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Should I Keep Operating This Service?

A service can work and still be the wrong thing to operate. Use this worksheet to compare the current system with a managed or rebuilt alternative using the work, risk, and user experience that actually exist.

1. Name the service and the decision

Service or stack	________________________________________
People who depend on it	________________________________________
Current operator	________________________________________
Decision date	________________________________________
Choices being compared	Keep / rebuild / managed service / retire

2. List the work users are trying to finish

Describe tasks, not product features. Include outside customers, partners, mobile users, shared accounts, and accessibility needs.

User task	Current path	Failure or friction	Required outcome
________________	________________	________________	________________
________________	________________	________________	________________
________________	________________	________________	________________
________________	________________	________________	________________

3. Record the operating work

Use tickets, calendars, logs, and invoices when available. If the number is an estimate, label it. Include the interruptions that never became tickets.

Work	Hours/month	Who can do it	What happens if it waits
Updates and security	______	________________	________________
User and access changes	______	________________	________________
Monitoring and incidents	______	________________	________________
Backup and restore tests	______	________________	________________
Client and integration support	______	________________	________________
Capacity and renewal work	______	________________	________________

4. Compare complete boundaries

Boundary	Current system	Alternative	Evidence needed
Identity and MFA	________________	________________	________________
Public exposure	________________	________________	________________
Data location and retention	________________	________________	________________
Backup and recovery	________________	________________	________________
Support and escalation	________________	________________	________________
Exit and portability	________________	________________	________________

5. Build the real cost comparison

Keep recurring and one-time costs separate. Count only savings tied to a service, license, server, or labor demand that will actually disappear.

Cost	Keep	Alternative	Confidence
Licenses and subscriptions	________	________	Low / med / high
Compute, storage, network, power	________	________	Low / med / high
Operator and support time	________	________	Low / med / high
Migration and coexistence	________	________	Low / med / high
Backup, recovery, and compliance	________	________	Low / med / high
Training and process change	________	________	Low / med / high

6. Decide who can operate the result

Routine administration owner: ________________________________
Privileged administration owner: ______________________________
Incident and vendor escalation owner: _________________________
Recovery authorization owner: _________________________________
Documentation and handoff date: _______________________________

If the alternative merely moves work to a person who has not been trained or granted a clear boundary, the operating problem is not solved.

7. Define migration milestones before starting

Milestone	Proof	Owner	Rollback point
Inventory complete	________________	________	________________
Pilot complete	________________	________	________________
Data synchronized	________________	________	________________
Traffic cut over	________________	________	________________
User workflows verified	________________	________	________________
Old service retired	________________	________	________________

8. Record the decision

Decision	________________________________________
Reason	________________________________________
Evidence still missing	________________________________________
Maximum one-time cost	________________________________________
Maximum recurring cost	________________________________________
Review date	________________________________________
Stop condition	________________________________________

This worksheet grew out of a completed mail cutover for roughly 150 users. The companion article explains why I moved that self-hosted mail and collaboration stack to Microsoft 365, what the move did not solve, and where the evidence ends.

How to use it: Print this page or copy the headings into a working document. The blanks are prompts, not a numerical score. A decision that cannot name an owner, recovery path, and retirement plan is not ready.