I'm slowly working through Peter Block's The Answer to How is Yes. It is one of the very best things I've read, ever.

Block illuminates the way in which real change is stifled by "how" questions. Here's how Block puts it:

Despite its rhetoric, the culture does not value independent action. The culture wants to ask the family of How? questions: What does it cost? How long does it take? Where else has this worked? And we may have no good answers to these questions. When we say Yes instead, we acknowledge that acting on what we choose costs us something, which is what gives it value. If there were no price in saying Yes, to acting in the face of our doubts and meagre methodology, then the choice we make would have no meaning.

Here's another quote that is right on the money

Also, remember that the question of "How do you do it?" is more often an indirect expression of our doubts than real curiosity. So let the doubts be stated directly and let them be owned by the doubter as an internal struggle in their thinking rather than detached observation of the external world.

And this thought rang loud bells for me:

When we do talk about money, or a budget, is is usually other people's money we will be spending. If we want to raise the stakes so that the decision is of some consequence, better to make it a personal question.

I have painful memories of a hugely expensive branding campaign run by a guy who prided himself on his budgeting prowess. It was a complete failure, though never has £30 million been wasted with such efficiency. His focus was entirely on book-keeping, and he put not a whit of his personal credibility on the line for getting a project that actually meant something.