vCIO Technology Roadmap Review Checklist Template

Start eight to ten weeks before the client’s budget is set. A roadmap that arrives after the budget is fixed waits a year.

• Open the annual review — client, fiscal year start date, budget deadline, and the vCIO and account manager for the account
• Pull last year’s roadmap — approved, completed, deferred and declined items, and the decision records from the last four QBRs
• Book the strategy interview — with the owner, managing director or finance lead, at least six weeks before the budget deadline
• Run the business strategy interview — growth and hiring plans, new sites or services, systems being replaced, and what worries the leadership team
• Record compliance and insurance obligations — frameworks, customer contracts and cyber insurance renewals that fall due in the next 12 months

• Export the asset inventory — devices from the RMM and the documentation platform, with purchase date, warranty expiry and operating system
• Flag end-of-support software — operating systems, server versions, Office editions and line-of-business applications whose support ends within 36 months
• Review hardware age — devices already past the client’s refresh cycle, and those that will pass it during the plan
• Review licences and subscriptions — Microsoft 365 plans, line-of-business renewals and any SaaS the business pays for outside IT
• Review open risks — findings from the latest security risk assessment, and accepted risks that are due for another look

• Score the client against your technology standards — each standard aligned, partly aligned or misaligned, with evidence
• Identify gaps that carry business risk — not every misalignment is worth fixing this year, so note why each one matters
• Record agreed exceptions — standards the client has deliberately declined, with the reason and the date of the decision
• Group gaps into candidate projects — one project per business outcome, not one line per device

Shown only when a compliance assessment or cyber insurance renewal falls in the plan year. Conditional logic keeps it out of the other reviews.

• Confirm the requirement and deadline — the framework or insurer, the current version of its requirements and the assessment or renewal date
• Compare current controls with the requirement — the gaps that would fail an assessment or answer an insurer’s question badly
• Add mandatory items to the roadmap — marked as required, with the deadline that drives each one
• Schedule the evidence work — assessment preparation or the insurance questionnaire, booked with time to fix what it finds

The vCIO owns this phase. The internal pricing approval halts the review until someone other than the author has checked the numbers.

• Draft the 12–36 month roadmap — projects by quarter in three horizons: this budget year, next year and year three
• Estimate each project — one-off cost, the change in recurring cost and internal labour, with assumptions written down
• Align the budget to the client’s fiscal year — quarters labelled by the client’s financial year, not the calendar year
• Approve the roadmap pricing internally — the service manager or owner checks costs, margin and resourcing before the client sees a number
• Write the executive summary — one page with the three priorities, the total budget by year and the risk of doing nothing

• Present the roadmap to the decision-maker — business goals first, then projects, budget and the end-of-support dates that drive them
• Record a decision on every project — approved, deferred to a named quarter or declined, with the client’s name and the date
• Record declined items as accepted risks — with the reason the client gave, so they can be raised again if circumstances change
• Send the decision record — the roadmap as approved, within two working days of the meeting

• Create the approved projects in the PSA — a quote, project and budgeted hours for each approved item
• Brief the project team — scope, decision record and anything the client said that shapes how the work should be done
• Add the roadmap to each QBR — progress against the approved plan becomes a standing item at the next four reviews
• Book next year’s review — timed to the client’s budget cycle, with the interview date in the diary