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Where AI Actually Earns Its Place in Enterprise Transitions

5 MINS

Where AI Actually Earns Its Place in Enterprise Transitions

"AI-driven" is easy to say and hard to mean. After studying AI for leaders and now building AI-enabled transition products, I've become allergic to AI that's bolted on for the pitch. In transition management, where mistakes are expensive and trust is everything, AI has to earn its place by removing real friction.

Transitions generate enormous, messy context

A large transition is drowning in information: scope documents, application inventories, knowledge-transfer notes, risk logs, dependency maps, ticket histories. Senior people spend a huge share of their time just assembling and re-reading that context to make the next decision.

This is exactly where AI is genuinely useful. Summarising knowledge transfer, surfacing risks buried in documents, flagging dependencies a human might miss, drafting the first version of a transition plan from prior engagements, these are the boring, high-value tasks that slow good transitions down. Automate the assembly of context, and you free experts to do the judgement.

Intelligence should assist the decision, not hide it

The fastest way to lose trust in an enterprise product is to make AI a black box that tells people what to do. In transition management, the person on the hook for the cutover needs to understand *why* a risk was flagged or a sequence was recommended.

So I design AI as an assistant to the decision, not a replacement for it. Show the evidence. Cite the source document. Let the experienced transition manager accept, adjust, or overrule. The goal is to make a good decision faster and better-informed, never to remove the human who's accountable for it.

Service-management discipline keeps AI honest

My ITIL and service-management background turns out to be a useful counterweight to AI hype. Service management is obsessed with process, accountability, and not breaking things in production. That discipline is exactly what AI-enabled products need so they stay reliable when the stakes are real.

The combination I'm after is intelligence with guardrails: AI that speeds up the work, sitting inside a process that's still auditable, repeatable, and safe. Speed without discipline is just risk delivered faster.

The bar I hold

Every AI feature I ship has to pass one test: would an experienced transition manager actually trust it on a live, high-stakes program? If the answer is no, it's a demo, not a product. AI earns its place in enterprise transitions by being useful, legible, and safe, in that order.

Background

Aneesh skipped presentations and built real AI products.

Aneesh Yashodharan was part of the April 2026 cohort at Curious PM, alongside 18 other talented participants.