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- Hello everyone.
And welcome to Boss Talks
a series featuring candid career advice
from some of the best in the business.
Today's episode is all about making moves.
And our careers are made up
of all the small decisions
we make every single day.
Whether it's where we wanna work,
what role we wanna take on
or how we address
something with our manager.
Every small decision matters.
And it can be hard to know
if you're making the right one.
The good news is most of these decisions
won't make or break your career.
It's called a journey for a reason
and the experiences along
the way are often greater
than the destination itself.
So don't be afraid to just go for it.
To help me navigate this topic,
I've invited someone who has
made some serious boss moves
in their career.
Sukhinder Singh Cassidy
has helped build some of
the best known companies
including Google, Amazon, StubHub, and more.
She's also the author
of "Choose Possibility"
and the founder and
chairman of The Board List.
Sukhinder welcome to Boss Talks.
- Well, I'm so happy to be here Ebony.
Thanks for having me.
- The way you've just
navigated your career
is like goals for many of us.
So we're here to learn from you.
So I wanna just jump
right into today's topic
and ask what are some of the
most memorable experiences
and moves you've made in your career?
Good, bad or indifferent
because they can all be really
great learning experiences.
- Absolutely.
And I think one of the things
that's probably most worth appreciating is
not every great move looks
great at the moment you make it.
And sometimes we go
through multiple moves
to get the reward we want.
And so if you measure it on day one,
they may not all look great.
But when we hindsight, you know
what those moves brought us
we often find it's
something pretty magical.
So probably one of my earliest
and most memorable moves
was the move to Silicon Valley.
I was living in London at the time
and working for BskyB Media Company.
And all of my roommates,
I was in my mid twenties
had actually moved back to the states
to go to business school.
But two of them were California girls.
And so I visited one at
Stanford Business School.
And let me just say, I fell
in love with the weather.
I fell in love with the esprit de corps
around entrepreneurship
and I really wanted be an entrepreneur
but I didn't know how.
And so I upped and moved to California.
You know, I wasn't really thinking
about what was happening
in Silicon Valley at the time
other than I wanted be an entrepreneur.
But unbeknownst to me,
obviously 1997 was the start
of another, you know, really major
let's say surge in internet usage,
mainstream internet usage.
And it turns out that moving
to Silicon Valley at that time
you have lots of opportunities to succeed
and quite frankly a lot
of opportunities to fail
and it'll still turn out okay.
So that's probably one
of the most memorable.
- So you've written a lot about
the myth of the single choice.
Which is the idea that one decision
can make or break our career.
And I think you and I
are both living proof
that that's not true.
So what's a more constructive way to think
about decision making.
- Sure.
So first of all, I think
in the book, I read a lot
about what I call this
myth of the single choice.
We often think that,
you know, a single choice
will sort of lead us to
glory or abject failure.
And of course, like popular
press kind of creates myths
around the big risk
that people take in their careers, right?
So in hindsight, everything boils down
to that one big move that somebody made.
When if you turned it inside out
you'd find that between any major reward.
And I can guarantee
whether you're Jeff Bezos
whether you're Elon Musk,
whether you're Sukhinder
whether you're Ebony
between us
and any major reward is not one move.
It's often, you know,
one choice that leads
to another choice that
leads to another choice.
It's probably a hundred
to a thousand choices
you make in order to optimize, right?
Every move towards this ultimate reward
that you once imagined.
And so I will say to people, first of all
the most constructive
way to think about it is
maybe stop subscribing to
the myth of the single choice
and recognize that between you
and what you're ultimately
seeking is that big reward
is probably your a hundred
or a thousand chances
to make another move.
Because all of those linked
together to get the reward.
And so stop over
weighting the initial choice.
And maybe the most important thing to do
is just to get into motion
with, you know, a smart choice
but then realize you have many, many
many more moves to make.
- I love that.
Get into motion.
And as you were talking
what I thought was these micro moves,
you just have these like the series
of moves that you said.
Could be one to a thousand, you know
moves that we make that ultimately lead us
to where we wanna be.
And then we're making moves in there.
We're always in motion.
Hopefully we're growing in learning
and we're always in motion.
- You got, and by the
way, you hit one other thing
like everybody presumes,
it's one mighty move, right?
You and I both know you can move, you know
you can move 360 degrees all at once,
or you can move a degree at a time
and you'll still, you know
have pivoted 360 when's
when all is said and done.
And so I think we often
think that every move is
of a big size.
And I think that moves of
micro sizes, medium sizes
large sizes, right?
And you're moving in
like their combination
steps is sort of my point
- I love that.
And you know, so much
of navigating our own career
is rooted in this risk taking.
And for some people, a small
micro move might be as big
as a huge leap for someone.
And I know it doesn't
come easy to everyone.
So tell us some of your tips for building
that risk taking muscle.
So we can get a little bit
more comfortable doing that.
- Well, first of all, I think
we tend to boil risk taking
to like, what's the
ambition I want to achieve.
And what I say to people is
often there are four reasons
people take risks.
Number one, to achieve some ambition.
Number two, to discover.
So risk taking for discovery
is really underutilized.
And we'll talk about that.
Number three is risk
taking for learning, right?
You and I might say, hey,
somebody offered us career move.
That looks lateral, but you
get to learn a whole new skill.
And so, you know, in my career,
I've certainly taken a lot of those moves,
which don't at obvious, you know
at first blush seem the obvious move.
And then the last reason
we take risk is to avoid harm.
I mean, think of all the
risk taking that happened
in COVID when people
were literally like, wow.
My business cannot go bankrupt.
What am I going to do?
And people learn their own agility
and risk taking maneuvers
to avoid serious harm.
So there's these four reasons.
But if you think about the
three of the four for upside,
right, learning, discovery ambition.
So I would say to people find
a reason to take a risk today.
And that could be as simple
as something's bothering you at work.
And you stay silent about it.
It could be as simple as
you need more support
at home yet you don't
raise the conversation
with your boss or your partner.
It could be, you're thinking
about a career move
but you think it's one mighty move.
And I'm like, well
what's the risk taking you
could do today for discovery?
Like, what's the thing you're imagining?
What's the smallest move
you could make today
to learn something new
and discover what's possible?
These are all micro
risks you could take today.
And again, we tend to
wait and think like, oh
we're gonna pile this
all up into one big move
we'll make one day.
And I'm like, but what if I told you
you could find a reason
to take risk today
under any of those fears.
What little risk would you take today?
- I'm sure everyone out here wants you to
be their career coach
because already it's just
already in these few questions.
- I can just give my own advice trust me.
- Oh, it's awesome.
And I really just admire,
I think that the theme
that I'm getting so far,
that through line is just get in motion,
do something, right?
Like just be an action.
- Yeah.
You'll start to make
your choices like DNA.
Right.
And as those choices link,
you're either gonna come
to a small outcome, a bigger
outcome, a bigger outcome.
Some of those outcomes,
maybe failing outcomes
but it kind of doesn't matter.
Right...
- [Sarah] It's doesn't matter.
- It's...
- [Ebony] Yeah, you're learning.
So what techniques do you have
for just pushing past that fear to focus
on the opportunity itself?
- Yeah.
You know, you're hitting the biggest risk
of course.
I think the irony of risk taking
is there arguably two big risks
in my mind that people fail to estimate.
One is the risk of staying still.
I.e literally doing nothing
and data would tell us
that one of the best stats I've seen is
from the world economic forum
that talks about the fact
that any of our single skills
degrade by 50% over a five year period.
So simply by staying still
you're actually falling behind.
Right.
So if nothing else, let that remind you
that any move is a good move when compared
to staying still any move, right.
As long as it increases your learning
- That gave me chills.
- Yeah, second, I know it's crazy.
Right?
And then the second big
risk is taking only one risk.
Like literally I'm like
if you think you're gonna
be a smart risk taker
it's like learning, saying
I'm gonna be a trader
but I'm gonna make one trade.
And that trade better work because of it.
You know, that trade's
gonna make me a millionaire.
And I'm like, well, the
best traders, you know
they build a portfolio of trades
and they learn from each trade.
They try to get smarter and they know
that they just need to
build a winning portfolio.
And so I think that like part
of what keeps us, you know
not acting is this, we think
stability is safe, untrue.
And then we also think like,
hey, it's one big move untrue.
You know?
So if you need help getting into action
those are two things
that you should fear more
than making multiple
moves, fear making no move
and fear of putting all your
eggs in a single winning move
because that's what I call luck.
- Yeah.
- So those are two ways
to get yourself in action.
And then I think there's
more concrete sort of
as you're trying to make a decision
also things you can do
to get yourself into action.
I'll say to people instead of
just visualizing the positive
which a lot of people do,
they visualize the positive.
And I get that.
I'm a visualizer too.
I wanna like, imagine what's gonna happen.
But if you can't overcome
your fear of failure in acting
it doesn't matter if you
visualize the positive.
And so there, I would say to people,
try to pre-morteming the failure
try literally, you know
pre-morteming the choice
you make it fails.
And then what you do.
And sometimes pre-morteming
is a very specific way
in which we can realize .
That if there are multiple
choices after a failing choice
you likely have more
freedom than you think.
- I love that because most people think
about doing a post-mortem,
but you're getting ahead of it.
So you're doing a pre-mortem
and it reminds me of something.
One of my mentors and coaches said to me,
she used to tell me, play it
through to the end, you know?
- Yes, that's the right case.
- Best case, worst case,
play it through to the end.
Right, and you just try to
imagine different outcomes.
And so I, well, I love
that, but now I have it.
Now I have a term for that.
We're gonna pre-mortem it.
(both laughing)
- Pre-morteming failure,
I think is a really great technique.
- Yeah.
- As opposed to visualizing the positive.
- That's right.
- Yeah.
- All right, Sukhinder,
we've come to my final
but favorite question and that
is what is your superpower?
- Hmm. What is my superpower?
I think I'm probably a
net energy transmitter
meaning I think I can give
people energy and a feeling
of momentum and a sense
that something is achievable.
So I'd like to think that
most people, you know
will say an interaction
with me can bring them not
just insight, but maybe
some feeling of possibility
and like five more things to consider.
So I'd like to think I'm
your net energy transmitter.
Now, my husband may
not say that 'cause I maybe
a pain in his ass but generally speaking,
I think will bring a lot
of energy to situations.
And I hope I distribute it
to the people I work with.
I know for me, you've expanded my horizon
and the art of what's possible.
And I just wanna thank
you for being so thoughtful
and helping us navigate our careers
and to make those boss
moves that we all wanna make.
So thank you again for being here today.
- Well thank you for having
me so much fun to see you.
I hope you all enjoy today's conversation.
And to watch more episodes of boss talks,
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With that thank you so much for tuning
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I'll see you all next time.
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