Your Digital Status

Section 1: Goals

1. Which business goal do you expect technology to unlock in the next 6–12 months?

2. How will you measure success (revenue, cost, speed, customer retention, etc.)?

Section 2: Current Pain

3. Which day‑to‑day process feels slow or error‑prone?

4. Where do customers or staff complain most about delays or work‑arounds?

Section 3: Systems & Architecture

5. What core systems (ERP, CRM, bespoke apps) run your operations today?

6. How old are they, and when were they last upgraded or patched?

Section 4: Data

7. Where is your critical data stored, and who owns its quality?

8. Can you access a single, reliable view of customers or inventory right now?

Section 5: Cloud & Infrastructure

9. Which systems are already in the cloud, and why were those chosen?

10. What stops you from moving more (cost, compliance, skills, legacy code)?

Section 6: Security & Compliance

11. What are the top two security risks you worry about this year?

Section 7: AI & Analytics Readiness

12. Do you have labeled, trustworthy data sets big enough for machine‑learning or AI use?

YesNoNot sure

13. Which decisions today rely on gut feel that you’d like to back with data?

Section 8: People & Skills

14. Which tech skills are missing in your team?

15. How do you keep staff up to date on new tools and practices?

Section 9: Budget & ROI

16. What is your yearly technology budget, and how flexible is it?

Section 10: Change Management

17. How does your organization handle change—formal training plans or “figure it out”?

18. Have past tech projects failed? If so, what was the main cause?

Section 11: Vendor & Partner Landscape

19. Which external vendors do you rely on most, and how satisfied are you with them?

20. Are there contracts expiring that present an opportunity to rethink tools?

Section 12: Customer Experience

21. Where do customers interact with you digitally, and what frustrates them?

22. What is your mobile versus desktop traffic split?

Section 13: Future Vision

23. In three years, what must be true for you to call your tech investment a win?

24. Which disruptive trend (AI copilots, edge computing, zero‑trust) worries or excites you most?