653: Sukhinder Singh Cassidy - Becoming a CEO, Transforming a Company, Earning the Promotion, Knowing Your Non-Negotiables, & Hiring Excellent Leaders

Go to www. LearningLeader.com https://www. LearningLeader.com for full show notes This is brought to you by Insight Global https://insightglobal.com/learningleader/. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Sukhinder Singh Cassidy is the CEO of Xero. Xero is a cloud-based accounting software designed for small businesses. They did $2.1 billion in revenue last year. Over the past 25 years, Sukhinder has had leadership roles at Google, Amazon, and StubHub. Notes: Key Learnings Strategic CEO Job Search Criteria – Sukhinder had four non-negotiables: macro tailwinds/good market, customer she could be passionate about, strong business model, and a role where she could "learn for miles" for 5-8 years. Only two companies met her criteria in 18 months of searching. "Sell, Interview, Sell" Hiring Process – First meeting is 50% selling the opportunity to attract top talent. Only after candidates lean in do you shift to intensive interviewing with leadership team exposure. The Virtuous Cycle Framework – Customer at the top, supported by "high purpose, high performance, high people" culture. "It's an 'and,' not an 'or'" - you don't get to choose just one element. Back-Channeling is Critical – Reference checking happens throughout the entire interview process, not just at the end. "The most important thing is not just front channel... it's all the back channel." Values Alignment Over Pure Qualifications – "Go where my values fit and my strengths are valued." Cultural fit becomes the deciding factor in close hiring calls, not competence. The Layoff Leadership Test – Six weeks after joining, Sukhinder laid off 900 people based on McKinsey benchmarking. Showed consistency between the outside-in analysis presented to the board and transparent communication to employees. Portfolio of Bets Strategy – Balance growth, profitability, and customer happiness through diversified initiatives ranging from "safe moves" to "flyers," with clear probability assessments. Consistency as Culture Foundation – "Culture means consistency of message and what's important." Authenticity through change, not resistance to change. The 10-Slide CEO Interview Deck Framework: Vision statement (destination in 2-3 years) Outside-in market analysis Competitive landscape SWOT analysis of current position Five key strategic moves Implementation approach ("the how") Estimated outcomes with probability ranges Practical Application: Job Search Strategy – Define 4-5 non-negotiable criteria upfront. Be willing to wait for roles that truly meet your standards rather than taking "the job before the job." Interview Preparation – Always build a comprehensive thesis deck even if not requested. Use it to clarify your own thinking and demonstrate strategic capability. Hiring Excellence – Spend equal time selling the opportunity and evaluating candidates. Use diverse interview panels and back-channel extensively throughout the process. Cultural Leadership – Be consistent in messaging across all stakeholders (board, investors, employees). Authenticity enables trust during periods of change. Strategic Planning – Frame initiatives as a portfolio of bets with clear probability assessments. Balance growth, profitability, and customer satisfaction rather than optimizing for one. Leadership Hiring Process: The CEO interviews top 2-3 levels even without hiring authority Diverse interviewer panels with "bar raisers" Business problem-solving presentations in the final rounds Multiple leadership team interactions before the final decision Life Lessons: Patience in Career Progression – Sometimes the right opportunity requires waiting. Sukhinder was frustrated during 18 months of searching but found the perfect fit. Preparation Separates Candidates – The depth of strategic thinking demonstrated in final presentations often determines CEO selections. Culture Survives Through Consistency – Not avoiding change, but maintaining consistent values and communication approach through inevitable changes. Leadership Requires Tough Decisions – Laying off 900 people six weeks into the role, but doing it transparently and based on clear data/analysis. Value Creation Through Alignment – Finding roles where your strengths are valued and values align creates exponentially better outcomes than pure skill matching. Systems Thinking Builds Trust – Sharing appropriate "behind the scenes" context helps teams understand difficult decisions and builds long-term credibility. Early Career Focus – "Do great work for great people." Find talented leaders to apprentice under and work exceptionally hard to maximize learning. Authenticity Enables Performance – Being genuine about challenges and changes builds stronger relationships than trying to maintain artificial stability. Strategic Communication – Frame personal asks in terms of organizational benefits. Make it about solving their problems, not your desires. The Xero Transformation: Financial Performance: $2.1B revenue, 21% YoY growth while maintaining profitability Cultural Approach: "High purpose, high performance, high people" - no choosing between them Strategic Moves: Pricing/packaging optimization, sales motion transformation, customer experience reimagining (new dashboard with 3000+ customer inputs) Leadership Philosophy: Provide a "systems view" to employees, share investor-level insights appropriately, and maintain authenticity during difficult decisions

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Ryan Hawk?

  I've just opened applications for my once per year Learning Leader Circle. And one of the questions I get asked quite a bit is, what is the ROI? What is the return on investment? And one of my longtime members and now friends, Liam Murray, who's been in our Learning Leader Circle for more than five years, actually sent me a note about the ROI, and I'm going to read it to you. He said, "When discussing ROI, most start with a financial analysis, so I will too. The Learning Leader Circle can be compared to any MBA, curriculum, or graduate degree in executive leadership. When coupled with the podcasts and books, the education you receive through the Circle

• 0:42Ryan Hawk?

  is comparable with any Ivy League graduate coursework, and I'd argue better, and it's at a fraction of the cost. Next for me, I believe your WHO is the most important place you can invest. As an adult with children and a full-time job, networking can be difficult. However, a Learning Leader Circle does all of the heavy lifting for you. Calls are scheduled for you along with an annual in-person growth summit. Most importantly, everyone is vetted beforehand, so you do not have to spend your most precious resource, your time, to figure out if someone in the group is worth building a relationship with. They all are." Last, if you put in the work and effort, ROI for the business is significant.

• 1:26Ryan Hawk?

  I can speak for myself, but Circle members have come into my business to serve as keynote speakers, consultants, advisory board members, and informal sounding boards. My firm quite literally has dozens of champions because of the Circle I have joined. One of the most rewarding things is seeing Circle members become friends with my work colleagues. All of this aside, the best ROI for me has been the friendships. Ryan has been a great friend and someone I call and text with regularly. I've also developed meaningful friendships with other members, have golfed, seen concerts, been to baseball games, et cetera, just to be around great humans. That comes from Liam Murray, longtime Learning Leader Circle member.

• 2:09Ryan Hawk?

  If you'd like to apply to be in my next Learning Leader Circle, go to learningleaderscircle.com. That's learningleaderscircle.com and apply today.

• 2:21Ryan Hawk?

  Welcome to the Learning Leader Show. I am your host, Ryan Hawke. Thank you so much for being here. Go to learningleader.com for show notes of this and all podcast episodes. Go to learningleader.com. Now on to tonight's featured leader, the great Sukhinder Singh Cassidy is the CEO of Xero. That's X E R O. Xero is a cloud-based accounting software designed for small businesses. They did $2.1 billion in revenue last year, including some from

• 3:01Ryan Hawk?

  me, as I am a Xero customer. Over the past 25 years, Sukhinder has had leadership roles at Google, Amazon, and StubHub. During our conversation, we discuss what Sukhinder looks for when hiring a leader, some of the must haves, then how to make a big ask and get what you want. And then Sukhinder takes us inside the exact process for her to earn the CEO role at Xero. The interviews, her thesis statement, and the final board presentation. She outlines what she put on each slide of her deck when presenting to the board. So

• 3:41Ryan Hawk?

  good. Then she shares how she earned the job. I think you're gonna love it. Ladies and gentlemen, please enjoy my conversation with Sukhinder Singh Cassidy.

• 3:54Ryan Hawk?

  I remember when I saw the press release come out that you chose to take the CEO role at Xero, and I thought, wait a second, Xero, that's what I use.

• 4:02Speaker 01

  Be so happy to hear that.

• 4:04Ryan Hawk?

  Yeah, I teamed up with my accounting firm that I work with, and they say, hey, we love Xero, and it's the best for our clients, and that's what we use. And I said, great, sounds good to me. And I've been using it ever since, and it's been great. So it's kind of cool that this product I already used before, and now you're the CEO. So I am curious, though. Last time we talked, you're kind of promoting your book, you're in between roles, you're thinking of what to do next. What made you say, you know what, I think zero is the place for me. That's where I want to go run that company.

• 4:32Speaker 01

  Well, first of all, you're gonna laugh because when I got the zero call, I said the same thing you did. I was like, oh, my tiny startup, The Board List, which was always been my side hustle, you know, a governance platform where people can find great leaders for boards, was also a zero user. So interestingly, when I got the call, I said to my husband, believe it or not, I was like, I know zero. I'm pretty sure this is the one. Now, I mean, if you zoom back and you say, why is it the one? You pointed out a couple of things that are important. You know, we'd sold StubHub, managed through the COVID crisis, I wrote the book, and I had been looking for CEO jobs, seriously, Ryan, for well over a year. So I was actually quite frustrated. I was like, and by the way, this is like 2020, 2021, like, stock market's booming. And I'm

• 5:17Speaker 01

  like, wait, I'm on the sidelines and like, everything is up and to the right. Like, am I missing my time? Interestingly, by the time I took zero, things were starting to already, you know, have crested and like, we were entering this era of profits plus efficiency. But okay, so all the way back to the story. Why did I say yes? I said yes because I not only knew the product, but because in my looking, I asked, I said, there are four things I want in this job. Number one, I want macro tailwinds and I want to play in a good market. And I'll say to people like, look, you can be the best person in the world, but you'd rather go where the fish are, you know, swim with the tide. And the digitization of small businesses, particularly their back office, is still a growing sector. Number two, I was like, I want a customer I can get passionate about. So I had told recruiters, look, I love consumer. Consumer's a hard business

• 5:59Speaker 01

  in tech. I said, I also love small business. I need to be able to empathize with the user. And as you and I both know, we're both small business owners. We've both been founders. So that resonate. I knew the product, to your point. I use the product. Number three, I said, it has to have a really good business model.

• 6:16Speaker 01

  Number four, I said, the CEO job has to be available and I need to be able to learn for miles. And the last one's important because, look, I'm in my 50s now and I think I have tons of energy, but maybe you can relate. For a lot of my career was like, well, if it's not this job, there's another job. You know, like I'm on a journey, right? And after StubHub, I was like, no, I just want the job. I don't want the job before the job or the job that leads to the next job. I just want the job for the next five, six, seven, eight years. Like, I feel continually challenged. And I've actually cut out a lot of choices, a lot. So I had this really high criteria and believe it or not, there was only zero and one other company in the course of a year and a half that met that bar.

• 7:00Ryan Hawk?

  I am fascinated by how people earn jobs and going like inside the process. Like, did you go after them? They come after you, mutual. What's the process like once you say, okay, they meet my criteria? How does it all work? How did this case all work for you?

• 7:17Speaker 01

  Well, interestingly, you say this. So first of all, you can imagine my worry, frustration, concern that I'm like, where are all the great CEO jobs? So first of all, CEO jobs are opaque. So while you can raise your hand, I mean, these processes tend to go the other way, which is you don't know where, it's not posted mostly on LinkedIn. This is a private process. It can be passive. It can be active. Almost all the big ones are run by headhunters. So generally, you tend to get these calls. You can't just say, gee, you know, I'd like to be CEO of your company. In the background, for whatever it's worth, I was working on two roll-up ideas because I was frustrated that like, if I didn't see the right CEO job, could I make my own luck? Could I go take a thesis and build a company at scale? Because I was looking for scale. So the way it happens is, you know, you typically get recruiter

• 8:00Speaker 01

  calls in both the CEO cases I was talking about, I got them. But the inside process for Zero was really fun for a few reasons. Number one, it went very fast. I think from the moment we started chatting, which is the beginning of September-ish to the moment I got the offer, which was mid-October. That's a three-month process. So they moved with intention, which I appreciated. It was very clear. You know, there was a first round, a second round and a final round in which there's always, if you're a CEO, there's almost always like a board presentation. And I had a board presentation. And in between, the fun second round was they said, come visit ZeroCon. ZeroCon is like the TED for accountants and bookkeepers. It's like a conference of three or 4,000 people. We do them around the world.

• 8:42Speaker 01

  So now, of course, I am at ZeroCon, but I attended the first ZeroCon in stealth. I was in the audience. Nobody knew. I was sitting among thousands of Zero customers, watching the current CEO. And by the way, it was the CEO had announced his transition. So, you know, to the board, not publicly. So it was a very managed process, like done collaboratively with the CEO. So I had met, I met the CEO. But I was sitting in the crowd and nobody knew I was the contender for the job, watching the current CEO present, which kind of fueled my conviction on the opportunity. And then like by the final round, yes, the board asked me to present a vision. And I think, I always say, on a CEO job, this is probably the most important thing because somebody just called me who's interviewing for a CEO role and asked for advice on what she should consider.

• 9:25Speaker 01

  And I said, hey, in the interview process, you should be building a thesis and you should build a deck for yourself, whether or not you ever presented to the board, such that by the time you enter your final rounds, you have like the 10 slides on what you would do if you were in the job. And those 10 slides are either going to give you the conviction that this is an amazing opportunity because you know what you would do and can imagine your game plan for the next 24 months. By the way, it's a thesis, of course, because once you're in, you're going to learn a lot more. But it's just like, you know, when people say imagine the first 100 days on the job. I'm like, if you're a CEO, I think you have to imagine the first 24 months on the job. What are the moves you would make? What's your thesis on how your coming to this organization can help unlock or accelerate its impact?

• 10:07Speaker 01

  And so I did have a 10 slide deck and luckily for me, the board, I guess, liked what I had to say and away we go.

• 10:13Ryan Hawk?

  Is that a deck that you're willing to share?

• 10:15Speaker 01

  Uh, you know, I'll ask the zero board. I don't know if they'd be willing to share. Probably not, but I will say I, I.

• 10:21Ryan Hawk?

  I would just, I personally, like, maybe we could talk separately. I'd love to see it because I, again, I love the process of how people earn big jobs. Maybe we could talk about some of the things that you are allowed to share. What goes in it? Let's say somebody, so could there, maybe not even a CEO job, but they're going for a leadership role. Cause I think you should do this, even if you're just going for your, like, your first ever management job, you should take it seriously, prepare, over prepare, have a thesis statement, create a deck. I mean, it couldn't hurt to do this, even if you don't end up presenting it, it couldn't hurt. So let's say somebody's in that type of job because it's more relatable than just, you know, going to be a CEO. What's that process look like putting it together?

• 11:03Ryan Hawk?

  What are some of the things that have to be in there? What are some things that you put in there that you're allowed to talk about? I'm really curious of how all that goes.

• 11:10Speaker 01

  Sure, sure. By the way, to your point, the format is almost always the same. So I think this is useful for anything and think about, think about, to your point, not just branching a CEO job, think about it trying to win a C-suite job. Think about having got the job, how you would write your game plan or your thesis. So first of all, I always believe in what I call like whiteboard plans. Whiteboard plans are like a plan on a page, like what's the starting thesis? Like by when? Like, so if you look at an organization or a group, you're, you know, going to inherit and you're thinking like, okay, first of all, identify like the destination. So with zero, it's a public company. So I could say, okay, it's, this is its current market cap. If I wanted to unlock shareholder value, which is the ultimate goal as a CEO, right? Or unlock customer value, my destination within some timeframe, like give yourself two years, three years.

• 11:53Speaker 01

  Just write a vision statement of like, what could success look like, right? And now you think about, so think about that as the goal for the deck and then you work backwards, right? So first of all, you need a goal and you can identify an outside in goal, or you can ask the person you're interviewing with, what does success look like? Do you see any goals set by in the timeframe?

• 12:09Ryan Hawk?

  For you, was that a? Number, a revenue target, what was that for you for this one?

• 12:14Speaker 01

  Yeah. So for me, as a CEO in that deck, I would be saying, hey, this is the current shareholder. So maybe this leads to kind of what I'm about to tell you on the journey on the way. So for a public company CEO, it's about unlocking customer value because I believe if you don't have customer love, just chasing shareholder value is nice. So for me, the three constituents that I'm trying to kind of improve are my customers, my investors and my employees. So think about the destination is having like those three constituents, right? And again, I know I'm talking in CEO speak, but for somebody who's crafting an internal vision, it might be this is my vision for my business in the context of the overall business. And maybe for my team or maybe for my customers, but I think you always need a customer view. You always need like, what does it mean to the business?

• 12:59Speaker 01

  What is financial success for the business? In our case, it's also measured by shareholders. And then you definitely need like for your team, what does success look like? Presuming these are the three constituents and you're like-

• 13:09Ryan Hawk?

  Are those three equal?

• 13:10Speaker 01

  Uh, you know, yeah, they're all equal, but look, look, you're all in service of the customer. So to me, the customer first, investors and-

• 13:19Ryan Hawk?

  Well, someone would say, take care of your employees. They will take care of your customers. So the employees are first. Now, that could be just a nice thing to say. You're actually in the seat doing the real job. You're a current operator, not a former operator, you're a current operator. So I'm curious from you, is that just kind of nice CEO speak that I put in the book after I retire? Or is there a chance that that, hey, take care of your employees, they will take care of your customer? What do you think about that?

• 13:46Speaker 01

  Well, let me tell you how we're talking about it at zero. First of all, it's a virtuous cycle. But if you think about a virtuous cycle and you said to me, what would I put at the top of the diagram of the circle? It would start with the customer.

• 13:56Ryan Hawk?

  Okay.

• 13:57Speaker 01

  Starts with customer. If we do right by the customer, you know, if you think of virtue cycle, you probably have two other circles on that like cyclical picture. And you'd say, okay, bottom left, you might be like, okay, to take care of our customers, you know, our investors will be happy, right? And then you have on the other side, like if we take care of our employees, you know, we take care of the customers. So I think it's, I do think it's a virtuous cycle. And what we talk about at zero is a high performance, high purpose, high people culture. We say all three. We say performance, people.

• 14:25Speaker 01

  Purpose. So now, look at those three words aligned to the circle I just gave you. Purpose. We're here to make small businesses, you know, more successful. That is the North Star. Make no mistake. And then we say, we want a high-performance culture, right? Because that is both great for our customers, but it's also great for our people. It's how do you come to zero and do the best work of your life? And we say a high people culture because we do care about our people. We do, we are known for being, I would say, a culture that where employees, like, we don't really have assholes at zero. We don't. Somehow, we do this remarkable job of lovely people who come together, who kind of want to do the right thing. I don't know how we do it, Ryan, but we've done it for 20 years. And my job as CEO is just not to mess it up. It's a remarkable culture.

• 15:09Speaker 01

  Every time people come in, they're like, wow, your people are so nice. Our customers say, your people are so nice, like, your brand is, like, really nice. So again, all I can tell you is I'm trying not to mess that up. So we correlate those three boxes I gave you. We say, we're going to be high purpose, high performance, high people. And we said, like, sorry, guys, you don't get to choose. It's an and. It's not an or. It's an and. And at the top is our purpose. So that means the customer, we all serve the customer. We all serve the customer. So that's the way we talk about zero. So anyway, back to the whiteboard plan. Hopefully, like, I know we digressed. So if you take the thesis that there is a goal you want to get to, you have to be able to say, like, success could look like this. And I know some people on this call are going to be like, well, I don't know what the goal is. Okay, we'll start the other way, which is every deck,

• 15:53Speaker 01

  every deck begins with the outside-in opportunity. Every single one. So to your point, like, how would you script a deck if you were building it for yourself? Always outside-in first. First of all, what's the market context? Is this a growing market, shrinking market? Are you participating in tailwinds or not? Remember I said this, like, where to play choice was my number one choice as a CEO? I think when you're running a business, start with the outside-in. What's going on? Then I always have a SWOT. I do, like, hey, what is our current hand? How are we doing against the opportunity? And it's always a SWOT. It always has four quarters. It's very classic, like, I write bullet points in each. This deck had it. I said, here's Zero's current, you're right.

• 16:33Ryan Hawk?

  Can you go through a SWOT real quick? I remember this from earning my MBA, but haven't really talked about it much since then. So can you just walk quickly like through what a SWOT is?

• 16:41Speaker 01

  SWOT is four or five bullet points on the company's strengths.

• 16:43Ryan Hawk?

  Strengths, weaknesses, opportunities and threats.

• 16:45Speaker 01

  That's it. It's just literally one page and you put four or five bullets in each box. Just stream of consciousness. By the way, in the outside in landscape, you also have to do the competitive landscape. So you can't just do the market. You have to do the competitors.

• 16:58Ryan Hawk?

  So part of what you're doing is you are showing them, one, I've thought about this. Like two, like I understand what I'm getting myself into. I have, I have an acute understanding of the market, of the situation, of the competitive landscape. I understand our strengths and weaknesses and opportunities and threats. You're in a way, you're kind of exhibiting, you're making the board probably be like, ah, okay, she's got this. I can go back to doing whatever else I was doing because you can just got this.

• 17:26Speaker 01

  They want to know that you see the way of any leader, by the way, and this is my core thesis. You have to be outside in and inside out. They want to know that you and you want to know, like, have you seen the picture? Can you see the movie before you think about the game plan? So can you see the forest? Okay, so that's your forest view. Then you have your SWOT. Okay. And then of course, like they want the critical thinking like, okay, if you saw this SWOT against the opportunity, what are the four or five moves you would make? And by the way, you know, remember you have, if you're public, you have a company's financials, or if you're private, you have your own financials. Now this is where you ask like, what's the goal line? Well, remember I said there's a vision? I typically put the vision on the first page. So I start with the ambition. Like every deck is like, here's where I'm trying to go. My thesis is we can be a blank organization by blank. Okay.

• 18:10Speaker 01

  Then I zoom out, I do market context. Then I do competitive context. Then I do a SWOT. Then I have one slide that's like my five moves. And believe it or not, I'm like, okay, if I do these five moves right, like this is my thesis. And then that's like the what, the what I'm going to do. There might be one slide on like, hey, here's the how, because I have to work with people. I have to work with investors. So it might be like, hey, in trying to make these five moves, here's like two or three things to consider. And then believe it or not, I estimate the end outcome. And that's it. It's like a six page deck. I think I remember doing for the board, I have to go back and check. I might have had six slides up front and I was like, that's the sizzle guys. And then I had the details and then I had like five more slides.

• 18:50Speaker 01

  So like the TLDR should be like in five or six slides, can you paint a picture of like where you want to go? What you considered, what you think the company's current position is, what are the five or six moves you think are most essential? And what could the yield be? And by the way, you can put a range on the yield. You can put a probability, you can say, hey, these are the three safe moves I'd make. This is like two more meaty moves and here's one flyer. You can even probability assess them. What do you think the person's looking for? I think most people think when you go in to pitch for a job or have the job. I think most people presume that the person on the other end is looking for the answer. They're looking for the quality of your thinking. They're looking to see like you could paint a range of probabilities and you have, you know, they're looking for your ability to assess.

• 19:35Speaker 01

  Solution pivot. So that's why you can put out, hey, here's five ideas. By the way, I'm going to give you like my probability on whether these will work or not. A couple here are really safe. A couple here are like flyers, a couple of here like are probably going to work, but they require significant investment. They're looking to see that your thinking can encompass all those things, right? And then mostly they want to know that if you're wrong, what would you do? They're going to ask you that question. You're like, well, if I'm wrong, I'll pivot.

• 20:01Ryan Hawk?

  Yeah. What you didn't mention there in that deck is like you as a person, your personal purpose, your core values, your behaviors that make those values true. Is that covered in previous interviews? You don't need to cover that anymore or?

• 20:17Speaker 01

  You hit it. The only reason I didn't cover it in a deck is because I wouldn't have even gotten to the final round.

• 20:22Ryan Hawk?

  If you didn't have all that, that's table stakes to make sure.

• 20:25Speaker 01

  All the personal time on like, so it's interesting, could it zero now a couple of times? We don't do consistently, but it's something we should consider. A couple of times more recently now is we're in the final rounds with leaders. We give them a problem to solve and they build us a deck. It is remarkable how much, because what happens, as you know, in early interviews, is you're chatting to somebody and you're talking and you get to feel who they are. You might get to feel like, to your point, how do they respond to the soft questions? And some people, you know, consulting companies do these like classic case interviews, as you know, which are hard because you're asking people to think on their feet and some people are good at that, some are not. But if you give a person a business problem and say, hey, you know what, for the final round, here's the situation we're really facing. We'd love you to just write a couple of slides and come back and tell us how you walk it

• 21:10Speaker 01

  through. You see the clarity of a leader's thinking, their solutioning, their problem solving, how they work their way around a business problem. That is a what, right? That's not a who, that's a what. And so, yes, I think by the end, they're testing the what. Now, of course, you know, you know this, right? In all leadership hires, like, the most important thing is not just front channel of like me chatting with you about how lovely I am and how lovely I think I'm. It's all the back channel. So like, so to be clear, I'm pretty sure the whole way through my interview, somebody is back channeling what all the people have to say in the valley about me who've worked with me, the lovers, the naysayers, the people who...

• 21:46Ryan Hawk?

  Wait, by back channeling, you mean references and people who know you?

• 21:50Speaker 01

  I mean references. So like, I think a good process for any, any leader, including when I hire, I'm back channeling all the way through because, because you kind of hit the other important point. There's like the what of how you think, the who of who you are, the why of why your values and your strengths, you know, are what this organization needs. Like, these are the questions that any person is assessing who's hiring a leader. Like, the what, can they do the job? Can they think about the next job? How would they think their way around a problem? The who, who are they? Well, how their values fit ours? What is our superpowers? And the why, like, why is this person going to be the right fit for the job at hand? So I like back channels all the way through because it tells you a lot about the who. It tells you, you can ask the person their why.

• 22:33Speaker 01

  You can assess your own why you would hire them, but you can also ask the person their why. Like, the zero, ask me my why, like, why zero? I listed the four things I talked about and I listed one, which was pretty freaking important to me. I was like, I want to go where my values fit. And my strengths are valued. This is why I say now I'm going to go where my values fit and my strengths are valued. So do my superpowers align to what the organization needs? I'm doing that fit, but you should also do that fit because I'm not perfect and there's things you're not gonna, you know, maybe if you wish for a leader of another's ilk, like you should know that going in. And then number two, do we share enough values in common that when the times get tough, we want to be in the boat with each other? Those are the only things I care about. Do you see my strengths as something that is additive to this organization? Do I see them the same way?

• 23:18Speaker 01

  Or accelerants? And number two, do we share enough values? And so I said that to Zero, I said, like, the reason I'm here is like, man, I look around, this place is full of lovely people. They want to do the right thing. They're diverse. They're humble. They're inclusive. Man, I would want to be a part of this tribe. By the way, the board is diverse. Like, yes. And I know maybe diversity is a bad word. I'm sorry. I'm a woman of color who's a leader. I want to go to a place that welcomes who I am, how I show up, and have heterogeneity, diversity of opinions in the room. So yeah, do I look for that when I interview? For sure.

• 23:55Ryan Hawk?

  Got you. I would love to go a little bit deeper on when you're making hiring decisions for senior leaders to work for you, because one of the commonalities I've found to Kinder and excellent long-term CEOs are that they're really, really good about surrounding themselves with excellent people, high character, high competence. So you mentioned backchanneling. So you're doing reference checks. You're checking on the people. That's one of the things. What are some of the other things you do? Like, take me inside the process. What is it like when you have an opening on your team, a direct report of yours? How does it work? What are some of the must haves? Like, they gotta have this to make it? What's that process like?

• 24:31Speaker 01

  Sure. And I interview anybody who's in our top kind of two to three leadership cohorts. So I care a lot that, you know, I don't just interview people who are in mine. Now, I don't have the hiring decision on some of those, but I do interview kind of the top two to three levels of Zero because it's very important to me that our leaders all exhibit, you know, the values and the traits that will make them successful at Zero.

• 24:53Ryan Hawk?

  I want to get to that in a second, but how common is it that you have disagreements? Let's say it's two or three levels below you and you're interviewing them and you're like, oh, my God, they're amazing. And if someone else is like, I don't know, or probably more common, no, I don't think they got it. And the other person says, yes, has that happened a good amount?

• 25:09Speaker 01

  It doesn't happen as much as you think, and I'll tell you why. Because you always have a diverse slate of interviewers and you always want to have bar raisers in your interviewers. So interestingly, you know, I'd say it's zero. In most of where I've been, if you have a high quality team and you have enough diversity on the interviewing panel, the right issues usually show up and it ends up being a close call. You know, I'd say the clear outliers are there. And then the controversy, to your point, I'll tell you where the controversy always is. It's always about maybe somebody's strengths and that they have superpowers and then the shadow of that. And does that fit culturally? It's almost never about competence at that point. Now, look, it could be about somebody's potential, you know, like have they done this job yet? You know, so you're betting on their potential

• 25:51Speaker 01

  versus like, I don't know, known experience. That's another dimension that people sometimes debate. Well, this person has all the experience and this person has all the potential. Like that sometimes shows up in the end interview rounds. But why the close calls are always like about culture fit. You know, they're like, wow, this person is excellent at this. Are they going to be able to get it done here? It's not about are they a great person? Or are they competent? It's almost always about culture when you get to these close calls. But they're always, I would say that the issues always surface when you have a diverse slate of interviewers, which I mean, it comes back to why I like diversity of perspectives. So what does the interview process look like for me? I'll tell you, my process is very specific and probably very funny to people. I always say sell, interview, sell. So when

• 26:33Speaker 01

  I meet with a candidate for the first time, I'm spending all my time selling the opportunity. People are like, what? I'm like, yeah. I'm like, talented people have choice. I am in full sell mode on my ZO is in the nation. Consider, I can't tell you how many times we've approached a leader who's like, you know, I'm not looking. I'm really happy where I am. I go into sell mode hard. And quite frankly, that's my most charming self is versus my most, you know, aggressive, intense, irritating self. So like, man, I got a bait and switch. But I hope not. And then the second interview, and then typically before I see them again, believe it or not, I put them through my whole leadership team. So I'm like, I'm going to see you again, but first I want you to meet a bunch of my team. So why do I let them meet a bunch of my team?

• 27:17Speaker 01

  Obviously, in my cell interview, I am getting to know who they are. But my point is, it's like, tell me a bit about yourself, and I'm going to tell you a lot about Zero. So that first interview is probably 50/50. Me letting them ask a bunch of questions and me kind of ask about who they are. But it's not like, what do you think about Zero, blah, blah, blah, because they're not even sure they want to come. And so in that, I'm doing a silent assessment of like, oh, would I want to work with this person? And then hopefully after that first call, they're like, you know what, it's your kinder, I would like to learn more. And then I'm like, great, now go meet five of my team members. Why do I do that? Because it makes it more efficient for me when I interview. You know why? They're going to go ask a bunch more questions. They're going to learn about the organization. They're going to be a bunch more informed. So by the time they see me again, now we're in interview time.

• 28:02Speaker 01

  Now I'm like, okay, you leaned into the process. You met each of my leadership team. You got to ask a bunch of questions. Now I'm going to ask you a bunch of questions. And then we get into the heart of it. And then I might meet with somebody one, two times. Obviously, if they're direct to me, they probably meet our board, a couple of members, not all, but I probably have a couple of board members interview. Meanwhile, of course, after my first interview, we're calibrating, we're shortlisting. And then I probably see them again, the board sees them. And maybe I have a couple more of my close in leaders. If it's a close call, spend more time with them. That's what it looks like. And then we make a call.

• 28:33Ryan Hawk?

  So when we talked about your book, you mentioned that you don't have to be specifically qualified for a specific job before taking it. Do you still believe that? Because like, this job you were overqualified for, I think, right? But you still want to give this advice to others. How do you feel about this idea of still going for jobs that maybe you aren't even specifically qualified for?

• 28:56Speaker 01

  Well, I think it comes to the quality of your thinking. So will I take somebody who's not specifically qualified for a job? Well, look, there are a couple of things, and you can appreciate this. While you might not be specifically qualified for this job, you need to be qualified for whatever the company is headed to. Okay, so let's say, you know, Zero is now a $2 billion plus kind of revenue organization. Let's say, and we've just told, you know, our investors, we're going to double by 2028. Like, okay, so like our fiscal 28. So we've already given, you know, we just said that with our recent acquisition. So if I'm thinking about the organization doubling, you would say, okay, well, there are some must haves and some options at the MI level. So must haves are like, can you operate at the next level of scale? Okay, if you haven't done it in this industry or this job,

• 29:40Speaker 01

  can you demonstrate to me where have you seen the level of scale or complexity we're going to? As an example, so I'd say in almost every job, Ryan, there's some must have skills. And the question is, you have to show that if you're not in this job, you have demonstrated the capacity for those skills. So, you know, if you ask me, would I take somebody, I don't know, I'm making it up. We don't have this job before. Who hasn't been a COO into the COO job? Sure, but I want to know that the summation of the skills that I need in that job, they have demonstrated individually. So I think like you want to know that you're hiring a person who can go where the puck is going, right, in hockey now, geez, without having to have done the specific job. Where do you typically find that?

• 30:20Speaker 01

  You'd find that in people who are agile, in their ability to learn, to grow, to adapt. And then, as I said, look, in the case of any company, including Zero, there are some must have. Is it likely as an example, you know, that at our scale, we would hire a chief revenue officer who has never managed revenue? I would say that would be a very high risk hire for us. You know, but you know, if you said to me, hey, again, would I take a COO who's never been in the COO role, but has managed discrete multiple functions over time at significant complexity, who is now going to put it all together in this job? I would say yes. So those are maybe like real and theoretical examples. The problem is, once you've had 20 or 30 years, maybe 30 years of experience, Ryan, you are qualified sadly for almost everything, because you're just old.

• 31:05Speaker 01

  Now I'm old. So sadly, most of the people I knew you are younger than me. So sadly, you know, I am going to be overqualified for a lot of things now. That wasn't always true.

• 31:18Ryan Hawk?

  You mentioned the fact that you're now a $2.1 billion company, 21% year-over-year growth. So you're just absolutely crushing it. I am curious about this balance between growth and we're getting into real operator stuff here. Growth and profitability as well as this obsession, this kind of Amazon-ish obsession for the customer that you've hit on a few times. How do you balance? I don't know if they're competing priorities, but how do you balance out growth profitability as well as customer happiness?

• 31:48Speaker 01

  Yeah, well, you hit, I think, the, and obviously this is now very specific when you're a public company CEO versus private, because when you're private, you might have more latitude. Where you're public, kind of hit the nail on the head. Unfortunately, it's not an or, it's an and. You know, I'd say in tech in particular, there was an era of growth at all costs, as you know. And then we moved to growth and efficiency. And if you look at today at multiples in in public tech and in SaaS, the category we play in, if you are high growth and profitable, you traded, you know, a bigger multiple. Right? So investors obviously benefit from that and investors like that because to get both is is hard. It's hard. To your point, it's hard. So now let's go to the fact that it's hard.

• 32:29Speaker 01

  Like, so first of all, it's an and not an or if you want to be a high performing SaaS company over time. And AI, of course, is only going to accelerate the expectations of how efficient you are, by the way. Right? So that benchmark is not going down, it's going up. Okay, so it's hard. So how do you do it internally? First of all, welcome, like we are going from being a teenager to like university. Welcome to the graduating class. Great that you're on the top of this stack. I just to be a freshman again in the next, you know, in the next class at university. And guess what? It resets. And so now it's growth and profitability. I think they understand that. I think the way you manage it internally is I think you do have a number of bets. I think you do have all things being equal. You know, and you know, I'm a believer in bets. So, you know, at zero, we do have.

• 33:14Speaker 01

  Portfolio of things we're doing and they run the gamut to things that are trying to improve productivity, to things that are trying to like, I'd say multiple bites at the growth apple and it making customers happy. And so I think if you have a good CFO and if you have a supportive board, we luckily do, you know, they allow us to manage a portfolio of bets and we give, I would say ourselves latitude with investors. We've been clear with investors, hey, we're going to try and be balanced, but all things being equal, you know, we're not going to give you, I don't know what we call it. Rule of 40 for us has been an aspiration, not guidance. And people say, well, why isn't an aspiration not formal guidance? And we're like, well, because at the end of the day, we want the room within these two sectors to flex between growth and profitability.

• 33:56Speaker 01

  So we're going to promise you both, but the level of both, we want to flex between where we see opportunity. And again, the best you can do with investors, I think, is if you have supportive investors, we are lucky that we do, is to be able to say, this is, this is what we're doing internally. Let us give you examples of decisions we might make. Trust us to be thoughtful allocators of capital and to be optimizing between, but we're not going to give you a specific number on each, because that takes away our flexibility to make the right decisions for zero. Now, again, I realize I'm giving you an ideal case, right? Sometimes as CEO, you don't have that latitude. Let's say you're doing a turnaround or what have you. Internally, though, I think you need to manage a portfolio. Of course, you know, you need, I'd say, your own constructs and you need buffer in both.

• 34:39Speaker 01

  I believe that if you're going to get to the right outcomes, you need to be, I'd say, shooting, you know, past your target on both profitability and growth. And it's a balance. It's not easy. It's all about being what we call an allocator of capital. And like, what does that mean? That really means like you have to have a set of focused bets. You have to say to everybody, these are the bets we're focused on. These are the ones we're not. I'm sorry, we can't afford to do everything and you know, and a portfolio of focused bets.

• 35:03Ryan Hawk?

  What are some examples of bets you've actually made? Would the recent acquisition be a bet? Like, what are some examples of bets?

• 35:11Speaker 01

  Yeah, that's we've made. Well, first of all, I mean, as we talked about, remember we talked about building that ideal business plan? And we said bets can be smaller moves, they can be bigger moves. So obviously we just announced the acquisition of Melio, which is a leading bill pay player in the US. That would go be called the biggest of big moves. Like you don't move, make that move every year, you know, it is, we're super proud of it, but it was many, many months, almost a year in the works. But in organically, like, let's not talk about M and A, or we can talk about smaller M and A, because, you know, Melio is an outlier in terms of its size. I mean, bets are very simple. Like, if you read our Investor Day presentation, we're like, here's some of our bets. We are going to, you know, now use pricing and packaging to try and deliver more value to customers each year. That's a bet. We listed out, like, literally, we had five

• 35:56Speaker 01

  themes. We had about three bets under each. We said, these are the bets we're making. Number two, we're going to try and transform our sales motions. So they'll just focus on acquiring a subscriber, but helping subscribers pick the right product on the way in and improve our mix. Like, by the way, do these bets sound quite operational? Sure. That's what I mean about a fundamental bet. I'm like, here's some smaller moves we're making. But when you compound these moves, we see that we can unlock a lot more value in a zero subscriber, not just keep adding subscribers without increasing the amount of products they take from us. So you change your sales motions, you change your pricing and packaging. These are literally discrete bets we listed in our investor presentation. We had another one. We said, yeah, we're going to reimagine the small business experience. I don't know

• 36:39Speaker 01

  if you know that, Ryan, but this past week, Zero just launched a reimagine dashboard for small businesses. You should go check it out. It's like, it was designed with 3,000 customers. We said a year and a half ago, we're going to do that. We just shipped it. Now, by the way, that's for customer happiness. We're not betting on it having financial yield, but man, our customers want an easier to use dashboard with customizable widgets that they can control, that gives them more insight. And so, like, that was a bet. So remember, we talked about customer happiness, financial performance, people. Imagine if you, if I sent you our investor presentation page of like, five themes and 15 bets, you would see there are bets allocated to each of those things that are meant to drive each of those things. Some are for customer happiness, some are for financial revenue accretion,

• 37:21Speaker 01

  some are for productivity, some are for future growth. So that's what bets look like. And again, on a page, you ought to be able to write down like the, and I think most zeros would say they could understand our bets.

• 37:34Ryan Hawk?

  Let's talk about the people side of things, and specifically, culture. This is hard to get it right, but vital and super important. What's your overall mindset and philosophy on building? I mean, you're in charge, you're the CEO on building an excellent culture at Zero.

• 37:53Speaker 01

  Well, first of all, I think culture means consistency of message and what's important. So I think, you know, people will say, oh, culture is what you do, not what you say, or what, how people act when no one's looking. I told you, like, there's some important, first of all, my first goal is to not, excuse me, screw up, I think I swore before, not to really like screw up the thing that Zero does uniquely right, which is it attracts, really, I don't know how else to say, it attracts really wonderful people. That's all I can say, and for me, wonderful people, like I say, they show up, they want to do the right thing, they care, they collaborate well, their natural inclination is to be helpful, and they're really unentitled. Like, those speak to my personal values, the type of people I would want around me. By the way, I also want people who are very diverse from my style and perspective.

• 38:38Speaker 01

  And so, like I said, I love that Zero attracts all different kinds of people from all different kinds of backgrounds for that reason. Okay, so that's one. So let's try not to screw up the thing the company does well. But I think in terms of the culture and how you kind of drive it, I think I really strive, as I said, to be consistent and authentic in my communications about what's important, to be pretty plain speaking on the things we're going to do and the things we're not going to do, right? And to make sure that what we say to investors, what we say to the board, what we say to employees, all matches up again and again and again. So for me, culture is about consistency, and maybe that is like a weird answer, but that's how I strive to, I would say, improve our culture. Of course, we did things like look at our values and we, we re-energized our values

• 39:23Speaker 01

  about a year and a half ago when we did our investor strategy, you know, the thing I talked about, our portfolio of bets, we made them public, we sort of said, hey, for the next era, what do our values need to be? How do we take them? How do we tweak them? How do we improve them? Yes, but you don't change your values every year. Mostly you try and live your values. And the best way I know how to live my values is to be consistent as a leader in my messaging, in doing what I say I'm going to do, and keep closing the loop for our employees. And we talked about it, we press on all three, purpose, performance, people, you know, we try and, like I'd say, manage all three in concert, and I try and move them as a system. And honestly, I just keep, believe it or not, in culture, I just keep trying to repeat the same thing again and again and again.

• 40:06Ryan Hawk?

  It was funny. I love that you said this. In all relationships in life, I think one of the key components to trust, which is the foundation of our relationship and it's mandatory that you have it if you're gonna have a relationship with somebody is being consistent, is doing what you say you're gonna do day after day after day, right? Is continuing to show up, continuing to do the thing, continuing to do the work, to being dependable, to being reliable, to consistently being there. All these unsexy words. It's funny, but man, it leads to trust. It leads to the formation of a strong and powerful relationship. So it's interesting

• 40:47Ryan Hawk?

  that that this consistency of messaging is so important to you. It makes a lot of sense that you've been able to build excellent cultures wherever you go because you're so focused on being consistent.

• 41:00Speaker 01

  Yeah, I mean, I think you said there's one other word that goes with trust, which is authenticity, right? So like, I believe, like, just say the thing. You earn people's trust when you do it. And by the way, there are times you make unpopular decisions for culture. Like, let's not forget that, you know, like, this does not mean that things don't change. This is in fact quite the opposite. This is the challenge. This is the challenge in building a culture in today's tech that's enduring. Things change all the time. You have to pivot. You have COVID. You have AI. You know, you have efficiency. When I arrived at Xero, we laid off almost 900 people six weeks after I arrived. Do you think that's a popular decision or an easy decision?

• 41:37Ryan Hawk?

  What happened? Why?

• 41:38Speaker 01

  I laid, I basically remember that plan we talked about with the board. I said,

• 41:41Ryan Hawk?

  Was that in the plan? Like, I'm gonna chop off 900 people?

• 41:44Speaker 01

  What was in the plan was not, I'm gonna chop off 900 people. What I was in was in the plan. Remember that outside in view? I said, here's where's where it does well. Here's where's your benchmarks last well. So I was just very clear. My outside in analysis of the company is, it's amazing here. Now, keep in mind, again, you don't make a decision like that lightly. I arrived, and by the way, this is all public knowledge. There's nothing here. I'm not saying that I that employees haven't heard. When I arrived, I said to the board and I said to the current CEO, because we had an overlap period. I'm like, I'm gonna bring in McKinsey and I'm gonna benchmark Xero because I'm pretty sure we're overly large. But I don't think this isn't that kind of decision. You just say, well, you know, this is my thesis. Like, think about the impact to employees, right? So we bought in McKinsey. We did a six week go round and I took over the CEO seat officially

• 42:28Speaker 01

  on my birthday, which was like February 1. And the very first all hands employee said to me, are you gonna do layoffs? And in my very first all hands, I had SaaS benchmarks in my deck. And I said, look, I'm not going to tell you about whether we're going to do layoffs or not, but I'm going to show you an outside in view of where zero does well and where zero doesn't do well. Put it out there. I was like, this might, you know, I was like, I tossed about how excited I was. Maybe it was my first or second, but my point was within my first two all hands. It was either the day I did it or two weeks later. And a month later, we did a layoff and it was brutal. But again, coming back to consistency, I thought like, my God, if this is my thesis and the world was heading there, you know this, this was an era by like was untold number of layoffs in the beginning of 2022.

• 43:09Speaker 01

  But I was like, wow, can I really stand up in front of this team that I am about to be the CEO of? And people are like, are there going to be layoffs? And I am doing a McKinsey study in the background. What is the data I can give these folks that gives them a clue to how I'm thinking about the business? That's still authentic, right? So my point is like authenticity serves you through change. So consistency is about consistency of like, what are your North Stars? What are the principles you're trying to uphold? How are you making decisions? Consistency does not mean nothing changes. Quite frankly, as I said, this is the hardest thing in culture. We are in an era where everything is changing and you're trying to bring your employees along. But you gotta go. Are you not going to go on AI?

• 43:52Speaker 01

  If the whole market is value efficiency, can we afford not to make the decision? If we're unprofitable to cut our headcount? No. So the question is, how do you maintain culture? And how do you maintain care for employees in a world where everything is changing? Quite frankly, that is a seminal question. And the only thing I know how to lean on is be consistent on the why, be consistent on your messaging. What are you aiming towards? And I'd say be transparent, you know, within the bounds of what you can do and authentic in your messaging. I mean, that's it like that. So I think it is really hard to just, you know, say nothing changes. That's actually the problem. I think people are like, well, in a great culture, nothing changes. I said, no, unfortunately, in a great culture, you have to adapt to what's changing.

• 44:35Ryan Hawk?

  It's easy to criticize a CEO who has to lay people off when you're not the CEO. Cause we don't see it all. We don't know what's going on. We don't understand the probability numbers. It's so easy to criticize that person. But that's why it's not for everybody and you've got to be tough and you've got to be willing to do what it takes to keep the company in business first and foremost and set the company up to succeed in the future. And that's why that job isn't for everybody and you've got to be willing to make those tough calls. And I admire that. I think that would be so hard to do. Usually though, anything worthwhile in your life that you've ever done is preceded by something really, really hard.

• 45:17Speaker 01

  Yeah, and it's hard throughout. It's not just preceded by something hard. It's hard throughout, right? But let me give you the, the hope I have. And again, I'm going to come back to the quality of the zero team that I inherited and the people I get to work with every day. Like, we have something called a global all hands, right? It's our monthly all hands and we do it live and I play a pretty big part in it. But you know what? In those all hands, employees sometimes ask me tough questions and occasionally I'm like, hey, this is not appropriate. But by and large, in those all hands, I get to talk to employees about the system view. Remember, we talked about that, Ryan, the system view? You're right. As a CEO, you do see the system. And often you get criticized because everybody doesn't see the system.

• 45:57Ryan Hawk?

  Right.

• 45:58Speaker 01

  But if your employees are smart, and they usually are, you know, and you're willing to have an authentic conversation with them, you can give them a system view and they are grateful for it. Like, every time I have a conversation with zeros and I'm like, hey, I'm going to zoom back and show you a piece of the picture I'm seeing. So again, just a simple example, we just did this big acquisition of this company called Melio. And as you can imagine, I mean, my God, for eight months, you have a bunch of people in secret working on a deal. And then we launched it last week. And in our first GH afterwards, I had a whole script and I went off script because we had a GH and instead of presenting the same slides we printed investors, we're like, let us tell you what investors asked us about. Let us zoom back and give you a view of what investors were

• 46:41Speaker 01

  asking us about. And people are grateful. They're like, wow, thanks for bringing us in the room. And when you can be placed, and you know, I always start those GHs and look, I'm going to knock on wood because I could be proven wrong, but I start those GHs. I said, I'm going to share a view with you that of course is confidential. You know, this is stuff I'm never going to write in a book. I'm never going to talk about on a podcast, but let me give you a feel for what it's like. That has never served me wrong with employees, not at Xero, not elsewhere. If you're willing to be authentic and you can give them a system view. Now, you can't give them everything, to your point. There are things that are confidential, what have you. But the more you can help, you know, your team see the forest and give them view of the forest. They're smart people. You know, you think they're not thinking about these things? Of course they are.

• 47:24Speaker 01

  So I would just say, as a CEO, if you can be willing to answer tough questions or zoom back and give your team the occasional systems view, I think it will come back to serve you really well on the why when change happens.

• 47:37Ryan Hawk?

  Yes. I want to close by talking about making a big ask. Okay, you did this earlier in your career to Eric Schmidt at Google, which I think is super inspiring. You're pregnant and you want to keep running an international business at Google, but you told him, I need to pay for me and my nanny to travel the world business class. And I would imagine, knowing you, you backed it up with great reasoning and a deck, probably, or a presentation. But I think it's inspiring to hear of people who make a big risky ask. There's a lot that goes into it, so you don't come across as some entitled person who feels like they deserve the world when you haven't fully earned it.

• 48:18Ryan Hawk?

  So can you go into that story and how it could be helpful for maybe somebody else who's scared, even though they have earned the right to make that ask? And what you would say to them?

• 48:30Speaker 01

  Well, first of all, just for complete accuracy, I made that ask to Omid Kordistaney, who was my boss and Google's chief business officer, who I think shared it with Eric. And definitely aware. And I was on at least one business trip to Korea where Eric actually kindly offered to take me and my daughter and my nanny with him on his travel. So he certainly was aware and very supportive. And I will, I'm eternally grateful, actually, to Google for their support of my family situation in that time. How do you make a risky ask? Well, I think you hit the nail on the head. First of all, don't be entitled. You don't deserve it. Well, I take it back. You might deserve it, but don't go in like you deserve it. Go in and understand, just be like, hey, I know this is a big ask. Now, to your point, I think in any risky ask, you have to first say, how does it

• 49:13Speaker 01

  Serve the person you're asking and the organization you're asking. So why did Google say yes? I think they said yes, because they're like, wow, the cost of losing Sukhinder in this job and replacing her with someone else and the cost of that time versus, you know, the cost of helping support her six-month-old at the time, baby, traveling with her as she dug, moves around the world to every pretty 180 different countries I was managing. So first of all, I think you have to say, what's the benefit to you? What's the upside? And then I think you, I mean, I think in any risky ask, you also have to outline the downsides and how you would mitigate those risks. So I think if you want to be a very thoughtful asker on a big risk, by the way, remember, we just went through the board with a big acquisition. Do you think we didn't go through, like, here's a big, we want you to support this acquisition, here's why.

• 49:59Speaker 01

  You have to be, I would say, and I think I write about this in my book, you have to list the downsides as much as the upside. So first of all, go in and say, why is it beneficial to you? Number two, what are the downsides of this risk to you? How would I mitigate them? So somebody might say, well, gosh, the downside is, you know, blah, blah, blah. And you're like, okay, well, here's how I thought about that downside and how I'd mitigate it. You know, so on balance, that you've considered it all. And I'd say in most risky moves, is there a way back? So often there is, like, you can say, look, if this doesn't work out, here's something we can consider, but let's try it. I think in very risky moves, in the case of the Google one, there's a way out. If it's a personal question, there's a way out, right? So I think you have to paint the upside for them. You have to be really clear on the risks and the mitigants. That shows you've been thoughtful.

• 50:42Speaker 01

  And I think I would end with the ask again, from a tone of gratitude and realizing they don't have to do it, but you would appreciate if they do it. And inside of that, yes, of course, you can talk about your value, of course. But if you make it all about you, I'm not sure that's the right point. The point is, it's about them and your value in that equation.

• 51:00Ryan Hawk?

  That's the key, key point. Whether you're going for a job or you're going for a big ask, if you're going for a job, you're essentially solving someone else's problem and you need to talk with them about how you're going to solve their problems and make their life better, to make it as simplistic as possible. When people mess this up, they focus on themselves and why maybe they're awesome or they deserve the raise, or they deserve the job, or they deserve the business class ticket, as opposed to saying, this is how it solves your problem. Be others-oriented, others-focused, not, look at me, I've earned this, I'm entitled. It's, no, this is how it's going to help you.

• 51:38Speaker 01

  Yeah. And of course, look, I am of course, a fan of if people want to advocate for promotion or raise, or I would never say, don't advocate. I would say, when you advocate, think about, you know, what you have done, what you still can do, and how you've demonstrated impact in the past, and how you're going to demonstrate impact in the future. Like, if I was going to go ask for a raise or ask, I'd be like, look, I'm so excited to be here. You know, this is what I've accomplished. Yeah, this is, I think, what people would say about my work. I think I'm already operating at this level, you know, but you judge, you let me know, like, I also would love the feedback. Okay, there's an ask, I'd love the, you know, and what I'm so excited to do, if I, if you were going to give me the premise, it's like, I can't wait to unlock more value here. Here's some of the things I think I could still accomplish. Like,

• 52:22Speaker 01

  again, it's about the tone of the ask and your recognition that you are part of a system. To your point, it's not you in your own system. You are part of a system. Paint the vision of you in the system and how it's better for the system and for you.

• 52:37Ryan Hawk?

  One more. You're meeting with someone who's earlier in their career. Maybe they're early twenties, just graduated college, maybe business school, and they want to leave a positive dent in the world, but they're not fully sure how. What are some general pieces of life slash career advice for that person?

• 52:54Speaker 01

  I always say, early on, if you don't know how to leave a dent world, I'd be like, do great work for great people. Sometimes you don't know where you want to go. You don't know what industry, right? So you might say, this company is interesting, or this person's interesting. I'd be like, go find a way to, I'd say apprentice, under somebody super talented. Now, talented doesn't mean easy. It doesn't, you know what? It doesn't mean like there's like the world's nicest boss. But I always say, if you end up doing great work for great people, you're going to be fine. And if in that equation, you don't even know what great works looks like, go find a great person in a category you find generally interesting, and apprentice. And by the way, and when I say great work for that person, means like, work your tail off. Like, work your tail off. If you work your tail off for somebody who's highly talented, you're going to learn disproportionately more.

• 53:38Speaker 01

  That's it.

• 53:40Ryan Hawk?

  Yeah. Get after it and be a value-added person to the team, right? How, I think the question you're going to ask at the end of each day is, what did I do to add value to my boss today? What did I do to add value to the person I'm apprenticing under today? And write those things down and think about it. Have conversations about it, like strive for that. I think that is crucial and really good advice.

• 53:59Speaker 01

  And look, and by the way, if you're, let's say you're doing great work for somebody that you don't respect or whatever, maximize learning opportunity. And in your next, say, man, you know what? This is what I was capable of here. I maximized the opportunity. I got a great reference, again, pretty much early in your career, right? And then be like, now I'm going to go find somebody great to work for. And great is usually defined by pattern of success, you know, maybe outsized capability in one area or another, known for either like the people who that, who've like worked with that person go on to do great things. So you can see outside end markers of someone's success. Again, it doesn't mean they're easy to work for. But if your goal is to find accelerated impacted learning, it usually is around people who've done the same.

• 54:39Ryan Hawk?

  Love it. So Kinder, this is amazing. I am so glad you came back. Let's keep checking in. I don't know, let's make it more frequent because you're like right in the seat, doing the thing. It's really, really hard and you're killing it. And I love talking to current operators who are getting after it, making a difference, building great cultures, building great value for not only your employees, but your customers and shareholders. It's awesome to talk to you. I'd love to continue this dialogue as we both progress.

• 55:08Speaker 01

  For sure. And of course, I couldn't end this call without saying, thank you for being a zero customer.

• 55:12Ryan Hawk?

  Of course. Thanks so much.

• 55:18Ryan Hawk?

  It is the end of the podcast club. Thank you for being a member of the end of the podcast club. If you are, send me a note, [email protected]. Let me know what you learned from this great conversation with Sue Kinder Singh Cassidy. A few takeaways from my notes. If you are going for any leadership role, treat it like Sue Kinder did to earn the CEO position at zero. Present a vision. What is your goal for the company? What did the first 24 months look like? Build a deck for yourself that outlines how you're thinking about. About the situation and then share with them how you will execute on that and make their life better. Remember it's about them and helping them. Then the four things Sue Kinder

• 56:01Ryan Hawk?

  looked for when deciding on her next job. Macro tailwinds, a good industry, right? Customers she can get passionate about, a great business model. And then I love this quote, learn for miles. She wanted to learn. What are some of the must haves for you when thinking about your next leadership role? And then going for the big ask. When she worked at Google, she asked for business class travel for herself, her baby and her nanny, and she got it. How? Well, she focused on the person she was asking, how she was going to make their life better. Don't be entitled. Don't walk in there thinking you deserve anything, right? Think about how you're going to help the person you're asking. Make it about them,

• 56:45Ryan Hawk?

  not about you. Always tie it back to the value that you will add for the company and why it benefits that decision maker to say yes. Once again, I want to say thank you so much for continuing to spread the message and telling a friend or two, hey, you should listen to this episode of the Learning Leader Show with Sue Kinder Singh Cassidy. I think she'll help you become a more effective leader because you continue to do that and you also go to Apple Podcasts and Spotify and you subscribe to the show and you rate it hopefully five stars and you write a thoughtful review by doing all of that. You are giving me the opportunity to do what I love on a daily basis and for that, I will forever be grateful. Thank you so, so much. Talk to you soon. Can't wait.