“We make our world significant by the courage of our questions and by the
depth of our answers.” – Carl Sagan
“The question isn’t who is going to let me; it’s who is going to stop
me.” – Ayn Rand
As I turn 35 and think of my life so far and what’s to come, I realize how
much I’m shaped by the questions I ask. I’ve always been insatiably curious.
These are the 35 questions that have made the biggest impact on my life.
What are you pretending not to know? This was perhaps the
most powerful question I was ever asked (by my best friend @bengleib). All possibilities open up when we
stop deceiving ourselves.
Why don’t you do the things you know you should be doing?
Life isn’t about figuring out what to do. The real challenge is (not so) simply
doing the things we know we should be doing.
What are your values and are you being true to them? Write
down the 3 most important aspects of each of these areas: family, romantic
relationships, friends, work, health, sex and spirituality. These are your
values. When we don’t act congruently with what we value, symptoms of
In what ways are you being perceived, that you’re not aware of?
Perception is reality. Make sure, for better or worse, you know
what people really think of you. (TIP: Watch “How to Persuade People”)
What don’t you know, that you don’t know? It’s always the
obstacles that we don’t even see coming that are the biggest challenges in life.
Get in the habit of asking people that have been there and done it before for
Happiness / Peace of Mind:
Are your “shoulds” getting in the way of your happiness? The
desires of our ego are often in conflict with the emotions of our heart. You’ll
always have what you want, if you want what you have.
If you achieved all of your life’s goals how would you feel? How can
you feel that along the way? The discipline of delayed gratification is
one of the most powerful habits of successful individuals. But most actions we
take are meant to elicit an emotion in the now. We’re happier striving for our
goals when we let ourselves feel that which we want to feel when our outcome is
What did I learn today? Who did I love? What made me laugh?
I try and ask myself these 3 questions at the end of each day.
Regardless of anything else that happens, if you learned something new, loved a
good person and got to laugh heartily, it was a day worth having and
If you weren’t scared what would you do? Use the rocking
chair test. What would your 90-year-old self, looking back on your own life,
advise you to do in the moment?
If you were dying, would you worry about this? We so easily
lose perspective on what takes up our energy and focus. We’re all dying.
Sometimes we need to remind ourselves of this to enjoy living. (TIP: Read “The Last
Lecture” and “Tuesdays with Morrie”)
Should you be focused on today or tomorrow? Savor the
present but don’t forget your future. Life is a balance of knowing when to
enjoy the moment vs. when to plant seeds for tomorrow’s harvest.
Influence / Achievement:
Why not? What would happen if…? Don’t accept that things
just are the way they are. Question why something can’t be done. And when you
get pushback to these questions, reframe the negative answers with
possibilities. (TIP: Watch “Steve Job’s Vision of the World”)
What/Who did you make better today? The way to measure your
worth may just be to give more than you take. Asking what/who you made better
each day is a simple litmus test we can all measure ourselves by.
What do you want your life to be in 5 years? If you
don’t know where you’re going, you’ll never get there – Lewis Carroll.
Write down 5-year goals. They’re close enough to grasp for, yet far off enough
to achieve almost anything.
What can you do today to improve? Consistent, incremental
improvement is the secret to achieving the greatest of feats.
Business / Entrepreneurship:
What’s your WHY? If you have a big enough WHY you’ll always
figure out the What and the How. If you don’t have a BIG WHY, you’ll always use
the What and the How as an excuse for not doing that thing you said you were
going to do. (Watch “What’s Your Why”)
What’s the one most important thing to get done today/ this
week/month? Write this down on a Post-it note at the beginning of each
day/week, and hold yourself accountable for completing this above all other
Stuff To Do.
What questions must you consider before starting a business?
See my list by watching “The 10 Questions” or reading the document.
What’s the potential upside? What’s the effort involved? What’s the
likelihood of success? What’s the strategic value? This is the
framework I came up with 3 years ago on “How to Make the Right Business Decisions”.
Whenever there is an opportunity cost, I have my team go through this
What are we talking about? What problem are we solving? I
try to start off every meeting by putting this on the whiteboard. In group
settings we too often we find ourselves having completely different
conversations. Sometimes when answers are difficult to come by, it’s helpful to
question if we’re solving for the right problem.
Can you get it done now? If something is important or urgent
and you can get it done now, do it. (TIP: Read “Getting Things Done” from the productivity guru
What do you need to make it happen? This is one of my
favorite questions to ask as a manager. It creates ownership to make sure the
goals will be achieved. And it creates a shared responsibility to provide the
resources required (time, money, talent, etc.) to achieve those goals.
If we could wave a magic wand and do anything together, what would
that look like? I use this question all the time with potential
business partners. By removing the perceived constraints that bind us and
focusing on mutually desired outcomes, we often discover new pathways of
How would your role models act and carry themselves? Act as
if. Act as if you have the experience, wisdom and swagger of your role model,
and you’ll often find even the most unchartered of situations more
When can we meet? We’re often this one question away from
engaging with someone who can open up limitless avenues of possibility.
The most important aspect of business is still to always get
it done in person. (TIP: Read “Business Development Advice”)
Will you be my mentor? It’s one question that, when asked in
earnest, almost nobody will turn down. Reach out to a person in a position and
industry you admire, and ask them if you can take them to coffee and hear about
how they got there.
What will I only know about you after we’ve worked together for a
year? This interview question comes from the awesome Wendy Lea (CEO, GetSatisfaction). This may be the best interview
question I’ve ever heard. (Watch “Fireside Chat with Wendy Lea” and check out my
previous 8 Awesome Interview Questions)
What would get you interested in our product/service?
Selling is the art of asking good questions, listening, and matching
your value to people’s needs. Sales is very easy when others explain what they
want and need from you. (Watch “The 5 Step Sales Process”)
What else? Such a simple but powerful question with so may
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