Organizational structure: if you're an organization that has pretty much wholly outsourced your IT – particularly if your contracts-style is base-year + Option-year 1 + ... + Option-year N chances are, you've been structuring your contracts to be focused on end-of-project-year deliverables. Worse, each option-year may be bid out to a different consulting company. This means that, not only are your contractors focused on delivery-boundaries (rather than continuous mid-term deliverables), the teams on either side of an option-year boundary may be wholly different from each other.
base-year + Option-year 1 + ... + Option-year N
The above is typical of government orgs with their "hard" FY-to-FY funding-models.
Yes, organizational structures are the biggest challenges. Also, I heard the DevOps principles are hard to apply in financial and health industries?
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