Questions to Ask the Customer:

  1. Describe the scale of your computing environment?
  2. What’s the break-down by OS?
  3. What’s the break-down by form factor?
  4. How many user accounts?
  5. What’s the user-to-device ratio?
  6. How many roam between locations?
  7. How many are used outside the perimeter by default?
  8. How are you licensed for desktops, mobile and servers?
  9. How big is your IT staff?
  10. How big is your IT budget?
  11. How is your staff organized for CM, AD, DB, InfoSec, and Applications?
  12. Is it documented?
  13. Do you have an existing management solution in place?
  14. Do you use it?
  15. How ‘up to date’ are your workstations on patches?
  16. How about your servers?
  17. Describe your servers by physical, virtual and clustering.
  18. Describe your IP addressing scheme.
  19. Do you segregate server and workstation address blocks?
  20. Is it documented?
  21. Describe your AD environment, forests, domains, trusts, and so on.
  22. Describe your Group Policy environment.
  23. Is it documented?
  24. Where’s your restroom?
  25. Where’s your snack machine?
  26. Do you use Azure or AWS?
  27. Do you have Express Routes or Direct Connect services?
  28. How many sites and site-to-site connections?
  29. Describe your storage environment(s).
  30. Where’s the nearest Starbucks?
  31. How do you handle end-user device provisioning?
  32. Is it performed in a centralized or distributed manner?
  33. How many platform configurations do you deploy and support?
  34. Are they documented?
  35. Where’s the nearest bar?
  36. Describe your antivirus protection environment?
  37. Who manages it?
  38. Do they have a chainsaw they’d like to sell?
  39. How much did you pay for that smartwatch?
  40. Where were we?

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