The GenAI Rollouts That Look Successful on Paper… Until You Look Closer

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Authored byRaeann Bilow

Last week, our contract web developer, Luca Ottolini, forwarded us a post he’d seen on social media. His note was short: “I think this perfectly explains, in a funny way, why your help matters…” 

We smiled, but we also paused, because it hit a little harder than we expected. When someone outside your team puts words to the value of what you’re trying to do, it’s both affirming and clarifying. It’s a reminder that the problem you’ve been tracking isn’t niche or theoretical. It’s widespread, and it’s quietly costing organizations real money and momentum.

The $1.4 Million “Ghost” Rollout

The post Luca shared described a hypothetical scenario that felt familiar almost immediately. A company rolls out Microsoft Copilot to 4,000 employees at roughly $30 per seat per month, adding up to about $1.4 million annually.

The board approves the investment quickly after hearing the phrase “digital transformation.” The executive sponsor repeats the promise that it will “10x productivity.” What never happens is the pause. No one defines what success looks like or which parts of the business are expected to change. Emails go out. Licenses are provisioned. And then the organization moves on to the next urgent priority.

A Pattern of Leadership Breakdown

What resonated about the story Luca shared is that it isn’t an outlier. We see this across B2B organizations of all sizes. The tools change. Copilot may become Gemini or a bundle of point solutions, but the outcome is a quiet stall.

This happens because GenAI doesn’t fit neatly into a single function. It cuts across Strategy, IT, Operations, HR, Finance, Product, and Customer Experience.

When responsibility is spread across leaders who already have full-time roles, no one has the time or authority to connect the dots. In this leadership vacuum:

  • The Experimenters: People who want to innovate don’t know what’s allowed.
  • The Skeptics: Those who doubt the tech feel validated by the lack of direction.
  • The Signals: Early warnings that the rollout is failing get missed because no one is looking for them.

This is where the absence of clear GenAI executive leadership becomes visible.

Why This Isn’t (Solely) a Training Problem

When usage data finally comes back and shows that only a handful of employees are using the tools, the conclusion feels obvious: Employees didn’t adopt because they weren’t trained.

Training matters, and organizations that invest in thoughtful enablement see better results. But in these situations, training is rarely the root cause of failure. Training assumes that foundational decisions have already been made.

Training assumes someone has already defined:

  • Which tools actually matter to the specific business model.
  • Which use cases deserve focus.
  • How impact will be measured in a way the business respects.

Without that foundation, training can increase awareness, but it can’t create momentum. Employees may learn how to use the tool, but they still don’t understand why it matters to their work.

The High Cost of “Wait and See”

The most obvious cost of this gap is unused licenses, but the hidden costs are more damaging:

  • Damage to Perception: A poorly led rollout teaches employees that GenAI is either irrelevant or just another “initiative of the month” that leadership will eventually stop talking about.
  • Shadow AI: When people see the potential but don’t have clear guidance, they find their own tools. Security and compliance risks increase, and fragmentation becomes harder to unwind later.

The Solution: Establishing Executive Ownership

Most leadership teams recognize GenAI is strategic, but hiring a full-time Chief GenAI Officer can feel premature. Yet, spreading the work across existing executives doesn’t work because GenAI requires sustained attention and cross-functional authority that doesn’t fit into an already full job description.

This is the gap a Fractional Chief GenAI Officer fills. The role exists to provide focused executive ownership without the permanence of a full-time C-suite hire. It means defining success in business terms, not vendor promises. It means coordinating efforts so learning compounds instead of fragmenting, and creating the space for training to actually work because enablement is tied to real priorities.

From Deployment to Transformation

The story Luca shared resonates because it makes a painful pattern visible, but it also points to a solvable problem. Buying GenAI tools doesn’t make an organization AI-enabled. Leading the transformation does.

If your leadership team is already stretched thin, that doesn’t mean lowering your ambition. It means getting support from people who focus on guiding organizations through this shift with clarity, realism, and care.


Ready to make your GenAI investment real? If you’re ready to move from deployment to measurable impact, our Fractional Chief GenAI Officer service provides the leadership B2B organizations need to turn investments into outcomes, grounded in nearly 20 years of research into how technology adoption actually works.

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