The AI Conversation CHROs Need to Have With Their CEO

AI is giving CHROs a rare opportunity to fundamentally reshape how their company operates. The amount of influence HR ultimately has over those decisions will depend on when HR leaders engage with their CEO.

Kelley Steven-Waiss

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The AI Conversation CHROs Need to Have With Their CEO

AI is giving CHROs a rare opportunity to fundamentally reshape how their company operates. The amount of influence HR ultimately has over those decisions will depend on when HR leaders engage with their CEO.

A conversation with your CIO and CFO might seem like the natural place to start when you’re beginning to design an AI transformation plan. Building consensus with your colleagues before going to the CEO is a familiar way to work, and finance and IT will play a major role in deciding how your company uses AI. But as a former CHRO and current CEO, I would reverse that order. Your first conversation should be with your CEO, while they’re still deciding which direction they want to take.

Timing matters. Introducing an idea while your CEO is weighing their options can help shape their final decision. But presenting that same idea after they’ve settled on a plan can feel like a request to start over.

Even a good plan can miss the mark

A companywide AI transformation is going to need the CEO’s backing. That’s an obvious point, but what’s obvious from a 30,000-foot view can get lost in the details of our day-to-day work. We’ve all spent days or weeks on a project we thought would impress our boss, only to learn that we completely misunderstood what they wanted.

Even a proposal that has enthusiastic support from finance and IT can die on your CEO’s desk if it’s not aligned with what they believe the business needs to accomplish. Getting on the same page as your peers can’t resolve a fundamental misalignment with your CEO’s vision.

Consider an executive who builds an AI proposal around helping employees save time on routine work. If your CEO’s priority is getting products to market sooner, they may not want to fund that plan even if they believe it will produce a positive ROI.

That first conversation with your CEO should connect the business outcomes your CEO wants with what needs to change in the organization to achieve them. You can bring a view of where the current way of working is holding the business back, and why new technology alone won’t fix it. Your CEO can challenge that diagnosis and clarify which changes they’re prepared to support. The result will be a shared direction for your organization’s AI transformation, including where HR can help lead it.

An opportunity to shape your CEO’s thinking

Engaging with your CEO early will also give you a chance to shape their view of what your organization’s AI initiatives should accomplish.

If your CEO wants to launch products faster, you still need to understand where the current bottleneck is. Maybe employees are finishing their work quickly, then waiting around for another department to approve the next step. Automating their tasks won’t remove that obstacle. You could help your CEO see that getting products to market sooner may require giving teams the authority to make more decisions themselves.

Conversations with your CEO should shape your thinking too. When I was a CHRO, I always saw myself as a businessperson first and an HR leader second. My responsibility was to help the company achieve its goals. From that perspective, any conversation I had with my CEO was an opportunity to fill in my blind spots about what was happening in the business outside HR.

A CEO’s support gives HR room to lead

When your CEO backs your ideas for a companywide initiative, their support gives you clear authority to make decisions that impact other functions. Proposing changes to how other departments work is different from improving processes within HR. It helps to have explicit support for both the direction of the change and HR’s role in leading it.

When you’ve already secured your CEO’s support, you can begin a discussion with your peers with a clear mandate tied to your company’s priorities. That’s a strong foundation for working across functional boundaries and advocating for changes that HR can’t make on its own.

But that doesn’t mean you should dismiss what your colleagues have to say. Any AI initiative will still need the expertise of your financial and technical leaders. Your CFO can help connect an investment to measurable business value, while your CIO can assess whether your company’s systems can support new technology and determine what you’ll need to introduce them securely.

Their ideas may change what you originally proposed. They’ll also give your plan a better chance of succeeding. When collaboration produces stronger business results, a CHRO builds credibility as a leader who can help make the whole company more effective.

AI is creating an opening for HR to help redesign how work gets done. CHROs will have the best chance to shape that process if they engage their CEOs while they’re still deciding what they want to accomplish.

©

2026

— Copyright

©

2026

— Copyright

©

2026

— Copyright

©

2026

— Copyright