Why Most Leaders Aren’t Ready for AI

Ryan Flanagan
Jun 05, 2025By Ryan Flanagan

TL;DR
You’re being asked to act on AI before your team has agreed what “AI” means. Readiness isn’t about tools. It’s about whether your organisation can make decisions with confidence, manage risk, and apply AI where it adds value. This blog shows you how to start building that readiness across leadership.

What AI readiness really means

Here’s the mistake: leaders assume AI readiness means hiring technical talent or signing a pilot deal. It doesn’t.

AI readiness is about organisational fitness: can your people make good decisions about AI use cases without adding confusion, reputational risk, or unnecessary cost? The World Economic Forum offers a framework for this: seven domains that must work together from strategy to governance to operations. But the real takeaway isn’t the list. It’s the order of operations.

Start with the leadership conversation. Then build capability around use cases. Only then should you consider tooling. If your organisation hasn’t had this sequence of steps, then no matter how much experimentation is happening you’re not ready.

 
Before buying AI, ask: “Can our execs explain where it fits?”

Most teams start with procurement. But the first real move is aligning your leadership team around three questions:

  • Where does AI make sense in our workflow?
  • What risks or unintended consequences could surface?
  • Who will be accountable for outcomes?
  • When these questions are left unanswered, projects drift.

Risk teams raise red flags.

People leaders get nervous. CIOs are left to make strategic calls in a vacuum.

You don’t solve this with a better demo. You solve it by building a shared internal vocabulary, grounded in your business context. That’s why AI Fundamentals sessions exist, not to teach tech, but to get your leadership team on the same page before money is spent.

Readiness is measured in workflows, not models

Here’s a practical reframe: AI is not something you “implement.” It’s something you apply to specific tasks.

Take one example from the WEF report: an APAC government agency used AI to triage service requests. The success didn’t come from the algorithm. It came from understanding the flow of work — and identifying where time and talent were being wasted on rules-based queries.

That’s the kind of capability you want to build across your operations, HR, and compliance teams: how to spot the task-level patterns that AI could handle — and how to assess risk in context.

If your team doesn’t think that way yet, don’t invest in tools. Build this muscle first.

What changes when you have real readiness

When your team has gone through a proper assessment and capability uplift, decision-making gets easier.

Instead of debating vague possibilities, you’re working with:

  1. A baseline understanding of what AI means in your setting
  2. Agreement on where AI can help, and where it shouldn’t
  3. A prioritised view of risks, gaps, and opportunities

This doesn’t just speed up AI work. It reduces internal friction. It gives your executive peers permission to move without fear of reputational damage or misaligned priorities.

That’s what readiness looks like: not enthusiasm, but clarity.

The path forward: what to do this year

If you’re not sure where to start, here’s what a good sequence looks like:

  1. Assess your organisational readiness
  2. Map your team’s capability across the seven dimensions. See what’s strong, and where decisions could break down.
  3. Run a leadership fundamentals session
  4. Use it to build shared language, clarify misconceptions, and make space for cross-functional concerns.
  5. Pick one process to explore with AI
  6. Don’t start big. Start with a use case that’s safe, operational, and visible.
  7. Document what you learn.


This sequence creates alignment, reduces internal pushback, and gives you a real basis for investment.

→ Check your team’s readiness with our AI Readiness Assessment
→ Align executives with our AI Fundamentals Masterclass
→ Move from concept to consensus with our Business Case Workshop

If you’re expected to lead on AI, make sure you’re leading from a place of structure.