Lessons from a Botched Upgrade

[frommagio]

Now that 2+2 is operational again, I thought I'd post a few technology 101 thoughts. I'm only scratching the surface here; these are just the ones that occur to me quickly as I type them in. Believe me, I'm probably going to miss 25 rookie mistakes in this quick list.

There are lessons to be learned, from a business and systems I/T perspective:
- Choose your technical staff wisely.
-- You know your business, techies know technology.
-- Many techies will be able to understand your business.
-- It's your job to find one.
-- Remember that your techie works for you.
- Consider your reasons for upgrading.
-- What are you trying to accomplish? What are you risking?
-- What are the drawbacks to upgrading? The benefits?
-- What if you decided just to stand still? Any problems?
-- Is this for business reasons, or for your techie?
-- If it's your techie, does he understand your business?
- Plan your upgrade.
- Test your upgrade first
-- Your customers are not a testbed.
-- Use a separate staging area.
-- Use artificial load generation to simulate real life.
-- Be sure that the new features are working as you hope.
-- Remember to check that the basic stuff still works.
-- Make a testbed beta available to some helpful customers.
-- Review the planned benefits, every point. All proven?
-- Review the risks, every point. Satisfied?
-- If your techie didn't do all of this, you screwed up; bad hire, learn the lesson.
- If things look good, announce your planned upgrade
-- Give plenty of warning to your customers
-- Give yourself plenty of time to back out
-- Remember that the software works for you, not vice-versa
- Finish your testing
-- Don't hurry.
-- Don't be afraid to back out; believe your own eyes.
-- Accept a schedule slip if it's too early to decide.
-- Remember that you are in charge.
- Go for it
-- After all your worries are satisfied, pull the trigger.