Insights
These articles help you ask better questions, evaluate the answers, and decide what your organization should do next. To record what you find, use the free Security Reality Snapshot checklist.
New here? Start with Five questions to ask your IT provider this quarter.
Planning your security for 2027, with AI in the picture
A plan for next year should start from how you and your staff already use AI, and from what you owe the clients who trust you with their information.
Ask your provider or team
Which AI tools has the business approved, and for what kind of work?
Microsoft 365 needs a security plan of its own
Check how accounts, access policies, and operational responsibilities protect your use of Microsoft 365.
Ask your provider or team
Which authentication and device-access policies apply to which users, and what is excluded?
Who owns the gaps between your security providers?
Trace shared security work from trigger to completion so responsibility does not disappear at a handoff.
Ask your provider or team
Who receives the signal, and who decides what it means?
Fit your security program to what you can operate
Right-size governance to the owners, providers, and evidence-review capacity a small organization has.
Ask your provider or team
What do you do without asking us first?
What a patch report does and does not prove
A completion percentage is not the same as evidence that exposure is going down. Ask for the record that shows it.
Ask your provider or team
Which systems are outside the current inventory, and how would we find out?
When the patch loses the race
Exploitation can now start before a fix exists. Ask what limits what an attacker can reach, not just how fast you patch.
Ask your provider or team
Which systems are internet-exposed, and could any of them be made not internet-exposed?
Who is allowed to remote into your network?
Remote-access tools are normal. An unmanaged list of them is a gap. Ask which are approved and what stops the rest.
Ask your provider or team
Which RMM tools currently have access to any device on your network?
Who owns your edge equipment?
State-sponsored actors are opportunistically compromising routers through defaults nobody rotated, not exotic tradecraft. Ask who owns the configuration.
Ask your provider or team
Who holds administrative access to the device, and is that access reviewed on any schedule?
What a backup report does and does not prove
Separate successful backup jobs from evidence that your organization can recover a usable service.
Ask your provider or team
Which systems does the report cover, and what is excluded or failing?
Five questions to ask your IT provider this quarter
Use these questions to turn a provider update into clear responsibilities, evidence, and next steps.
Ask your provider or team
If a serious alert arrives Saturday night, who reviews it, who can contain it, and who contacts us?
What your MSP contract actually covers
Read your managed service agreement alongside operational evidence to understand coverage and responsibilities.
Ask your provider or team
After an alert, which of human review, investigation, and containment does the service include?
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