695: How to Take Risks Confidently with Sukhinder Singh Cassidy

Pete Mockaitis
Sukhinder, thanks for joining us here on the How to be Awesome at Your Job podcast.

Sukhinder Singh Cassidy
Thank you for having me.

Pete Mockaitis
Well, I’m so excited to dig into your perspectives associated with your book Choose Possibility. Can you tell us, what’s the big idea here?

Sukhinder Singh Cassidy
The big idea is that we all have a rather terrible relationship with risk-taking and a rather kind of, I would say, ill-conceived view of what risk really looks like. And so, the book was written to help us reframe risk for what it is, really the pursuit of possibility, and offer really pragmatic ways to rethink how you approach risk-taking in order for you to be able to unlock more of its benefits.

Pete Mockaitis
Well, I’ll take right away the pursuit of possibility feels a lot better than the word risk just in the gut, as you sort of feel the words side by side and their valance. So, very cool. Now, your own career has had some interesting possibilities and risks and wild successes and disappointments. Can you give us a little bit of view for some of the wildest rides and how you’ve thought about risk and what happened for you?

Sukhinder Singh Cassidy
Sure. Sure. Well, as you noted, I consider myself someone who’s taken hundreds of risks in my career. I have been at large companies when they were growing, like Amazon and Google. I’ve been a CEO of large companies like StubHub, but I’ve also started three of my own, been an early-stage investor, a mid-stage investor, a late-stage investor, a board member at startups, a board member at large public companies, and so I feel like I’ve navigated and traversed risk-taking throughout my career.

And if you said sort of, “What are some of the wildest rides?” Well, they include quitting my job as a president at Google when I was arguably among the top 15 executives in the company, and going to a startup as a CEO, and, honestly, having it fail ferociously as a career move within six months, only to have to figure out how to recover and navigate my way to my next career choice and, ultimately, find the unlock for myself in terms of the rewards I took for the risks I took. As you can imagine, that career left me feeling like risk-taking is not what people think it is, and the reward relationship with risk is anything but linear, which is how we tend to conceive it.

Pete Mockaitis
Well, I absolutely want to ask about that specific point, so let’s roll with it. So, the risk-reward relationship is not linear. What does it look like?

Sukhinder Singh Cassidy
I think of the relationship between risk-taking and reward is not only non-linear but, in some ways, very circuitous. And so, let me explain what I mean. When we make a move, any move, or take any choice, I bet you we’re looking for not just one reward but multiple rewards. We might be making a career choice that we’re hoping will fulfill us financially, that we’re hoping will unlock some outsized career, win like a title change, or step up in responsibilities, and maybe brings us a lot of personal happiness. So, we’re making a move that has effectively three choices within it that we’re trying to optimize for.

Yet, when it comes to sort of how things unfold, as we execute our way through a choice we’d made, the reality is we’re measuring it on these three different choices or goals we have, and we won’t get the results all at the same time. We maybe figure out if it’s going to be a financial win for several years. We may figure out if it’s a happiness win within a year. We may or may not achieve the career ambition we wanted in terms of title.

And so, when you think about all the reasons we take the risk to begin with, the rewards don’t unfold in sequence, they don’t unfold at the same time, and each reward may have its own relationship to our execution or to the factors that are entirely outside of our control on whether or not we sort of achieve we originally intended against that specific goal.

So, when I say it’s non-linear, I mean it unfolds at various points in time, big and little risks don’t correlate to the size of the ultimate reward, and so you look at the whole thing, and you say, “Gosh.” Whatever you imagine going in, you may or may not achieve it going out, but I bet you that you will still be able to collect the benefits of risks even if they don’t look like the rewards you originally imagined.

And I think that is the key, how you take risks and make sure that if it’s a non-linear and circuitous relationship, you can still gain benefit from the risk you take and understand what the relationships and the benefits might be every time you take a risk even if it’s not the ones you originally imagined.

Pete Mockaitis
Well, boy, I think you could chew on that for a while and really get to some great places. It’s funny, when I was thinking about a non-linear relationship doing risk and reward, I was just thinking from a strictly kind of a finance thing, it’s like, “As there is a higher standard deviation and the returns of the given asset class, risk, there is a higher reward, like percent, money, return.”

Sukhinder Singh Cassidy
Yeah, percent return. Right. Yes.

Pete Mockaitis
But as you sort of zoom out and think about kind of the long game and your life and time and how things unfold, it doesn’t look like that at all.

Sukhinder Singh Cassidy
Yeah. Well, it’s interesting. So, actually, let’s back away, let’s look at your asset, my view versus your view, and back way. First of all, there is a thesis that I have in the book that if you actually look over the extent of your lifetime, you will actually find maybe that linear relationship but through multiple choices and multiple cycles.

So, if people were to chart my career, they’d say, “Wow, Sukhinder, there’s a pretty linear relationship between risk and reward because you started at one place and you took a risk and, gosh, look where you ended up.” So, it looks like a straight line over your lifetime but, really, what you’re doing is mapping through a bunch of cycles of choices and individual risks and individual rewards, each of which may or may not have worked out.

So, to your point, it’s like a stock pick. Any given stock pick may or may not work out. You and I would agree. When you’re building a stock portfolio, what are you trying to do? You try and actually make multiple choices. You’re diversifying your risks in order to maximize your overall return. By the way, as you keep picking stocks and watch pattern matching, I bet you become a more calculated stock picker over time.

And over the course of a long timeframe, let’s say 10 years, in which you are managing a stock portfolio, you’re getting better and better, though never perfect, at picking stocks, diversifying risks, taking parallel risks at the same time. And over the course of that entire period, you may say, “Wow, there was a relationship between starting to be a stock picker in my ultimate value of my portfolio.” But that doesn’t mean every individual stock you picked worked out.

And I think therein is the opportunity, and therein is the miscalculation of how most people think about risk. Most people think about risk as one mighty choice for one mighty reward. And I think, to take your analogy further, you will see the compounding benefits over a long period of time, but it will be an amalgamation of many individual choices or risks taken, each of which may or may not have worked out. And that’s why I think risk-taking has to become a skill rather than a single event we imagine.

Pete Mockaitis
So, when we think about risk-taking as a skill, how do you recommend we go about getting better at this skill of risk-taking?

Sukhinder Singh Cassidy
First and foremost, it’s probably no surprise, I think about starting early and often. I will say to people, you imagine and look at the biggest risk-takers in the world, and we somehow celebrate their biggest choices and we act like that’s the only choice they ever made and that’s why they’re such a mighty risk-taker when, in fact, most started taking risks long before we knew it, and they took risks of different sizes.

So, if I were to say to you, “How did you become good at managing your portfolio?” or whatever it is you’re doing, I bet that it started by doing it early and often. So, I say to people, first and foremost, find reasons to take risks in your everyday life, in your everyday career. And most people will say, “Well, I took a risk. I made this choice to go into this career. I took a right turn and decided to join a startup.” Okay, well, that’s one risk but we have opportunities to take risks every day.

I always say to people you could take the risk to learn something new. You could take the risk to discover more opportunities. You could take the risk certainly to achieve an outsized ambition, or you could take a risk to avoid harm. Like, those are four different reasons we might have to take risks every day. And so, I say to people, early and often is the way to really build your risk-taking muscle.

The second thing I talk about with people is many people believe that risk-taking first requires a lot of planning. I don’t know. Have you ever seen this, Pete, the person who plans a lot, and plans judiciously, and plans in great detail before they ever take a risk? Because we think the more perfect our plans, the better our risk-taking will be and the more we can control the outcome.

And one of the other pieces of advice I say to people when they’re trying to get going and just start to take risks is, “Hey, as oppose to the perfect plan from afar, spend less time planning, create a rough plan, and then the most important thing you can do is get proximate to the choices you’re thinking about making, or the risks you’re thinking about taking.”

If you’re thinking about taking a risk to be an entrepreneur in a big company, one of the best ways to do it might, first and foremost, be proximate to people who are entrepreneurs. Learn what it looks like to be an entrepreneur. Get proximate by joining a startup. Become an apprentice before you make a final choice.

And so, I think people presume that risk-taking requires a perfect plan. And, instead, I kind of advocate for a rough plan, what I call a whiteboard plan, “What’s the direction in which you want to head?” And before you make your choice, take the little risks to get proximate and closer to the opportunities you seek, and learn before making your final choice.

Pete Mockaitis
Now, we’re using the phrase take risk a lot, so let’s get clear with definition, shall we? When you say, “Take a risk,” what precisely do we mean by that?

Sukhinder Singh Cassidy
Well, I think of a risk is anything that has an uncertain outcome in pursuit of a goal. So, if you look at the standard definition of risk in Merriam-Webster, it’s to avoid injury or harm. That’s the kind of risk-taking we all imagine that keeps us from ever acting. If you look at the definition of risk-taking, it talks about literally entering an uncertain situation for the pursuit of a goal.

So, for me, a risk could be speaking up in a meeting. That’s ego risk. That’s psychological risk. It’s not financial risk but why don’t people speak in meetings? It’s because there’s a risk involved to their psyche or to their sense of what others think of them. And then risk-taking obviously follows more classic definitions if you know. You might decide to, as we said, empty the money from your bank account and put it in your first startup. That’s a bigger risk but it’s still a risk.

So, I think of risks as micro-actions, medium-sized actions, and larger-sized actions, all of which are uncertain but they’re decisions you make to try and unlock more impact. And what keeps you from doing it is obviously these fears we have, whether they’re related to our ego, financial, or kind of personal risks.

Pete Mockaitis
Well, yeah, so let’s talk about the fear. And maybe we’ll zoom out for a moment and get to a conceptual or theoretical optimal relationship to risk. Like, is your take that we should neither be fearful and take zero risks nor reckless and just do every nutty thing that we think about? Or, what does optimal look like in the realm of risk-taking?

Sukhinder Singh Cassidy
Sure. Well, let’s start with what I call the universal risk-taking equation.

Pete Mockaitis
All right.

Sukhinder Singh Cassidy
So, I want you to imagine two phrases, they’re pretty simple. One is FOMO, fear of missing out. I’m sure you know FOMO. The other of FOF, fear of failure. So, many people have fear of failure, many people have FOMO. So, I think of the universal risk-taking equation, put this in your head, the one that guides us all.

It’s goes something like this. If our fear of missing out on something is greater than our fear of failure, we’ll likely act, we’ll likely move in the direction of a choice we’re contemplating that has some uncertainty. If our fear of failure is greater than our FOMO, we’ll likely fail to act, it will equal inaction. So, let’s imagine risk-taking framework that looks like that.

First of all, you’ll notice two things. In that universal risk-taking equation, there isn’t the absence of fear. There are actually two fears that we are managing at any point in time – our fear of missing out, which is kind of what we would all think of as a positive fear, it’s the fear that induces us to act, and this fear of failure.

So, if you think about that concept, I think the world largely tells you that if you want to act, you just have to visualize the positive. Keep visualizing the positive because we’re going to ramp our FOMO. Makes sense. It’ll be like, “Hey, if you want to get that risk-taking equation working in your favor to act, just ramp your FOMO.” That doesn’t really do much for the way most people live, which is with a lot of fear.

So, just visualizing the positive doesn’t really do anything to help shrink the denominator in the equation, which is fear of failure. So, you could have a lot of FOMO, like you could have a lot of positive visualization, but if you can’t conquer or find a way to shrink your fear, you just won’t act, even though you know intellectually that there are all these things you’re excited about.

So, I often say to people, first of all, embrace both fears. I have an executive coach that I’ve worked with for 10 years through a number of my career choices, and he says to me, that I think is absolutely right, most people have a rather immature relationship with what he calls our inner risk manager, that voice inside of us that is, on the one hand, sometimes goading us forward, but more often our risk manager is trying to keep us from acting by sort of signaling all the dangers that’s going to happen to us, they’re trying to keep us safe.

So, he always talks about this immature relationship with our risk manager, and managing that formula I just talked about is about having a more mature relationship with your risk manager. And so, while it’s all good to kind of visualize the positive and ramp your FOMO, and I certainly recommend it when you’re creating goals, or when you’ve made a big choice and you’re trying to keep yourself motivated every day. What I often say to people is, “Let’s work actively on reducing our fear of failure,” and, “What are the strategies we can use that would help us reduce our fear of failure and allow us to act also?”

And there are a couple that I strongly recommend. One comes from our favorite risk-taker of all time, Jeff Bezos. Bezos wrote in his very famous shareholder letter to investors when he was going public, that most decisions Amazon makes, and he says that, “Most decisions we make, as people, are what we call decisions with two-way doors.” We often imagine that we make a decision and it’s a one-way door, there’s no way back. But the vast majority of things we do or try, there’s a way back. If you say something in a meeting that it doesn’t work out the way you want, it’s not like you can never say anything again.

Pete Mockaitis
“You’re fired.”

Sukhinder Singh Cassidy
Yeah, “You’re fired. Are you kidding? You said that terrible thing. Nobody thought you were smart.” Like, that’s absolutely ridiculous. If we said, “Hey,” you want to take a new job opportunity and it’s at a startup. If you’re very employable, and your current company lets you, it’s not like there’s not a way back if you go and it doesn’t work out.

So, the vast majority of things we think about are not one-way doors; they’re two-way doors. And so, I often advocate, and I advocate certainly in the book, that if you want to have a good relationship with your fear of failure, let’s start by not avoiding what those risks are. Let’s name them. Let’s size them. And they get sized as big if they’re one-way doors. If they’re two-way doors, they’re likely smaller, medium-sized risks, and go one step further.

I say, like, imagine the choice after the choice. Imagine you say that thing in a meeting and it doesn’t work out. Well, what’s the very next thing you would do? Imagine you go to that startup and you hate the job. What’s the very next move you would make? And the minute you can imagine the choices after the choice, and if you can come up with several, well, that’s probably not as large a risk as you think it is. And imagining what you would do actually helps us confront those fears of failure as opposed to avoiding them.

So, I often think about that universal risk-taking equation, and while I’m all for FOMO, I actually believe that we own each strategy to sort of look and shrink our fear of failure in order to get us into action. And those are some of the things I think about a lot and talk about a lot when I advocate for people to take more risks.

Pete Mockaitis
And so, you say you advocate for people to take more risks, is it fair to say that most of us don’t take enough risks and relatively few of us are wild and reckless? Or, what’s your take about the breakdown of the…we’ll just say United States professionals?

Sukhinder Singh Cassidy
Well, you’re asking a question that’s near and dear to my heart. If you want to go to the website for the book called ChoosePossibility.com, you can take a risk quiz, interestingly, to figure out what your natural risk-taking style is because I wanted to know the answer to the same questions as I was writing the book and certainly bringing it to market as we launch it.

And so, we actually created a simple risk survey, and then we surveyed the US population, obviously not the entire population but a sample, before putting the risk quiz on LinkedIn and on the site where you can take it. And to your point, what we found is that we sort of named four archetypes for risks, and we found that the vast majority of people taking the risk quiz, like 60%, are what we call contemplators, which is very good at being calculated and measured in laying out the pros and cons of any decision.

But where they self-identify is having challenge is in actually making a decision. And these people self-identify saying, “Hey, I can look back and I have a decent amount of regret about choices I didn’t make and actions I failed to take.” So, the majority of the population in our risk quiz are contemplators. And then let’s think about what comes on either side of a contemplator.

A contemplator who is more negative, who sees more easily the cons of any given situation, who’s always trying to keep safe and keep away from harm, we call a critic. On the other side of being a contemplator is what we call the calculator, the person who also does the analysis of pros and cons in any big decision, and certainly probably does a faster analysis or more efficient analysis on smaller decisions, but is comfortable making a decision within a given time period. So, they’re always calculating and kind of biased towards making a decision more than the contemplator.

And then the last archetype we identified is what we call the change seeker. And you and I probably know lots of change seekers, which are people who are so easy to see opportunity that, in fact, they may move very spontaneously. Some would call them reckless, some wouldn’t. Some would say that they’re the life of the party and the people who never miss an opportunity even if it costs them overcommitting or, in some ways, moving rashly.

And so, when we look at these four archetypes, and as I said, you can identify which you are by taking the quiz on the site, I think the majority of people certainly are comfortable with the idea of a pros and cons list, but when it comes to action, they maybe sit on the sidelines a little bit more than they wish they would. And, obviously, that’s what prompted me to write the book.

Pete Mockaitis
Okay. Well, let’s talk about some particular strategies and tactics when it comes to doing some decision-making. So, I liked how you discussed how we can shrink our fear of failure by thinking through, “Hey, is this a two-way door? If this went south, what would be the very next step?” What are some of your other favorite approaches? Or, do you have a master framework when you sit down and say, “Okay, Sukhinder, decision time”? How do you get to your answers?

Sukhinder Singh Cassidy
Well, let’s put it this way. First of all, in our risk quiz, I’m a calculator, which means I’m never without my own spreadsheet. Make no mistake, I think of my own relationship with risks as, “Yes, here’s that formula.” But to answer your question, I do believe that for smaller choices, it’s about doing the rapid formula and moving yourself to action because as soon as you realize that a risk is of rather small size, hopefully you can get into action fairly quickly without needing a gigantic spreadsheet.

But, believe me, when it comes to bigger choices in my own life, I have a pretty gigantic spreadsheet too. And some of the things that you would find on it might surprise you. So, in my frameworks for taking risks and making bigger choices, there are probably two things that I do, and I weigh in my framework that most people don’t weigh.

When most people create a framework for making a bigger choice, they really do a pros and cons of like what we might think about like how they will execute, they say, “Gosh, this could go right and this could go wrong.” But they really act as if the entire risk and thing worth rating are like their own execution ability. Like you say, “Oh, this could go right or this could go wrong if I do this or I fail to do this.”

In my own risk-taking frameworks, actually, I not only look at how something compares to my goals or my own skills and capabilities, like, “Gosh, am I likely to succeed or fail in my efforts?” But I have two dimensions that I think most people fail to add. Number one is what I call the people factor. So, most people try and make a choice sort of on the what of the thing they’re pursuing.

So, let’s put it this way. I want to go to a startup. I’m thinking about the what that that startup does and is that startup likely to be successful or not? Is that a winning idea? I often, and this has certainly been something I’ve learned the hard way in my career, but I’ve also had the benefit of, I’ve really, in all of my frameworks, I overweight the people I am going to join in any new choice or endeavors. So, I call that the “I put the who over the what,” and that’s one big piece of advice I have for people when creating around framework and doing your own pros and cons list. You have to add and rate the people factor of any dimension.

And people say, “Well, why is that important?” I think it’s important because many of us have been told to take risks in the direction of our passions, as an example. Like, “Hey, go overweight moving towards something that’s in the direction of things you enjoy.” That’s great. But 99% of our careers and how successful we are on the job are done in collaboration with others, with peers, with a boss, with a CEO who might be guiding the direction of the company, so with people who share or don’t share our values, let alone complement our strengths.

And so, when I overweight the people, what I’m really overweighting is, like, “Hey, I’ll get to have fun in my job or do the things I’m passionate about or good at dependent on the people I go to work with every day. And if I go to work with extraordinary people, people who have skills I seek to acquire, or people whose values fit my own, there’s a far better chance that I’m going to enjoy the day-to-day of my job and do my best work.”

And, yes, all the better if it’s in the direction of my, let’s say, stated passions in terms of topic area. So, putting the who over the what is one big factor in my frameworks that most people don’t really rate enough or rate highly enough when they make their choices. And the other one that I often tell people is missing from their frameworks, and I would add to any framework or pro-con choice, is what I call the things that aren’t in your control, the headwinds and tailwinds of any situation.

We tend to believe that we go into any situation, and what I call the neutral state, like it’s just waiting there for our immense and amazing execution in order for us to be successful as if that is the only factor at play in things that work and don’t work. But if we take the time to rate the situation we’re entering, as it’s like, “Does it have momentum and tailwinds?” People often give me a lot of credit for my choices, but my friend, I came to Silicon Valley in 1997. Ahh, that was a good time to come to Silicon Valley.

Let me tell you, there are so many tailwinds that if I made a bad choice, I could still pivot into good choices. And, in fact, that happened to me in my first job in the Valley. I quit in six months but there was so much opportunity that I could pivot into and so many companies that had tailwinds, that I had plenty of what we call room to fail and still be successful.

And so, I think objectively rating the situation you’re entering, “Does it have headwinds or tailwinds? And what does that mean for your ability to execute?” is a huge other factor in the frameworks I build around any big choice.

Pete Mockaitis
I like that concept right there, room to fail. I guess I could just flip it around. As I was contemplating, “Should I launch this podcast? Oh, it’s going to be a lot of work. And, hey, I’ve tried a lot of business initiatives that didn’t work out.” And one of the things I loved about this, as a concept, was that there were just so many ways to win, financially. I already knew it was going to be fun talking to people like you about stuff I love.

Sukhinder Singh Cassidy
Of course, right?

Pete Mockaitis
But I thought that there are so many ways that this can win, whether it’s just from sponsorship, or selling courses, coaching and training, licensing and monetizing. Like, there’s a lot of ways. As opposed to a lot of businesses are like, “Well, hopefully people like this thing,” whether a product or service, and if they don’t, then that’s kind of all there is to it.

So, room to fail or many ways to win is a cool parameter to embrace and to value and to consider.

Sukhinder Singh Cassidy
I love it. This comes into like embrace your inner calculator. Like, lay out all of these things because sometimes, as you know, like one of the things I found in the book is if you look at the research, people often make decisions quickly because uncertainty feels so uncomfortable.

But when you lay out all of these paths, as you said, all the ways your podcast could monetize, like you’re not only ramping your FOMO, you’re also, in many ways, like dealing your fear of failure. You’re saying, “Oh, my goodness, here are like the three ways. If this one doesn’t work, this one could work. If this one doesn’t work, this one could work.” So, I bet you, that thought process got you into action by confronting all of these thoughts early and being calculated in taking this risk, not just like a hope and a prayer, but laying it out in order to get yourself into action.

And so, I mean, I love it. Yes, room to fail all the time. But room to fail means you take the time to confront the things that not only you would love about doing this, but the things that you fear, and laying out all the possible paths you could pursue. That’s what gets me into action, it’s not just sort of dreaming in the abstract.

Pete Mockaitis
And that’s a really compelling point right there about folks moving quickly because they don’t want to linger in the discomfort of those, the moments of uncertainty.

Sukhinder Singh Cassidy
Yes.

Pete Mockaitis
I think there’s some real wisdom there. And so, any pro tips with regard to if folks are in a position, like, “Ah, I’ve just been thinking about this too long. Aargh!” How do you recommend sort of calming the system, or, maybe just in general, like when emotions are running hot, like to get back to a place of calm, wise rationality?

Sukhinder Singh Cassidy
Well, I’ll tell you what I do because I certainly love to act and I’m somebody who makes decisions, relatively speaking, fast. But when it is a weighty decision, or when there is something bothering me, the first thing I do when something is like I’m prompted to act quickly, almost too quickly, and I feel myself becoming reckless, is I try and step back and ask myself, “What am I trying to solve?”

And, often, what reveals itself is that there is not a one-stepper but a two-stepper. So, first of all, when we’re feeling anxious, it’s because something in our current situation is maybe feeling threatening or negative to us. You know people who are like, let’s say, take the first job offer they get. And you say, “Well, why are you going to jump into that job? Like, just step back. What are you trying to solve?”

And when you ask yourself the question, “What are you trying to solve in making the decision now?” usually, what you find is you’re trying to solve in a one-stepper something that’s effectively of two-stepper. So, what do I mean by that? Let’s say your current job sucks. Like, you’re fighting with your boss. So, the first job that comes up, you feel like, “I’m going to take that. That’s the one. I’m saying yes on Monday.”

I would say, “Okay, figure out why you want to say yes on Monday. Before you say yes on Monday, figure out what you’re trying to solve.” So, first of all, you’re trying to solve your current discomfort at work. That might involve going in on Monday and having an honest conversation with your boss about something that’s not going right. That is a distinct decision and risk to take from the risk of what job to go to next. That’s the two-per. Like, number one, solve the current discomfort. Number two, then decide if you were in “a neutral state” and try and pick the best possible job choice, “Would you pick this one? Or, would you now take the time, having solved your immediate discomfort, to go lay out five job choices because maybe you’re going to find one that’s even better?”

And, certainly, I say to people, like, “Step back. Forget what you’re trying to solve. And if it’s a two-per, lay out your two independent goals because they may be solved separately. And that allows you then, my friend, to setup the next choice, that next possibility, and I’m not like, “Hey, go live forever in uncertainty,” then I’m more in there like, “Hey, if you were in a neutral place, maybe you would have the time to go figure out the three jobs that would be your dream job. Go have two more conversations and set yourself a timeframe to still make the decision but it doesn’t need to be yesterday.”

Pete Mockaitis
Well, I think that is an insight that’s applicable in many circumstances, that this isn’t a one giant leap but rather maybe two or three or four steps and components. And in asking that question, “What are you trying to solve?” you can see that and take appropriate action. And what’s fun is that you may feel all the more empowered and emboldened and equipped to have that conversation with boss because, like, “I don’t know if this is going to go well.” It’s like, “Well, hey, if it’s horrible, at least I have something.”

Sukhinder Singh Cassidy
Yeah, I have something. I have a bird in the hand. Yes, absolutely. But it’s just about forcing those things apart when we’re feeling reckless. So, the point is that I think our relationship with risk tends to be risk is for the risk-takers among us. Okay, not true. Risk is a skill that anyone can build, point one. And then, number two, on this point of like, “Okay. Well, if you want to build those risk-taking muscles, think about these choices in increments.” You’re often not making, as you said, one choice. You often have the opportunity to make two, three, four choices.

And you know what that does for us when we know we have the ability to make two, three, or four choices? It frees us from the pressure of one big choice, which is what people think it needs to be – one big choice. I call this the myth of the single choice, “I’m going to make one big choice and it’s going to be either a raging success or an abject failure,” and then there’s so much pressure on that one choice. The minute you say, like, “I have multiple choices and risks to take or choices to make,” it really frees us up from this myth of the single choice. And, in fact, we can get the compounding benefits of choosing again and again and again.

Pete Mockaitis
That’s beautiful. Well, Sukhinder, tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Sukhinder Singh Cassidy
Well, I think mostly it’s what I said. If you think that risk-taking is for the risky among us, reframe your thinking about what risk really is. It’s a small or big choice that you can make multiples times a day, a week, a month, a year that get you into action now and sort of unlock your learnings so you can choose again. And it’s about this freedom to choose and choose and choose again that really helps us create compounding benefit to the risks we take.

Pete Mockaitis
Lovely. Well, now, could you share with us a favorite quote, something you find inspiring?

Sukhinder Singh Cassidy
My favorite quote is probably one from the book, which is, “When nothing is sure, everything is possible.” And so, we often think about, as I said, this idea that uncertainty is daunting, but let’s just remember, like, uncertainty is literally the definition of possibility. When nothing is sure, everything is possible. So, that’s a pretty awesome place to dwell, right?

Pete Mockaitis
Yeah, thank you.

Sukhinder Singh Cassidy
And we don’t tend to think of it that way.

Pete Mockaitis
And how about a favorite study or experiment or bit of research?

Sukhinder Singh Cassidy
Well, one of my favorites is actually, I don’t know about, but have you ever read the book Good to Great from Jim Collins?

Pete Mockaitis
Oh, yeah.

Sukhinder Singh Cassidy
So, that’s one my favorite older books, but one of my favorite newer books, in fact, I had it in our book club at StubHub. I made the entire leadership team read it, it was this book Growth Beyond the Hockey Stick from a set of McKinsey partners. It’s one of my favorites. It’s a 30-year study of companies that non-linearly outperform over time.

And what it really finds, which I think is so fun, is it sorts of reinforces or validates through data the research that the companies most prone to failure over a long period of time are companies that fail to take any move rather than companies that made multiple moves, some of which were wrong, actually have a much better chance of what they call, what McKinsey calls moving up the power curve to become non-linear, you know, outsize successes over time in terms of shareholder returns. So, failing to move is far more likely to have you, what we call go, whereas making multiple moves, imperfectly, is far more likely to get you to grow. Very neat analogy, obviously, to the book.

Pete Mockaitis
And how about a favorite tool, something you use to be awesome at your job?

Sukhinder Singh Cassidy
My favorite tool to be awesome at my job, you would laugh, but it’s my iPhone notes. Like, when people talk about having, like, “I always have a plan,” but I’m moving all the time, so although I’d love to have a whiteboard. The reality is my iPhone notes is my whiteboard. If you went into it, you would see notes on everything from business ideas, to what I need to get done today, to my grocery list, to tips for what are the things I want to remember to mention on this podcast. So, I would say one of my favorite tools is a pretty simple one – iPhone notes. All the time. Goes with me all the time. I can erase it, modify it, but it’s always there.

Pete Mockaitis
And a favorite habit?

Sukhinder Singh Cassidy
These days it’s tennis. I don’t know what your favorite COVID habit is but I have become much more regular as a tennis player, and I’m loving it.

Pete Mockaitis
And it sounds like you may have already shared a couple of these, but is there a particular nugget that you articulate that gets quoted back to you frequently and people are loving?

Sukhinder Singh Cassidy
I have a quote I often give people that does get played back to me all the time. It’s called, “You manage me or I manage you. Which would you prefer?” And when people are like, “What do you mean by that?” I often say in leadership talks, “Okay, like literally, if you’re a leader, you have a choice, you can say to your people, ‘You manage me or I manage you. What would you prefer?’”

And most people presume that the right answer is, “Well, gee, like I would prefer to manage others.” And I say to folks all the time, I’m like, “Really? I prefer for somebody to manage me.” They’re like, “What do you mean?” I’m like, “No, no, I really prefer that they manage me. Like, I’m a CEO, so if you walk into my office and expect to be managed, and I’m an opinionated person, there’s a pretty good chance I’m just going to spit out whatever is in my head and tell you to do it. That doesn’t mean it’s the right answer. It’s also not a super empowering place to be.” So, if you presume that my job is to manage you, that’s not a particularly fun place to be.

Now, let’s reverse it. Now, if I say, like, “Gosh, your job is to manage me. That means you’re likely to walk into a meeting with me with an agenda of your own. You take control of the conversation. You probably have a problem and a solution you’d like to propose. You’ve thought it out. You lay it out.” Now, guess what that means for me as your leader and manager? It means that I get to have a really highly leveraged interaction with you where you’ve clearly thought it through. You get to lay out your vision. I get to respond to it and add to it my vision and my insights. And then you leave out my office in 10 minutes versus an hour. You’re feeling super empowered. And guess what? I’m feeling pretty leveraged and we both go on to have a better day.

So, I always say to people, like, reverse your thinking on management. If you think the purpose of management is for you to manage down to others, imagine what life looks like when you ask people to manage up to you, what it looks like for them and what it looks like for you. That, to me, feels like real leverage for both parties.

Pete Mockaitis
That is a beautiful perspective. And one of my mentors, Victor Cheng, in episode 500, he said that that’s how he would approach his conversations with new direct reports. So, he’s the boss, he’d say, “I work for you and here’s how it works. You tell me what you need, what resources, what decisions I need to provide to you so that you can do your best work. And then that’s what I want to with them, and get out of your way, and we’re going to have great things happen.”

It’s sort of a reframe but it is lovely. I could tell you, with employees, it is refreshing and wonderful for all of us when they say, “Hey, Pete, here’s what I need from you.” I was like, “Okay, cool. Well, hey, you’ve got it. Is that it? That was quick.”

Sukhinder Singh Cassidy
Isn’t nice? It’s awesome, right? It’s quick and efficient. Now, make no mistake, your friend sounds pretty graceful and patient. My problem is I’m actually impatient and fairly opinionated. So, I always say to people, “The problem is if you walk in with a blank sheet, you’re far more likely to walk out with my sheet, and I’m not sure that’s a good thing. It may or may not be but the problem is I always have something to say, so I would much rather you come in with what you have to say because that is a fun place for me to be as well.”

And sometimes personalities like mine, you definitely don’t want to be walking out just presuming that because I have an opinion, it’s always the right one. What I’d really love to do is get into an interaction with someone, which is quick, efficient, highly leveraged, and fun because we’re both learning something from it.

Pete Mockaitis
And if folks want to learn more or get in touch, where would you point them?

Sukhinder Singh Cassidy
Well, you can always find me on LinkedIn, just at Sukhinder Singh Cassidy. You can find me on Twitter but, honestly, I hang out more on LinkedIn because it’s a fun place to have career conversations with folks. And, certainly, you can, if you are so inspired, you can always preorder the book Choose Possibility on the website, and it comes out August 17th.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Sukhinder Singh Cassidy
I would say my call to action is take the risk quiz but, more importantly, understand that it doesn’t matter what your natural style is. Every single one of us can be what I call a chooser. And so, my call to action is be a chooser versus kicking the can down the road. Make the little choices today that unlock incremental possibility.

Pete Mockaitis
Well, Sukhinder, thank you for this. This is a real treat. And I wish you lots of luck in all your possibilities.

Sukhinder Singh Cassidy
Well, thanks so much. Thanks for having me.