Pitfalls
The big challenge here is that not every organization has rules that can be perfectly replaced with a technology change. Although my previous story was based on an actual occurrence, I haven’t seen too many of them. These are rare but worth it when they come up.
The other challenge is creating a group of like-minded people with enough power to overturn the rules. Typically the further away the policy enforcers are from your team, the harder the change is to make.
If rules are self-imposed by the development group, then it’s a snap. If rules are dictated by human resources, good luck. In between there is a continuum of difficulty levels that you’ll have to judge and counter to be effective.
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