1.1

What is your primary AI objective?

What are you hoping AI will achieve? e.g. reduce manual work, speed up a process, improve customer response times, unlock insight from data.

1.2

What is the single most important business problem you want this to solve?

If we could only fix one thing, what should it be?

1.3

Where do you expect AI to be in your business in 2–3 years?

Paint the bigger picture. Is this a one-off automation, or the first step in a broader shift?

1.4

Have you tried any AI tools already?

e.g. ChatGPT, Copilot, an internal experiment, another vendor. What worked, what didn't?

2.1

What software do you use to run the business?

List all of it: accounting, CRM, project management, email, industry-specific tools, etc.

2.2

Do these systems currently talk to each other?

Are any integrated or automated today? Or is data manually re-entered between them?

3.1

Where is your data stored outside of software?

Select all that apply.

3.2

How is your data structured?

Organised and consistent (clean spreadsheets, a database), or scattered and inconsistent? Be honest, messy is normal.

3.3

Does any of your data need special handling?

e.g. customer personal information, financial records, health data, contracts, regulated or confidential data. Any privacy or compliance obligations?

4.1

Describe one task you want AI to automate or assist with.

4.2

How does it happen today, step by step?

Walk us through it as if explaining to a new staff member. Include who does each step.

4.3

What triggers this task, and how often does it happen?

e.g. every time an email arrives, daily, 50 times a week, end of month.

4.4

What is the output or end result?

What gets produced? e.g. a report, an email reply, an updated record, a document, a decision.

4.5

Who does it now, and how long does it take?

4.6

What does "good" look like, and what's the cost of getting it wrong?

What level of accuracy is acceptable, and what happens when this task is done incorrectly today?

4.7

What time savings or cost reduction do you expect?

A rough estimate, e.g. hours saved per week, headcount freed up, faster turnaround, fewer errors.

5.1

How will you measure whether this is a success?

The specific metric or outcome. Not just "it saves time," but the number or result you'd point to.

5.2

Who are the decision-makers and the project sponsor?

Who signs off on budget and direction, and who will be our main day-to-day contact?

5.3

Who can grant access to your systems and data?

Is there an internal IT person, an external provider, or any security approval process we'll need to work through?

5.4

What is your biggest concern about adopting AI?

e.g. accuracy, security, staff adoption, cost, loss of control. Naming it helps us address it.

6.1

When do you want a solution rolled out?

6.2

What's driving that timeline?

e.g. a busy season, board or leadership pressure, a competitor, a contract renewal.

6.3

Do you have an expected or preferred budget?

A range is fine. This helps us recommend the right approach for your situation.

6.4

Anything else we should know?

Context, constraints, ambitions, past experiences. Anything that helps us understand your business better.