How to win C-Suite buy-in for legal AI: 5 questions every GC must answer

Lynette Ooi, Founder and Principal Consultant at BetterWiser, suggests that successful legal AI adoption starts with trust, not just technology.

When I first brought up AI in a leadership team meeting, I expected curiosity – maybe even excitement. Instead, I got crossed arms, cautious glances, and a lot of uncomfortable silence.

It turns out, this reaction isn’t unique.

According to a March 2025 Axios report, enterprise AI is now a top source of internal tension. While most C-suite leaders believe AI is essential to long-term growth, nearly half say it’s creating discord across their organisations. Employees worry about job loss and lack of transparency. Executives push for AI adoption but often without a clear path for responsible implementation.

In short: AI isn’t just a tech issue. It’s a trust issue.

For General Counsel, this makes the task even trickier. You’re not only championing a technology shift – you’re navigating cultural and organisational headwinds. And to bring your legal department into the AI era, you need more than a good pitch.

You need a strategic conversation – one that answers the right questions in the right way.

Here are five powerful questions every GC must be ready to answer when approaching the C-suite about legal AI.

1. What’s the audience’s starting point on AI?

Before you walk into that room, do a mental pulse-check: Where is each executive really at with AI?

According to a report by the Deloitte AI Institute, while 78% of executives surveyed expect to increase their AI spending in 2025, respondents cited a range of challenges, including building trust and addressing data issues. That gap reveals both a challenge and an opportunity. Some execs may be AI optimists. Others may worry about reputational risk, job displacement, or compliance breaches.

Your job isn’t just to pitch a legal solution – it’s to read the room.

Prepare by working backwards from your audience:

· What are the hopes and fears about AI across functions?

· Who are the blockers, who are the advocates, and who’s sitting on the fence?

· What objections are likely to surface, and how can you respond without jargon or defensiveness?

Try punchy responses grounded in business impact:

· “This isn’t about replacing judgment. It’s about reducing the 40% of our work that’s repetitive and low-value.”

· “We’re not racing into risky automation. We’re piloting a tool that’s already used in 100+ legal departments with clear governance in place.”

Start where they are – not where you want them to be.

2. What are current legal department pain points costing the company?

It’s easy for GCs to make the mistake of focusing their presentation on legal pain points and resourcing challenges. But identifying a problem isn’t enough – you have to connect it to business consequences your peers care about.

Ask yourself: What is our current legal friction costing us in terms of:

· Speed to market? A slow contract cycle can delay revenue and erode competitive advantage.

· Inconsistent advice? When different business units get varied interpretations of the same regulation, you increase both risk and confusion.

· Regulatory overload? With rules evolving monthly – from privacy laws to ESG mandates – manual tracking creates blind spots and missed obligations.

And yes, of course, there’s the question of cost. Legal departments often allocate a substantial portion of their budgets to external counsel, much of which could be reduced through automation of routine tasks. Getting specific about potential cost savings makes it easier for executives to support your vision.

 By linking legal pain points to enterprise risk, cost, and agility, you shift the conversation from “we’re overwhelmed” to “here’s how this impacts you.”

“The biggest risk isn’t the tech. It’s human resistance to change.”

3. What are the most-needed legal AI solutions?

Many C-suite leaders still think AI in legal means a chatbot answering FAQs.

It’s your job to paint a more complete picture.

Show – don’t tell – what legal AI can do when it’s applied to real, high-impact workflows. Focus on 1-2 “big rock” use cases:

· Contract lifecycle management with AI-assisted clause detection and risk scoring

· Regulatory horizon scanning using AI to track evolving laws across jurisdictions

· Litigation readiness with AI sorting and tagging e-discovery data

Choose tools that solve a clear pain point and can be piloted fast. This isn’t about a perfect, all-in-one solution. It’s about building confidence and proof of value. Start with a targeted, measurable improvement, e.g. fully automating the drafting and closure of 80% of NDAs. Once ROI is proven through measurable time and cost savings, scaling to more complex processes becomes feasible.

4. What’s your change management plan?

The biggest risk isn’t the tech. It’s human resistance to change.

Your executive team wants to know: How will you ensure adoption, accountability, and safe deployment?

That means having a clear, thoughtful rollout plan:

· Stakeholder engagement: Which business leaders, legal ops partners, and IT teams will be involved?

· Training and enablement: How will you upskill your team, from senior lawyers to paralegals?

· Governance and controls: What policies and guardrails are in place to supervise AI outputs, ensure data privacy, and monitor risk?

Think of it like implementing a new regulatory framework: you need communication, compliance, and culture change.

Frame AI not as a one-off project, but as part of your legal department’s evolution into a modern, data-driven function.

5. Why are you the right leader to transform the legal department?

You were likely hired before generative AI became mainstream. So the final – and perhaps most personal – question is: Why you?

To lead your team through this transformation, you need to show:

· A foundational understanding of how AI works (take that Coursera course, follow legal AI thought leaders, speak at a legal tech summit).

· A strategic view of risks – regulatory, operational, cybersecurity – and how you’ll address them.

· A bias for action: launching pilots, measuring outcomes, refining as you go.

This doesn’t mean you need to walk this journey alone. One way to gain credibility is to admit your own knowledge gaps and seek the right help – through internal hires or external consultants. This shows your willingness to prioritise the department’s future over your ego – building trust in the process.

The Opportunity Ahead

The future of the legal department isn’t about choosing between lawyers and AI – it’s about amplifying your team’s impact through technology that works for them, not instead of them.

Yes, the path requires courage. Yes, the questions are hard. But the prize is real: a faster, smarter, more strategic legal function that’s deeply embedded in the business.

When you walk into that next C-suite discussion, bring your questions, not just your answers. Invite conversation, build trust, and lead with vision.

Because the legal leaders who win the future won’t be the ones who waited for certainty.

They’ll be the ones who asked the right questions – and moved first.

About the author:
Lynette Ooi is the founder of BetterWiser Consulting, a boutique practice that supports senior professionals, founders, and leadership teams through coaching, corporate speaking, and strategic advisory work. She brings 18 years of in-house legal and business leadership experience, having served as Head of Legal for APAC & MEA at PayPal, and Head of Legal for ASEAN at Amazon. With a strong track record navigating complex regulatory and commercial challenges across 100+ countries and supporting > USD 1 billion in business, Lynette now helps clients lead with clarity and build with intention. Her current work spans 1:1 executive coaching, startup consulting, and leadership development for corporates. For more details, please click here.

Email: lynette@betterwiser.com

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