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Chart It · Step One of the Dragon Bay Process

Your AI Readiness Questionnaire.

Your answers shape the written AI Readiness Assessment we prepare for you: where AI can save your team time, what company data is exposed, and what to fix first. Plain questions, mostly multiple choice.

About 15 minutes
Can save on this device as you goOne page, send when you're done
"Not sure" is always a fine answer
No passwords or account details needed

Your Course

About You
Goals & Timing
AI in Use Today
Your Data
Files & Access
Rules & Training
Accounts & Sign-Ins
Devices & Backup
IT Support & Software
Your Team & AI
Insurance & Obligations
Review & Send

Answers save on this device as you go.

Step 1 of 12About You

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Step 1 of 12

About You

Who we're talking to and the shape of the company. This is how we tailor the findings to your industry.

Your name *

Your title or role

Work email *

Phone

Company name *

Company website

City of your main office

Industry *

Which industry?

How many employees does the company have? *

1–1011–2526–5051–100101–250250+

About how many people use a computer or company email for work?

Office and field staff who sign in to email, Microsoft 365, or company software.

Where does your team work? Choose all that apply.

In an officeOn job sites or in the field, using phones or tabletsFrom home or hybridOn a shop or plant floorAcross more than one office

Step 2 of 12

Goals & Timing

What prompted this, and what you'd like AI to do for your team. Your answers here shape the use cases in your report.

What prompted you to look at AI readiness now? Choose all that apply. *

Staff are already using AI and we want rules around itOur cyber insurance application or renewal asked about AIA client, GC, owner, or partner asked about our AI or security practicesWe want AI to save time and keep up with competitorsA security scare or incidentLeadership asked for a planSomething else

Where would AI help your team most? Choose up to three.

Drafting emails, letters, and noticesSummarizing contracts, specs, submittals, bids, or leasesEstimating and takeoff prepMeeting notes and action itemsExplaining financial and job-cost reports in plain EnglishProposals, marketing, and bid packagesAnswering questions from our own files, SOPs, and past jobsClient, tenant, or customer communicationsNot sure yet. We'd like ideas.

Choose up to 3.

Which tasks eat the most time for your team each week?

A sentence or two is plenty. For example: "Project managers spend hours writing RFIs and chasing submittals."

When would you like to have AI rules and tools in place?

Within 30 daysIn the next 1–3 monthsIn 3–6 monthsWe're just exploring

Step 3 of 12

AI in Use Today

Most companies have more AI in use than they think. Best guesses are fine, and "Not sure" tells us something too.

How many of your staff use AI tools for work? *

None that we know ofA few peopleAbout halfMost of the teamNot sure

Which AI tools do you know or suspect are in use? Choose all that apply.

ChatGPT (free or personal paid accounts)ChatGPT Team or Enterprise (company paid)Microsoft Copilot (free, in the browser or Windows)Microsoft 365 Copilot (paid add-on)Google GeminiClaudePerplexityGrammarly or other writing assistantsAI meeting note-takers (Otter, Fireflies, Read.ai, Zoom or Teams AI notes)AI features inside software we already use (Procore, Bluebeam, Adobe Acrobat, Canva and others)AI browser extensionsAI image or video toolsNot sure

When staff use AI for work, which accounts do they use? *

Personal and free accounts sit outside the company's control. You can't see, manage, or delete what goes into them.

Company-managed accounts onlyA mix of company and personal accountsMostly personal or free accountsNo one uses AI for workNot sure

Does the company pay for an AI tool for staff? *

A company-provided tool is the most effective way to steer people away from personal accounts.

Yes, for everyone who uses AIYes, for some peopleNoNot sure

If someone asked which AI tools your staff used last month, could you answer? *

Insurers, clients, and auditors are starting to ask this exact question.

Yes, from a report or a monitoring toolRoughly, from asking aroundNo

Do AI note-takers join your calls and meetings, including ones clients or vendors bring? *

Note-takers record and transcribe conversations, often to accounts the company doesn't control.

No, and we'd know if they didYes, an approved one we set upYes, people add them on their ownNot sure

Step 4 of 12

Your Data

What information your company handles and how it moves. We never need the information itself, only how it's handled.

Which of these does your company handle? Choose all that apply.

This tells us which mistakes would cost the most if they ended up in an AI tool.

Bids, estimates, and pricingContracts, change orders, and legal documentsDrawings, plans, CAD files, and specsEmployee records (SSNs, payroll, benefits)Client, tenant, or buyer personal information (IDs, SSNs, bank details, credit applications)Financial statements and bank recordsPayment and wire instructionsGovernment or defense project informationProprietary designs, methods, or processes

Has anyone pasted or uploaded company information into a public AI tool? *

An honest answer here is the most useful one. It isn't a test.

No, and we'd know if they hadProbably notProbably yesYes, we know it has happenedNot sure

Do any client, owner, GC, or partner contracts limit how you can share or process their information? *

NDAs and confidentiality clauses often cover AI tools even if they don't mention AI by name.

Yes, and we know what they allowYes, but we haven't checked them against AI useNo, none that we know ofNot sure

How do people share files with people outside the company? *

Through approved company tools with controlled linksMostly as email attachmentsWhatever works: personal Dropbox, Google Drive, WeTransferNot sure

Is anything in place to stop sensitive details, like SSNs or bank numbers, from being emailed or uploaded where they shouldn't go? *

Microsoft 365 and other platforms can warn or block automatically. Many companies own this and haven't turned it on.

Yes, it's set up and we've tested itSome basic rulesNoNot sure

Step 5 of 12

Files & Access

AI tools that work from your company files only see what the signed-in person can see. If file access is loose, AI makes it easy to find things people shouldn't.

Where do your company files live? Choose all that apply. *

SharePoint or OneDriveMicrosoft TeamsA file server in the officeGoogle DriveDropbox or BoxEgnyteProcoreOn individual computers or USB drivesNot sure

How organized are your company files? *

Clear structure. People find things quickly.Somewhat. Depends on the department.Hard to find things, with lots of duplicate versions

Who can open sensitive folders, like HR, payroll, finance, and bids? *

This is the biggest single factor in whether an AI assistant can safely search your files.

Only the people who need them, and we review accessLimited, but we've never reviewed itMost people can see most thingsNot sure

Do people share files with "anyone with the link" links? *

No, those links are turned off or restrictedSometimesYes, oftenNot sure

Is there one place that holds the current version of your templates, SOPs, and standards? *

AI answers are only as good as the documents behind them.

YesPartlyNo

Step 6 of 12

Rules & Training

Rules turn AI from a risk into a tool. These questions cover what's written down and who decides.

Do you have a written AI acceptable-use policy? *

A short written policy is what insurers and clients ask to see first.

Yes, and staff have read and signed itYes, but staff haven't signed it or been trained on itWe're working on oneNoNot sure

Is there a list of approved AI tools and what information can go into them? *

Yes, written down and shared with staffIt's understood informallyNo

Who decides which AI tools are allowed? *

A named person or teamLeadership, case by caseNo one in particular

Has your team had security or safe-AI training in the last 12 months? *

Yes, both security awareness and safe AI useSecurity awareness onlyNoNot sure

Does a person review AI output before it goes into a bid, drawing, contract, or client message? *

AI drafts are fast but can be confidently wrong. Review is the safety net.

Always. It's expected.UsuallyIt depends on the personWe don't use AI for that kind of workNot sure

Have clients asked whether you use AI with their information?

Yes, and we had a clear answerYes, and we didn't have a clear answerNot yet

Step 7 of 12

Accounts & Sign-Ins

AI can only be governed on accounts that are managed and secured. Attackers also use AI to write convincing fake emails, so these basics matter more now.

What does your company use for email? *

Microsoft 365Google WorkspaceBothSomething else (GoDaddy email, hosted Exchange, an in-office server)Not sure

Which Microsoft 365 plan are most people on?

It's on your Microsoft invoice or in the admin center. Not sure is fine.

Business BasicBusiness StandardBusiness PremiumE3 or E5A mixNot sure

Is multi-factor authentication (a code or app prompt at sign-in) required on every email account? *

Stolen passwords are one of the most common ways into business email. MFA blocks most of those attempts.

Yes, for everyone, and it's enforcedFor most peopleOnly for some people or adminsNoNot sure

Do the people who manage your email admin settings use a separate admin account, not their everyday email? *

YesNoNot sure

When someone leaves the company, how quickly is their access removed? *

The same day, using a checklistWithin about a weekWhenever someone remembersNot sure

Do people share logins, like one account for the front desk, estimating, or a software license? *

NoA few shared accountsYes, it's common

How does your team keep track of passwords? *

A company password managerSaved in the web browserSpreadsheets, notes, or memoryNot sure

Can staff get company email and files on personal phones or computers? *

No, or only through protected company appsYes, on personal phones, with no extra controlsYes, on any deviceNot sure

When a vendor, sub, or client emails new payment or wire instructions, how do you confirm them? *

AI makes fake invoices and payment-change emails much harder to spot, and voice cloning can fake a phone call.

We always call a known number before payingSometimes, for large amountsWe usually go by the emailWe don't send payments that way

Step 8 of 12

Devices & Backup

AI rules are enforced on the computers people work on. These questions cover how those computers are protected and how you'd recover.

What protects your company computers from threats? *

Security software monitored around the clock by a security teamAntivirus only, like Windows DefenderProtection on some computers, not allNothing in particularNot sure

How are Windows and software updates handled? *

Installed automatically, and someone checks they workedAutomatic, but nobody checksManually, or not reliablyNot sure

Can staff install apps and browser extensions on work computers without approval? *

Unapproved AI apps and extensions are one of the main ways company data leaks into AI tools.

No, installs need approvalSome people canYes, most people canNot sure

Is your email and cloud data (like OneDrive and SharePoint) backed up by a separate backup service? *

Microsoft and Google keep their services running, but restoring deleted or encrypted data is largely up to you.

Yes, and we've tested a restoreYes, but we've never tested itNo, we rely on Microsoft or GoogleNot sure

Are any computers or servers running Windows 10 or older, or more than five years old? *

Microsoft ended regular security updates for Windows 10 in October 2025.

No, everything is currentA fewManyNot sure

Step 9 of 12

IT Support & Software

Who looks after your systems today and the software your team relies on. We'll suggest AI uses that fit the tools you already run.

Who handles your IT today? *

An outside IT companyAn in-house IT person or teamBoth an in-house person and an outside companyA tech-savvy employee or a part-time helperNo one in particular

How well is that working?

Very wellIt's OKNot well

When does your agreement with your IT company come up for renewal?

Within 3 monthsIn 3–12 monthsMore than 12 months awayWe're month to monthNot sure

What runs on servers in your office? Choose all that apply.

We don't have servers in the officeShared filesSage 300 CRESage 100 ContractorQuickBooks DesktopOther business softwareEmail (Exchange)Our servers are already hosted in the cloudNot sure

Which software does your team rely on? Choose all that apply.

Sage 300 CRESage 100 ContractorTimberscan, Office Connector, Liberty Reports, or PrintBossQuickBooks DesktopQuickBooks OnlineProcoreBluebeam RevuAutoCADGlazier StudioPartnerPakEgnyteAdobe Acrobat or Foxit PDF EditorMicrosoft Office (Word, Excel, Outlook)

Any other software your business runs on?

Step 10 of 12

Your Team & AI

Tools only help if people use them. This shapes how we'd roll AI out and how big a plan would fit.

How does leadership feel about AI? *

We want it, with guardrailsCurious but cautiousSkepticalAgainst it for now

How does your team usually handle new software? *

Picks it up quicklyMixed. Some people take longer.Change is hard here

Is there someone who could be your internal point person for AI? *

Yes, we have someone in mindPossiblyNo

If you gave your team an approved AI tool, about how many people would use it? *

1–56–1516–3031–6060+Not sure

How often would most of them use it? *

A few times a monthA few times a weekEvery dayMany times a day

Have you set aside budget for AI tools or IT improvements this year?

YesWe'll set it after this assessmentNot yetPrefer not to say

Step 11 of 12

Insurance & Obligations

Cyber insurers are adding questions about AI at renewal. Knowing your dates and obligations helps us put the right things first.

Does the company have cyber insurance? *

YesNoNot sure

Which month does it renew?

Did your last application or renewal ask about AI use?

YesNoNot sure

Could you answer those AI questions confidently?

YesPartlyNo

Do any of these apply to your company? Choose all that apply.

Clients, GCs, or owners send us security questionnairesWe work on government or defense projectsWe handle escrow, trust, or tenant deposit fundsWe take credit card paymentsWe collect SSNs or IDs from customers, tenants, or buyersNone of theseNot sure

In the past two years, have you had a security incident, like a hacked email account, payment fraud, or ransomware? *

NoYes, a minor oneYes, a serious oneNot sure

Anything you'd like to share about what happened?

Optional. A sentence is plenty.

Step 12 of 12

Review & Send

Last step. Check your answers, add anything we should know, and send it over.

Anything else we should know?

Concerns, deadlines, or questions you want answered in your report. Please don't include passwords or account details.

How would you like us to follow up? *

By emailA phone callA video callIn person, at our office

Where should we meet you? *

The office address for an in-person meeting. We visit businesses in the Tampa Bay area.

Which times usually work for a conversation?

Weekday eveningsWeekendsWeekdays during business hours

By sending this form you agree to be contacted by email about your request. See our privacy policy.

Answers Received

Thanks. We've Got It From Here.

Your answers are with our team. Here's what happens next.

We Review Your Answers
We go through everything you told us, including the "Not sure" answers, which often point to the most useful things to check.
We Prepare Your Written Assessment
Your readiness score, the gaps to close first, and where AI can actually save your team time, in plain English.
We Walk You Through It
We'll reply by email to set up a time to go over the findings and answer your questions. What you do next is up to you.

Reference:

Read how AI governance works

Your AI Readiness Questionnaire.

Thanks. We've Got It From Here.

We Review Your Answers

We Prepare Your Written Assessment

We Walk You Through It

Your Privacy, Your Choice