The CEO signed off on company-wide AI training. Then quietly skipped every session.

His assistant handles his AI interactions. He approves the outputs without understanding how they’re generated. When problems arise, he defers to “the technical people.”

This pattern is more common than anyone likes to admit. And it creates real problems.

Why This Matters

Senior leader disengagement from AI training undermines the entire effort:

It signals AI isn’t important. When executives visibly skip training that everyone else must complete, the implicit message is clear: this isn’t really mandatory for serious people.

It creates knowledge gaps at the top. Decisions about AI investments, risk tolerance, and strategic direction get made by people who don’t understand what they’re deciding.

It disconnects strategy from reality. Executives set ambitious AI goals without appreciating implementation complexity. When projects stall, they blame execution rather than unrealistic expectations.

It concentrates power inappropriately. The people who do understand AI (often junior staff) can’t effectively advise leaders who don’t share basic vocabulary.

Understanding the Resistance

Senior leaders resist AI training for reasons they rarely articulate:

Fear of looking incompetent

Executives built careers on expertise and confident decision-making. Sitting in training sessions where they know less than junior colleagues threatens that identity.

One CFO admitted privately: “I didn’t get to this position by asking questions in front of my team.”

Time scarcity (real and perceived)

Senior calendars are genuinely packed. But the “I’m too busy” excuse often masks discomfort. These same executives find time for golf, industry events, or board meetings.

The question isn’t whether they have time. It’s whether they prioritise this particular learning.

Scepticism about personal relevance

“My job is strategy, not tools.” This framing positions AI skills as implementation details beneath executive concern.

It’s a defensible position—until strategic decisions require understanding AI capabilities and limitations.

Generational dynamics

Not universal, but present: some leaders feel technology skills are for younger workers. They see AI proficiency as a task to delegate, not a capability to develop.

What Doesn’t Work

Standard approaches often backfire:

Mandatory attendance without engagement. Leaders show up physically while mentally absent. They check emails through sessions, leave early, or send proxies.

Public pressure. Calling out executives for non-attendance creates defensive reactions and political complications.

Dumbed-down content. “AI for Executives” programs that oversimplify create the impression there’s nothing substantial to learn.

Peer comparison. “Your competitor’s CEO just completed AI certification” might motivate or might trigger dismissive responses.

What Works Better

Executive-specific sessions

Design separate experiences for senior leaders:

• Small group or individual format
• Peer-level facilitators (other executives, board members)
• Focus on decision-making implications, not tool mechanics
• Confidential environment for questions

The Australian Institute of Company Directors has seen strong uptake of their AI governance programs precisely because participants learn alongside other directors.

Connect to strategic concerns

Frame AI skills around decisions executives actually make:

• Evaluating AI vendor proposals
• Assessing AI investment business cases
• Understanding AI risk profiles
• Interpreting AI project updates

This isn’t “training”—it’s “strategic briefing.” The reframe matters.

Use trusted messengers

Executives respond better to:

• Board members who’ve invested in AI learning
• Peer CEOs from respected companies
• Advisors they already trust
• External experts without internal political agendas

Sometimes the L&D team’s most effective move is arranging the right external voice.

Create private practice opportunities

Provide access to AI tools with no oversight:

• Personal accounts separate from company systems
• No monitoring of usage or mistakes
• Time to experiment without witnesses

Leaders will practice when nobody’s watching. Make that easy.

Focus on risk, not opportunity

Executives are often more motivated by downside risk than upside potential. Frame AI literacy around:

• Avoiding costly failed implementations
• Identifying vendor misrepresentation
• Understanding regulatory compliance requirements
• Managing reputational risks from AI mistakes

A Sensitive Conversation

Sometimes direct conversation is necessary. Approach it carefully:

Acknowledge the discomfort. “I imagine training sessions feel different at your level” opens space for honest discussion.

Make it about the organisation. “Your team is watching how you engage with this” connects personal action to leadership responsibility.

Offer alternatives. “What format would actually work for you?” invites problem-solving rather than resistance.

Be patient. Behaviour change takes time. One conversation rarely shifts deeply held patterns.

When to Escalate

Some situations require board or ownership involvement:

• CEO resistance undermining company-wide AI transformation
• Strategic decisions being made with fundamental AI misunderstandings
• Competitive risk from leadership knowledge gaps

These conversations are delicate. Document concerns carefully. Seek HR guidance on appropriate channels.

A Realistic Outcome

Perfect executive AI literacy is unlikely. More realistic goals:

• Leaders can ask informed questions about AI initiatives
• They recognise when they need technical input
• They don’t make obviously uninformed statements publicly
• They model learning orientation even if skills remain basic

That’s not transformation. But it’s meaningful progress from executives who genuinely can’t distinguish machine learning from macros.

L&D’s Role

Learning and development teams should:

• Design executive-appropriate formats
• Identify and recruit trusted messengers
• Create safe practice environments
• Frame learning around strategic value
• Track engagement without creating surveillance anxiety

The goal isn’t forcing participation. It’s removing barriers and providing motivation for executives who are willing to engage once the path is clear.

Some will never get there. Focus energy on those who might.