In The Answer to How is Yes, Peter Block identifies six How? questions that he says are “always reasonable, but when asked too soon and taken too literally may actually postpone the future and keep us encased in our present way of thinking.”

1. How do you do it?

“When I ask this question, I take the position that others know, I don’t. The question carries the belief that what I want is right around the corner; all that prevents me from turning that corner is that I lack information or methodology.”

“The rush to a How? answer runs the risk of skipping the profound question: Is this worth doing?”

2. How long will it take?

“The question How long? drives us to actions that oversimplify the world.”

“The most important effect of the How long? question is that it drives us to answers that meet the criteria of speed.”

3. How much does it cost?

“The question of cost is first cousin to the question of time. Instead of instant gratification, we seek cheap grace.”

“The most common rationalization for doing things we do not believe in is that what we really desire either takes too long or costs too much.”

4. How do you get those people to change?

“This is the power question. . . ‘Those people’ need to change for the good of the organization, they need to change for their own good, for the good of the family, for the sake of the next generation, for the sake of society.”

“We may say we want others to change for good reasons. But no matter how we pose the question, it is always a wish to control others.”

“The behavior we describe in others may be an accurate description, but that is not the point. The point is, our focus on “those people” is a defense against our own responsibility.”

“When we honestly ask ourselves about our role in the creation of a situation that frustrates us, and set aside asking about their role, then the world changes around us.”

5. How do we measure it?

“This question makes the statement ‘If you cannot measure it, it does not exist.’”

“Many thing that matter the most defy measurement. When we enter the realm of human nature and human actions, we are on shaky ground when we require measurable results as a condition of action.”

Isn’t this one of the difficulties in church leadership? We have trouble figuring out what we can legitimately measure. How do you measure the fruit of the spirit? Needing to measure something, we start focusing on things we can count. Only the things we can count aren’t necessarily the things that really count.

6. How have other people done it successfully?

“‘Where else has this worked?’ is a reasonable question, within limits. It is dangerous when it becomes an unspoken statement: If this has not worked well elsewhere, perhaps we should not do it. The wish to attempt only what has been proven creates a life of imitation. We may declare we want to be leaders, but we want to be leaders without taking the risk of invention.”

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So how many times have you been in meetings where these questions have dominated? What was the result? My experience is that we use these questions to talk ourselves out of inspiring ideas that require great risk and could actually make a difference.

In a future post, we’ll look at a different set of questions that can take the conversation in a completely different direction.

In The Answer to How is Yes, Peter Block writes that “transformation comes more from pursuing profound questions than seeking practical answers.”

He argues that our culture is too obsessed with how? questions.

“My premise is that this culture, and we as members of it, have yielded too easily to what is doable and practical and popular. In the process we’ve sacrificed the pursuit of what is in our hearts. We find ourselves giving into our doubts, and settling for what we know how to do, or can soon learn how to do, instead of pursuing what most matters to us and living with the adventure and anxiety that this requires.”

“This has led me to the belief that the questions about How? are more interesting than any answer to them might be. They stand for some deeper concern. So in this book, the starting point is to question the questions.”

“If we were really committed to the pursuit of what matters, we might well be served to hold a moratorium on the question How?”

“If we could agree that for six months we would not ask How? something in our lives, our institutions, and our culture might shift for the better. It would force us to engage in conversations about why we do what we do, as individuals and institutions. It would refocus our attention on deciding what is the right question, rather than what is the right answer. It would also force us to act as if we already knew how–we just have to figure out what is worth doing.”

“In any of its hundreds of variations when we ask How? we are really making a statement: What we lack is the right tool. The right methodology. We are mechanics who cannot find the right wrench. The question How? not only expresses doubt about whether we know enough and are enough; it also affirms the belief that what works is the defining question, a major source of our identity.”

We’ll look at some of the How? questions that Block says we ask too soon and too often in a future post.