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Staff proposes two‑year strategic planning calendar tying budget, CIP and work program; council presses for fewer priorities and operational metrics
Summary
City staff and consultants presented a proposed timeline to align the two‑year work program, operating budget and five‑year CIP, with key milestones Nov–Dec 2026 (post‑election input), May 2027 (proposed budget/CIP/work program) and June 2027 (adoption); council urged realistic item counts and better integration with operations.
City staff and consultants presented a proposed strategic planning timeline at the Feb. 28 Cupertino council retreat that would align the two‑year work program with the operating budget and the five‑year capital improvement program (CIP).
The outside consultant described the process: staff will develop the 2026–27 operating budget and next five‑year CIP this spring, begin year‑two work‑program activity in July 2026, solicit council priority input in November–December 2026 after the election, consolidate proposed priorities in January–March 2027, deliver the proposed budget, CIP and final work program in May 2027 and proceed to adoption in June 2027. The consultant emphasized aligning resources across the work program, operating budget and CIP so projects are not double‑counted or overcommitted.
Council members asked procedural questions about how the "five‑year CIP" functions as an outlook (year‑one focus, years 2–5 subject to yearly adjustment) and how midcycle updates will work. One council member cited a low execution rate—"only 3 out of 30" year‑one work‑program items completed—and urged the council to set fewer, higher‑priority items and to rescore priorities after year one. Staff and the consultant proposed periodic check‑ins (September/October and February/March) and suggested categorizing initiatives as high, medium or low priority so staff can propose tradeoffs when resources are constrained.
Council members also raised operational concerns: projects that emerge during the year (legal issues, contracts, public‑safety work) can consume staff time and are not always captured on the work‑program dashboard, so several members asked for an operational performance report or more frequent dashboard updates to show what staff accomplished.
Members discussed adding AI and operational tools as a focus area to improve permitting, 3‑1‑1 ticketing and budgeting scenarios; staff said AI could be treated as a focused theme and folded into the operational plan if council so directs. The consultant recommended a case‑based, scenario approach to workshop difficult accountability questions.
There were no formal votes. Council members agreed to follow up with staff on timelines, midcycle checkpoints and a possible early retreat for onboarding new council members.
