can unlock new funding opportunities, leverage its networks, and serve as influential ambassadors for the organization. When donors feel connected and the board is fully invested, fundraising efforts become more strategic, sustainable, and successful.

Embracing AI

From predictive fundraising to automated grant reporting, AI is rapidly changing nonprofit operations. According to the 2024 Nonprofit Standards Benchmarking Survey, 82 percent of organizations have implemented AI technology. AI is quickly becoming a valuable tool in the not-for-profit sector, enhancing an organization’s ability to anticipate donor needs and recommend targeted actions.

Strategic CEOs understand the urgency of thoughtfully investing in AI across everything from software to leadership positions, such as Chief Innovation Officer. Smaller organizations are forming committees that may include board members to explore how to use AI synergistically with various functions.

Employing AI to do everything from the tedious to the time-consuming leaves staff open to connect in a more meaningful way with the organization’s donor base. Forward-looking not-for-profits are using AI-assisted donor segmentation, chatbots for volunteer engagement, and automated analytics for board reports, building AI literacy among their team members.

Digital fundraising solution OneCause works specifically with not-for-profits and found organizations are most successful when leaning into AI from a solid foundation of personal connectedness. In 2024, 75% of organizations hosting in-person events met or exceeded their fundraising goals, and 76% of those using hybrid models also achieved their targets.

Mission-Minded, Future Focused

It’s a challenging time for the modern non-profit CEO/Director, but within this sea change lies opportunities to serve and grow the organization’s mission.

The mission is the motivator.

“Every nonprofit begins with someone on a mission. To grow the organization, the mission must resonate with others, and someone must articulate the mission in such a compelling way that others embrace it and are willing to support it, not just with their hearts and their volunteer time but also with financial donations,” said Amanda K. Brady, Chief Client Officer/Managing Director. “Whether it is the Founder, a CEO, or a development leader, someone must craft and evangelize a message that brings others into the community and keeps them engaged. It is an existential imperative. In today’s times, leaders must seek, embrace, and utilize innovative tools that build on the organization’s mission.”

With 2025 just around the corner, we’re looking to the future of legal industry trends, anticipating and planning for what’s next. While we don’t have a crystal ball, we do have 40 years of executive recruiting experience, a deep well of data, and the trust of our clients, who express their leadership needs to us as they plan for 2025 and beyond.

Managing Directors John Lamar, Amanda Brady, and John Mann, Directors Sarah Mitchell and William Lepiesza and Senior Associate Anthony Ott share their thoughts and insight on expectations and trends for 2025.

John Lamar, Managing Director, The Alexander Group

“AI continues to dominate people’s thought process in making the firm efficient and profitable. Tech is a driving force, but it’s not where it needs to be. Everyone’s doing window dressing right now, hiring chief innovation officers, but in reality, firms are buying off-the-shelf software products. That will change in the years to come.

Another trend garnering attention concerns partners getting paid ungodly amounts of money. They are offered multi-year 25- to 30-million-dollar deals. How long can the industry sustain that?

I’m hearing a lot from chairs about work-from-home. It’s interesting in Europe; they all comment that everyone’s back 100 percent; the U.S. is the only country with three days in the office. It’ll be interesting to see what happens next year. Do firms hammer the idea of return to office? Maybe you will spend four days in the office, but you won’t be sitting at home on a Monday. The associates will give them the best work in the office, but the partners are not leading. It starts with them. They are in a bit of a conundrum. People are struggling with it. You have to hit them in the pocketbook so that people can start showing up.

Mergers and Acquisition activity is not slowing down within legal as the industry continues consolidating. A few firms at the top are leading the way–and there’s more to come.

Amanda K. Brady, Managing Director/Chief People Officer, The Alexander Group

“Synthesizing data to inform strategic growth. (Some) law firms are becoming more sophisticated around coordinated growth initiatives. Business intelligence is evolving beyond the typical matter, partner, or practice profitability analysis into deep dives into all that touches firm and practice growth. It combines knowledge management on the practice side with knowledge management on the business side, merging information from CRMs, experience databases, historical financial metrics, targeted industry research, and honest assessments of the firm’s talent. It’s all data. This is most successful at firms with cultures that allow their leaders to be innovative – not business as usual, set ambitious business goals, develop corresponding growth strategies, and pull the puzzle pieces together to make things happen.”

John Mann, Managing Director, The Alexander Group

“In 2025, strategic legal recruiting functions will be crucial for law firms, as they focus on proactively identifying and recruiting top talent with specialized skills aligned with client needs.

Artificial Intelligence will continue to impact the legal industry by automating routine tasks and enabling more efficient client service. It will ultimately transform how legal professionals work and deliver value.

In 2025 and beyond, law firms will continue to build sales-focused client development teams who generate revenue much like public accounting firms and are responsible for driving business growth by developing client relationships, identifying new business opportunities, and promoting the firm’s legal services.”

Sarah Mitchell, Director, The Alexander Group

“The return to office push/pull is still strong, but law firm leaders seem to be “over” the discussion. Unlike the trends we see with technology companies and banking, very few firms seem willing to implement any mandate. They are shifting to making the office space somewhere that lawyers and business professionals want to be—not with pizza parties, but fresh, thoughtfully designed office space that feels “alive” and opportunities to connect.

Discussions around generational differences are being discussed more forthrightly, and I think it might become more pronounced in the next couple of years. We currently have four well-defined generations working together, and they each tend to have distinctive attitudes concerning technology use, adaptivity to change, RTO expectations, dress, and communication. One law firm COO mentioned they have introduced training around generational differences as part of their professional development curriculum, and it has been well received and actionable.”

Bill Lepiesza, Director, The Alexander Group

“As I consider legal industry trends for 2025, I believe we will continue to see the rise and evolution of the Chief Innovation Officer role.

We will see the further integration of firmwide talent/strategic human resources functions across lawyer and business professional populations and the continued elevation in caliber, leadership expectations, and strategic value-add of law firm business executive roles.

Anthony Ott, Senior Associate, The Alexander Group

“Each year, there is a swing of trends. I anticipate seeing more Baby Boomers retiring, and vacant leadership opportunities will be available for those who have earned a right to be in consideration.

As work-from-home policies shift, so will their impact on the candidate pool. Jobseekers will be willing to explore new industries in order to receive job title advancement and increased compensation. Similarly, law firms will look at candidates from other professional services companies outside of their industry.

We will also see people on the move to improve their quality of life. As the cost of living increases, it may encourage people to explore opportunities in new cities for a better quality of life and employment opportunities. For example, people may be able to afford larger homes less expensive in major metropolitan cities, so they move to grow their families or be open to other career opportunities.”