Strategy and leadership : What are your pain points?

Continuing the discussions from Who are your leadership role models?:

As mentioned in the topic above, next month our theme is going to be strategy and leadership. This time I’m interested to hear what your challenges or pain points are. How is strategy developed and handled within your organisation? Do you work cohesively with your leadership team? What parts are hard.

I’ve noted @gillian_halba’s related [challenge](and UX strategy - What is it? What’s in one?:).