Strategy question

You’re inheriting four teams across Code Context, Design to Code, Code to Design, and Code Platform. How would you set a 12-18 month strategy for Roundtripping: define the target user outcomes, choose where to invest first, and decide which platform capabilities must be built centrally versus within each workflow as customer demand and the technical path are still emerging?

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What this question tests

Whether you can set a multi-team platform strategy under real ambiguity about both customer demand and technical feasibility.

Define the target outcome first: designers and engineers spend less time manually re-implementing or re-documenting each other's work, measured across Code Context, Design to Code, and Code to Design.
Sequence investment: start with Code Context, since accurate underlying representation of design and code state is a prerequisite for both translation directions to work reliably.
Decide centralization: build shared primitives (file parsing, token mapping, diffing) centrally in Code Platform, but let each workflow team own its own translation logic where the technical approach is still unproven.
Use staged bets: run Design to Code and Code to Design as parallel experiments against the shared Code Context layer rather than committing to one direction as the flagship.
Set checkpoints every quarter to reassess which workflow shows stronger technical feasibility and customer pull, and reallocate accordingly.
State explicitly what is deferred, for example full bidirectional live sync, since that depends on both directions maturing first.

Justifies Code Context as the first investment because both other workflows depend on it, a genuine sequencing argument rather than an arbitrary pick.
Distinguishes 'build centrally' (shared, stable primitives) from 'build in the workflow team' (unproven, still-changing logic), with a clear reasoning rule rather than a static org chart.
Uses quarterly reallocation checkpoints to keep the 12-18 month plan responsive to which direction proves out.
Names a concrete outcome metric, for example reduction in manual re-implementation time reported by design and engineering pairs on pilot teams.

Trying to fully centralize or fully decentralize all four teams' work instead of reasoning per capability.
No sequencing logic for why one team gets investment before another.
Vague target outcome that cannot be measured at the 12-18 month mark.

How would you decide it is time to centralize something currently owned by one workflow team?
What would you do if Code to Design turns out to be technically infeasible at the fidelity customers need?
How would you measure progress at the 6-month mark before the full 18 months plays out?