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cover of episode Ask Simon Anything: Part Two

Ask Simon Anything: Part Two

2023/1/3
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A Bit of Optimism

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Simon discusses his strategy for dealing with overwhelm by focusing on one task at a time and reaching out to friends for support.

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Hey there, I'm Dr. Maya Shankar, and I'm a scientist who studies human behavior. Many of us have experienced a moment in our lives that changes everything, that instantly divides our life into a before and an after. On my podcast, A Slight Change of Plans, I talk to people about navigating these moments.

Their stories are full of candor and hard-won wisdom. And you'll hear from scientists who teach us how we can be more resilient in the face of change. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hello, and welcome to Haunting, Purgatory's premier podcast. I'm your host, Teresa.

We'll be bringing you different ghost stories each week straight from the person who experienced it firsthand. Some will be unsettling, some unnerving, some even downright terrifying. But all of them will be totally true. Listen to Haunting on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Welcome to Cheaters and Backstabbers. I'm Shadi Diaz. And I'm Kate Robards. And we are New York City stand-up comedians and best friends. And we love a good cheating and backstabbing story. So this is a series where our guests reveal their most shocking cheating stories. Join us as we learn how to avoid getting our hearts broken or our backs slashed. Listen to Cheaters and Backstabbers on the iHeartRadio app, Apple Podcasts, or wherever you listen to podcasts.

Welcome back to part two of Ask Simon. For the holidays, we decided to gather a whole bunch of questions and take an opportunity to answer them. So hope you enjoy part two. This is a bit of optimism.

I have a member of my team here. Say hi, Zach. Hey, Simon. Thanks for having me. And Zach is going to ask the questions that have been coming in. Let's jump right in. Simon, when you feel overwhelmed or unfocused, what do you do? You'll hear this as it's a repeating pattern in a lot of my answers. But when there is an emotional anything going on,

you know, an overwhelm is emotional. I reach out to a friend. I find somebody that I can call and I say, hey, I am overwhelmed. What that does is it helps me make me feel not alone in my overwhelm, which for some reason helps me feel that I can sort of tackle whatever it is I'm dealing with. Sometimes they'll offer me some strategies. But the best thing is also when I'm feeling overwhelmed to recognize that overwhelm comes from looking at everything that I have to do and thinking, how am I going to get it all done?

And so my strategy for beating overwhelm is to not look at everything, but to look at one thing. Okay, I'm just going to do this one thing. Think of it like a marathon. It's very hard to say, I'm about to run 26 miles. It's absolutely overwhelming. We can say to ourselves, I'm just going to run one mile.

And then we do. And then you run another mile, then you do. So what I find the best solution to help me overcome overwhelm is to actually get rid of all the stuff that's overwhelming me and get it to one thing that I can absolutely take care of. Next question.

Do you think the American education system is broken? How would you improve it? The simple answer is yes, for a couple of reasons. If we're talking in high school, one of the big problems we have is that education, schools, we compare it to leadership theory of the modern day. They're about 10 or 15 years behind. You have a high school principal, for example, says, my number one priority are my students. No, it's not. Your number one priority are your teachers. Your teacher's number one priority are your students.

And when you have teachers who fear the principal or teachers who fear the administration, that's going to trickle down in how they teach and how they treat each other. It's an administrator's job to create circles of safety for the teachers so they can teach to their best selves so that they can invest all of themselves in their kids. That's number one. Number two is, weirdly, parents are one of the biggest obstacles to any kind of

reform in education. I think most parents, I've seen some of the data, most parents agree the way we teach our kids has to change. And this industrial revolution, treating schools like factories system doesn't serve most. It doesn't foster creativity and things like that.

I think a lot of parents agree with that. They just don't want the schools to experiment on their kids. So we're kind of a little bit stuck there. But when we go to universities, I think it gets even worse. Too many university presidents are more preoccupied with their fundraising than they are with creating a fantastic culture of learning and cooperation and creativity.

We know a lot of schools are doing a bad job of serving kids who are struggling with mental health challenges, depression or anxiety, for example. Sometimes they'd rather kids take the leaves of absence rather than offer the service to take care of them. But I think the universities, unfortunately, seem to operate more like businesses than places that want to foster creativity and innovation. Look at how they market themselves. Universities literally will market themselves at the average starting salary of their graduates rather than

the graduates that contribute to society and help society grow and become active and valuable members of community. Maybe I'm just a crazy idealist here, but I want to go to a school that makes me a better person, doesn't just make me fit some

corporate mold for the next job I'm going to get. But hey, that's just me. Are you noticing any cultural shifts as organizations start having millennials in leadership positions? What's really, really funny is as millennials are entering leadership positions, they're complaining about millennials. They're also complaining about Gen Z. It's just really funny. I just appreciate the irony so much now that millennials are becoming the leaders. Look, this generational thing is going to go on. But to answer your question about cultural shifts, yes, of course there are cultural shifts.

Society, companies are living, breathing organisms that necessarily have to change with changing tastes, changing politics, changing technology, changing culture. Organizations have to keep up with the times. These are not the 1950s. These are not the 1850s.

Of course, it's a modern culture and new generations are helping to shape the norms and values of the day. So yes, there are cultural changes and our organizations hopefully are becoming more modern because of the young generations. If we want something specific, for example, younger generations now are the most inclusive generation. They don't care where you're from, what the color of your skin is. They don't care what your gender identity is, what your sexuality is. They understand that gender and sexuality are different things.

For them, it's a big nothing. They're just a very inclusive generation. And it puts a lot of pressure on organizations because this young generation expects that other organizations are as inclusive as they are. And they're perplexed when those organizations are not. So yes, I think that's one example of young generations exerting positive pressure on the changing culture of companies. And there are others, of course.

Simon, what continues to surprise and delight you? I love people. When COVID happened and a lot of people went to TikTok just to sort of let off steam, I guess, I just loved how much creativity there is. People are really funny and smart. Like when I get down on anything, I'm reminded of just how great people are. And one of the great things about living in a post-lockdown world is I'm getting to meet people again.

And I'm inspired by people. I'm inspired by the conversations. I think one of the greatest attributes any one of us can have is the realization that we know a tiny, tiny, tiny little bit. And no matter how much we know, we don't know so much more.

I love hearing the ideas of other people. And I love the intellectual banter and advancing ideas. So yeah, people are my thing. How do you deal with people that choose pessimism? Like how do you move forward and make sure that they don't drain your energy? One of the nice things about being an optimist is a pessimist is not going to change my mind. Likewise, being an optimist probably won't change a pessimist's mind. I'm not inherently against pessimism. You know, one of the things I think is really funny about pessimists is they all say, I'm not a pessimist, I'm a realist.

Well, I'm a realist too. We're both talking about the unknown future. I believe that the unknown future is more likely to be bright. Pessimists believe the unknown future is more likely to be dark. We can both be realistic. We can both be realistic about the good times. I think they'll last or the bad times. I think they won't last opposite for pessimists, I guess.

The thing that I think is great about pessimists is they offer an alternative point of view and they often cover my blind spots. I like pessimists when they're in the fight, when they're going to be with me shoulder to shoulder, fixing whatever we need to fix, working through whatever we need to work through. Where pessimists are not helpful is when they just lob grenades. They stand on the sidelines and point out all the problems, but they don't actually get involved in rolling up their sleeves. I'll take a working pessimist over a sideline pessimist any day.

How can you be a new kind of leader in companies where old managers only want to keep doing things in the old way? I get this question all the time. Senior leadership doesn't get it. What do I do? How do I influence them? And the answer is, you don't. You cannot influence other people, especially if they're multiple levels above us in the organization. What we can do is be the leaders we wish we had. What we can do is...

is take responsibility for the people to the left of us and the people to the right of us, regardless of where we are in the corporate hierarchy. We can be the lowest level. We still work with or for someone. And we can come to work every day and work tirelessly to see that those people rise, to see that those people feel seen and heard and understood. That's called leadership.

And if we have an infinite perspective, then these teams are going to be really high functioning and high performing. And one of the people in those teams may be promoted out and join another team. And they'll take everything they've learned and bring it to their new team. And then they'll move on to another team and they'll bring everything they've learned and bring it to their new team. And before you know it, the tail's wagged the dog. Before you know it, the whole organization has changed. So as long as we are willing to take an infinite minded perspective,

We can affect profound and positive change in an organization, especially when senior leadership doesn't get it because our work will outlast them. Did you have a failure in college that looking back on it now, you feel like it set you up for success later? Yes. One of the biggest mistakes I made in college was as a freshman. I made a real freshman mistake. So we had a book that rated all of the classes. All the outgoing students of a semester would rate the class that they just took and we'd publish the results. The school published the results.

And my first semester freshman year, I chose my schedule based entirely on workload. In other words, the lowest I could find. And let's just say I was bored out of my skull because there may have not been a lot of homework, but the professors were dull as dishwater and boring. And so I was not engaged. And my grades actually weren't that great either because I wasn't engaged.

And so the next semester I learned the lesson, which is it's not about the workload, it's about the professor. And so I picked my entire course load based solely on the professor, even if the workload was through the roof.

And I had a blast because the professors were amazing and I was engaged and I was interested and curious. And so now if I look at how I've navigated my career since I was entry level, I've always tried to pick the people. I never focused on the money that was being offered by a company. And I sometimes turned down a company that offered me more money to take a job from a company that offered me less money because I wanted to work for that person. Because I recognize that working for a great person, great leader is going to have better long-term effects on my joy, my inspiration, my performance, right?

I'm going to have a champion for me who's going to teach me and coach me, not just somebody who I'm getting paid to be bored. That's a go nowhere job. So yeah, I've worked very hard to choose who I work for, not necessarily make decisions based on money or workload. What's one thing you've changed your mind about in the last 12 months? This one's an uncomfortable one because I've thought about this for, I kid you not, like 10 years.

the importance of someone whose value set is different to ours. You know, I'm an idealist. I want people to believe that

in the idealized state of the future and be driven by that, you know, full of inspiration. But the reality is the future is ethereal. The future lives in our imagination. And it's hard to be driven on a day-to-day basis simply by looking to an idealized future. What helps us know what our values are is when we can see visually, tangibly, something that represents the opposite of our values.

So, for example, during the Cold War, Democrats and Republicans were at each other's throats and there was division in the country and all of these things were still the case. But at the end of the day, we could all agree that the Soviet Union was a greater threat to us than we were to ourselves.

And that really helped. And when the Soviet Union went away, we have no sense of an external existential threat. So you can see what human beings do. We look to define what we stand for by looking for the people who we stand against, which is unfortunate when we look internally. And I think human beings are all looking for a sense of belonging and purpose. And if you look at our country, instead of just defining ourselves, what we stand for, we find it easier to find

what we are against to help us know what we stand for. So I recognize that having a balance of power is important. This is why we don't like monopolies in business, right? Because the monopolies lose sight. They lose sight of the customer. They lose sight of their employees. They just lose sight. And having competition

a competitor is good for the customer. This is the whole spirit of capitalism, that competition is ultimately good for the customer. And I think that is as much true for ideas as it is for products. Someone on social media asks, pasta or noodles? Noodles. I like the taste. I like the texture. It's a little healthier. I like noodles.

Okay, Simon, what is the role of creative thinking in leadership and in organizations? You know, I think we forget that creativity matters everywhere. Creativity ideas is as important as creativity of creating stuff. And creativity thrives in the face of problems, obstacles, or chaos. And if anybody has ever led, there are problems, there are obstacles, and there is chaos.

And I love when leaders get together and they face a challenge that they may have faced before. And somebody says, what if we tried this this time? And I love the risk tolerance that goes along with trying something new in a leadership context. Because like any kind of experimentation, any kind of innovation, there is a risk doing something differently because it may fail and it may make a new problem, but it might actually work better.

So I don't believe in blind risk taking. I mean, I think you have to consider what will happen if it does fail. What's the backup plan? But one of the greatest joys I've had in being a leader is when I faced very difficult problems to try entirely new ways of solving that problem that are counterintuitive. When people use lawyers to advise them on what they should do, that's like following the old thing. And take, for example, medical malpractice.

A significantly high number of medical malpractice lawsuits occur because the doctor simply refused to apologize.

And I can guarantee you, the lawyer said, whatever you do, don't apologize. Sometimes just doing the human thing and saying, I'm really sorry, is all anybody wants to hear. And so I think trusting your gut. If you think the right thing to do is say you're sorry, then say you're sorry. And that's just one little example. But yeah, I think mixing it up makes for better leaders, like experimentation makes for better anything. Are some organizations beyond redemption? It's not about the organization being beyond redemption. It's about the leader, right? Organizations are simply collections of people.

And if we say, are some leaders beyond redemption? Sadly, the answer is yes. I've talked about this before, which is I'm not against letting people go from a company, but only when they have proven themselves to be uncoachable. They may have performance issue or behavioral issues. And we sit down and say, hey, listen, I need to bring this to your attention and we're going to coach you to be better. But if they think they're perfect and they think there's no room for improvement and they prove themselves to be wholly uncoachable, then yes, we should ask them to find joy at another company. But the

But the same goes for leaders, and I've seen this. I've seen leaders who reach a level of success where they believe simply because of their rank or fortune that that means that they have nothing else to learn. They start surrounding themselves with yes men. They start surrounding themselves with people who only agree even to their worst instincts, and there's no creative tension anymore. They start to believe that they are right and they are always right and they're the only ones that can save this organization.

sometimes just talking to those people is so difficult that yeah, they can sometimes be beyond redemption because they just can't listen. And if anybody's ever been in a relationship with somebody who refuses to listen and think they're right all the time and can gaslight you better than anybody else, well, imagine that person running an organization and treating all their people the same way.

How can people in distressed companies keep an infinite mindset even when the need to cut costs and drive immediate results is real? One of the good things that can come out of a distressed organization is camaraderie, believe it or not. Human beings actually can form close relationships.

during shared hardship or shared struggle. This is how bootcamp works in the military. You know, they form strong bonds with people who go through the shared hardship of bootcamp. Anybody who's ever lived through a natural disaster, you're friends with your neighbors. You may not have liked them yesterday, but today you're friends with them. Any family that's ever had a family tragedy, for example, it brings the family together. So a good leader in a distressed organization will challenge the people to contribute and be a part of the solution.

Where it doesn't work is when the leaders think that they have to solve all the problems themselves and start

start making dictations about we have to do this, we have to do that, they don't provide context, that produces fear in the organization as if there's not enough. And that makes people sort of shy away and go into self-preservation mode. In a truly distressed company, if you need cost cutting, for example, before cutting the people, which is the easy one, say to the company, hey, here's the reality of where we are. If we continue on this path, all of us lose our jobs. We have to save this amount of money. The easy thing for us to do is to just

start cutting jobs, but we want to make that the last option, not the first option. So we're challenging all of you. Where can we, where can we find the money to keep this business afloat? How can we be creative in how we spend money and how we make money? And when people are challenged to work together and find solutions together, it's amazing what happens, not only the creativity, but the camaraderie in writing the ship.

So yeah, I think sometimes distress is a massive opportunity to build strong team ethic and also creativity. Crisis is a terrible thing to waste, which, you know, the old trope. All right, Simon, someone says, I miss the book clubs you did during lockdown. Will you be doing anything like that again?

Funny you should ask, Zach. As you know, because you played a major role in it, we launched a book club. I stand on the stage all the time and I hear people say, Simon, we believe in what you talk about, but we can't afford a leadership training program, for example. And I always sort of cynically say, can you afford a book?

start a book club. Book clubs are a wonderful way to learn about leadership. And we also know that a lot of book clubs, kind of they're hard to get going in companies, not because the idea doesn't work, but because nobody wants to quote unquote lead it because everybody wants to sort of

be even Steven. And like, so finding somebody to lead, it's a little hard, but also the depth of conversation. You know, a lot of book clubs are like, so what'd you think of chapter three that we just read? There's really an opportunity to go deep. And that's what we did with our book club. It's me guiding it. And I force people to have conversations about themselves and their organizations based on the subject of the book.

that they really have to have difficult conversations about their organization. And our first book club I probably should mention is The Infinite Game. I do hope to do one of the big public book clubs again we did on YouTube. Those were really, really fun. So yeah, I'm sure we'll find a time in 2023 to do one again. Simon, here's the last question I've got for you. Are there any questions that you wish you had been asked?

So there's a huge difference in the questions that I get asked from businesses versus the military. Businesses ask me all the same questions and military, every time I go see them, I get asked different questions. Businesses ask me questions that help themselves.

And military asked me questions about how they can use my work to help each other and how they can better themselves. So for example, one of the questions I was asked in the military was, how do we compete against an enemy who's really good at everything that I speak about and write about? So an enemy with a clear sense of why and an enemy with an infinite perspective. I've never, ever, ever been asked by a company, how do we compete against another company who's really good at all the stuff I talk about? That's a really good question.

That's a really hard question. I find that there's intense honesty in the military. I don't get intense honesty in private sector. Military will say, we are really struggling at this. How do we get better at it? Where business, they rarely say to me, we really suck at this. They'll never say, our leadership is just failing left and right. Where in the military, they will. And so I think the questions that I would love to get are ones grounded in blunt honesty about the reality of the situation that everybody knows, but you're not talking about.

and better ways to improve the organization, not just the results? Those are the questions I want to get asked.

I think that's all we've got, Simon. So thanks for tuning in. Thanks for listening. I hope this was interesting. I hope that you had some of the same questions that people have been writing in. But here's one of the things that I've learned from all of these questions. One, people are taking themselves on. A lot of the questions were about self-growth, becoming a leader, what it means to lead, how to lead, how to take care of people. I love that.

If we go back 30 years, all the questions were, how do I hit my targets? How do I be more efficient? How do I increase productivity on my team? And now the questions are really about that core, beautiful, magical human leadership. I love that. I also love that people are being very open about uncertainty. What does the future hold?

We're not pretending that everything's perfect. And we're out loud saying, I don't know and I don't understand and I'm asking around. So I really appreciate those questions as well. And at the end of the day, what I'm learning is we're entering in a time where we believe constant self-improvement for ourselves and our organizations is a real thing. And that's something I want to be a part of. If you enjoyed this podcast and would like to hear more, please subscribe wherever you like to listen to podcasts.

And if you'd like to learn more about the topic you just heard, please check out the Optimism Library at simonsenik.com, where you can get access to more than 35 undemanded classes about leadership, culture, purpose, and more. Until then, take care of yourself. Take care of each other. Thank you.

Hey there, I'm Dr. Maya Shankar, and I'm a scientist who studies human behavior. Many of us have experienced a moment in our lives that changes everything, that instantly divides our life into a before and an after. On my podcast, A Slight Change of Plans, I talk to people about navigating these moments.

Their stories are full of candor and hard-won wisdom. And you'll hear from scientists who teach us how we can be more resilient in the face of change. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hello, and welcome to Haunting, Purgatory's premier podcast. I'm your host, Teresa.

We'll be bringing you different ghost stories each week straight from the person who experienced it firsthand. Some will be unsettling, some unnerving, some even downright terrifying. But all of them will be totally true. Listen to Haunting on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Welcome to Cheaters and Backstabbers. I'm Shadi Diaz. And I'm Kate Robards. And we are New York City stand-up comedians and best friends. And we love a good cheating and backstabbing story. So this is a series where our guests reveal their most shocking cheating stories. Join us as we learn how to avoid getting our hearts broken or our backs slashed. Listen to Cheaters and Backstabbers on the iHeartRadio app, Apple Podcasts, or wherever you listen to podcasts.