How to Convince Your Legal Team and CEO to Get Started With AI
AI holds real promise for HR, freeing up time, sharpening decisions, and helping your team focus on what really matters. But moving forward often depends on getting two important partners on board to get started with AI: legal and executive leadership.
We can’t hand you a step-by-step plan since every organization has different needs and AI use cases. What we can do is give you the questions and framing that can help you start productive conversations and build shared trust.
Why HR leads this conversation
HR’s role is uniquely positioned at the intersection of people, data, and culture. That makes HR a function equipped to ensure AI doesn’t just drive efficiency, but also equity and impact.
From designing AI-augmented performance systems to developing leaders who can thrive in tech-enabled environments, HR can turn what might feel like disruption into a competitive advantage. AI will change how decisions are made, but HR decides how those changes affect humans, teams, and long-term business strategy.
This is important because the next five years will be a proving ground for HR. Those who lean into this moment, learning how to guide, govern, and scale AI use, will elevate their influence in the C-suite and reshape the future of work for the better.
Those who wait to get started with AI risk being reduced to policy stewards while real decisions are made somewhere else. HR has the opportunity right now to lead the AI transformation, not as tech experts, but as outcome architects and human enablers.
What your legal team is thinking about
Legal’s role is to protect the business. If you’re introducing new tools or workflows, they need to understand how risk will be managed, not just what the tech can do.
Start by exploring how your chosen tools handle employee data. Are you clear on how information is collected, stored, and used? Can you speak to vendor compliance with applicable regulations like GDPR or CCPA? You don’t need to have every legal detail memorized, but showing that you’ve asked the right questions builds credibility.
Fairness is another priority. Legal teams want to understand how the use of AI avoids bias, especially in areas like hiring or performance reviews. Be ready to explain how you’ll review results, flag issues, and document outcomes.
And finally, accountability matters. If a tool is making recommendations or informing decisions, how will your team track and audit those outputs?
What your CEO needs to hear
Executives aren’t looking for a product demo. They want to understand how something will move the business forward.
That’s why it helps to start with the “why.”
Will AI help your team move faster or make smarter decisions? Will it improve retention, engagement, or manager effectiveness? The strongest business cases focus on real pain points, like slow hiring cycles, overloaded managers, or low trust in performance data, and show how AI can help address them.
Scalability is another important angle. Executives want to know whether AI will reduce friction as the company grows. Can it reduce your team’s dependency on manual work? Will it help streamline workflows or support more consistent decision-making across departments?
And finally, consider how AI fits your company’s culture and competitive identity. Framing responsible AI use as part of a thoughtful, employee-centered strategy can help position your team and your company as future-ready.
How to bring legal and execs together
You don’t have to pick a side between caution and action. Your job is to show that both can exist together when you lead with intention.
That starts by naming your approach. You’re not rolling out tools for the sake of novelty. You’re exploring low-risk, clearly scoped use cases that support business needs, like summarizing survey comments or drafting onboarding messages. These are real workflows where the risk is low, and the value is clear.
You can also invite collaboration. Offer to draft an internal AI use policy in partnership with legal. Frame it as a shared effort, not a compliance checkbox. And when you talk with execs, stick to outcomes like improved retention, more manager capacity, and faster insight into what your people need.
Bringing both sides into early reviews or pilot retrospectives can help build long-term trust.
Talking Points to Try
When you’re ready to bring your legal or executive teams into the conversation, use language that reflects both care and clarity.
With Legal:
“We’re starting with a narrow use case and a trusted vendor. We’ll make sure the pilot stays compliant, create a shared use policy, and make sure those engaged in the pilot are aware of the policy and receive training.”
With the CEO:
“This is about giving our people more time for high-impact work. With the right guardrails, we can use AI to move faster, reduce admin, and retain great talent.”
Moving toward the future
For many teams, AI is already working in the background. Traditional performance management tools can collect survey responses or run performance reviews, but they leave HR teams stuck in analysis paralysis or chasing one-size-fits-all solutions.
AI-powered platforms like 15Five bridge this gap by turning people data into personalized, timely, and scalable recommendations for both HR leaders and managers. That means faster insights, more targeted actions, and better outcomes across performance, engagement, and retention.
There’s no one-size-fits-all strategy for AI in HR. But start by asking smart questions, inviting partnership, and staying rooted in business results. The more clearly you can frame what you’re solving for and how AI helps, the more likely your legal and executive teams are to say yes.
This is part 3 in our series about AI in HR. Check out the guide to AI readiness, and what to think about when crafting your AI in HR policy.
Disclaimer: This document is meant to be for illustrative purposes only and does not constitute professional and/or legal advice. Always discuss use of AI tools with your legal department and other stakeholders prior to using AI tools with employee data.
