How to Tell Your CEO a $50M Program Is Actually Failing (And Keep Your Job)

Your flagship digital program is four months behind and $3M over budget.
The PMO says amber. Risk says red. And you’re the one who has to walk into next week’s executive committee.

If you’re a COO or CRO reading this at 11pm on a Sunday, you already know the problem:
Dashboards are telling different stories, your SI vendor keeps saying “we’re on track, just a few minor issues,” and your gut is screaming that something’s seriously wrong.

But here’s what makes it impossible:
You championed this program. Your credibility is attached to it.
Telling the CEO it’s failing feels like career suicide.

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What 25 Years Fixing Troubled Transformations Has Taught Me:
The conversation that saves programs isn’t about status reporting, it’s about diagnosis. 🩺

The difference sounds subtle, but it’s everything:
Status reporting is “We’re behind schedule and over budget.”
Diagnosis is “We have three competing views of delivery health because we’re measuring effort, not outcomes.”

One approach makes you look like you’ve lost control.
The other makes you look like the only adult in the room.

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When you need to have the hard conversation, lead with what you’ve discovered, not what you’ve failed to deliver.
Instead of saying, “The digital banking program is 4 months behind,” say, “I commissioned an independent diagnostic on our digital program. We found that PMO is tracking task completion, Risk is tracking control gaps, and the vendor is tracking hours billed. None of them are tracking actual business outcomes. That’s why the board gets three different stories.”

Rather than, “We’re $3.2M over budget,” say, “Our diagnostic shows $3.2M of spend on ‘discovery’ that should have been done before contracting. The SI’s green status is technically accurate—they’re delivering what’s in the SOW. But the SOW was based on assumptions that turned out to be wrong.”

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Key insight:
This approach only works if you’ve brought in someone with no skin in the game. Your PMO can’t diagnose themselves. Your SI vendor can’t investigate their own delivery approach. Internal teams are too close to see clearly.

The role of independent transformation assurance is to give executives the ammunition they need to have career-preserving conversations about program reality. 🦺

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Executives don’t fail because they don’t know their programs are in trouble. They fail because they can’t prove it’s in trouble without looking incompetent. Independent diagnosis is your proof. It separates “I lost control” from “I discovered a systemic issue no one else spotted.”

If you’re sitting on a major program that’s showing warning sign, competing dashboards, vendor contracts up for renewal, APRA asking questions, you probably don’t need more governance; you need diagnostic clarity.

That’s a very different conversation.