The Book of Beautiful Questions: The Powerful Questions That Will Help You Decide, Create, Connect, and Lead

by Warren Berger

Almost every bureaucratic process in an organization should be subject to the fundamental “Why?”: Why does this rule (or this process) exist in the first place? Having considered why it was first implemented, the necessary follow-up question is: If it made sense once, does it still make sense now?

What stupid rule would you most like to kill?37 Provide

TO SHARPEN YOUR LEADERSHIP FOCUS, ASK THESE QUESTIONS What is the one thing I can do that would make everything else easier or unnecessary?38 Ask this “focusing” question at the start of any new challenge or project. (Gary Keller) What should we stop doing? Practice “systematic abandonment.” (Peter Drucker) What do I want to go big on? Ask this instead of “What am I giving up?” (Greg McKeown) Which stupid rule should we kill? Share this question with employees to see what they choose. (Lisa Bodell) At this moment, what is the highest, best use of my time? Use the “HBU” question to maximize personal productivity. (Angie Morgan)

RELEASE YOUR “INNER STEVE JOBS” BY ASKING “VISIONARY” QUESTIONS How can we become the company that would put us out of business? Start by envisioning a threat that doesn’t exist (yet). How can we brace ourselves for the third wave? It’s not the wave you’re on now or the one you can see breaking; it’s the big one yet to break. If an oracle could tell us about our business five years from now, what would we ask? Think of the most critical questions; then go to work on them (because you’re the oracle). What would the seventh generation think about what we’re doing? Take a lesson from the Iroquois about long-term planning. How might I make tomorrow visible? Inspire people by giving them a glimpse of a better future. What is our “vision question”? Forget the vision statement. Pursue the future with an open-ended query.

He wandered the building and at each stop, he inquired about what was going well, what were the biggest challenges that person was facing, and eventually culminating with the clincher: How can I help?

WHEN DOING “AMBULATORY INQUIRY,” A LEADER SHOULD NOT ASK … How’s it going? This is a rote question and elicits rote responses. Why did you ___? When you ask “why?” questions directly of employees, it shifts them into “justify” mode. Who screwed up here? Rather than focusing on a scapegoat, inquire about how best to address the issue and move forward. Haven’t we tried this already? Often uttered wearily by “Been there, done that” leaders. Say it enough times, and people will stop offering ideas altogether. AND SHOULD ASK … What’s the biggest challenge you’re facing? You can make the “challenge” question more specific (“on this project”) or more general (“in your job”). Are you making progress? If employees feel “stuck,” frustration sets in. Help me understand what led to … Instead of asking “Why?” about a problem, start the question this way—it’s wordier, but less accusatory. Is it clear what we’re doing and why? Ask employees this question with regard to company goals, directives, policy changes, and the vision for the future. How can I help? Per Doug Conant, the “ultimate leadership question.” But only ask it if you mean it.

If you observe a chronic problem of an employee being unable to make progress or meet expectations, don’t assume the worst. Instead, consultant John Barrett suggests you ask yourself the “Can’t, Won’t, Don’t Question” about this employee’s failure to perform: Is it because they can’t do it, they won’t do it, or they don’t know how to do it?56 If it’s the last one, that’s not the employee’s fault—it’s your responsibility to make available the needed instruction or training.

TO ENCOURAGE A CULTURE OF INQUIRY, ASK THESE FOUR QUESTIONS How can we make it safe to question? Institute a strict “no judging” rule; all questions welcome, the more the merrier. How might we make questioning rewarding? Celebrate productive questions by verbal recognition. To go further, offer bonuses and other tangible incentives. How might we make questioning productive? Train people in how to question in ways that produce results. How can we make a culture of inquiry stick? Make questioning a central part of meetings and other regular activities.

amorebeautifulquestion.com/Q-cards

The three types of questions do three different inquiry jobs: “Why?” questions help us to understand a problem; “What if?” questions help us imagine possible alternatives; “How?” questions, which tend to be more practical and action-oriented, lead us toward a solution.

What’s going on? (Tell me about the challenge you’re facing.) What have you tried already? If you could try anything to solve this, what would you try? And what else? (Repeat this question several times, as needed, to surface additional ideas.) Which of these options interests you most? What might stand in the way of this idea, and what could be done about that? What is one step you could take to begin acting on this, right away?