Ask Five Good Questions

imgresIn May of 2016 James Ryan, Dean of the Harvard Graduate School of Education, gave a commencement speech  about asking good questions.  While his words were directed at future teachers and leaders in education, they are invaluable to a much broader audience.
His speech includes a reference to Raymond Carver’s poem “Late Fragment.” In just thirty words, Carver beautifully articulates the simple desires that so many of us want at the end of our lives: “to call myself beloved” and “to feel myself beloved on the earth.”

Seems simple.

And it is.

The challenge is how to get there.

Late Fragment
by Raymond Carver
And did you get what
you wanted from this life, even so?
I did.
And what did you want?
To call myself beloved, to feel myself
beloved on the earth.

I’d like to suggest you get there  — there being “successful and happy” and being able to say “I did”– by following Dean Ryan’s advice:

Ask five good questions:

  1. Wait, what?
  2. I wonder…?
  3. Couldn’t we at least…?
  4. How can I help?
  5. What truly matters?

1.   Wait, what?

Ryan explains it clearly:

“Wait what” is actually a very
effective way of asking for clarification,
which is crucial to understanding.

When do you need clarification? More often than you think. How about before you do any of these actions:

  • draw your conclusions
  • make a decision
  • accept a job
  • judge others
  • agree to a meeting
  • accept an assignment

As Ryan says, “slow down to make sure you truly understand.” Not only will your purpose be clearer, but you won’t waste time going to an unnecessary meeting, chasing a job you don’t want, or trying to complete an assignment that you don’t fully understand. This applies to the 20-something intern and the 50-something executive.  Wait, what? Pause, get clarification, then act.

2.  I wonder… 

The wonder question is about curiosity AND making the world a better place.

Curious:  I wonder why…
Make the world better:   I wonder if…

Ryan’s example is “I wonder why students often seem bored in school, and I wonder if we could make their classes more engaging?”

In business and in education, it’s not always about the whole world, but about your immediate world. And in business the questions might be:  “I wonder why the employees in Joe’s division always arrive late” and “I wonder if they would change their behavior if they felt more relevant and appreciated.” Or, “I wonder why I didn’t get that job” and “I wonder if I could improve my interview techniques.” Wondering opens up space, creates hope, and encourages optimism, rather than focusing on criticism and defense.

3.  Couldn’t we are least…

If you reach an impasse, try to find common ground as a foundation to move forward.

Ryan’s example is “couldn’t we at least agree that we all care about the welfare of students, even if we disagree about strategy?”   In business it might be  “couldn’t we all agree that employee attrition is a problem.” This works equally well for quality control, lost accounts, lack of diversity,  and an unsustainable work pace.   Whatever challenge you and your team or opponent is faced with, starting from common ground might just be what you need to get moving.

4.  How can I help?

This is not a typical C-suite question bu it could be an invaluable one.

What if your CEO walked into a working meeting and rather than trying to take charge, said “How can I help?”  Or what if you’re the junior person on a team and unsure of your role. You could re-phrase this as “what can I do to be most effective”  It works when you are junior — but I think it works even better for executives, particularly in the execution phase, as opposed to the strategic phase.  If you trust your plan and your team, the team can direct you to where you are the most valuable and effective.

5. What truly matters?

Ask yourself what truly matters and let that be your guide.  What truly matters to you? What matters about this project, this job, this neighborhood, this work, this life? And pursue what truly matters.


  1. “Wait, what” is at the root of all understanding.
  2. “I wonder” is at the heart of all curiosity.
  3. “Couldn’t we at least” is the beginning of all progress.
  4. “How can I help” is at the base of all good relationships.
  5. And “what really matters” gets you to the heart of life.
The list is worth repeating
until it is committed to memory, and then
until asking these questions becomes a habit.  

The video of Ryan’s commencement speech is only 25 minutes — and well worth watching.  If you want to skip the school-centric reflections for the new graduates, then you can start around minute 9 and then it will only be 16 minutes long.  A worthy 16 minutes if it helps you ask better questions and focus on what truly matters.

P.S.  Dean Ryan’s speech has over 8MM views on Harvard’s facebook post and he has now published a book, “Wait, What?” about his questions.

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