Most Enterpise Transformations Stall Before They Fail
Detect loss of momentum before it shows up in reports, budgets or escalations
Teams Busy - Funding is approved - Backlogs are full - And yet - delivery slows, dependencies surface late and nobody can clearly explain what must move next - That is not failure - That is stall
This checklist is what we use to detect that stall early, while there is still room to act:
What this checklist actually does
This is not a best-practice list.
It is a stop-or-go decision gate designed to surface problems most organizations avoid naming.
The checklist will:
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Force named business ownership (not “the business”, not committees)
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Expose avoided decisions upstream
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Make cost of delay visible, even when delivery looks “busy”
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Stop work that is moving forward without clarity
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Create an explicit moment to decide: continue, correct, or stop
If the checklist feels uncomfortable, it’s doing its job.
When this checklist is typically used
Organizations use this checklist when they sense that something is “off”, but cannot yet point to a failure:
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Delivery feels slower, but nothing is formally blocked
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Refinement meetings increase, outcomes do not
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Dependencies appear late and repeatedly
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Product ownership exists on paper, not in practice
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Steering conversations revolve around status, not decisions
If you wait until metrics turn red, you are already late.
Who this is for — and who it is not
This checklist is for:
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CIOs and IT leadership
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Transformation sponsors
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Senior program and portfolio leaders
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Executives accountable for outcomes, not activity
This checklist is not for:
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Teams looking for agile tips
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Lightweight templates
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Training material or process documentation
It assumes senior accountability and real consequences.
What you will need to complete it
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30–45 minutes
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Willingness to answer honestly
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One or two people who can actually say “no”
You do not need: More data - More tools - More reporting - You need clarity