By Ben Dewar
Chief Legal Officers are being evaluated on a moving target. Expectations that have defined the role for decades still apply, but a new one is stacking on top of them faster than most executive hiring processes have caught up to.
I practiced corporate law before moving into executive search, and I’ve spent over two decades running CLO searches since. Over that time, the core of the role has stayed remarkably consistent, but what’s expected on top of it keeps shifting, and AI is driving the fastest-moving shift yet.
This piece breaks down how boards, CEOs, and investors should be evaluating CLO candidates, how to spot AI depth, and how AI is changing what relevant regulatory experience looks like in some industries.
The Bar for Legal Executives Is Higher Than Ever
There’s no doubt that AI is impacting the legal executive role considerably. But aside from AI, expectations have been rising on the whole. Employers, particularly in PE- and VC-backed environments, expect CLOs to have proven legal expertise, leadership capabilities, business acumen, and financial fluency.
- Legal expertise. No lawyer is an expert in every area of the law. In most legal leadership searches, what matters more is having the right depth where it counts most for that specific business, whether that’s regulatory, commercial, or complex transactions.
- Leadership. Paired with that legal expertise needs to be the ability to build and lead a high-performing legal function that’s tightly aligned with the business and staffed with lawyers who operate with the same clarity, judgment, and commercial mindset as the CLO.
- Business acumen. The best legal executives are business leaders first and functional experts second. A CLO should spend as much time advising CEOs and boards on business strategy as they do on the law itself, helping think through decisions, weigh risk in real context, and push the leadership team toward stronger outcomes. That strategic judgment is something CEOs can’t do without, and it’s often the hardest quality to find, because lawyers aren’t traditionally trained to think this way.
- Financial fluency. This goes along with business acumen. You can’t be a credible business leader without understanding the numbers behind the business, including P&L, financial models, unit economics, cash flow, and capital allocation. Without that grounding, even great legal advice can miss the mark.
None of the above goes away because of AI. What’s changing, however, is that the legal function is being built around a different mix of humans and technology than we’ve seen before. Legal-specific AI tools are taking on work that used to require a person. Companies need to be screening CLOs for how well they can run a function where people and AI produce work together, with an output that outpaces what either could do alone.
Screen for Real-World AI Results
Even though AI technology in the legal function is still in its early days, legal executives are being evaluated on their ability to harness and get the most out of the tools, while building a modern legal team around AI.
As recently as a few months back, legal leaders were mostly expected to show AI curiosity and a willingness to experiment. The expectations have shifted. Investors, boards, and CEOs are looking for proven success marrying AI with the legal function.
- Tangible results. Clients and search teams alike have moved from asking candidates about their point of view and plans for AI use to their actual results using it.
- A way of staying current. The tools themselves are moving fast enough that what’s relevant today may look different a year from now – or even a few months from now.
Strong CLO candidates will be able to:
- Point to specific tools they’ve piloted.
- Name what’s changed in the space in the last six months.
- Highlight relationships they’ve built with legal tech vendors.
- Show they’ve designated someone on their team to track AI and legal tech developments.
- Understand when AI can be most helpful and when to hold back. With the costs of enterprise AI rising, CLOs are expected to be judicious about spend.
Over the last year, the NU team has run 100+ Practical AI sessions – hands-on workshops on using AI day-to-day – for PE and VC firms, portfolio companies, and executive teams across industries. What we’ve found is that even among engaged, motivated groups, true AI depth is still rare. Asking for specifics around a candidate’s AI use and results will help you gauge how advanced they really are.
Agents Vs. Chat
Earlier in the year, AI expectations were mostly around adoption. Was the legal leader using AI and encouraging their team to experiment with it? That bar has already moved. The question now is whether they’re putting AI agents to work across the legal function, automating workflows rather than only using AI as a chat interface.
Using an LLM for research, drafting, or summarization is becoming commonplace. But can the candidate point to a legal process they’ve automated end-to-end, explain what changed as a result, and quantify the time, cost, or work it eliminated? Ask for specifics. What can their legal team accomplish today with AI that it couldn’t a year ago?
In Some Industries, AI Is Changing What Relevant Experience Looks Like for CLOs
For AI-native businesses, particularly in regulated sectors like healthcare and financial services, the profile of the ideal legal leader is changing.
- Traditional industry experience can matter less. Historically, a healthtech company, for example, might prioritize candidates with deep healthcare regulatory backgrounds. AI-native healthtech companies, however, are increasingly open to looking beyond the sector, prioritizing legal leaders who understand the regulatory questions that come with building AI-native products.
- The ability to navigate the future of AI. With AI regulation still developing rapidly, companies want legal executives who can anticipate where regulation is headed and help the business make decisions without a clear playbook.
Bringing It All Together
While legal expertise, leadership capabilities, and business acumen will continue to be table stakes, the future of the function will be led by CLOs who can bring people and AI together to produce more than either could alone, and translate that into business outcomes.
If you’re planning a CLO or General Counsel search, we’d love to connect and share what we’re seeing across the space.
NU Advisory Partners is an AI and tech-led retained executive search and advisory firm focused on senior executive, operating, and board positions. If you’re interested in learning more, get in touch here.
