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The Reward of Risks in Leadership

By August 12, 2021 September 4th, 2021 No Comments

Sukhinder Singh Cassidy (@sukhindersingh) has been a CEO many times over, most recently of StubHub. She is also an author and her newest book is called Choose Possibility: Take Risks and Thrive (Even When You Fail). Today she and Mark talk about what it means to take risks and to thrive in business leadership.

Hear how:

  • The best and highest use of a leader is to have other people manage them
  • Being less perfect, and displaying authenticity, imperfection, and transparency nurtures an environment for risk-taking
  • Risk-taking isn’t about the higher risk, the higher reward—it’s about taking many risks for the ultimate reward

Listen to this episode so you can truly understand risk and embrace it for this VUCA world.

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Hey folks, welcome back. This is Mark Divine with the Unbeatable Mind podcast. Thanks for joining me today. Super-stoked to have you here. As you know, I don’t take it lightly, with all the things vying for your attention. So, we’re going to bring you some valuable information and not waste your time.

If you do enjoy this podcast, please go rate it wherever you listen – iTunes is a great place to do it. We have over a thousand five-star reviews. So, it helps other people find it and also value the podcast. And so I appreciate that as well.

I’m excited today to be talking to Sukhinder Singh Cassidy – I hope I got your name correct…

Sukhinder: You did.

Mark: Awesome. Sukhinder is a leading tech exec, entrepreneur, investor, board member… she’s got over twenty five years of experience with a couple of small companies such as Google, Amazon… she’s recently served as president of Stub hub… helped to sell that in 2020 for a few billion bucks…

And that company’s thrived under her leadership. She is the founder and Chairman of the Board list… she’d been profiled in many, many publications… and has a new book out called “Choose Possibility,” which I’m excited to talk about.

Sukhinder, thanks so much for your time. And for doing this podcast while you’re travelling in LA, from a hotel room…

Sukhinder: It’s all good. I wish I could come to San Diego. Next time. But thank you for having me.

Mark: I appreciate that. So there’s a lot that we could talk about – but I always to start out just getting to know and having listeners just get to know little bit about why you became who you are today. Like, what were your formative experiences?

Both the good and the bad… the challenges, as well as the opportunities that you’re presented with. That help you become a tech executive and entrepreneur and then rise to the highest of ranks, so to speak, in the corporate world.

Sukhinder: Well, that’s a flattering way to describe it… first and foremost I would say to people if you want to know what formed me, many people, I am the daughter of entrepreneurs… in particular my father. My parents were both medical doctors, immigrated to Canada when I was young, from Africa.

But my dad loved running a medical practice, as much as he liked serving people. And he loved the fact that it was a small business. When I was maybe seven or eight my dad started us, all doing entries into his ledger, so that at tax time – because remember, you still used to write out …

Mark: Double entry bookkeeping. That was exactly…

Sukhinder: Double entry bookkeeping. It’s absolutely true. So he had his whole family do it – we were three girls, and we would all be entering into his ledger expenses from his checkbook.

And by the time I was 12 or 13, I probably understood how to do his tax return…

And so you’re , what does that have to do with possibility and being an entrepreneur? And turns out it’s everything, right? Because when you witness somebody who goes to work every day on the one hand – dreams of building a big business – my dad dreamed of opening walk-in clinics, probably 15 years before that became a mainstream business concept. He saw the possibility for what an always-open medical clinic could be.

Yet I mean possibility was also , “hey, it’s as simple to run a business as figuring out your expenses and your costs. And making sure that one exceeds the other.”

And so I think that in my formative years – my father loved working for himself, he loved being an entrepreneur – he married impact with his vocation. And those were all my formative lessons.

And I remember when I was young, he used to tell me to work for myself. And then I went off to university and went to undergraduate business school. And I wanted to be a corporate executive – I didn’t know what it was to be … I didn’t know what it meant being an executive. But I wanted to do it.

But probably by my mid-20s I wanted to be an entrepreneur – , I came all the way back to those lessons once I had a little bit of a taste of corporate life. I’m , “I do want to create something.”

So that was probably the most formative thing if you would dial all the way forward. And then you’re…

Mark: Can I pause you for a second?

Sukhinder: Sure.

Mark: What age did you come over from Africa? And where did you grow up in Africa?

Sukhinder: Well, first of all my parents are both Indian – but my father’s family immigrated to Uganda. My mom was raised in India, and I was born in east Africa – my parents ran a medical practice there. And then they immigrated – and so this comes to this point, right? About this immigrant mentality.

My parents immigrated to Canada relatively late in their life – my dad was probably early 40s, my mom was late 30s, maybe – they gave up prosperity in Africa to kind of start over and make sure their kids got a great education. They did their residency, they moved into an apartment, and they restarted their life.

So you didn’t have any… did you have any formative experiences in Uganda that shaped your thinking at all?

Sukhinder: I didn’t – I would say my father certainly did, but I think I was too young – I was two years old when my parents moved to Canada. But I think that… were my parents risk-takers in a classic sense? Well, no – but they took one big risk – to start over, right? And that worked out.

And then, as I said, my father lived kind of taking little and big risks every day as an entrepreneur. And I appreciate that now more than ever. That was the formative experience.

And then everything since – we can certainly go through my career – but there was some formative decisions to come to Silicon Valley at a time that in hindsight was really good. Like, I moved here in 1997 and unbeknownst to me from a macro-economic perspective – that was a great time to move to Silicon Valley, right?

The tailwinds around internet usage were lifting every tide. And it continued to do so – by the way. So of course, there’s some bigger decisions I made. Or choices I made. And some smaller ones.

But certainly, the credit goes to my dad.

Mark: So as you got into Silicon Valley and starting to navigate that – , what were some of the biggest challenges that you faced? I mean what was hard for you? And what did you have to overcome?

Sukhinder: Yeah. Let’s talk about what was easier, and then what was harder…

Mark: Sure.

Sukhinder: So, I think what was easier is finding a place that welcomed my – generally speaking – aggressiveness. A relatively meritocratic environment, where you could be in your mid-20s and be a founder, right?

So I would say, a lot of my values and how I operate were welcome. So I would say that is the macro-context. For the last 20 years, I’ve lived in an environment where who I am authentically mostly is rewarded, right?

And you say, well what are the obstacles…? And keep in mind, , I always believe that you have to have some sense of clarity about your own life. Like, the obstacles I faced… in the context of the world’s problems, these are not obstacles, right?

Mark: (laughing) I feel the same way…

Sukhinder: Yeah. And you’re , “what are the obstacles.”

I’m , “well, gee…”

So let’s put it in perspective – but in a podcast about career development and being your best self – let’s just appreciate that I know my obstacles are all put in perspective.

But I’d say there were two – number one – I mostly thrived as we talked about, but a couple times in my career, I didn’t, right? My first job in the valley I quit at six months.

Fast forward 12 years into my career – I was having lots of success – I became a first-time CEO… I was out within six months. And if I were to look at those experiences and say , what were the organizations where I didn’t thrive? I would say my values fit was fundamentally missing.

Maybe I put the what, “oh, I really want to work in this industry or at this company,” over the who. And when I put thewhat over the who – and I ended up in situations where I felt myself either subordinate to or inextricably tied to somebody with whom my values didn’t fit.

In a startup there’s no place to go, right? It’s not it’s a division where you’re , “hey, myself and this person don’t share the same worldview. I’m just going to move to another division.”

And so twice in my life, I quit startups.

Mark: Yeah, there’s one division. (laughing) make this thing work.

Sukhinder: So I would say one big obstacle set in my career – which many of us have – is , when you take a risk what do you bet on? And I would say betting on the who is a disproportionate bet for most of us. And twice I think I’ve gotten the who wrong – and we can talk about that.

So, I think that’s one macro-theme. And then I think the other thing is just recognize – I will say to people, “it’s called risk for a reason,” right? We all try and take risks. The best we can do is be a calculated risk-taker.

And so often we believe that when we succeed, or we fail it’s about us. People are , “oh, Sukhinder, you must be great.”

And I’m , “well, let’s be clear. We choose our responses to the environment we’re in.” But reading the macro headwinds and tailwinds and trying to time your entry or exit into a situation right, is itself either a huge proponent of your success, or an obstacle.

So, I would say, the other places I haven’t succeeded, it’s not because I didn’t pivot and try and iterate. Sometimes – particularly in a world of internet tailwinds and headwinds – I was too early.

My first company Yodlee we were way too early as a fintech app. Luckily for us, we survived and raised enough money. And then fintech became an enormous category, but it took us 15 years to build a public company.

My second company – Joyous – I mean, I was doing video commerce in 2010 – let me tell you – nobody believed you could sell something through video online. When I tried to raise money for my company in 2017, I couldn’t get it done. And look, the unit economics weren’t working out.

Four years later video commerce is everybody’s new sweetheart category. Everybody wants to build a video conference company.

So sometimes when we have obstacles, it’s because we think it’s all about us, but in fact, you have to be reading the tea leaves about what’s going on around you.

So, I believe in two things – I believe that a) we can position ourselves really best for success when we find people and environments in which we can thrive. And when we read the macro headwinds and tailwinds and try and ride tailwinds and identify how to pivot in headwinds.

And yet despite all that, there are some times when macro beats micro and you can be perfect on execution, but you can’t execute your way out of a bad market, right?

So, if I were to look at obstacles – some are very business driven, and some are obviously choice-driven by choices I made where in hindsight I’m like, “okay, if I had to redo that choice, what are the lessons I take away from it?”

Mark: Right. To lead a technology company, do you have to be a technology person? I mean, do you consider yourself techy? Do you understand the underlying nuts and bolts of how the tech works?

Sukhinder: Well now – I’m not an engineer, I had a business undergrad – I don’t think you have to be a technologist, but I think you have to love creative problem solving. I think you have to be able to have empathy with whoever your end-user is.

And I think you have to be curious, right? So now I know enough to be dangerous, because I’ve been a co-founder to multiple technologists. I’ve been a CEO who’s had to manage technologists. And now I guess I love product design enough that if a product team comes in to me and is designing a new service for consumers, I have a lot of opinions on the UEX, because 20 years of looking at it.

But am I technologist? No. I’m somebody who falls in love with problems around empowering or delighting people. And I have empathy for a lot of different problems, and a lot of curiosity. And now, just enough knowledge to be dangerous.

But no, I’m not a technologist,

Mark: So you’re describing some really important qualities that a CEO or a leader needs to bring to the team. And so I’d love to kind of get your take on when you look at the role of the leader or the chief executive, what should you not do? And what should you do more of?

Sukhinder: Yeah, it’s a great question so… and keep in mind, I show up in most rooms as one of two types of leaders, depending on the situation – number one, is I’ve been a founder three times – so I have a lot of founder genes, you know what I mean? For good or for bad.

Mark: Founder as a CEO is going to be different than a hired gun CEO…

Sukhinder: You got it, right? So I’ve been a founder CEO and I’ve been a hired gun CEO. So, I’m going to try and identify what’s in common. I’d say when I show up with my founder hat on, it’s mostly because I love to create. And start things from scratch. And I get a lot of creative energy.

And then when I’ve been a hired gun CEO, it’s because I can own the end to end of kind of creating a delightful experience. And I can scale it.

I get a lot of leadership joy from trying to solve different problems at the same time – in parallel. It’s very intellectually stimulating.

What should a leader do more of? Well, I say to most leaders… if I were to give you one principle, it would go something like this – you enter most situations as a leader presuming that your best and highest use is to manage other people. And I think in many cases the best and highest use of a leader is to have other people manage you.

People are like, “well, what do you mean?” Well, leaders think that the leverage… especially if you’re a first-time leader, you think the leverage is… “I’m going to manage people directly and get the most out of them.”

But sometimes getting the most out of them is letting other people author and come to you with their vision. And then to add your insight on top of it.

And many leaders – myself included – I have lots of opinions. If you walk into an office with me, and you have no opinion – I always say, “you’re going to leave with my opinion.”

I’m not really sure that’s the most empowered place to be for you or me, because then I am directly managing you all the time, telling you what to do…

And most leaders would tell you they get frustrated… they feel like they have to drive everything.

Yet, the definition of leadership for a lot of people is managing people. And I’m like, “okay, just stop for a moment. Imagine if you said to everybody ‘your job is to manage me. Now here’s what that means – you walk into a room with your agenda, you walk in with your vision and your questions. You control the conversation with me.’”

Which is not the way most people think about an interaction with their CEO – “’and then tell me what questions you have. And then we’re going to get into a really fun dialogue.’”

Now I will say to people, “’by the way if you want to come when your plan is perfect, and then you’re offended if I give you any feedback, that’s probably not a great way to go.’”

But if you come in with no plan, you’re going to leave with my plan. Also not a very empowered place to be. ‘How about you come when you’re 75% baked, and then you can actually actively manage me. You have conviction, you have a thesis. You have ideas, you have questions…’”

And for me that’s a really fun interaction – it’s really leveraged – we have a really quick, efficient, effective conversation. I learn a lot. Maybe I can give some insight that’s useful.

And you will leave feeling like, “oh, maybe my plan is a little bit better.” Or “I thought about this.” Or “Sukhinder challenged me this way.”

But it’s still “I came in holding my own and empowered.” So I think about one thing that people should do more of, it’s try and turn around that principle. Don’t presume that your main job as a leader is to manage people tightly. What would happen if you ask people to manage you in a structured way?

And come in empowered, right? But that means empowered prepared for other things… it kind of shifts the dialogue.

So that’s the thing I think you should do more of. I call that “you manage me, or I manage you” principal. Which would you prefer? (laughing) do you want to manage me, or do you want me to manage you? Honestly.

And then I would say the other one that I think people should do less of I think leaders believe they have to be perfect sometimes. And I think what people value is – constructively nobody wants to be spooked – authenticity, transparency, imperfection… because it gives other people the permission to do the same.

So I think if the example we set as leaders is “you have to be perfect” or “I need to look perfect,” it sets a standard where everybody thinks they need to look perfect. And people don’t take risks when they feel they need to be perfect. People don’t pivot and iterate. They don’t come to you and say, “my range of estimates on this product launch is actually we could do 10 million next quarter, we could do 30.”

“And the variation in that those numbers is going to be this and this and this situation. So I’m going to try and manage for them.”

But if you come in and you say “the only good answer for Sukhinder, is it has to be 30. And I’m going to protect that it’s 30.” Think about all the dynamics that creates, right? So I believe less of perfection, more of authenticity, transparency, being clear about the volatility in the situation. While having a solution mindset.

Mark: I love that. In fact, I wrote a book about that topic I called it “staring down the wolf” and the premise is kind of what you just said is that oftentimes leaders are the limiting factor in the team. Because they do think they’re supposed to have all the answers. And they suck all the oxygen out of the room.

Sukhinder: Yeah.

Mark: And so I broke it down into a few different principles, and I used my glorious screw-ups to kind of highlight how not to do things.

But one of the things that I really talk about is it takes great courage as a leader to admit that you don’t have all the answers… and to admit that you have biases and also sometimes traumatic things that cause you to react in certain ways.

Or project certain things onto people. Because guess what? You’re human.

Sukhinder: Yeah, exactly…

Mark: And that’s what we mean by authenticity, is to recognize that you’re a freaking human. Who also happens to be CEO that day. So get over yourself.

Sukhinder: Absolutely. Well, first of all get over yourself is a pretty good principal. And look I love that you talked to talk about learning from your screw-ups. Make no mistake, you can probably read it right through this video – I am opinionated, I am impatient, I am a driver… so you can imagine all of the goodness of that – but you can imagine the badness of that…

Mark: Yeah, I saw a note that you scared your secretary…

Sukhinder: Somebody told me that, and I was like, “okay.” Really, that’s ridiculous. But anyway – I was 27 years old at the time so it was a weird thing to say to me.

But the point being, the derivative of my own leadership style is lots of people come in and think the only right answer is my answer, right? Or, if I have an opinion that must be the truth…

As opposed to it’s my opinion, or if I ask five questions that I must be trying to get to something. When often for me the way I learn, is I just ask lots of questions…

Mark: So you’re saying there’s an attribution bias placed on you because of your success already – your past success…

Sukhinder: Actually, I would say there’s a lot of biases placed because of my style… let’s not put it on anyone else. So I think to your point let’s go further… what should you do more of as a leader?

Be more self-aware and I would just say own your own biases to your point and your style… so that you can give people permission to say, “hey, this is who I am. This is what it’s going to be like to work with me.”

Now when I hire new leaders who are going to work closely with me, I want them to know what it’s like.

Because I’m looking for my compliment, right? I’m looking for people who understand how to hold me -and they’re not afraid of it. Look, this is who I am. That doesn’t mean it’s wrong or right, it just means that you have to be able to hold your own and give me feedback. Don’t presume that because I have this style, I think I’m always right. Or what have you.

So, I think you kind of have to own your flaws. And be relatively clear with people. I’m like, “yes, these are the good things about my style, and these are the things that can create angst.”

I learned long ago that when I’m in brainstorming mode – you think you can be in brainstorming mode as a CEO? Guess what? When you’re in brainstorming mode as a CEO, everybody walks out of the room and thinks like, “we have to do that, and that, and that, and that.”

Mark: I am such a victim of that. Oh my gosh. I have to recluse myself, because everyone takes it as a direction.

I’m like “no wait, wait, wait. I’m just talking.”

Sukhinder: (laughing) yeah… “wait, I was just brainstorming. Hold on a second, right?” But were all the derivative impacts would have as CEO, so you can’t just think that’s on other people. That’s on us.

So, you kind of want to create environments where you acknowledge your own style and what that might be doing. And you also want to create structures around it.

So, the last thing I would just say is for somebody like my own style and my team… you were saying – you wrote a book based on your flaws. There’s no doubt, it’s very easy for a whole room to attune to what I’m saying, because I have a lot to say on anything.

The converse is if I actively want to make the team brainstorm, I literally have to pick myself up out of the seat on the table I’m sitting in as the CEO – and I go to the white board, and I pick up a pad. And I’m “okay, what do you think?”

I have to move myself mentally to scribe, in order to get people to shift out of that mode where everybody is turned to me and listening to what I have to say. Those are the types of tactics you have to use, for yourself, once you know your style as a leader.

So it’s not on your team, it’s on you… (laughing) to be clear…



Mark: How have you handled the negative nilly, or the individual on your team who happens to be the person who’s bringing everyone else down to his or her lowest common denominator? Because that’s something I learned in the SEAL teams – the teams that are firing on all cylinders, that are operating at an elite level, is where everyone – every individual – is willing to admit their own shit.

Every individual is willing to receive feedback, every individual is willing to check their ego at the door. And the teams that couldn’t operate that way, it was often just one guy. And they didn’t have the courage to get him off the team.

So how do you handle that?

Sukhinder: Well, I think you’ve hit it. The reality is once you have been a leader long enough – to your point – you learn that the hardest cost and the regrets we often have are like when there was a person who should have been given feedback. Or who should move on.

Or wasn’t a fit and wasn’t able to take the feedback. And after repeated attempts, we all sort of shy away from that conversation.

And the cost to the organization is quite high. So to answer your question, I’m probably pretty similar to you. I’m like, “okay, how do you get this person feedback…”

But keep in mind, I think when we say you’ve got to get that person feedback, it’s hard to give people feedback once. You have to give people feedback early and often.

You can’t say “it’s on this person.” Well, I don’t know about you, do you know how many boards I’ve sat on where the CEO never gets feedback from the board? It’s incredible how scared we are to give feedback.

So, you can’t just put it on that person if you’ve not given them the opportunity for feedback early, often… and what I’ve often found is if you can find them receptive to feedback and coaching – like we all are, I have to take a lot of coaching – I’ve had it all my life, I continue to have a coach.

Then, I think it’s redeemable. But I always think that what is irredeemable is people who put themselves ahead of the team. That’s really hard. Somebody who’s optimizing for the I, not the we.

If it’s somebody who’s inherently pessimistic, but well-intentioned, then I think it might be coachable if you give them feedback and they want to take it.

I think really hard to get out of team, is the person who’s always optimizing for the I and is negative. That’s a really…

Mark: That’s problematic. Yeah, that’s a deep character issue.

Sukhinder: Yeah, that’s it. And you do see that. People are optimizing for what makes them look good.

But I think what you’re identifying is if there’s a toxicity in a team driven by one individual you have no choice but to get into a feedback cycle with them. And a pretty definitive time frame in which to solve it.

I don’t know of any better… I have no secret sauce other than you got to do the hard work of…

Mark: Gotta have the critical conversations…

You mentioned coaching… and coaching and team development, and personal development or leadership development… whatever label you want to put on it are starting to become more and more – I was going to say “popular” – but almost looked at as necessary – especially kind of post-pandemic. Because what seemed to be working before doesn’t seem to be working now.

And so I’m curious have you leveraged coaching in your organization? Besides yourself – have you thought, or do you bring coaching into your organization? Do you have a developmental model? What does that look like for you guys?

Sukhinder: Well, I’ll tell you what it’s historically looked when I tested Stub hub, and what I think it’ll be what I test in whatever company I run next as well because I think it has some teeth. So I’ll come to in a moment.

My own coach came from YPO. So I was in YPO 2009 – almost 11 years ago – because I was a first time CEO and looking to figure it out.

And ultimately, I thought YPO was good, but it was very time heavy. So I kept the coach and left YPO. And that coach has been with me for 11 years.

And so the first thing I did is – because we talked about whatever your strengths are as a leader, likely to have their all their negative ramifications as well, right? So, I would bring my coach into every organization I was in to meet my leadership team and do my 360. Because I didn’t trust that the board would do it, and often boards don’t. Particularly of startups – they’re very unorganized – generally, unfortunately.

They’re scared to give their CEO’s feedback – particularly when their CEOs are founders – they’re even more scared, which is not helpful, right? So it’s the opposite of early and often feedback. It’s zero feedback.

So if you’re a CEO, where do you get your feedback? And nobody wants to tell you directly… so I brought my coach in, and I had my coach interview my leadership team.

Because I knew two things would be true – number one) they would trust him or her to take the feedback, anonymize it and deliver it to me in the way that it would best land. And I knew that that person had my best intentions at heart, and I didn’t have to worry about whatever they were going to say to me, because they weren’t also sitting on my board, right? A coach is a great person to give you that feedback, because there’s no other agenda than your success. You don’t have to worry about any of that stuff.

So my first model was bringing a coach in to get feedback on me. Then to your point – you’re like how do you create a feedback system for your organization… so first of all, at any large organization, I’ve always had learning and development organizations where you manage your training and so on.

But I think as you get into the leadership levels – coaching, I think, is historically done as a one-on-one thing… and then what we tried at Stub hub which started to work.

And then we ended up selling the company, but I want to try again is for my leadership team my coach created a mini-YPO type model – and I think this is why it’s so powerful, and it was starting to work…

So, this is one thing for all of you to try if you have any curiosity around this…

Mark: More than curiosity – I mean, I can’t wait to hear this… but this is what we do as a company.

Sukhinder: Yeah, exactly. You’re hitting on it. So here’s the thing – most people who I’ve had in my career will come to me and say “Sukhinder, you have an executive coach. I’m an SVP – I want an executive coach.”

So you pay for them to get one-on-one coaching… but that coach is missing the context of the organization…

Mark: That’s right.

Sukhinder: So, that’s really hard. So, what you really want is a coach who maybe knows all the execs – so they can understand the back channels and the politics… and each person’s personality and gifts. And then they can facilitate your team, because they have the context.

So I found one) maybe a coach who is there and understands the context of the organization is a more interesting coaching model so they’re coaching several members of the team. So there’s synergy, that’s one option.

But the second thing my coach did – and we had multiple different my coach was at Stub hub, but at one point had an external coaching organization… so, this idea that you’re coaching a team as well as individuals – there’s synergy there.

But then number two) what my coach did, I thought, was brilliant. Is he created many YPO forums – where they peer coach each other.

So let’s say they’re all having trouble with Sukhinder. As long as I’m comfortable in them all having a peer coaching session, where they’re coaching each other – what I know is they’re teaching each other how they navigate situations. And that’s pretty powerful, right?

So, the next organization I go to – I want to continue that model. Because I think there’s something pretty powerful about bringing leaders together to peer coach each other. They’re all learning from each other – as well as the facilitation of having a coach there, to give them one-on-one coaching when they need it. But with context.

Because I think otherwise you have your coach, I have my coach… we all have our coaches, but that doesn’t help the team dynamic in a company. Which is – by the way – where all the challenges are. The challenges aren’t like, “am I great?” Or “what could I do better?”

The challenge is “I’m in a situation where I’m getting triggered. Somebody else has their agenda, I have my agenda – we’re butting heads.” Most of our challenges come in team situations, with other people who are also trying to make their way through the world. And together we have to accomplish something.

So I really like this model.

Mark: It’s a great model. In fact, what I was alluding to is we’ve been doing this now for several years as a service. Unbeatable. So what we do is we go into organizations and our coaches will then go and form with the support of the team – the teams.

And then those internal teams have curator facilitated sessions with our coach, but then they also have sessions alone, where it’s just peer group. And then our whole objective is not just to help them work out their interpersonal issues and whatnot, but also to help them grow individually and as a team. So we work on that vertical growth, so we’re giving them the skillful means to use mindfulness and breath work and stress reduction strategies like that.

And then also get their exercise and their sleep, and all the things that that degrade performance will lead to breakdowns over time. So we bring those specialized skills in the team environment.

And then on top of that, they get all these interpersonal dynamics and having the crucial conversations in that facilitated crucible or the container of the forum of the group is really, really powerful.

Sukhinder: It’s very powerful. I think the key is how do you keep it going in a frequency model? Because what happens is somebody will parachute in a team and then you’ll have this moment of truth and sharing, and then they disappear, right? And a lot of the conflict and the frustration is in the day-to-day.

So I like this idea of some ongoing support, right? And some structure to a point – so they can even solve among themselves, because often as a leader you end up diving in to solve among two people, right? And what you want them to do is have the skill set to navigate with each other.

Mark: That’s right, yeah. That’s neat – one of the principles that I’ve kind of been working on now is I think as we head into the VUCA world – which all have been VUCA – but it just it’s kind of been hidden under the surface – but there is no one person or one leader or one genius who can see through the complexity and deal with the volatility and the uncertainty…

So the team is the new leader. And to your point – the team should be the voice; the team should be the main thing… not me versus them – it’s we. And so that’s a mindset shift – so it takes a little bit of time to get everyone kind of into that model – “hey, this is about us. It’s about the mission first – it’s about the team, second.”

“Within the team, my teammates are first and I’m second.”

Sukhinder: Yeah, I mean that is… there are a few different leaps in there to be made, right? And you would know this well, because of your background. It’s ironic, because people always say to me “Sukhinder, how do you form the relationships at work?”

And I always chuckle, I’m like, “all the relationships I have at work given my natural intensity where I don’t stop and necessarily ask people about their families which sounds terrible, but my head is filled with stuff – I come into work and I’ve got to get this all done.

But I always say to people I have the best relationships, because I’ve been through fire with people… I don’t know how else to describe it… often, we go through these experiences together and as a result of going through this… solving this problem together, we are bonded.

Anyway, so I totally get it. I wouldn’t say I’m as great at it as you are, but I think as a leader so much happens when you solve a hard problem together that gets you bound and committed. Because you’re sort of on a mission together. And by virtue of being on that mission, you then end up with these kinds of unbreakable bonds. Which is pretty cool.

Mark: Right.

“Choose Possibility.” So where did this book come from and what’s your main message, and the reason why you wrote it?

Sukhinder: Well, I’ve been wanting to write this book for almost 10 years. And I think the main reason I wrote it is as follows – most people – I think – have an ill-conceived notion of what risk is.

And you say, “what does that mean?”

What I observe when people ask me how I’m successful or what have you, is they want to identify the single choice I made. The single choice. Because they imagine – and by the way although all the stories of risk we celebrate, seem quite binary from the outside – think about all the risk takers you celebrate or look to.

People think of people as mighty risk takers, and there must have been one choice that was the difference between success and failure.

And I was “not really.” If I thought that there was just one choice, I’d put a lot of pressure on myself to get it right. And by the way, I did.

But what I really found throughout my career is it was about my commitment to continually choosing that I found success. So if you looked at any single choice I made – some might fail, some might succeed, right?

So if you measure yourself on a one-time choice, it’s very hard to think about becoming a risk taker.

But if you feel risk-taking is about the inevitability that the relationship between risk and reward is actually far from linear, it’s not the bigger risk you take – the bigger the reward…

It’s that you start choosing and you keep choosing. And there’s probably a hundred or a thousand choices between you and the ultimate reward. And so choosing is not about choosing once. Choosing is about continuing to choose the next possibility, and that’s how success unlocks.

It’s not a single choice – it’s not binary – and I call that the myth of the single choice. People live on this… one perfect choice they’re going to make… one perfect risk, one massive risk between abject failure and immense success.

And I’m like, “it doesn’t really unwind that way.” I know that, because I’ve made hundreds of choices and taken hundreds of risks.

Mark: Right. And all those choices influence the quality – all the small choices influence the quality of the big choices you get to make…

Sukhinder: You got it, right? And so why would you think…? So, if you think that between you and success is a big choice and a big failure, it’s pretty daunting. You never choose. You just think, “I’ll choose tomorrow. I will make a more perfect choice tomorrow.”

Like, you keep kicking the can down the road.

Mark: Yeah, or the world will make a choice for you…

Sukhinder: Yeah, and that’s the problem, right? The world makes a choice for you… and so, you can’t really avoid risk, you might as well embrace risk…

But not risk as a one-off – risk as a process. That’s the main message of the book. Risk is a process, not a one-off. It’s a learnable skill and there are repeatable things you can learn about how to become a great risk taker.

That doesn’t mean you win every time. It means you get compounding benefits, and you win overall.

Mark: That’s right.

Sukhinder: And I don’t think people think about choice that way. I think they put a lot of pressure on the first choice.



Mark: I think I read a stat recently – 40 some odd percent of people are wanting to change their careers right now. Because of the pandemic. They’ve had a lot of time to think, they’ve had to face a lot of suffering and that that causes us to think “what’s important in my life?”

But it’s risky, right? There’s financial risk, there’s reputational risk – there’s all sorts of things. So, I think right now – more than ever – we need to learn how to be risk tolerant.

Sukhinder: Well, here’s the irony of the whole thing. I sold this book before the pandemic, like literally we had sold Stub hub, announced the sale – it was a great outcome for the company, but I was sad, because I wasn’t going to get to be CEO of the consolidated company, right? Very clear that when you’re the acquired as the CEO of the company that got acquired – you may come or go.

And in that case, I wasn’t, and I was disappointed. I was two years into the job, we were just getting started. And so I’d wanted to write this book, and I sold the book before the pandemic.

And then the pandemic happened. And two things became true in the pandemic that make this book even more relevant than ever. Number one) when we’re looking to avoid harm, we often become more agile and risk-taking than we are when we’re safe.

So let’s just think about that for a moment. You try and build a culture where people take risks when they’re safe, and they have every reason to. But they can imagine all the downside.

And then comes the day when you have what’s called a coconut event. Coconut event is literally… it’s a research term…

Mark: The coconut falls on your head?

Sukhinder: You got it. It kills you, right? And so people think coconut events never happen, but unfortunately, they actually do happen more often than you think.

But the coconut event comes, and all of a sudden you have to respond. And people learn their agility and their real ability to take risks and make fast decisions and choices when they’re trying to avoid harm, right?

So it’s ironic that when we want to achieve ambitions, we’re afraid to take risks. Yet when we’re forced between having further harm or doing nothing, we pivot and find our way out, right? And we learn our agility.

So actually the reason this book is so relevant is covid taught us a lot about our ability to respond and be agile and take risks… at the threat of further harm.

Yet most risk taking opportunities we have in our day-to-day lives are for upside. Yet we fail to take them. So I’m like, “okay, this is your moment. You’ve learned something about your ability to be agile and take risks.”

Yes, to avoid harm. But in that, there’s the opportunity… it’s like, “okay, well now you have an opportunity to take risk for the upside again.”

Mark: That’s interesting. What are some of the actionable steps that you offer readers to help them learn to take risks?

Sukhinder: Well, I has three sorts of main – I would say – areas of focus.

Number one is get going. How do you literally – to your point – get going? And I often say to people number one) you’ve got to find an opportunity to take risks every day. And people are like, “well, what do you mean? I don’t have a big career ambition every day?”

I’m like, “well, hold on. Let’s just break this down.” You can take risks for one of four reasons: achieve an ambition – that’s what most people think about it – to learn – risk to learn are almost never a wrong risk. Discovery – literally discovery of opportunity. Before you make the big choice – what risks are you taking to discover what’s possible?

People don’t really consider that a risk, but you could make that choice today. It’s not even asking you to choose yet, it’s just asking you to invest a little bit of time to discover, right? It’s not even a big risk to take.

And then fourth, to just avoid harm – that’s what we think about what we just went through with the pandemic – we had to make a quick action to avoid harm.

So, I’ve just given you four – you should be able to find a micro-risk that you can take today and start practicing. Number two, I always say to people put… I would say if you don’t know quite what to do, get proximate before you start planning.

Most people think that taking a risk starts with a plan. And they create a plan and write it down and have this perfect plan. And they research and so on. But it’s pretty abstract, right? So if you don’t even know yet what to do – get proximate to something you’re interested in. That’s it. Get proximate.

You want to be an entrepreneur – get proximate. You can read a book, you can go spend an evening at an incubator and listen, you can shadow with a friend who’s starting a company – moonlight…

Whatever you’re going to do, get proximate. Because it turns out that we don’t know how to achieve what we want to achieve, getting proximate gets you a lot of data. It’s just a risk of your time, right?

Mark: Pause there. Two quick things that come to me from my SEAL training. One is this idea that no plan survives contact with the enemy – the enemy gets to make a choice, right? So why spend all the time planning, when it’s not going to make any sense anyways as soon as you execute it.

And then the other one is doubt is eliminated through action. So getting proximate – that’s the same thing. Move toward the sound of the gunfire – that’s where the answers are. It’s not running in the opposite direction.

Sukhinder: Absolutely. And then the third way to get started is sort of what you noted – I said, if you put proximity before planning, well then, you’re like, “well, what’s the plan.” I was like, “the best plan to me is a whiteboard plan.”

It could be on your iPhone, it could be on a whiteboard – I mean, a whiteboard or an iPhone… it is meant to be erased and modified as you go. It’s the absence of these long detailed plans… people put in OKRS -objectives and key results – and quarterly plans and annual planning…

I’m like, “what would happen if your plan was literally a whiteboard plan or an iPhone plan. And then you can keep modifying it to your point as you go, right?

So those are some of the tips and then the middle of the book is really getting smarter, how to become a really calculated risk taker as you start to contemplate bigger choices. And then the third part of the book is really the models, how to reframe your mental model for once you’ve made a big choice. How to optimize your execution – those are other risks we take – execution risk. To really have the impact we want once we’ve made a big choice.

And then also the way risk and reward unfolds. It’s not quite the linear relationship you imagine, but there are patterns to how it unfolds.

So those are some of the things we talked about in the book.

Mark: And reframing your mental model – what are some of the frames that you found to be really effective?

Sukhinder: Well, it’s ironic that I say to people – I just went through obviously the Stub hub, CEO experience and then the sale, and then the pandemic. And it’s really weird. If you were to look at that cycle of my life and then rewind and if I were to put my career arcs – highlights and lowlights – on a graph… you would find pretty quickly that it looks a lot like a sine wave.

So it doesn’t look… like, people want to call it a straight line, because it’s easier to just look at the peaks, right? But if I were to show you the graph of my career, it’s a sine wave so it’s the same freaking sine wave, just repeating.

And yes, over the course of my career that sine wave is up and to the right – it’s not lateral, but it’s a series of repeating experiences… that’s why I say risk is a process and it is repeatable. And your goal is obviously over the course of a lifetime to be moving up and to the right with your choices. And having increased impact with your choice set.

But you will still experience the same volatility in your career. You think volatility goes away the more senior you get? It doesn’t.

Mark: It does not, does it?

Sukhinder: It keeps repeating… but it repeats in an arc that gives you some confidence at your low points that there is an end that will come. And at your high points it sort of reminds you, you’re not all that you think you are, so buyer beware if you think it’s all about you. Like, covid will come along and knock you on your ass. And remind you that you’re not nearly as great as you think you are.

But then it will also teach you that you can recover. And you have way more skills than you thought possible in times of difficulty.

Mark: Right. This is more interesting than anything else, but you’re Indian by… your heritage – the yogi tradition says or claims that these ups and downs in our lives happen in roughly seven year increments or seven year time frames.

And when I’ve looked at my life, it’s kind of proven to be sort of six to eight years – I’m riding high and then all of a sudden there’s kind of this valley I started descending into.

Sukhinder: It’s so funny you say this – I would say when people ask me my cycles, they’re typically five to seven years…

Mark: There. Yeah. It’s gonna be a little bit different for everybody, but that’s fascinating…

Sukhinder: Yeah, that’s probably the one framework that I feel is true and think about how it unfolds. Now again, I think the challenge for most people listening to a podcast or reading a book is “okay, this is all well and good, but give me some pragmatic tips for how I navigate it,” right?

And so hopefully there are both frameworks, but more importantly there’s things you can do to build this muscle but trusting in the cycles is an important thing to recognize.

Mark: Right, and the sine wave doesn’t slant upwards unless you have that relentless commitment to learning from both the down cycles as well as the up cycles. Because then the decisions become a little bit more refined every time. You still have the ups and downs, but they’re more refined for whatever you’re trying to execute, to achieve.

Sukhinder: Absolutely. And just to be clear there’s one other thing that’s really important in cycles, right? It goes up and to the right because you have to play a game of probabilities. So you have to be focused in any given cycle – you know this – you want to make a choice, maximize its impact, get to the rewards you imagined – or a different reward or impact – but you’re playing through a cycle with focus. In a given cycle.

But it’s true that the best… the people who are successful in any realm – whether you’re an NBA athlete, whether you’re playing major league baseball, whether you’re a SEAL, whether you’re a CEO, right?

Enduringly there are probabilities – this means that you have to play through enough cycles to have a winning season – it’s not one game, right?

And that doesn’t mean the probabilities don’t matter – if your win/loss ratio is not in the upper quartile of whatever you’re playing, yeah, you can go sideways – so, you are playing to win. Make no mistake.

But you have to understand that probabilities might be three out of ten, might be a winning season or a winning batting average, if you’re a baseball player…

The odds are just different in any given category in which you play. So it doesn’t mean you have to be perfect. It just means that at the top of your game, you need to understand there are probabilities, but it’s all dependent on how many at-bats you get and take.

And then how you optimize each at bat.

Mark: That’s fascinating. So and what’s next for you?

Sukhinder: I don’t know. I love to lead, so I’m sure there will be one more cycle of leadership for me. And another leadership challenge. As I noted – I loved running Stub hub. I’ve loved every leadership opportunity I’ve had.

I loved being an entrepreneur so… yeah, I have one more in me at least. I don’t know what it is I’ll run next, but I’m excited to figure that out. And I mostly wanted to take…

I used my covid time to really do something else that was meaningful for me, which was write this book, right? Before that next chapter begins, I felt like this might be my opportunity to put pen to paper on these ideas that hopefully can unlock for other people the kind of success they want to have across a career.

Mark: Right. Obviously, you’re very passionate about leadership and growing organizations and the people and the mission. What would you consider to be your impact mission – if you were to pan out and say, “how am I making the world a better place?” What would you consider that to be?

Sukhinder: I’d say two things – first of all, I love building services that empower, delight users… and in some cases those have been startups that succeeded like Yodlee or didn’t make all their impact Joyous but we’re the first of their kind…

Or went all the way, right? I mean, I’ve had all sorts of experiences where I’ve been able to build services that were either the first of their kind, or actually went on to be the winning service. That changed people’s lives in either a happiness way – I love platforms that purely delight people, make people happy – Joyous made people happy through shopping, Stub hub made people happy through live experiences, Yodlee empowered people in their financial lives, the board list empowers people to get access to leadership opportunity…

So I just love creating services like that. So that’s one level of impact I hope that I’ve had.

But the second is as important. In running organizations and teams and being a leader, I really hope that my impact has been that I got to work with a tremendous number of tremendously talented people and accelerate their impact. I mean, that gives me a lot of joy.

I feel really privileged to work with really smart, awesome people in almost every job I’ve been at. Privileged to be their leader… but also feel like my unique opportunity is to help them accelerate their own journey, right? And if I’ve been a part of that, that makes me feel good. It makes me feel good that maybe one day people will say, “oh okay, I was going to get there anyway, but Sukhinder helped me get there faster.” Or “something that she said unlocked.”

I would like that to be the other impact that I could point to at the end of my life.

Mark: That’s awesome. Sounds you’re already doing that. So – is that the website that people can learn about the book?

Sukhinder: Yeah, they can learn about the book. You can take a risk-taking quiz on your natural style as a risk-taker. Just get yourself thinking about how to do it.

You can obviously buy the book or download the book, if you like audible. It’s out august 17th and most importantly I hope it gets people thinking about how to unlock their own journey.

Mark: Right, well thank you so much for your time. Thank you for your contribution and for being on the Unbeatable Mind podcast, Sukhinder.

It’s just been a delightful conversation. Really appreciate it.

Sukhinder: Thanks so much.

Mark: Yeah. Thank you. Hooyah.

All right folks. That’s Sukhinder Singh Cassidy. Check out her book “Choose Possibility.” You can learn more at… take a risk-taking profile…

Yeah, let’s go improve our chances of having better possibilities, so we have that upward arc – continue our growth. And until next time thanks for being here, thanks for your support.

This is the Unbeatable Mind podcast. Stay focused and be unbeatable.


Divine out.

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