Strategy question
You inherit a newly signed enterprise account where support workflows are fragmented, requirements are unclear, and the VP of Support, Operations, and IT all want different things first. What roadmap would you set for the first 90 days, how would you prioritize which workflow to launch first, and what milestones would you use to keep the account moving toward a production go-live?
- Decagon
- Strategy
- Hard
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What this question tests
Tests setting a first-90-days roadmap for a newly signed account with conflicting stakeholder priorities, and defining milestones that keep the deal moving toward production.
How to approach it
- Run structured discovery separately with the VP of Support, Operations, and IT to surface their actual priorities and any hidden constraints, like IT's data access concerns.
- Find the workflow that satisfies the most stakeholders at once, likely the highest-volume, most operationally painful ticket type Support cares about, that IT can approve quickly.
- Sequence the 90 days: weeks 1 to 3 discovery and data access setup, weeks 4 to 8 build and internal testing, weeks 9 to 12 limited production pilot with a defined ticket volume.
- Set milestones stakeholders can see progress against: data integration complete, first agent passing internal evals, first live tickets handled, and a go-live review date.
- Keep Operations and IT engaged throughout with brief recurring check-ins, not just Support, so no stakeholder feels sidelined by the chosen first workflow.
- Define the go-live criteria explicitly, for example resolution rate and escalation rate thresholds, agreed with all three stakeholders before launch.
What a strong answer includes
- Picks the first workflow by finding the intersection of stakeholder priorities, not just the loudest stakeholder's request.
- Builds in IT's data access and security review early in the timeline instead of as a late blocker.
- Sets concrete, dated milestones (integration complete, first evals passed, go-live review) instead of a vague ship in 90 days plan.
- Keeps all three stakeholders engaged throughout so the account doesn't stall on one side's disengagement.
Common mistakes
- Choosing the first workflow based only on the most vocal stakeholder, alienating the others.
- Leaving IT's security and access review until late in the 90 days, risking a late-stage blocker.
- Setting no concrete milestones, making it hard to tell if the account is on track.
Likely follow-up questions
- What would you do if IT blocks data access in week 6?
- How would you handle it if Support and Operations want different first workflows?
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More questions from Decagon
Learn the skill behind it
Chapters of the AI PM course that teach what this question tests.
- Chapter 4: Discovery and strategy for AI products
- Chapter 9: Prove it paid off: outcomes, economics, and pricing
- Chapter 14: Get the job: the AI PM interview loop