Questions to Help You Decide, Create, Connect & Lead

I place very high value on the ability to ask good questions, so when Scott Mann mentioned The Book of Beautiful Questions, it was a must read.  Author Warren Berger sums it up: “When we are confronted with almost any demanding situation, in work or in life, simply taking the time and effort to ask questions can help guide us to better decisions and a more productive course of action.”  He recommends we take our lessons from the expert questioners – 4-year-olds.


What am I really trying to decide here?

Why do I believe what I believe?

What would I like to be true?

What if my beliefs or assumptions on this issue are just plain wrong?

How can I see this with fresh eyes?

How do I open up more options?

What is the counterintuitive option?

If the current options were unavailable, what would I do?

If my friend had to make this decision, what advice would I give?

How do we generate more ideas?

What am I missing?

What if cost were not an issue?

If I am saying yes to this, what am I saying no to?

What struggle or sacrifice are you willing to tolerate?

What matters most?


What is happening that doesn’t make sense?

What’s ripe for reinvention?

What might I notice if I were encountering this for the first time?

What is the upside if I do solve the problem?

Why hasn’t someone solved this already?

When is my creative prime time?

Who would look at this problem from a different angle?

How would this look in the future – ten or twenty years from now?

Where is my petri dish?

Connect with Others

Am I genuinely interested in the other person?

Am I prepared to truly listen?

What was the best part of your weekend?

What’s the strangest/most interesting thing about where you grew up?

What’s the best thing that happened to you today?

What problem do you wish you could solve?

What would constitute a perfect day for you?

What was the most difficult problem you had today?

What have you always wanted to try?

What do you struggle with on a day-to-day basis?

Stronger Leadership

Do I have the confidence to be humble?

Am I courageous enough to abandon the past?

Do I surround myself with inspiring, sometimes even odd, big thinkers?

What could I have done differently?

When have we, as an organization, been at our best?

If we disappeared tomorrow, who would miss us?

What do we do that other organizations can’t or won’t?

What if we stopped celebrating being busy as a measure of importance?

What do I want to go big on?

What should we stop doing?

What stupid rule would you most like to kill?

What is one thing I could do that would make everything else easier or unnecessary?

How could we become the company that would put us out of business?

What if we created the ideal workplace for our employees – what might their day look like?

What is the implication of this decision 10 minutes, 10 months and 10 years from now?

What is going well?  What are we doing right?

What if we had the capability to do what we do now much faster and more efficiently?

What’s the biggest challenge you’re facing?

Is it clear what we’re doing and why?

What culture do I want, and what actions and conditions are likely to produce such a culture?

Whose voice might I have missed hearing – and how might I amplify this voice?

Family Purpose questions

What does it mean to be part of this family?

What are our family values?

Of all the family members you know or have heard stories bout, who do you think lived the most interesting life?  Why?

What are some traditions that have been passed down through our family?

What difficulties did the family have to bounce back from?

What are some of the greatest accomplishments of family members through the years?

Final Big, Beautiful Questions

What is your sentence (if you had to summarize your life in one sentence, what would it be)?

What is your one ‘big, beautiful question’?

– One you devise for yourself and pursue the answer to.  It should be bold and ambitious and actionable.  Typically, these will start with “How might I” or How might we.” Put an aggressive goal in question form – your big, beautiful question – and then write it down, tell your friends/team, share it any way you can.  Then start the journey toward the answer and stay with it.