Enterprise AI Strategy & Roadmap Playbook
- Executive
- Intermediate
- Template Included
- Workshop Ready
Build a defensible 18-month AI roadmap: inventory pilots, size value against feasibility, sequence by dependency, and get budget signed off in one steering session.
How is this different from a generic digital transformation roadmap?
It's narrower and more mechanical on purpose. A digital transformation roadmap tends to bundle infrastructure, process redesign, and culture change into one narrative. This playbook isolates the AI-specific prioritization decision — which model-driven or agentic initiatives get funded next — using a scoring method built around AI-specific readiness factors like data availability and model risk exposure.
What if business units refuse to submit honest value estimates?
That's exactly why finance validates every value score independently rather than accepting the sponsor's number. In the workshop, require sponsors to show their calculation method, not just the final figure — inflated estimates usually collapse under a two-question follow-up about the underlying assumption.
How many initiatives should realistically be in Horizon 1?
Five to seven, sized to what your engineering and change-management capacity can actually support simultaneously. Organizations that fund more than that in Horizon 1 consistently see slower delivery on every initiative because the same integration and data engineering teams are shared across all of them.
Does this replace the need for an AI governance function?
No — this is the prioritization and sequencing layer. Responsible AI governance (risk tiering, model oversight, compliance) is a separate, ongoing discipline that should review every Horizon 1 initiative before it scales, not after.
How often should the roadmap actually change?
Re-score quarterly, but expect the Horizon 1 list itself to be genuinely stable for two to three quarters at a time. If your Horizon 1 list is reshuffling every single quarter, that's usually a sign the initial scoring wasn't rigorous enough, not that the business is moving unusually fast.
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