How does your organization avoid to fall into the alignment trap? Or what should it do to avoid the trap?

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Is there a clear alignment between your organization’s business strategy and investments in technology? How does your organization avoid to fall into the alignment trap? Or what should it do to avoid the trap?
In the Octo case, which inhibitors played a critical role in the wobbly alignment process? Can  an alignment process actually reach some kind of steady state?
What mistakes did the CIO make in this whole process? What should the CIO do in the future to avoid similar mistakes?

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