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OakCress • Independent technology advice

Owner’s Technology Checkup

A plain language review for family owned and owner led businesses.

Use these questions to identify where the company needs clearer technology ownership, stronger documentation, or an independent second opinion. Answer based on what leadership can verify today.

15 questions • About 5 minutes • No email needed to see your results

Your quiz answers are calculated in this page and are not saved or sent to OakCress. Reloading or leaving this page clears them.

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How the score works

Count each No or Unsure response. The score is a discussion guide, not a certification or guarantee of security. This is the same scoring used in the downloadable PDF.

0 of 15 answered

Access and Ownership

1. Do you know who has administrator access to every critical system?

Leadership should know who can make high impact changes.

2. Are important passwords stored in a secure company controlled system?

Critical access should not depend on one person’s memory or personal account.

3. Is access removed promptly when an employee or vendor leaves?

Former access can create avoidable financial and security risk.

4. Does the company own its domains, software accounts, and cloud subscriptions?

The business should control the accounts it pays for.

Backup and Continuity

5. Has anyone successfully restored data from your backups?

A running backup does not prove that recovery will work.

6. Do you know how long the company could operate without its main systems?

Leadership needs a realistic view of downtime.

7. Is there a written plan for a technology outage or cyber incident?

Employees need clear first steps and contacts.

8. Could the business operate if its primary technology contact were unavailable?

The company should not depend on one person.

Vendors and Spending

9. Can leadership explain what the IT provider is responsible for?

The agreement and actual service should match.

10. Does leadership receive a useful technology report?

Reports should explain risk, work completed, spending, and next priorities.

11. Can every major technology expense be connected to a business need?

Licenses and services should have a clear owner and purpose.

12. Has an independent person reviewed the IT provider’s work?

A second opinion can identify gaps without requiring a provider change.

Growth and Planning

13. Is there a written technology plan for the next 12 months?

Technology decisions should support the company’s actual growth plans.

14. Are technology responsibilities assigned to named people?

Every important task needs accountable ownership.

15. Can leadership identify the three technology improvements that matter most?

A clear priority list prevents scattered spending.

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