#110—Sukhinder Singh Cassidy: Embracing Risk, Agility, and Resilience for Success

Sukhinder Sing Cassidy is the leader of the growth and performance of Xero globally. With more than 25 years’ experience in Silicon Valley as a CEO, digital leader and board member, she has experienced building and scaling global companies including Google, Amazon, Yodlee, Joyus and StubHub. She currently serves on the board of publicly traded fintech, Upstart with previous experience serving on the boards of Ericsson, Trip Advisor, Urban Outfitters, Stitchfix and J.Crew. 

Working across such a diverse, prominent portfolio of companies has given Sukhinder a unique counter-perspective on how leaders and business owners look at risk and reward. Her book, Choose Possibility: Take Risks and Thrive (Even When You Fail) sheds light and dives deep into what she’s learned in her extensive career as a leader in tech, where risk-taking and volatility is the norm.
 
In this discussion, we journey through the art of risk-taking and decision-making, with its intricate interplay of creating a portfolio of bets, understanding variability, and fostering an environment that embraces ambiguity and iteration.

In this episode, she shares:

• The interrelation between possibility and decision-making, and how it’s too-often wrapped up in the “myth of the single choice,” as she calls it 
• How taking a big risk often starts with building and evaluating a portfolio of small possibilities—and how you build this 
• How, as a leader, you shouldn't force people to give you false precision—which often results in failures, plus three more mistakes leaders make that inhibit risk-taking and the exploring of possibilities 
• How the best risk-takers aren’t successful from an absence of fear, but rather, by learning to master what Sukhinder calls “the universal risk equation.” 

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Episode Timeline:

00:00—Highlight from today's episode
1:14—Introducing Sukhinder + the topic of today’s episode
3:06—If you really know me, you know that...
4:10—What's your definition of strategy?
5:26—Why did you name your book, Choose Possibility?
6:53—What is the "risk of the single myth"?
10:18—What advice do you have for someone that realizes they're falling into the trap of narrowing on too few ideas?
12:00—How do you know if you have too few or too many ideas?
15:18—What are the first steps someone should take in pursuing new ideas?
16:48—How should leaders create a risk-taking environment?
19:36—Could you talk to us about the psychological impact of taking small bets?
21:59—What is "the universal risk equation"?
25:09—What can a company do at zero to maintain agility as they grow?

27:55—How can people follow you and continue learning from you?

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Additional Resources:

choosepossibility.com book
LinkedIn: https://www.linkedin.com/in/sukhinders
Twitter: https://twitter.com/sukhindersingh

All content © 2024 Outthinkers.

Thank you to our executive producer Zach Ness, our producer Nazanin Homayoun Jam and our editor James Pearce. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening.

Follow us at outthinker.com/podcast

Transcript

Kaihan Krippendorff: Sukhinder, thank you so much for being on the podcast. It's great to be with you.
 
 Sukhinder Singh Cassidy: Thank you so much for having me.
 
 Kaihan Krippendorff: We have so much that I wanna talk about from your role as an entrepreneur and that start up and contrasting that you being an entrepreneur, you being a CEO, you being on the board, you've done everything from licking stamps to just advising people to lick stamps right all the range in between. But I do wanna start with 2 questions that I start my podcast with always. The first is just for us to get you know you a little bit better personally. Could you complete this sentence for me? If you really know me, you know that.
 
 Sukhinder Singh Cassidy: If you really know me, you know that I love to bake, knit, and play tennis, you can get me to cry at a moment's notice by saying something.
 
 Kaihan Krippendorff: Wow. Bake, knit, and what was the third 1?
 
 Sukhinder Singh Cassidy: Play tennis.
 
 Kaihan Krippendorff: Play tennis. Awesome. I'm looking for a commonality between them, but it doesn't matter.
 
 Sukhinder Singh Cassidy: That's hilarious. My ears are enough.
 
 Kaihan Krippendorff: Yeah. Yeah. As you say, like, put you know, with regard to career, after the fact, you can thread the logic through, but that's not what gave it to you.
 
 Sukhinder Singh Cassidy: Yeah. Yeah.
 
 Kaihan Krippendorff: And what is your definition of strategy?
 
 Sukhinder Singh Cassidy: My definition of strategy is, like, living, working, rough plan of where you wanted, it evolves.
 
 Kaihan Krippendorff: And tell us more about why you say rough plan.
 
 Sukhinder Singh Cassidy: Because life never goes as you wanted to. And so, you know, as you know, and many people on this podcast. Now you can write a perfect deep piece of strategy on paper, but it sort of presumes the world is constant and conditions are constant, but that's just never true. And so it looks wonderful, and you have a destination, and it's only as you start going that, you know, you get tailwinds or headwinds. Somebody gets off the bus.
 
 Somebody gets on the bus. What looked easy from afar is hard from within. And so get there by sort of, you know, roughly thinking about where you wanna go, and then you just keep adjusting. By the way, you make it all the way there, you may not. But, you know, I'm never 1 to not have a purpose at the end, but, I guess, I've been smacked around enough the life.
 
 No. But it's just never like that.
 
 Kaihan Krippendorff: So, like, taking it a scream, you could say, hey, if it's messy how we're gonna get there, let me set the goal and let me just hope or let me just plan, but you break down some really practical things that we can do as decision makers to be an action despite the messiness. If you don't mind me maybe just opening up with, it took me some reading of your books, I'm listening to podcasts to really appreciate why you named the book, what you named the book. And so could you tell us why choose possibility?
 
 Sukhinder Singh Cassidy: Sure. Well, I I named the book two's possibility on the thesis that we're always aiming ourselves towards the next possibility and winning comes by choosing through successes and failures. And so the way I think about the world It's very simple. You know, you have a big goal, whatever it is. But, like, let's just talk professionally.
 
 You have a big goal for yourself or, you know, a business, and you said it. Okay. You decide you're gonna you know, take this you're not done when you said it. Right? Then all the work begins.
 
 And so then you are just picking your way through smaller choices. Make a choice, see the results, you know, you either get learning, you get the results you want, or learning, and then you choose again. And the answer turns out is you just keep choosing through a bunch of obstacles And if you look even more deeply at the hero's journey, which, you know, is off to refer to. People always remember the singular what looks like big risk, big return, it's never really like that. Even in detail, the hero's journey is about a number of obstacles, you know, that a protagonist goes through on the way to, you know, the top of the mountain.
 
 So I picked to choose a possibility because you're always orienting yourself, like, through the current possibility, choose the next possibility. But if you're open to the next possibility, then you know it's not a single choice game.
 
 Kaihan Krippendorff: So what is the risk of the best myth? So I'm kind of imagining an entrepreneur working in a company, Andy Jassy, at Amazon. Right? Before he became, you know, as well known to out people outside of the tech world as you as, you know, he sees this opportunity, I think, target says, hey. Can you run our platforms?
 
 And he kinda sees this thing. Right? After the fact, the myth is he saw, and he said, we'll do this. And then it happened. And what is I understand what's wrong about the myth because it's not I can see that what's the problem with that myth?
 
 Sukhinder Singh Cassidy: Sure. The problem with that myth is sort of like you're waiting for the singular big uh-huh. Right? And if it doesn't come, if you don't get it, you don't act. And people wait to act for the single, like, light bulb idea.
 
 And as you know, Often, you take a little risk. Andy Jassy takes that call. He listens. Maybe he sets up a small team and to be like, okay. Target will try this.
 
 On the basis of a little data, he gets a little bit more conviction. Right? So people always assume somebody made a massive choice and took a massive risk. And often, people are choosing a possibility. Maybe it's a small possibility.
 
 They get themselves into action. They see the results. Right? And they keep choosing their way. And I bet you at some point, Andy and Jackie did have to make.
 
 Truly take a big risk. You know? Somewhere in there, he went to Jeff Bezos and I'm sorry. I don't know the story of AWS. I should again, but I don't.
 
 And said, Jeff, you know, I want 2000000000 dollars. Right? By the time you did that, I could guarantee he had a bunch of data points. He built conviction. He had iterated his way through a bunch of choices before he made that ask.
 
 Oh, and by the way, you know, even in the context of Amazon, no fact. 2000000000. What might be a big risk somewhere else? It's probably medium sized risk for Amazon. Because these would be the first to say, okay.
 
 We'll try it. And if we fail, like, we'll dial back. It you know, we'll shut down, you know, we'll shut down and we want. So even our assessment actually of a big risk is often that it's not as think if you can retrofit out a bit if it fails. But I think the biggest point is it likely isn't that Andy Jassy rolled in his bed 1.
 
 Tight and said, oh my god. You know? It's likely that he had an inkling of an idea, or it was bought to him by a customer or employee or some and he started, you know, playing through that idea and getting data points. Right? So most of that's I I think what's wrong with the myth of a single choice, which is what I call it in the book is many people wait to act until they have a big idea.
 
 I'm like, okay. Like, I mean, just hold on. You know, when I left Google, many people come and be like, I wanna be an entrepreneur. You know? Suki and driving Google, I wanna be an entrepreneur.
 
 I'm like, okay. Couple things here. Leave it Google's a big choice. You're leaving a lot of money on the table. Like, being an entrepreneur is really hard.
 
 So before you make the big choice, why don't you play through a bunch of small choices? And then you will today, we have to decide, but that day is not today. Like, if you want to be an entrepreneur, we'll start advising startups. If you want to be an entrepreneur, start a side hustle. If you're not willing to spend 5 hours at night doing it, I'm not sure what makes you think you should go do your day job.
 
 If you wanna be an entrepreneur, go talk to 10 startups and compare them to each other. Link, so but people are waiting for some miraculous big choice or light bulb moment, and I'm gonna say, like, hey. Why don't you start choosing your way through multiple possibilities? Take little smart risks, and then 1 day you might need to take big risk. And maybe that's a 1 way door.
 
 Even then, it you know, which is an Amazon phrase. 1 way door is 2 way door is 1. Can you go we would come back if it doesn't work? So
 
 Kaihan Krippendorff: Yes. Yeah. And there's research that shows that 1 of the big barriers for entrepreneurship and insurance for entrepreneurs as well as that we focus on too few ideas. And when you have just 1 idea, there's a French philosopher who said there's nothing more dangerous than an idea, but it's the only 1 you have. And then you just wanna keep driving that idea. Even if the you're getting feedback, it's a bad idea. So what advice do you have for someone who maybe recognizes that they're falling into that? How does 1 generate enough ideas?
 
 Sukhinder Singh Cassidy: Well, first of all, you kind of hit the key point. I would say you need a pipeline. Right? So it's sort of like, you know, I'm like, you have to build a pipeline because it's a game of probabilities. Right?
 
 And probabilities with increasing data points, that applies to a job search, that applies to an idea you think is great. Because if you only have 1, you're attached to it. Right? It's like, as I said, if you apply the same logic to your, you know, to your career or to work. If you go through and you're only advocating for 1 idea.
 
 And the data points, it's a bad idea, but it's the only idea you have. You're singularly attached to it. You have nothing to compare it to. So I think this idea of probabilities is pretty important. Now, by the way, juggling 10 ideas also hard if you have limited resources.
 
 But, you know, this is why you want a brainstorm, maybe you get down to 2 or 3, and then just be open to getting an action on 2 or 3 and getting data. Points. Right? And then building your conviction. So, again, by the time you take a bigger risk, it's a calculated risk.
 
 By the way, it might still fail. It's okay. But you're a smart risk taker. I hope the book teaches people to be smart risk takers in favor of opportunity. But mostly, I think the worst kind of risk to take is 1 risk, and let's just see what happens.
 
 I and if it fails, well, I'm never taking risk again. I'm like, oh, gosh. How about the world of probabilities?
 
 Kaihan Krippendorff: Great. Oh my gosh. Yeah. There's 5 questions that come out of that. But let me start with 1, is you just touched on a little bit.
 
 How do you know if you have too few or too many, how would you think about knowing? Yeah.
 
 Sukhinder Singh Cassidy: Well, look. First of all, again, even the process of idea generation, like, if you're inside a company. Right? The price of idea generation, get a bunch of smart people in the rule room who have different perspectives, but experience inside the company. By the way, you know, in a place like 0, lots of ideas might come out of customer support because every day for customer problems.
 
 Right? So make sure you get the right I'd say smaller set of people in the room who have diverse perspectives, but maybe experience. Right? And I get to 9 out of 10 of the ideas that we generate anyway will be generated from insights about customers or what's already working in the So first of all, there's this myth you need to come up with something totally new. Often, there's insights in your own business, as you know, about green shoot opportunities.
 
 Right? So if you get the right people around the table, you know, I would say, by the way, I don't spend my time brainstorming. Spend my time. But you know, maybe brainstorm 10 ideas. Like, look, this is now we've got, you know, as a leader.
 
 You know, they get money to test all 10. You probably need to you know, brainstorm 10, create criteria. Your criteria might be, you know, what evidence do we have already that this is working even before we put, you know, dollar of effort into it. Great the ideas. And, again, I'm a big fan of, you know, I always think of risks in this, like, corporate risk and strategy risk in this 3 buckets.
 
 It's very simple. Low hanging fruit type risk, high probability of rewards, they might be small, but you have enough data to know, like, hey. If I just put, I don't know, a million dollars more into marketing in this channel or region, I have pretty good evidence that I'm gonna get yield. Then there's sort of, like, roots that are, like, fundamentals, you know, like, medium probability, you know, medium size returns. And then you have sort of, like, I don't know.
 
 It comes to people call it your 10 percent risks, your flyers. I call it, like, obtain glory. Like, ideas that you don't mind if they'll work. But if they worked man, right, So I think about, like, brainstorming, like, all of them. It's sort of, like again, the simplest way for me to describe is college applications with your kid.
 
 You go all the way from stretch to the schools. Down to, like, safety schools. Like, you decide you're gonna test 3, 1 in each bucket. Again, I think it matters less. How perfect you are.
 
 This is like, get to 10, get to 3, figure out how many can afford to fund in some way. You know, create a time you're gonna come back together and look at the results, and then go. So and you can have a thesis that 1 of those 3 is the biggest deal. It's and then you might be right. The point is just, like, go get some data.
 
 So I don't know if that is, like, you know, but I again, I think in, you know, I guess, I think in portfolios and how we've been.
 
 Kaihan Krippendorff:. Yeah. But that's really interesting. Yeah. Portfolios. And then, you know, as you have you've written about as well, with portfolio managers, they make lots and lots of trades. And you know, as you diverse yeah. 1 of my favorite Bezos quotes is if you have a 1 in 10 chance of a hundred times payoff, you gotta take that bet every time, but you gotta be ready to lose 9 times out of 10. Right?
 
 Sukhinder Singh Cassidy: And then you have others that are 5 and 10 bets or 8 and 10 bets, and that's okay. By the way, that's the bread and bread and butter of, like, you know, how you might build yields. Right? They're all not 1 in 10 bet. That's what I mean about this kind of big choice or no choice.
 
 I'm like, no. No. There's a portfolio of choices.
 
 Kaihan Krippendorff: Right. Right. Yeah. We do see entrepreneurs and strategists if they're working inside a large established company, they lean really heavily to those first 2 buckets. And don't want to spend a lot of time investing in or talking about those that other 1.
 
 You write also about in in order to in order to have a full portfolio to generate a lot of ideas, And what are some you know, you talk, for example, about having a tribe around you. What do you suggest someone do that maybe recognizes that they need more ideas. They don't just sit in a bathtub. Right? Yeah.
 
 I do. I do.
 
 Sukhinder Singh Cassidy: Again, if you're talking corporate strategy specifically. Remember, we talked about bringing that smart and diverse group into a room. You have to, like, you wanna diaspora of type. Right? Like, I would say, like, you might want in the room the naysay or the pessimist.
 
 You might want in the room more particularly creative. That's okay at a certain stage. Right? You wanna pull, I'd say, different types of people to give you different lenses in both generate ideas and maybe even rating the downsides of those ideas. But I think that you sort of have to just first create an environment, which you can pull some of the more diverse sets types of bakers.
 
 In the company getting diverse functionally and maybe diversify personality type. Like, you know, somebody like me lives in possibility. My issue is the opposite. Right? My issue is, like, frame up 10 ideas, but, like, we're constrained.
 
 You know? So constraint is hard for me. There are other people who can see very clearly what to do inside a constrained environment. But if like, piece of paper. They're just, like, a little lost until you give them thought starters and, you know, and other things.
 
 So I think it's about the diversity of the group, the diversity of their Tanya and the diversity of their, I'd say, thinking styles, only in a brainstorming session needs some, you know, very creative, you know, I'd say things who are willing to, you know, put that into the mix.
 
 Kaihan Krippendorff: Yes. And you as a leader need to create the space for that to happen. Yes.
 
 Sukhinder Singh Cassidy: Yeah. You need to but you there's 1 important thing. I think more than creating space, what I always say to leaders at companies is if you wanna create a risk taking environment, small risk big or medium base, risk big whatever that is, you have to understand that you have to let people I'm not expect people to give you false precision. So, like, this is 1 of the things that drives me crazy. People brainstorm, and then they come out and, like, we need to set a plan that's exactly how much we're gonna generate from these IDs.
 
 I'm like, this is false precision. Nobody knows. So you can say, like, hey. CEO, I wanna take 5 percent of our resources and create ideas, and this 1 is low probability. This is medium.
 
 This is, like, could be a complete width, whatever it is and say, like, So I can give you a range of what I think will happen, but until I get an action, I don't know. So companies also need to expect depending on the nature of the badge. Allowing people to give them a range in volatility. I feel like so many leaders ask for preciseness, and I'm like and I'm like, come on, guys. Like, you could spend all your time trying to create a perfect forecast.
 
 The reality is nobody knows. Nobody by the way, even on the businesses run really well, there's still a range of volatility because of all those things we talk about. So I think as the leaders, you you wanna create an environment, you can't just go ask people to brainstorm. You ask them to do a little attitude whether it's in how much capital, for how much return, showing you a range of return profiles, showing you hypothesis, and saying, like, this is what I think. This is what I'm gonna measure.
 
 Now so this talks this is very much about the capital envelope. Right? Financial envelope when it comes to certain size risks. And, like, let's say, ink even incubation risk. Right?
 
 It's like, you just have to think about that way.
 
 Kaihan Krippendorff: Yeah, you give us 3 or 4 very specific things that a leader can do to allow for those ideas that can't yet be proven. Avoiding that proof plan execute approach versus the act learn build approach. But that's where you clarify. You're not talking, but fall that rule you're talking about taking actions that aren't you said get information, but sometimes information's not there. Right?
 
 It's not look up a report, it's not right a business case. You're talking
 
 Sukhinder Singh Cassidy: I'm talking about getting the execution mode and get it's like an MVP. Right? It's like get the most minimal data points you can to sort of keep validating. Right? And then it so, again, this podcast makes it sound like all the risk taking I'm advocating is iterative.
 
 That's, like, I think that once you've made, you know, a big choice or a small strategy choice, you're iterating your way through anyway. Sometimes that iteration precedes. Right? It's precedes a big choice to your point. Sometimes, you can only get certain data points, and then you you're forced to make a bigger call.
 
 Right? And then in any event, you're executing all the way through that. Right? And you wanna be iteratively kind of executing on that big rest even if you make the call before you had a lot of data points. But the overall point is it's iterating through small and big risks.
 
 Kaihan Krippendorff: Perfect. And you write something that I hadn't thought of before. I'm sure other people have or you this for you is just, you know, obvious to you, but for me, it was a big insight. You know, I know, like, taking lots of risk, we can diversify, reduce our risks. We can create a more predictable return by putting multiple bets and 1 thing.
 
 But you also talk about, like, the psychological impact of taking these small bets, making these small steps. Could you just describe that to us.
 
 Sukhinder Singh Cassidy: Sure. So I always say, if you think the relationship between risk and reward is the bigger the risk, the bigger the reward, I'm not sure I agree. What I mostly say is the reward for risk is not what you think it is. So we make a big choice. Again, strategy choice, career choice.
 
 Right? And then we move. We start taking action and we iterate our way, execute our way, write little choices, little actions, get the learning succeed, and keep building upon them. And 1 day, 3 or 5 years later, we're either gonna have the outcome we wanted or we won't. Okay?
 
 But in the process of iterating through things that they work and don't work. You build 2 skills that are actually long term predictors of success. 1 is agility, 1 is resilience. And with the result of agility and resilience is confidence. Right?
 
 And it's not confidence that you're always going to get the result you predicted. But it's confidence that you believe you of agency to keep moving your way through success and failure. Right? And then 1 day you look back and you'll either say, I achieved that thing or I didn't achieve take that thing. But I bet you will be more resilient, resilient, incompetent leader.
 
 Guess what the number 1 skills are that are predictors of the long term success? Not singular success. More on tympanic. You know? Go read, you know, articles.
 
 Like, I think then you're talking about 1 on, like, the path of the COC does a winding. It's people in order to risk sometimes laterally. So, like, in ways you don't expect, and that's how they got this. It wasn't linear. And so that quicker to the point, but what they've done through that nonlinear journey is built, agility, resilience, and the result of having those 2 things confident.
 
 Right? Confidence, we can deal with obstacles and failure.
 
 Kaihan Krippendorff: Yes. And I just wanna not have a question here. I just wanna accentuate how important what you just said is. If you do that for yourself, amazing transformative. If you then do it for a hundred people, 10000 people, and you can to themically build that confidence and willingness to what will that do to the, you know, amplify the fasting.
 
 What is the universal risk equation? Sounds like it applies.
 
 Sukhinder Singh Cassidy: And, by the way, just all the way back, not today, but, certainly, I would say historically, Google was you know, this is on their whole 70, 20, 10. Portfolio risk taking, training was taking, you know, the many like, literally being clear to the company about the portfolios. Right? Yep. Yep.
 
 Of returning capital now. Anyway, the universal risk equation I think you asked about is there's an equation on what that I call kind of fear of failure and FOMO. These are things you both know well. If you have take 1 take a risk, you have a fear of failure on the 1 end. You have FOMO on the other.
 
 And the and if you're FOMO, if you're missing out on something, you know, is greater than your fear of failure, likelihood is you'll act. Okay? Any risk. If your fear failure exceeds your FOMO, likely as you won't, likely as not, you won't at. So it's, you know, FOMO greater than fear failure equals you know, and if it reverses 2 equals inaction.
 
 But I think the myth for most people is that risk takers don't have fear. I'm like, no. No. They're mastering that equation. Most people think they're mastering that equation by just visualizing the positive.
 
 If you look at the worlds, I'd say, more sophisticated risk takers you know, they visualize to a certain extent to get excited about the next possibility, and then they turn themselves into pre morteming failure. This could be anyone from in my book, I write about Allan Eustace, who is an ex Googler who became in the world record holder for, you know, the longest a free fall from space. And if you, Alan, who's an engineer, he'll tell you about all of the testing he did for 5 years in a suit. And, you know, going up to the edge of this, you know, stratosphere. And so by the time he took the jump, the actual jump, which he's it didn't set the world record on.
 
 He's like, I'd only pre mortem to every use case. Right? So he got into action because he hadn't, like, spent all his time visualizing the positives, but the you know, after a mad thing, it's spend most of the time promoting failure state, which in this case is a massive risk. It's like the risk of death. Right?
 
 For most people, if you can imagine you make the choice, and the choice fails, and generate all the ideas of what you would do after. Like, let's say you quit your job and go be a startup entrepreneur, and it fails. If you can be more to them right now, what would happen after? Can you go back to a big company? Okay.
 
 Can you, you know, sort of playing it all out? Do you have a specialist who has an income? Like, okay. Then you can really figure out what you would do in all those failure states, and it helps you size the risk appropriately. And in most cases, it helps people shrink their fear of failure.
 
 To get low enough to act.
 
 Kaihan Krippendorff: Both because they realize, oh, the risk is not as bad as I thought, or they see how they can mitigate that risk and create that risk asymmetry. And you point out as well that business development people, they do a lot of focusing on what could go wrong. It's like a key success factor. Right?
 
 Sukhinder Singh Cassidy: I'm like, you know, you're in love with each other on a deal until the time the contract comes. And then third from a complete optimist to a complete pessimist. If you've ever been in a negotiation with a biz, that person. Then they just negotiate the Jesus after the contract to make sure that every failure state is attention. It makes about the other end and you do a deal and you get into action.
 
 Kaihan Krippendorff: Yep. Oh, gosh. So so much for you to go over there. I know we're I know we're reaching the top of our time with you. So I'm just gonna ask you Just 1 last quest just web question.
 
 So you are leading what looks like an amazing, fascinating company Xero, helping entrepreneurs, around the globe, and you are scaling rapidly. You've been at a huge, huge company, Google. What can a company do? Or what were you gonna do at Xero? What can a company do to maintain this kind of agility and experimentation as you get bigger?
 
 Sukhinder Singh Cassidy: Well, first and foremost, I wanna come back to that con comment I gave on Google and the way I talk about things at Xero. I'm like, look, guys. We have a portfolio of bets. In our case, it's countries and products and segments. And I'm like and there are different states of maturation, and that's okay.
 
 Our first job is to to a point, look at it like a portfolio. You know? And because that portfolio is what you all allows you to take low, medium, and high risks. So we talk a lot at 0 as we're, you know, as we'll investors. And, generally, they're like, okay.
 
 We have a portfolio of countries and products and segments, and we're gonna have to play some bets. And some of these are really high probability, and some of these are a lot probability. We can't place every bet. Right? So even what we're constrained in resources.
 
 So I think, first of all, just talking portfolio theory, you'd be surprised how much. It helps people just size and quantify. Right? The different bets 1 might k. Lower risk, lower return, low risk, high return, blah blah blah.
 
 It helped them churn it. I think that's I think that's what. Number 2 is the leader I keep coming back to it. And then I'm the third 1. You have to create conditions where people can tell you the variability of ranges on any given bat.
 
 It sounds so simple, but it's true. It drives me more crazy when people come in with, like, a plan on paper and, like, they spent weeks trying to get the precise number for forecast. I'm like, You don't know. You don't know. It's early.
 
 Just give me a range so we can plan for the range. Like, you just give me spend, like, half as much time playing for the range. Tell me the range. I will accept a range, and then go get it to action. And, like, because all of this perfecting of your plan on paper that takes weeks, if a leader expects a perfect plan.
 
 From something with highly imperfect data, I think it's I think it's it it's not creating conditions for for agility. And then I I always say to my teams. It's the most simple 1. Take little risks every day. I'm like, if you're sitting in a meeting and, you know, you don't understand something to speak up.
 
 It's a little risk. You know, I call that ego risk. What's the worst that can happen? The worst it can happen is, you know, somebody maybe thinks it wasn't the best idea. The best it can happen is so much better.
 
 You ask a question that everyone's worrying about. It's a little risk. But it unlocks learning for the whole room. Like, if people just took little risks every day, I think they would learn that there's not that much to fear. And then, obviously, in doing so even in taking little risks, you just took a little risk every day.
 
 You will build your agility, your resilience, and your confidence.
 
 Kaihan Krippendorff: Love it. Love it. Yeah. This is so practical, so specific, and the ripple effect of each of those is profound. I see that.
 
 So people should certainly buy your book. You've got a great website associated with the book as well. Choose possibility dot com. How else can people continue to learn from you and follow you?
 
 Sukhinder Singh Cassidy: You can always follow me on LinkedIn. I wouldn't cut myself the world's best influence or I left running a company in, you know, at Xero and but, you know, when I post thoughts, I post them there. And mostly, I hope, that the book is pragmatic and helpful for people in, like, actionable steps to just unlock your own risk taking muscle. Because the majority, as we talked about, is for upside. You know, unlike in a life threatening situation, most of the risk we contemplate taking every day or if possible.
 
 Kaihan Krippendorff: Wow. Thank you, Sukhinder. Smart, proven, and inspiring. Thank you for being here.
 
 Sukhinder Singh Cassidy: Thank you for having me.
 
 Kaihan Krippendorff: Thank you to our guest. Thank you to our executive producer, Karina Reyes, our editor, Zach Ness, and the rest of the team. If you like what you heard, please follow, download, and subscribe. I'm your host, Kaihan Krippendorff. Thank you for listening.