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Plan / operate / review

My CTO operating plan & templates.

I connect service ownership, risk, recovery and delivery to a small set of accountable decisions.

My approach

I start by listening and validating the operating facts. I prioritise a few changes with measurable outcomes before I commit the team to a large transformation.

My first 90 days

1

Days 1–10: listen to service owners

I ask what work must never stop, where users lose time, and what a successful quarter looks like. I map critical services to a business owner and technical owner and list the top dependencies.

2

Days 1–15: establish the operating facts

I reconcile headcount/capacity, support coverage, budget, supplier renewals, asset ownership, and admin access. I note uncertainty explicitly rather than turning assumptions into a dashboard.

3

Days 10–20: test the recovery assumptions

I pick one critical service and run a controlled restore or recovery exercise. I compare elapsed time and recovered data against the agreed recovery-time and recovery-point objectives. I record the gaps and a funded owner.

4

Days 15–30: agree the top five risks

I build a risk register with likelihood, business impact, current controls, treatment, owner, due date, and residual risk. I take the acceptance decisions to the person authorised to accept them.

5

Days 20–30: set the service contract

I agree support hours, a usable priority matrix, escalation ownership, and baseline service metrics. I use the SLA builder as a starting proposal and confirm staffing before making promises.

6

Days 30–45: cut the project list to capacity

I score current initiatives by outcome, risk reduction, effort, dependency, and available owner. I explicitly stop, defer, or fund work rather than expecting every team to absorb another priority.

7

Days 45–75: deliver two visible improvements

I choose one reliability improvement and one user-facing improvement. Each gets a starting measure, target, accountable owner, rollback plan, and evidence of the result.

8

Days 75–90: agree the next-quarter rhythm

I establish weekly operational reviews, a monthly service/risk review, and a quarterly roadmap decision. The board update explains outcomes, risks, money, and requested decisions in plain language.

Reusable working documents

Start with a useful template

I fill in the owner, scope, evidence, and next decision. I adapt these starting points to the organisation before approval.

Agent test cases

I record expected answers, permission checks, failures, and evidence before release.

Download CSV ↓
AI use register

I document the use, role, classification decision, and evidence for every AI system.

Download CSV ↓
Backup and restore test

I compare an actual recovery with the recovery-time and recovery-point objectives.

Download CSV ↓
Deployment pilot record

I capture device preparation assignments, application results, and rollout decisions.

Download CSV ↓
Microsoft 365 baseline evidence

I assign ownership and record the evidence behind each baseline setting.

Download CSV ↓
NIS2 control and evidence register

I map applicable measures to accountable owners, actual tests, and remediation.

Download CSV ↓
Operational risk register

I record likelihood and impact separately, then assign a treatment and acceptance owner.

Download CSV ↓
Supplier review

I connect supplier obligations, dependencies, access, evidence, and renewal decisions.

Download CSV ↓
CTO 90-day operating plan

I turn priorities into owned outcomes and decisions that fit the available capacity.

Download CSV ↓
Example SLA matrix

I use these as starting proposals, then agree coverage and targets with the service owner.

Download CSV ↓
Incident and reporting record

I capture the incident clock, ownership, impact, communications, and regulatory decisions.

Download MD ↓
AI acceptable-use policy starter

I adapt the scope, approval rules, oversight, and escalation route before approval.

Download MD ↓
Local read-only agent example

I allow one fictional status tool, validate its inputs, and cap the loop at three rounds.

Download PY ↓
My reference shelf

Useful Websites

Microsoft Learn & Docs ↗

Official docs for M365, Azure, Entra, Intune and Graph API.

LazyAdmin GitHub ↗

Practical PowerShell and M365 automation scripts and guides.

BleepingComputer ↗

Security news, malware analysis, and vulnerability writeups.

MXToolbox ↗

DNS, MX, SPF, DMARC, blacklist and SMTP diagnostics.

SSL Labs Server Test ↗

Deep TLS/SSL server analysis and certificate grading.

Have I Been Pwned ↗

Check if an email or password appeared in a known data breach.

VirusTotal ↗

Scan files, URLs and IPs with 70+ antivirus and threat engines.

Shodan ↗

Search engine for internet-connected devices and exposed services.

Regex101 ↗

Build, test and debug regular expressions with live explanation.

JSON Crack ↗

Visualize, edit and explore JSON structures as interactive graphs.

OneTimeSecret ↗

Share passwords and secrets securely — link expires after first read.

JWT.io ↗

Decode, verify and generate JSON Web Tokens in the browser.

Down For Everyone Or Just Me ↗

Instantly check if a website is down globally or just for you.

WhatIsMyIP ↗

IP address, ASN, geolocation and network info lookup.

Browserling ↗

Free online cross-browser testing across multiple OS and versions.

What changed

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