The chatter coming out of the CIO 100 crowd this week wasn't about launching more AI pilots.

Instead, they were asking: how do I get my board to believe this is actually working?

These are different problems and the CIO’s still focusing on AI implementation are going to be a part of some hard conversations.

Two years ago the board question was "what are we doing with AI?" That was an easy question. Most answered it with a roadmap and a couple of demos and everybody felt modern.

Now the question is "what did it return?"

Boards have learned the difference between a demo and a result, and they are not in a generous mood about it, the hype is waning.

Plenty of leaders are making real progress and losing the room anyway. The projects may be “on track”, but the board is still losing confidence.

A status update proves activity. Milestones hit, budget consumed, timeline green. It answers the question are you busy?

A confidence signal proves judgment. It answers the question should we believe you about what happens next?

As most seasoned CIO’s know, boards fund great judgement and promised results. And "we're on track" tells a board absolutely nothing, everyone is on track, right up until they aren't.

1. Lead with what surprised you.

This feels backwards, itt isn't. A leader who reports zero unexpected findings is either not looking or not telling, and boards will sniff out both. If you can say something like; "Operations adopted it in week two, but finance hasn’t touched it. So it turns out the bottleneck was our approval process, not the tool." That's a leader that continues to pressure test the project from the perspective of business outcomes.

2. Show the judgment, not just the decision.

Recap your decision making process. You started with a hypothesis and you’ve been granted the funds to test. A decision with visible reasoning earns trust for the next decision. A decision without it will just be graded on the results.

3. Define the bar before you clear it.

"We committed to a 15% reduction in ticket volume by Q3. We're at 9%. Here's why we still expect to hit it, and here's the date I'll come tell you we won't."

Don’t be afraid to name the failure condition, it’s a meaningful signal that you understand company risk and are trying to protect the company’s downside. Vagueness is what gets you replaced. If you never define the bar, someone else defines it for you.

Pull up your next AI investment update and do four things:

If you positioned yourself well in the beginning, your board likely knows that the AI play is a longer term investment. They won’t be focusing on massive returns in the near-term, but they will be trying to understand the risk profile of their investment.

If you’re just providing status updates and not a clear demonstration of your ability to problem solve your organization’s desire for an AI uplift, then you will be risking the confidence of the board. Most people understand the dynamic and even political nature of AI integration. As a CIO or tech leader, your responsibility is to cut through the noise and ensure your organization can confidently back the spend and mitigate the risk.

Your board isn't asking you for certainty. Nobody has certainty. They're asking whether the person spending the money can tell the difference between successfully executing a project and transforming a business.

If you can prove that, then the phrase “on track” won’t get you fired.

Until next week,

—Jared

Text Me: 314.806.3912

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