Beyond “What Tools Do You Use?” AI Questions Clients Should Ask Firms

How Leading Legal Departments Are Rethinking AI and Outside Counsel Value

For the past year, conversations about AI and outside counsel have sounded almost identical.

What tools are you using?
How much time does it save?
Are you experimenting with generative AI?

Those were fair questions… at first. But they’re already starting to feel surface-level.

In many organizations, AI isn’t just a curiosity anymore. It’s a mandate coming from the C-suite. Legal departments are being asked to show measurable efficiency gains, smarter spending, and clearer productivity stories. And because outside counsel represents a major portion of legal spend, firms are inevitably part of that equation.

The conversation is shifting.

It’s no longer: Are you using AI?
It’s: If you’re using AI, how does that change outcomes for us?

What we’re seeing now isn’t one big AI question. It’s a new way of evaluating law firm performance altogether.

Here’s where leading legal teams are focusing, and the AI questions they are asking of their firms.

AI Governance Is Expected. Operational Control Is the Real Question.

Most large firms now have AI policies. That’s become table stakes.

What’s less clear (and far more important) is how those policies actually show up in day-to-day work and specifically how purchasers of legal services will see those effects.

Forward-thinking legal teams are looking past the existence of governance and asking how it functions in practice. Who makes decisions about tool usage? How are client-specific restrictions enforced? What happens if something goes wrong?

Governance isn’t impressive because it exists. It’s impressive when it’s operational.

Questions clients can ask:

• Who ultimately owns AI usage decisions on my matters — and how is that oversight documented?
  
  
• How do you implement and enforce client-specific AI restrictions at the matter level?
  
  
• If an AI-related issue occurs, what is your escalation and remediation process?
  
  

“We Use AI” Doesn’t Mean Much Without Workflow Specifics

Many firms now say they use AI. That statement alone tells you very little.

The meaningful question is: Where?

Is AI used during intake and scoping? Research? Drafting? Discovery? Knowledge management? Billing? Reporting?

There’s a significant difference between a firm experimenting with tools and a firm that has redesigned how work actually moves through its system.

Clients are starting to notice that difference.

Questions clients can ask:

• At which specific stages of the legal workflow are AI tools integrated today?
  
  
• Have you redesigned any processes because of AI, or is it layered on top of existing workflows?
  
  
• How does AI usage affect how matters are staffed and resourced?
  
  

If Efficiency Isn’t Measured, It’s Just a Story

Nearly every firm claims AI “saves time.”

Fewer can explain how they know.

How much time? On which tasks? Measured how? Tracked consistently? Or estimated informally?

Legal departments don’t expect perfection. But they are increasingly looking for discipline. If efficiency gains are real, there should be some method — even a simple one — for understanding them.

Credibility now depends less on bold claims and more on measurable thinking.

Questions clients can ask:

• How do you estimate or measure time saved through AI on specific tasks?
  
  
• Is efficiency tracked systematically across matters, or anecdotally?
  
  
• How has AI changed average matter duration or staffing models in measurable ways?
  
  

Who Actually Captures the Economic Benefit?

This is where the conversation gets more direct.

If AI reduces effort, that efficiency has to go somewhere.

Either:

• The client benefits through lower fees or leaner staffing
  
  
• The firm retains the benefit as improved margin
  
  
• Or the gain disappears into more premium work
  
  

There’s no inherently “wrong” answer right now. But there should be alignment both in where the benefits show up and who they are flowing toward.

Sophisticated legal ops teams are beginning to examine how AI efficiencies flow through pricing structures — and whether incentives truly reflect partnership.

Questions clients can ask:

• When AI reduces effort on a matter, how is that reflected in pricing?
  
  
• Have you adjusted fee structures or AFAs to account for AI-enabled efficiencies?
  
  
• How do you ensure AI-driven productivity gains are shared with clients?
  
  

Transparency Is Becoming a Competitive Advantage

Historically, clients focused on outcomes, not process.

That’s changing.

Some legal departments now want visibility into whether AI assisted in the work, how efficiency assumptions were calculated, and whether projected benefits were actually realized.

Firms that can engage openly in these conversations tend to be further along operationally. Not because they’re perfect — but because they’re comfortable being transparent.

Questions clients can ask:

• Do you disclose when AI materially contributes to deliverables?
  
  
• Can you provide reporting on projected versus realized efficiency gains?
  
  
• Are you open to periodic reviews of how AI is affecting cost and delivery?
  
  

Incentives Drive Behavior — Not Technology

The best AI tool in the world won’t change much if internal incentives discourage adoption.

Clients understand this more than ever.

If partner compensation depends heavily on billable hours, efficiency can feel threatening. If AI reduces hours, resistance is rational. If compensation structures remain unchanged, adoption will stall — regardless of leadership messaging.

Technology matters. Incentives matter more.

Questions clients can ask:

• How do your compensation and evaluation models account for AI-driven efficiency?
  
  
• Are partners rewarded for improving productivity, even if it reduces hours?
  
  
• What internal barriers to AI adoption have you encountered — and how are you addressing them?
  
  

AI Is Reshaping the Client–Firm Relationship

At the most advanced level, this isn’t a technology conversation at all – it’s a relationship conversation.

AI is accelerating a shift away from input-based billing toward productivity- and outcome-based thinking. That requires collaboration. It requires experimentation. It requires a willingness to revisit pricing assumptions as service delivery evolves.

Some firms are ready for that shift. Others are still figuring out what it means.

The clients asking these questions early will shape which model prevails.

Questions clients can ask:

• Are you open to piloting AI-enabled delivery models tied to outcomes rather than hours?
  
  
• How often do you revisit pricing assumptions as workflows evolve?
  
  
• Would you collaborate on redesigning fee structures as productivity changes?
  
  

Why This Matters

For many legal leaders, these questions aren’t theoretical. They surface during budget reviews, audit discussions, or after a new CFO asks for clearer evidence of value creation.

When outside counsel claim AI-driven efficiency, that efficiency ultimately shows up — or doesn’t — in legal spend, predictability, and pricing leverage. The ability to evaluate AI use with discipline gives GCs something concrete: a way to connect service delivery changes to financial outcomes the C-suite understands.

AI governance is important, but it’s AI accountability that resonates in the boardroom.

The Bottom Line

AI is no longer just a technology discussion for legal departments. It’s a service design conversation, a pricing conversation, a transparency conversation.

Firms that treat AI primarily as a marketing story may be fine for now.

Firms that treat it as a structural shift in how legal work is delivered and how value is shared will define the next era of outside counsel relationships.

At PERSUIT, we’re seeing this shift happen in stages, as a series of smarter, sharper questions about how legal work is delivered, priced, and measured.

For legal teams exploring how to align AI adoption with outside counsel value, and how to bring clearer financial discipline into those conversations, contact us to see how PERSUIT can help.