AI Readiness Assessment AI Readiness w Booking Subscribe Step 1Step 2Step 3Step 4Step 5Step 6Step 7Step 8Step 9Step 10Welcome! This self-assessment helps your organization reflect on its current AI readiness, practices, and opportunities. It takes 5-10 minutes to complete. Please answer as accurately as possible—this helps you get the best recommendations for your AI journey.BackNextFull NameEmailPhone/MobileBusinessBusiness Size 1-10 employees 11-50 employees 51-200 employees 201-1000 employees 1001+ employeesBackNextCurrent Technology EnvironmentWhat platform does your organization primarily use for email and collaboration? Microsoft 365 (Outlook, Teams, OneDrive, SharePoint) Google Workspace (Gmail, Drive, Meet, etc...) Not sure OtherHow is your IT environment managed? Internal IT team External IT provider (MSP) Combination of internal and external support No dedicated IT support Not sureWhere is most of your company’s data stored? Cloud (Microsoft 365 / Google Drive / Dropbox, etc...) On-premises servers Mix of cloud and on-premises Mostly local devices (desktops/laptops) Not sure OtherHow confident are you that the right people have access to the right data in your organization Very confident Somewhat confident Not confident Not surePreviousNextAI Awareness & Current UseHow would you describe your organization’s current use of AI tools? Not using AI at all Limited experimentation by a few individuals Informal use across teams (not centrally managed) Structured and managed usage across the business OtherAre employees currently using tools like ChatGPT, Copilot, or other AI tools in their daily work? Yes – widely Yes – but only a few people Not sure NoIf AI is being used, how visible is that usage to leadership or IT? Fully visible and tracked Partially visible Not visible Not sureBackNextData Awareness & RiskDo employees clearly understand what information is safe vs. unsafe to enter into AI tools? Yes – clearly defined and communicated Somewhat No Not sureCould sensitive company data (client info, financials, internal docs) potentially be entered into public AI tools today? Yes Possibly No Not sureHow confident are you that your organization’s data would remain protected when using AI tools? Very confident Somewhat confident Not confident Not sureBackNextGovernance & PolicyDoes your organization have a formal AI usage policy? Yes – established and enforced In progress No Not sureAre there defined guidelines for (check all that apply): What tools are approved What data can be used with AI How outputs should be validated None of the aboveIf an employee misused AI or exposed sensitive data, would there be a clear process to handle it? Yes Possibly No Not sureBackNextIT & Security FoundationsHow would you describe your organization’s current IT/security maturity? Advanced and well managed Moderate Basic Needs improvementDo you currently have the following in place? (check all that apply) Multi-factor authentication (MFA) across users Device management / endpoint controls Data classification or labelling Data loss prevention (DLP) policies Centralized identity management Not sure / None of the aboveHow confident are you that your current IT environment is ready to support AI safely? Very confident Somewhat confident Not confident Not sureBackNextBusiness Value & StrategyDo you currently have a clear strategy for how AI should improve your business? Yes – well defined Somewhat No Not sureWhere do you most expect AI to create value? (select up to three) Employee productivity Customer service Sales/marketing Operations/process automation Data insights/reporting Not yet definedAre you currently measuring the impact of AI usage in your organization? Yes No Not sureBackNextReadiness ReflectionIf your organization adopted AI more broadly tomorrow, what concerns you most?What do you feel is the biggest barrier preventing your organization from fully leveraging AI?How “AI ready” do you believe your organization is today? Not ready Emerging Developing AdvancedPreviousNextIs there anything else you would like to add that may help in the assessment? Back Next
