Success & the Art of Developing Your Inner Coach
Storytelling advice from Akira Kurosawa

Five Essential Questions to ask Yourself

It’s graduation time around the United States, and while many speeches are forgettable, some of them stick. Dean James Ryan’s speech at the Harvard Graduate School of Education ceremony was one such speech. Dean Ryan’s central message is that developing an ability for asking good questions is key to one’s path to success and fulfillment. "I would urge you to resist the temptation to have answers at the ready and to spend more time thinking about the right questions to ask,” he says. The entire 24-min speech is here, but it is this six-minute section below that resonates most with me and many others. In this section Ryan says he believes there are five essential questions that we must regularly ask ourselves. Ryan's claim is that, if we get in the habit of asking these questions, we’ll have a great chance of being both successful and happy. And, he says, we’ll be in a better position to answer “I did” to the bonus question at the end of his list of five. (A summary of his list of five follow the video.)


(1) Wait, what?
"Wait what is actually a very effective way of asking for clarification, which is crucial to understanding,” Ryan says. "The wait, which precedes the what, is also a good reminder that it pays to slow down to make sure you truly understand.” Many of us often have an unconscious bias toward information which confirms our own views about the world. In the 21st-century where social media allows completely made up “facts” to be circulated unabated, it's more important than ever to slow down, and to stop, and to question anything which seems too good (or bad) to be true.

(2) I wonder, why/if?
"Asking 'I wonder why' is the way to remain curious about the world, and asking 'I wonder if' is the way to start thinking about how you might improve the world. As in, I wonder why our schools are so segregated, and I wonder if we could change this?” This is perhaps the most fundamental question of all. This is one of the most powerful questions an educated person—regardless of their schooling—can ask. Questions such as: Is it so (I wonder)? Is it really true? How do I know that it’s so? What would happen if__? We begin tackling the really big problems in the world—and the big problems in our personal lives—with the smallest of questions: I wonder why/if?

(3) Couldn’t we at least?
"It’s what enables you to get past disagreement to some consensus, as in 'couldn’t we at least agree that we all care about the welfare of students, even if we disagree about strategy?'” This is a way to obtain some common ground and make progress, no matter how small. Ryan says that it’s also an approach for getting unstuck or for getting started in the first place. I have found this to be a mind-hack of sorts. One of our biggest obstacles to progress in our work is procrastination. Most of us procrastinate because we focus on the enormity of the project or on it’s conclusion, a conclusion about which we are uncertain. So instead of focusing on finishing the project, simply concentrate on getting started instead. Just start it, you tell yourself, don’t worry about how it progresses or about the long road to finish it. Simply start. When you tell yourself that you’ll just get started for a bit and not worry about the size and perceived difficulties of the entire project, it’s very easy to sit down and just have a go at it. Often, we’ll surprise ourselves which just how much progress we make when our only aim was merely to "at least get started."

(4) How can I help?
 "We shouldn’t let the real pitfalls of the savior complex extinguish one of the most humane instincts there is,” says Ryan, "the instinct to lend a hand.” A yearning to help and to make a difference in the lives of others is what fundamentally drives most of us. But, says Ryan, we must remain humble and truly listen with our eyes, ears, and heart to see where we can help best. “…how we help matters as much as that we do help, and if you ask 'how' you can help, you are asking, with humility, for direction."

(5) What really matters?
"This is the question that forces you to get to the heart of issues and to the heart of your own beliefs and convictions.” This is a question that we need to ask ourselves more than only occasionally. These days, professionals and students are asked to do more (or at least are enticed to do more). It’s easy to get pulled in many directions and to attempt to do too much. I say it a lot but if everything is important to you then nothing is important to you. Life is about making hard choices. This is true for business and it is true in life. We must learn to remove that which is not essential to our answer to the question “What really matters to me?” Clarity, simplicity, and focus are crucial for staying on your own path to what really matters.

Bonus question: “And did you get what you wanted out of life, even so?”
Here Dean Ryan recalls a passage in a poem by Raymond Carver that reads: "And did you get what you wanted out of life, even so?” The “even so” tag, says Ryan, is a reminder that life even at its best is filled with pain, sorrow, and disappointments. Still, even so, are you living a fulfilling life? "My claim is that if you regularly ask: wait, what, I wonder, couldn’t we at least, how can I help, and what really matters, when it comes time to ask yourself 'And did you get what you wanted out of life, even so?' your answer will be I ‘did.'"

Full speech and transcript


Julie Kertesz

Thank you. My jewish grand-fother used to come and ask me (I was not yet 10 at the time) to ask him whatever question. He answered and if he could not "I'll look it up in my books" - No Google yet 70+ years ago.

"And did you get what you wanted out of life, even so?"
Yes, one of the most important questions, even more for me at 82.
Even so... we all experience. And make the best we could and still can is as important. As never stopping asking "And now what new thing I can do want to do, need still to do"?

Conor Neill

Wonderful questions, thank you for sharing this talk and your summary of his questions.

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