011 How do we do things we would never, ordinarily do?

Summary
Matt and I talk about lessons learned from almost a year of helping transform IT at Allstate. When it comes to scaling up agile and cloud-think the real challenges are in functions other than development, like budgeting, planning, training, hiring, and how the overall IT department is organized. We discuss those topics - esp. budgeting! - and also how to set one’s personal expectations about going on the transformation journey. Then we discuss an upcoming column on mine in The Register on the benefits of small batches thinking.
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Show-notes and Links

After a year, the question becomes “can it scale?”
How do we do: Budgeting, training, hiring, how do we organize teams
We only plan with good information, not bad information.
You need to establish an overall vision, but avoid being too specific on tactics. For example, with a claim application, we know the general product, the vertical, the line of business we have roughly an ide