Becoming a Superboss and Building Stronger Companies

October 5, 2022 Mimi Torrington

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What do Superbosses look like? What skills do they possess, how can you know you are becoming a superboss yourself? and how do they go about creating future leaders? Let's find out all the answers from one of the most exceptional leaders, Sydney Finkelstein.

Sydney is a Professor at the Tuck School of Business at Dartmouth College, a Consultant, a Speaker to senior executives, and an Executive Coach focusing on leadership, talent development, and corporate governance.

Sydney is also a fellow of the Academy of Management and is listed on the Thinkers50, the world's most prestigious ranking of leadership gurus, and the author of Superbosses: How Exceptional Leaders Master the Flow of Talent. Moreover, he is a columnist for the BBC and the host of his own podcast, The Sydcast.

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Welcome back to CFO Weekly, where we're talking with financial leaders about how to build efficiency in their teams, create time for strategy and ultimately get results with your host Megan Weis. Let's jump right in.

Megan Weis: Today my guest is Sydney Finkelstein. Sydney is a Professor at the Tuck School of Business at Dartmouth College. Additionally, Sydney is a consultant and speaker to senior executives around the globe, as well as an executive coach, focusing on leadership, talent development, corporate governance, learning from mistakes and strategies for growth. He is a fellow of the academy of management and listed on the thinkers 50. The world's most prestigious ranking of leadership gurus. He has been featured in The Financial Times, The Wall Street Journal, the Washington Post, Harvard Business Review, Business Week, The London Times, Toronto Globe and Mail Inc, Fast Company, and CNBC. He is also a columnist for the BBC and the host of his own podcast, The Sydcast. Sydney, thank you so much for joining me on today's episode.

Sydney Finkelstein: Thanks Megan, great to be on with you.

Megan: Yes. You are a professor at Tuck School at Dartmouth, author of Superbosses, and podcast host of The Sydcast, and I'm honored to have you on my show today. We're going to be hearing your story and looking at the role of a leader, the qualities great leaders possess and how they go about creating future great leaders. As I said, I've been really looking forward to this conversation so let's get started with you. First of all, can you tell us a little about you a little bit about your career journey and how it is you got to where you are today?

Sydney: Well, Megan, how many hours you have for this part?

Megan: [laughs]

Sydney: I'll keep it short. I grew up in Canada in Montreal and early after I went to college in graduate school and had a chance to actually be a teacher and instructor at the university I went to in Montreal which is called Concordia University which is a great school. Not that well known globally, but very good school. I was 23 years old and they wanted me to teach. I didn't-- I had a master's degree at that point and I thought, well, why not that sounds like fun. I was scrambling to figure out how to do all that because of course I didn't have very much experience. I hadn't really worked with very many organizations, very many companies by then, but I did it and I had a two year contract and I did really well.

What happened is my boss, who was at that time, the head of the department and the management department. I now call him a superboss, by the way. He basically fired me. He told me you're doing well, that you are doing great, the students really like you, but if you want to be serious about this career, you need to go get a PhD. You need to go work with companies more. You need to really get immersed into the field.

I wasn't happy to hear that because I was having a great old time, but sometimes, when you let somebody go that has a lot of potential, it opens a door to their opportunities and that's what he did for me. I ended up going to Columbia for my PhD. I used to teach early on at University of Southern California, now at the Tuck school at Dartmouth College for almost three decades. I do a lot of work on leadership on strategy and have worked with companies around the world and basically tried to do all those things that former department chair said I needed to do, and then some, and luckily it's all worked out.

Megan: Yes, it sounds like it has and sometimes we need that kick in the pants, I guess. Get us out of our comfort zone and change is scary, but good.

Sydney: Yes. Comfort zone is a funny thing, isn't it?

Megan: Yes, really is.

Sydney: We like it because it's comfortable, but I've spent my career trying to fight against that natural tendency to just get comfortable with anything and you don't always do it and sometimes you don't have to always do it because you have to be able to enjoy where your present circumstance, wherever it is. I've always found the best learning comes from challenging and pushing and questioning. It's certainly what I've advocated throughout my career for my students and for consulting clients and people that I coach as well as one of the themes of what makes for great leaders. It's a big point you're bringing up.

Megan: As you look back on your career and maybe you've touched on them a bit already, but are there any stories that stand out in your mind as turning points?

Sydney: Well, certainly being fired at qualifies, but I'll tell you one even earlier which is really interesting when I reflect on it. I once thought I would be an accountant. Which might sound a little bit strange for a guy that does a lot of work on leadership, but my older brother, Simon was an accountant and I looked up to him and so I decided, "Well, why don't I do that?"

In my first job doing that I was doing some-- Entry-level accounting is auditing type work. I hadn't gotten my CPA, it was called a CA in Canada, yet and I had my review with my manager and the manager said a lot of great things about that I was very analytical and definitely diligent and focused and getting the job done, getting it done quickly, but then he said, "If there's one thing you really want to work on it's one thing you want to change?" Of course, I leaned in to hear what that was because I wanted to get better. He said, "You really should stop asking so many questions." That was my last day in accounting. Which I'm proud of because I was young and what did I know?

Somehow, I had that intuition that asking questions, not only is this not a bad thing, it's an incredibly important thing. I've found that the best leaders ask the best questions because you can come up with a great you could spend forever trying to solve a problem or a strategy or direction or a project but if it starts off with a question that's fundamentally faulty or not creative enough or not out there enough, then you've been spinning your wheels.

Asking questions is not just important. It's central. It's of course how I ended up making my career that's my job as a professor, you ask questions then you go try to solve or answer those questions and that's called research. That was a pretty powerful lesson early on and one that was a real eye-opener for me.

Megan: Yes questions is the key to learning and once you stop learning life's pretty much over. I would like to think that the profession of accounting has evolved over the years.

Sydney: Of course it has. Maybe I was one of these kids that just I always wanted to know more and maybe I was starting to get annoying. It's certainly possible.

Megan: Sounds like my sone.

Sydney: [chuckles] It's very odd advice in any event but I thank him for it because if he couched it a little bit softer or so maybe I would've been there in a bit longer.

Megan: Yes. You would've missed your calling.

Sydney: Who knows?

Megan: What courses do you teach as a Professor at Dartmouth?

Sydney: I used to teach the core business strategy course for many years, and I used to teach a course on mergers and acquisitions as well. Over the last 10 years, my primary courses are one that I call strategic leadership, which is like a Sydcourse. It's my stuff. It's the things I do research on the things I work on with companies and I just created a course all around it. It has to do with developing talent, how to be a great leader how to hire and select talent how to build great teams, how to manage unexpected challenges as a leader then the other course that I spend that I teach now primary course is actually a two week intensive program for all of our incoming MBA students.

They all take this course and I teach, I lead this and I teach in it, but I have, there are other faculty that I brought in to teach other portions of it and it's like a bootcamp and an orientation at the same time to the two year MBA program. I've created all kinds of interesting experiential exercises as part of that to get to really send the signal that this is not school as normal. This is going to change you, this is going to challenge, you talk about comfort zone and this has potential to transform who you are as an individual and I want to start to send that you can't do that in two weeks, but I want to start sending that signal through a variety of different things that we do in that program. So those are the primary things I teach now.

Megan: That boot camp sounds like an amazing experience. Of course we can't all get into Dartmouth, but as we were talking about be before we started recording, you've recently released courses on Coursera. Can you tell us a little bit about those?

Sydney: This has been such a fun thing. There's so many online courses that are out there. It's exploded as an area. I resisted it for a while, but now that we created this partnership with Coursera, which really is a best-in-class global firm, they have a hundred million learners, which is a crazy number. I had a chance to put together four courses. They call a group or a set of four courses a specialization for which they, if you pass them and do them, you can get a certificate.

Three of the four courses are based on books and areas of work that I've spent literally decades working on. It's like my life's work in here and then the fourth course is brand new things that I haven't even written about yet but personal leadership and things that I'm thinking about now and the courses consist of a series of videos that I created from scratch, as well as something like 50 application exercises, which is my way of saying, if you want to use the ideas that I'm sharing with you and the thoughts and the techniques and the methods and all that, if you want to use it, you need to know how to use it. You need to apply it.

It's not enough just to be able to regurgitate it back. I'm not a believer in these quizzes that sometimes you see in online courses, multiple-choice questions. That tells you nothing for a topic like, like mine, which is about leadership, strategic thinking, making better decisions, living a better life even and so applying it to yourself and to the people around you is where the action is. I created those as well.

It's just launched, there are already thousands of people that have started these courses. It's very very exciting to see where it's going. Your listeners can find it, just by googling my name and Coursera and the specialization is called strategic leadership.

Megan: Awesome. I'm definitely going to look into it. You also have a podcast which is called The Sydcast. What's this podcast about in general?

Sydney: This one, I'm into my fourth season now, and it's just been so much fun. I call it informative and informal conversations with really fascinating people and often people that may not be as well known as some of the famous people that are out there. I feel like I know everyone has a story, has an interesting story to tell, and I help that person tell their life story. We talk about their career. We talk about lessons learned along the way, we talk about their life, sometimes their personal life, certainly growing up and I have people that are entrepreneurs.

I have some academics and different fields that are doing fascinating research from people that are graphic designers working on Pixar films to one professor, one academic who is working with NASA in sending an orbiter to land on one of the moons of Jupiter. Unbelievable topics. I have some sports people, both athletes and presidents of teams, entertainers, and of course, some good old fashioned leaders and CEOs. So really diverse types of people, great conversations and a chance for me to help somebody bring their story to a wide audience chock-full of lessons, and just an interesting conversation as well.

Megan: As you look back on the last four years, you have as an episode that stands out in your mind as maybe one of the more memorable or even your favorite?

Sydney: Wow. There's a lot. I'll share one that it's the most downloaded of all the episodes. I guess the audience or the marketplace has spoken on that one too and it's a very powerful episode with a young woman named Kate Speer. S-P-E-E-R. She talks openly about her struggle with mental illness for a very-very long time and misdiagnoses, and having to really struggle but she over time started to figure it out, started to get better, started to get the right type of treatment.

This is amazing, found that her dog, her pet could almost predict when she was going to have what she calls a psychotic episode, where she gets these hallucinations that are damaging. The dog warns her ahead of time that it's happening and comforts her before it even hits her and so she knows something's about to happen in her brain that is not real, and it helps her and it helped her deal with it, and lo and behold, that she got better and started talking openly about this. She started to help so many young people that have these. When you're in middle school, high school, early years. It's challenging anyways.

Then you have episodes that you just don't know how to deal with or not sure what to do with, and she is today, the CEO of a company called The Doggist which is so appropriate. D-O-G-G-I-S-T. I don't know if you ever heard of it, but it started as an Instagram account by an out of work photographer in New York city that will take photos of dogs and add some captions and they have now become a real business and she is helping them run and monetize the idea, and they have books and other activities as well.

It's a powerful story, a powerful journey that she shares bravely and openly, and a very happy story as well as it's turned out.

Megan: Absolutely. That sounds like a very brave story. Last month you focused on leading through times of crisis and change. What's your advice for this?

Sydney: Leading through crisis? Well, I've always been a believer in as hard as it may be facing up to the reality of the world around us. Just being willing somehow to say," Okay, this is not good. This is scary, but this is the way it is."

I call that intellectual honesty. It's being honest with yourself about the way the world is. Whether that's COVID and the challenges that have happened, whether that's people being in jobs that are not fulfilling or that they're looking to change, whether it's people dealing with personal life issues about their personal life, whether it's people in a more strategic sense looking at their business and saying, "It's not working the way I thought it was going to work, and I need to do something about this." You have to be strong to do this.

The way that I described Kate Speer just a moment ago, the woman from the Doggist, having to eventually, and it took a while, but recognize that this is her life, this is who she is. These are the challenges she has to face. Now let's figure out how to do it.

I think that's my number one bit of advice, and it's a hard advice. It's not that easy to take because all of us would like to sometimes pretend that what we're dealing with is not real. I understand that, but sticking our head in the sand and ignoring change, ignoring crisis, ignoring challenges, doesn't mean it goes away and so step one has got to be not acceptance that life is like this, but recognition or awareness that, "Yes, this is my challenge. Now let's figure out what to do about it."

Megan: The word authentic came to mind as you were describing that. It's hard.

Sydney: Absolutely. Not easy.

Megan: It's a quality. It's hard. It's not easy, yes. It's hard to be yourself and to be authentic.

Sydney: It is. That's a word that's used a lot also authentic and sometimes being authentic can get you in trouble. That's the bad part about it. Not everyone is open-minded, but I really believe that, especially in the modern economy that exists today, there are so many career tracks and so many things changing that we owe it to ourselves-- Every one of your listeners owes it to herself or himself to find the spot, the job, the situation that they find fulfilling. Work doesn't have to be just work.

I know maybe not everyone's gonna be able to get there and some jobs are just tough jobs but I think we should try and I could tell you also what those jobs look like by the way. There are several characteristics that you want to look for, or you want to try to create you want to create or look for as much autonomy as possible.

This is one of the reasons why this work-from-home world we're in now and hybrid has become such a big topic and it's not going away. It's not that COVID has gone away but most people are learning to live with life in a world where there will be some COVID, just like there's some flu and other things like that but it continues this issue about working from home and a lot of CEOs I talk to are still struggling with this.

The reason it's so central is because I think the underlying issue here is autonomy. People want to feel autonomy. They want to feel like they have some control over their work over their lives. When they do, they are going to be happier and more fulfilled in that job. That's what you want to look for. I would say number one, autonomy. Number two, impact a job where you can actually do something good for someone, something, some aspect of society.

I always say to leaders, to managers, you need to convey to the people in your team and the people around you that this work means something, that it counts and the question I always ask is you need to answer this question. Why do we exist? Why do you exist as a team or as a business? There's got to be a really good answer. If the answer is to make a lot of money. It's not a good enough answer. I'm a capitalist and I like a lot of money too, but that's not good, that's not where meaning comes from.

Autonomy, impact, and I'd say connection. A job that allows you to connect with other people in some way, people need people. We certainly have seen that in our two years plus of COVID with so much isolation and the problems that it created, and being able to work with either directly or indirectly people that you feel some degree of connection to that you get some value from adds a lot. Those are the characteristics of great jobs and that's what we should be looking for. I don't think people should settle for anything other than that whenever ever possible.

Megan: Yes. That's great advice and you brought up connection. How can companies create connections in a world that's mostly remote? Any advice for that?

Sydney: Yes, there, there are a few things you can do. I'll give you a couple of very simple practical tips. When people are working remotely, I think looking forward, most people will have some degree of hybrid. Even if you're working mostly remotely, there will be occasions where you will be face to face. In fact, my daughter started a new job in November of 2021. She met her boss for the first time, five months later, face-to-face and it's not unusual. She's a millennial, this happens.

How did they spend their time together? There were no long presentations and PowerPoint slides and formalities. They were face-to-face, they were talking. They had dinner together with some other colleagues to talk informally. We have to use our face-to-face time much better than we typically or historically have because it's so rare and that's my first tip. Don't fill up that time with PowerPoint slides and all the other stuff and meeting after meeting that could wait for other circumstances.

I think the second tip, and this gets to connection that's not just about accomplishing your goals, although it has a lot to do with it, but you're living your life and building that connection, is we've got to schedule some one-on-one time with people, where you could learn from your boss. You could learn-- I think so much teaching so much development of individuals on the job comes from that one-on-one, experience. You could even do it on ZOOM if you needed to, if it's one-on-one, but you could also do it outdoors. To the extent that we have another flare-up or people have different personal concerns about COVID, which are understandable, walk and talk.

I've had tons of meetings that are walk and talk, one-on-one and they're fun. You get a little bit of exercise and you get to know somebody at a different level. We got to use our time. We have to look for more creative ways to spend time one-on-one to build that connection. Also at the same time, advance our careers and advance our learning.

A lot of my students are worried about developing graduating students are, are worried about developing mentors and develop those strong professional interpersonal relationships that are so critical, getting anything done and they're right, if you're a hundred percent on ZOOM, it's going to be tough to do that. We got to be smart. We got to protect our time and use it well, and we have to be creative as well.

Megan: You're also the author of the best-seller, Superbosses: How Exceptional Leaders Master the Flow of Talent. First, let's start with the idea of a superboss. What exactly is that?

Sydney: Yes, so a superboss is a leader that sees the potential in other leaders often before they see it themselves. It's a leader that generates and regenerates talent really on a continual basis. It's someone that is great at scouting for talent, for looking for talent, for identifying talent, developing people, motivating and developing people, building strong teams as well.

It's not just a good leader or a good manager. Of course, they are that, but they have elevated the importance of talent to a level that stands out, and working for a superboss leader is one of the absolute best ways to accelerate your career as well, because they'll help you get better. They won't always make it easy. Sometimes people make the mistake of assuming that they want a nice boss.

Well, a nice boss is not necessarily a good boss. I'll take nice over nasty, I got that, but a good boss is someone that will push you, that will challenge you, will take you out of your comfort zone, as we talked about in the beginning of our conversation. That's what the best bosses will do. Superboss leaders will do that. Working for somebody like that is one of the best ways to advance to accelerate your career.

Megan: Let's talk about how they do that. How do they go about motivating, inspiring and enabling others?

Sydney: Yes. When it comes to motivation they do two things that in my experience should go together, but don't often go together. One is that they do create a strong performance-driven culture. They push people hard. the expectations are there for getting the job done getting it done at a high level but they do the second thing as well when it comes to motivation. That's that inspiration word that you reference. They inspire people to believe that they're the ones that could do it.

Ralph Lauren is one of my superboss leaders that I profile in the book. He used to say to his team and to people in the company, we are the ones that set the standard. We don't copy other people. They might try to copy what we're doing but we will not do that. We will always be a step ahead. He believed it. He was, again to use the word you brought up earlier, he was authentic. He was genuine about that and he inspired people to believe there's nothing they can't do.

What I learned from the superboss leaders is these two sides, the yin and the yang of motivation if you will challenging people, pushing people hard, creating that performance-driven expectation, and at the same time inspiring them to actually do it and to believe that that they can do it. I've seen managers that are good with one or the other, but you really need to be able to do both.

Motivating, of course, is not the whole story. It's how you get the train in motion. The other thing I'll say that they do, which is the day to day development of talent earlier when I referenced how important it is for people to have some time working one on one with their boss, that's where people really learn that is a superboss idea and that one-on-one time will involve teaching.

They'll teach people on their team about the business, sometimes about life, sometimes about how to manage other people. It will-- a good way to summarize it is that they've actually resurrected the most common method of developing talent in the history of I don't know of the world, but let's say for hundreds of years, so that's quite a statement. That is the master-apprentice relationship. They have resurrected a master-apprentice relationship so that when you work for a superboss, it's almost like you are an apprentice to that master and they are teaching you their crap. They're teaching you all about that business and they normally teach you, but they do two other things that are important.

One, they create opportunities for people. How many of us have had these great opportunities that a boss saw something, a leader saw something in us and was willing to take a chance? Many of these examples, many of these instances, we're probably afraid or concerned, and that's that comfort zone thing coming up yet again. We did it and we looked back and we said, "Wow, there's nothing I can't do now." It just accelerates your career.

Then the other aspect of developing talent that's part of this master-apprentice mindset, is that these leaders customize how they work with each person on their team. They spend the time to know who they are, to know how they think, what they like, how they behave, and then they customize their actions and their behaviors. Which is, if you think about it, a really big deal because we live in a world today that has customization of everything.

Type in a search term on Google and it completes the term for you. It knows what you're thinking even before you've written it down. It's spooky. But, when it comes to developing talent, where is that customization? We seem to fall into this trap of saying, and I bet a lot of people can relate to this. You have a new boss, what's the first thing you're going to do? You're going to talk to colleagues and say, "Okay, what's she like? What's this going to be like? What are we going to have to deal with now?"

We think about how we adapt, how we need to adapt ourselves to our boss, when in fact the superboss leader understands that it should be quite the opposite, that they need to adapt or to customize how they work with each person in their team, and they do that. The loyalty that they generate is tremendous. The ability to get more out of people and for people to feel again, meaning, fulfilled, and engaged in their work goes up. Those are some of the main things that we learned the superboss leaders do.

Megan: In this day and age when talent is so scarce seems like becoming a superboss would elevate the company in general. Do you think people are born superbosses? Are they raised to be superbosses or is this something that we can become later in life as an adult?

Sydney: First, a quick point on the premise of your question which is exactly right in our modern era, the talent, what do we call the great resignation? Has there ever been a more important-- First of all, has there ever been a better time to have talent at anything? The opportunities are incredible, but has there ever been a more important time for leaders to up their game and figure out how to really be a great leader? Because that is now expected, that is required. It's not an option anymore. A great leader helps other people get better. They advance their careers to the point of being, are you born, or can you do this? Not only do I believe that you could learn how to do this, I know you could for a bunch of reasons.

One of which is I've been doing that with teams and organizations and leaders now for several years. You could see the result, but just in an anecdotal way, I could tell you that before COVID, I was on the road a lot doing a lot of different work including book signings and people come up to me, "I'd like you to sign your book to my boss. Now that I heard you speak, I know my boss is a superboss." I signed the name to that person. I never heard of that person in almost every instance. I often didn't even hear about the company.

In other words, there are superboss leaders up and down every company, every organization that's there. They're not enough, but they're not that scarce. They're are there. We need to recognize them more. We need to value them more, I think, but they're there. That's an indication that in fact a lot of people have begun to figure out how to do this.

Every one of the, I call it the Superboss Playbook, a whole series of in fact, the books that I've written about superbosses, the first one's called Superbosses, then the follow up two or three years later is called the Superboss Playbook that has these tools and techniques and practices to help people become superbosses. Exactly to address the question you raised, about can you learn how to do that. In fact, you can and every single aspect of what superbosses do, they are learnable, they're teachable, and they're learnable. You have to want to do it and you have to work at it, but they're absolutely learnable.

Megan: Well, that's good to know. We've talked a lot about success, but you've also spent a lot of time studying why executives fail. What do you think is the biggest reason that this happens?

Sydney: Well, that's quite a big question. I wrote a book called Why Smart Executives Fail and did a lot of follow-up work on that topic. There are a lot of reasons, but if I were to drill down into the single biggest reason, it is that sometimes people, meaning leaders, forget that some of the flaws that all of us have as individuals. They could be biases in how we think, they could be believing we know more than we do. They could be arrogance and complacency. They could be believing our experiences even more powerful, more relevant than it actually is because the world is changed around us. It could be because we procrastinate. It could be because we sometimes stick our head in the sand.

All of those very human defects if you will, problems, biases. When we allow those things to take hold as a leader, that's when failure happens and that's what makes it tough because they're very natural. There are times in all of our lives when we probably have fallen into some of these traps. Being alert to them, being self-aware, surrounding yourself with people that are unafraid to speak up and to feel that psychological safety to share their point of view even if it's a different point of view than the one that you might have as a leader, these are the things that are needed.

The irony is that the number one reason why, what I call smart executives, managers, executives, leaders that have previously been successful or have had some degree of success. The number one reason why they derail, why they fail is because they allow those very human traits that all of us occasionally have to take hold, to take control of them and not to fight back and then fall into these traps believing we know more than we do and not listening, and arrogance and complacency.

Even to circle back to one of the first things we talked about, not willing to put ourselves out of our comfort zone to try something new, to change, to adapt because we are just so comfortable with where we've been and we're afraid that something might go wrong.

Megan: Yes, we're all born with biases and it it's amazing to me just how many there are and how strong they are.

Sydney: That's part of human nature, but we need to know that, we need to be alert to that and we need to be self-aware and you know what? We also need to do some of those things that are softy things. I use the word reflection, reflection is just thinking, taking a few minutes every day. You don't have take a lot of times to reflect and think about it. Sometimes even write down some of those things that happened to us during the day and reflect about why we did things the way we did. Why that's the case and learn more about ourselves.

People do this by the way, in lots of ways, it's not just sitting down for 10 minutes every day and reflecting. You can do it when you're jogging, you could do it in the shower. When you just let your mind go, you could do it through meditation and yoga. There are a lot of ways to do it, but we need to do it, and we need to try to capture that and do it in a purposeful way.

Megan: What do you believe is the most necessary skillset today for an executive to possess to succeed in the world of business?

Sydney: I would say the most important thing to succeed is to be unafraid of failing, and that's not easy as we know. Imagine what you could do if you were not afraid to fail? it would be spectacular. It's that fear. It's that concern. Again, it's a natural thing, for some people, it takes the form of imposter syndrome, for other people-- My podcast not that long ago, I was talking to a CEO of a company who said when I asked, "What do you wish you'd done differently?" He said, "I wish I wasn't so afraid." He was successful. "I wish I wasn't so afraid of making a mistake, it slowed me down and it took me a long time to get where I ended up and it didn't have to be that way." That's what I would say.

Megan: That's great advice.

Sydney: Stop being so afraid.

Megan: Absolutely. I look at my life and I know I'm still afraid of things, and it holds people back.

Sydney: It does. Again, like I said earlier, it's a very human thing, but we need to be alert to it. We need to know what it is, and we need to set ourselves up so that we don't let it dominate.

Megan: Sydney, lastly, as an expert on leadership and talent, what obstacles do you try to foresee for your students that are just starting out, or what's on the horizon and what do you think is holding people back?

Sydney: Well, all these questions you've been asking are great questions and I feel I can pontificate for a very, very long time because there's a lot of aspects to these great questions. What keeps me up at night is thinking about how I can continue to have an impact on the communities I care about. Which in my case, it's different for everyone who my case would be my students would be executives that I work with, and coach, it would be my family and friends. How can I keep getting better? How can I get continue to push myself to get out of my comfort zone so that I could do what I've set out to try to do in not just my career, but my life?

I would say that you can translate that idea in a much broader way to be the challenge for every one of us in whatever career track we're in, whatever work we happen to do we're always about impact. If we don't feel like we're having an impact on the world, or our friends, or our family in some way, we will be less happy. It is simply the way it is, and we'll have less meaningful lives and careers. I don't want that to happen to me. I don't want that to happen to anyone. That's what I advocate. That's what I want people to think about. It's not a one and done, it is pretty much a continuous process of challenge, of questioning, and even creativity and courage as well.

Megan: Sydney, thank you so much for being my guest today. I feel like I could literally talk to you all day.

Sydney: Megan, I really appreciate the time and the opportunity. It's been great to engage with you on these really, really important questions. Thank you.

Megan: Yes. Thank you. I appreciate you taking the time to be here with us today and I wish you all the best. To all of our listeners take care, and until next week when we're back again, I wish you all the best.

[outro music]

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In this episode, we discuss how you can learn to ask the best question, leading through crisis and change, finding the right job, what makes Superbosses stand out, among other interesting topics.

Learn Asking Good Question

Quote superboss asking good questions

Asking the right questions is the foundation of every problem you try to solve and every strategy or project you want to build. If you start with an inaccurate or uninspired question, you will work hard without many positive outcomes.

“I've found that the best leaders ask the best questions”

Leading Through Crisis and Change

Quote superboss Leading through crisis and change

When dealing with times of crisis or change, some leaders tend to ignore them. But that will only lead to bigger problems. You have to be strong to admit these challenges and search for ways of dealing with them.

“Sticking our heads in the sand and ignoring change, crisis, and challenges don't mean they go away”.

Finding the Right Job to Help Becoming a Superboss

Quote finding the right job to help in becoming a superboss

When looking for a job, look for these characteristics. Number one, as much autonomy as possible. Number two, identify the impact the job has. That is where leaders should step in and convey to people and teams their job's meaning. And third, find a job that allows you to connect with other people.

“Every individual owes himself to find the spot, the job, and the situation he finds fulfilling. Work doesn't have to just work”.

It's a Bird... It's a Plane... It's a Superboss

working for a superboss Quote

A Superboss is a leader who sees the potential in other leaders. A Superboss is also great at identifying talent, motivating and developing people, and building strong teams. Superbosses push people hard, inspire them, teach, create opportunities, and customize how they work with each person on their team.

“Working for a Superboss is one of the absolute best ways to accelerate your career”.

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