IT Environment Assessment Workbook & Dashboard

The #GoodwinGetsIT IT Environment Assessment Workbook & Dashboard is a practical Excel workbook designed to help IT professionals, consultants, MSPs, and technology leaders systematically evaluate an unfamiliar IT environment before jumping to recommendations.

A good IT assessment shouldn't start with:

"What should we replace?"

It should start with:

What do we have?
What matters?
What's actually working?
Where's the risk?
And what happens when something fails?

This workbook provides a structured workspace for answering those questions.

It includes 66 prebuilt assessment questions covering nine major areas of IT operations, security, infrastructure, resilience, and management.

Use it during IT assessments, consulting engagements, new-role onboarding, MSP transitions, infrastructure reviews, technology due diligence, or anytime an organization needs a fresh set of eyes on its environment.

The workbook includes:

IT Environment Assessment Tracker - Work through 66 assessment questions covering Identity & Access, Backup & Recovery, Patching & Vulnerabilities, Network & Infrastructure, MFA & Security, Documentation, Licensing & Spend, Disaster Recovery, and Vendors & MSPs.

Identity & Access Assessment - Review administrator access, privileged account separation, employee and contractor offboarding, joiner/mover/leaver processes, service accounts, shared accounts, and recurring privileged-access reviews.

Backup & Recovery Assessment - Evaluate backup coverage, restore readiness, recovery ownership, retention, configuration backups, recovery procedures, and whether successful backup jobs actually translate into a recoverable environment.

Patching & Vulnerability Assessment - Review patching cadence, remediation ownership, critical and exploitable vulnerabilities, exceptions, unsupported systems, and whether reporting accurately represents the entire environment.

Network & Infrastructure Assessment - Examine internet connectivity, firewalls, switching, wireless, virtualization, storage, cloud infrastructure, monitoring, dependencies, documentation, lifecycle risk, and potential single points of failure.

MFA & Security Assessment - Evaluate MFA enforcement, privileged access, security exceptions, endpoint protection, email security, logging, monitoring, legacy authentication, and other foundational security controls.

Documentation Assessment - Determine whether another qualified administrator could understand, operate, troubleshoot, and recover the environment without relying on knowledge that exists only inside one person's head.

Licensing & Spend Assessment - Identify unused licensing, overlapping products, upcoming renewals, legacy subscriptions, contract ownership, and opportunities to reduce unnecessary spending without automatically removing capability.

Disaster Recovery Assessment - Review restore priorities, RTO and RPO expectations, recovery plans, decision ownership, testing history, communications, and the organization's ability to operate through a major technology failure.

Vendor & MSP Assessment - Document responsibility boundaries, vendor administrative access, contracts, SLAs, escalation procedures, renewals, support ownership, and third-party operational dependencies.

Assessment Status Tracking - Mark items as Not Assessed, In Review, Needs Attention, Validated, or Not Applicable so progress is visible throughout the engagement.

Risk Prioritization - Assign Low, Medium, High, or Critical risk ratings to separate meaningful exposure from ordinary improvement opportunities.

Ownership Tracking - Assign an Owner or Subject Matter Expert to assessment areas so findings don't disappear into the dangerous land of "someone should probably handle that."

Evidence & Notes Tracking - Record supporting evidence, observations, configuration details, test results, limitations, and other information used to validate each assessment answer.

Recommended Action Tracking - Capture the next logical action directly alongside the observation instead of creating a separate list that eventually becomes disconnected from the assessment.

Completion Tracking - Track progress at the individual assessment-question level and measure overall assessment completion.

Automated Assessment Dashboard - Quickly view total assessment questions, validated items, open items, High/Critical findings, overall completion, items needing attention, unassessed items, and ownership gaps.

Configurable Workbook Settings - Customize assessment statuses, risk levels, domains, and completion values while maintaining consistent dropdown values throughout the workbook.

The goal isn't to walk into an environment assuming something is wrong.

The goal is to build an evidence-based understanding of how the environment actually operates.

Sometimes the answer is better security.

Sometimes it's documentation.

Sometimes it's ownership.

Sometimes it's licensing.

Sometimes it's architecture.

And sometimes everything is working reasonably well, but nobody has stopped long enough to prove it.

Because the recommendation should follow the assessment.

Not the other way around.