Asking Better Questions

[Excerpt from Hitchhiker’s Guide to the Galaxy]

“O Deep Thought computer,” he said, “the task we have designed you to perform is this. We want you to tell us….” he paused, “The Answer.”
“The Answer?” said Deep Thought. “The Answer to what?”
“Life!” urged Fook.
“The Universe!” said Lunkwill.
“Everything!” they said in chorus.
Deep Thought paused for a moment’s reflection.
“Tricky,” he said finally.
“But can you do it?”
Again, a significant pause.
“Yes,” said Deep Thought, “I can do it.”

[7.5 million years passes]

“You’re really not going to like it,” observed Deep Thought.
“Tell us!”
“All right,” said Deep Thought. “The Answer to the Great Question…”
“Yes..!”
“Of Life, the Universe and Everything…” said Deep Thought.
“Yes…!”
“Is…” said Deep Thought, and paused.
“Yes…!”
“Is…”
“Yes…!!!…?”
“Forty-two,” said Deep Thought, with infinite majesty and calm.”

Moral of the story being – if you don’t ask the right question, you will never understand the answer!

Lately, I have been doing a series called “career chats” with individuals both within – and outside of – Lyft that have been successful in their careers.  Although it is an AMA (ask me anything) style chat, the core question almost always seems to be, how do I get to where you are? Or to use the above analogy, what is the answer to life, the universe… everything!?

From self-help books to TED talks, we are in constant pursuit for the answer but rarely stop to ask ourselves what our question is. And the reality is that an answer given to a bad question rarely is the answer we want. Deep thought (the most highly intelligent computer in the book designed to give the meaning to life) gives the answer “Forty-two” to the question almost reluctantly… “you really aren’t going to like it”.

How do we stop looking for the answer and get to better questions?

A few thoughts (note, this advice is focused on career questions):

• Focus on self – Before coming to the conversation, ask yourself what do I really want? The quick answer to this might be – more money, a promotion, to be recognized for my work, more flexibility in my hours or to learn new things. All of those are valid answers (and I think everyone would say yes, I want all of those things!) If you reflect more deeply, you might really care about one of those, and using a technique like the 5 whys might bring you to the realization that your job is really a way to focus on and fund your other passions. Focusing on self and investing time in understanding your motivations, passions and desires helps you ask better questions and in doing so, helps others understand how to help you.
• Focus on others – generally the people answering the question do not know enough about your specific situation to give you the answer. Even if their career journey looks identical to yours, their answer to a specific question about your journey might sound like “42”! Great questions acknowledge and understand the difference between my journey and yours and seek unique perspectives on their journey. Great questions focus on the why versus the what. Why did they take that step in their journey and not… what should I do at this point in my career?
• Ask what you should be asking – when we focus purely on what we want to know, we miss on the general wisdom that those further along in their journeys bring. Some of my favorite questions here are “what advice would you give a younger you” or Guy Raz’s “Does your success come from skill or luck?” or even a simple “What question hasn’t been asked that you believe should?”

Let’s not stop searching for the answer, let’s just make sure we understand our question first.