Choices and Chances: Designing Successful Strategies - Featuring Jessy Hsieh

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This episode explores the importance of assumptions, choices, viewpoints, and purpose to formulate a successful strategy.

My special guest is Jessy Hsieh, Clinical Assistant Professor at New York University Stern School of Business. Jessy’s research interests include strategy, creativity, digital sociology, and philosophy of education.

A good strategy questions all certainties and assumptions with a curious, open, and flexible attitude. Strategy is not a rigid plan based on dangerous false assumptions but the smallest set of choices that optimally guide or force other choices.

The best strategic ideas require leveraging different points of view by listening to your people and giving them a voice. Strategy is about choosing, and choosing is the freedom to reframe challenges to make us feel we have agency in our personal and professional lives.

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Welcome to Pity Party Over the podcast for people teams and organizations seeking practical ideas for results in greater happiness. I'm your host, Stephen Matini. Let's pause, learn and move on. Pity Party Over is brought to you by ALYGN, A L Y GN . company.

Stephen Matini: Hi everyone I'm Stephen and welcome to Pity Party Over. This episode will explore the importance of assumptions, choices, viewpoints and purpose to formulate a successful strategy.

My special guest is Jessy Hsieh, Clinical Assistant Professor at New York University, Stern School of Business. Jesse's research interests included strategy, creativity, digital sociology and philosophy of education. Jesse teaches both undergraduate and graduate courses and she is currently pursuing her PhD in the department of Applied Statistics, Social Sciences and Humanities at New York University.

Stephen Matini: I am curious to know where you grew up, and what were your early experiences that somehow shaped where you are now.

Jessy Hsieh: I was born and raised in New Jersey, Parsippany New Jersey to be specific, but you know where I grew up, and who I am and where I'm from is a compilation of what I would say everyone before me. So a little bit about my, my parents were both in, one born, my dad was born in Southern China. My mom was born in Northern China.

Their families in 1949, they all went to Taiwan. They were both raised in a small, a small city in Taiwan, but it wasn't until they both came to the United States for graduate studies that they met. I might have been born in Morristown New Jersey and raised in Parsippany New Jersey, but the history of where I'm from is a confluence of so many chance occurrences that created me.

Stephen Matini: What would you say that has been the biggest contribution of your parents in the way you think, the way you are?

Jessy Hsieh: Strategies at the confluence of choices and chances, so chances, things that you don't have any control over and choices, those decisions that you make to kind of pivot or to make those moves. My dad was a, he's retired now. He was a biochemical engineer, and those that was really, not really by choice, but something that he was very good at and that he knew that he could get a scholarship to study here in the United States.

For my dad was always very interested in history and my mom was a very accomplished, she loved to paint in her in her free time. I come from a family of scientists, but always there was this artistry, humanities, there was a crux of people's interests that they weren't able to pursue. So for me, I think that where I learned to appreciate both scientific mindset and although also the artistry and interpretive mindset of artists, and putting them together in terms of my teaching as well, just a science and an art.

Talking about strategy and a confluence of choices and chances, things that you cannot control and things that you can control. One of the most salient memories I have was when my mom died from cancer when I was 17. That was a very, very big learning for me, because she was the only person whose opinion really mattered to me when I was growing up. And so having no longer be able to rely on that, I had to really make a lot of decisions for myself. That's important to me? What do I have at hand? What's the environment and then to make those choices?

Because I could not rely on the wisdom, the opinion of this person who matter so much to me. So that to me is a very formative experience. This person was removed from my life. It actually forced me really rely on my own thinking, my own decision, making my own kind of internal motivator, and also internal compass to make those decisions, to own those decisions, and to move forward.

Stephen Matini: Do you look like your mom?

Jessy Hsieh: I look like both my my dad and my mom I think.

Stephen Matini: In 2015 you said, you tweeted, “Strategic equals skeptic of false a certainty, citizen of enlightened ignorance.” So has that thought changed since?

Jessy Hsieh: Skeptic of false certainty, yes. And then also citizen of ...?

Stephen Matini: Enlightened ignorance.

Jessy Hsieh: That definitely works, still holds! I actually don't think that that could be mine. I must I must have been somewhere where I heard that or something. I should have, I should have credit that, or if it's mine, that could work. I mean ...

Stephen Matini: I think it sounds like you, yeah.

Jessy Hsieh: Yes because I think that one of the biggest challenges when people think strategically or when formulating strategy is false certainty. The moment somebody says like this is definitely the way we should go ... to me, it’s kind of like we're not cynical of that possibility, but the skepticism is really like, okay, why? Are these decisions in this statement ... are these based on assumption of the past that might not be true to reality, and that are basically guiding you to think something that is certain when it's not.

The only thing worse than uncertainty, is false certainty. That's kind of where I would think strategy really comes in. We're always going to live with uncertainty, because there are so many things that are out of our control. The only thing worse than living with uncertainty is being falsely certain that you know the right answer, that you know the right course, that you know, or assume that what you are doing is either wrong or right, right? So false certainty is the danger.

And enlightened ignorance. I think enlightening ignorance was definitely a phrase that I've heard somewhere before. I'm definitely not as poetic as that, be able to come up with that. But enlightened ignorance really is, constantly being in the state of asking questions, never being falsely certain about what you think is true, what you think is the right course, and being flexible. What's the next thing I want to know? What's the next thing that I can clarify. There's so many things that we don't know. Let me find out what I can know.

Stephen Matini: It is my understanding that strategy typically involves two major processes. One is formulation, which includes a strategic planning and strategic thinking. The second one is implementation, which refers to the action plan taken to achieve the goals. Do you have a similar approach or a different one?

Jessy Hsieh: The definition of strategy that I would use is from Eric J. Van den Steen. His definition of strategy I love just because it kind of encapsulates both. It can go for individuals, it can go for groups, it can go for organization. So his definition is that strategy is, “The smallest set of choices to optimally guide or force other choices.” I love this, this is about the formulation and also it guides action.

As an individual. What's your strategy for this? Sometimes it be like, I need to find a new job, I'm going to find a new job, right? That's in my mind, not a strategy, that's an action, maybe a tactic. That’s an implementation of something, right? Perhaps in terms of a strategy might be something like, I want to work in a place that utilizes my organizational skills or something like this. That is a decision to formulate that guide.

We want to be best in kind in this, or we want to develop innovative strategies. Even just using the word innovation is actually again, falsely certain. What are those choices you need to make in order to continue? Formulation. That set. That set of choices. Then implementation. What do you need to take action on those choices? A job is something you do to make money. A career is a job you're good at. And a profession is a career you want to get better at. It's about coming up with these constraints.

Again, another strategy thinker that has really influenced the way I think, the mindset, but also how I live my life, my work here, is Adam M. Brandenburger. Adam M. Brandenburger is a professor here at NYU, and he has this four seeds of creativity. What are your constraints? What are your context that you were in? How can you look around to see what you're in and do something opposite? And combination. What are those choices that you can actually take something and add it to something else?

Because if it's too broad, it's too vague, it's really hard to take action. It's almost in-actionable, un-implementable if you will. It’s about that sweet spot, formulating some sort of idea or action, formulating that set of choices, and then using that set of choices to implement. Formulation, implementation are all part of the thinking process and action taking process this idea of strategy really lends itself to.

Stephen Matini: One of the things that I used to hear a lot from clients in the past, what is a strategy for the next year? For the next three years? For the next five years? And somehow this concept has become almost ridiculous, in a world that changes all the time. How is a strategic approach changed in your opinion?

Jessy Hsieh: They always think about the strategic plan. I think I heard this from Adam M. Brandenburger, or he may have quoted somebody else, foolish is the person who comes into battle or comes into something with a plan. It's not flexible enough. Plan all you want, maybe schedule you want and have all these goals, but things often don't turn out to where you want them to be. Using time as a strategy is time-bound, is like a goal, by year one. This is what I will have done. Those are goals. Not necessarily strategies. Strategies are choices, like choices that you're making.

The key thing about strategy is these decision notes. Every little pivot, any one of those things could lead off two totally different timelines if you will. There's multiple outcomes that could come from any type of decision at any moment that you decide to take another course. If you're a retailer, are we going to be a fully organic or we only use organic cotton for our garment?

That's a strategy, because it limits what you will do. The best in kind in providing fully sustainable organic products. That gives you a direction, that guides other decisions that need to be made. That guides then who you're gonna get as your suppliers, who are you going to target as your customers, how you might have to price things in the future, like these are all those are the types of decisions that are going to guide other ones. Is it a plan? Not necessarily is it time bound? Not necessarily. Time is a helpful tool to help meet targets, or to meet goals, and to see if you're on the right track, or making progress. But strategy is decidedly not a plan. It's a set of choices that you're making. That you have to decide upon a set of choices. A set of decisions. Yeah.

Stephen Matini: With that said (laughter) ... the notion of choosing is so central in the way you approach strategy. What are the ingredients to choose well?

Jessy Hsieh: I want to say that about you Stephen, what do you think are the ingredients?

Stephen Matini: For me the first thing that I thought about is to be aware of how I look at things, because everything can be interpreted in so many different ways, you know. What is objectivity? It doesn’t exist. So for me to become mindful of how I look at things could be probably one of the most important steps.

The other one that I thought about is the multitude of points of view, or different ways that something can be can be looked at, to be mindful there could be other interpretations, other angles that I'm not aware of.

When you were talking before is about choosing. It's not just about a plan. For me, it's probably the soulfulness of why I do what I do. So if it's a company maybe it's something that is deeply connected with the vision, mission and values. Because to get there there could be so many different routes, but the soul of the organization, why we do what we do, probably is one of the components that is going to dramatically kick out some of the choices.

Jessy Hsieh: Yeah, for sure. I love, I love how you're talking about this choosing well and then also purpose. Why are you doing what you're doing? Simon Sinek, you know, always start with why. Because why, if you had that, then the what, the what comes from the why, and how is near infinite. It helps you limit those choices. So like why are you doing what you're doing.

In terms of choosing well I have had many, many jobs, many things I've gotten paid to do, investment banking, so many different things that I've gotten paid to do. From there, I'm like well what is it, what is it that I'm actually good at? I could have chosen, right. I probably could be good at it. I haven't really tested. But my last job for example, you know, working at an investment bank. I was getting paid, I liked what I was doing. You know, I was good at it. It's a career, but why am I doing this? Like do I want to get better at this? And that to me was fundamental kind of purpose question.

So now I'm in a profession, I'm teaching is something I get paid to do. That I believe that I'm good at, and I want to get better at it. Like every day is something I want to get better at. Why is fundamental, because that's something you can just go back to. It's not necessarily something that you decide on first, but it is something that is foundational. What is essential, what is foundational to your core business, to your organization? Then you go, okay then you can decide what, and how.

Stephen Matini: Recently I was talking to a general manager that I worked with in the past, and he said, results are really important, but results alone do not do the trick, especially if you want to have a long term strategy. So you have to look at results. Those are important indicators that allow me to understand, yes, I'm going the right direction, but there's so much more than that, you know. Managers, executives are so obsessed about results, and rightfully so. But that's not really a strategy. Not at all.

Jessy Hsieh: No

Stephen Matini: It's just getting by.

Jessy Hsieh: For sure. I think the results are observation, this is data. They're all data to see why did you achieve that excellent result. Why did your, your first quarter earnings outpaced your last quarter. The results are one thing, understanding what it was, and why you achieve those results are much more important, because those are the things that last. Organizations are sometimes just making broad, sweeping decisions. You must come into the office, you must be in person three days a week, four days a week.

However, so they are actually making decisions that are how are we going to do our work in person or totally remote? That’s a how question. You're going deeper into as a General Manager is why do I, why do I want people to come back in person? Is it because I really want to have more, increase a culture of collaboration? Is it because I wanted to increase those moments of spontaneity and generative ideas that can only be captured in spontaneous interactions?

Utilizing the data from when you were in person, when you were on Zoom. What situations lead to the reason why you're doing it? Were you able to build collaboration particularly on Zoom? Just like we're doing right now, right? We don't need to be in person to be able to have a meeting of the minds.

As companies are grappling with how to structure their work, other work time, they're going to these decisions without first deciphering when and how. When do we work best? How do we work best? And what do we want to achieve? Making decisions based off of past decisions, so that you can unearth why did this work well. Results are just indicators of things that work, or are things that don't work, the extent to where things work, and perhaps observation points for how things might be able to work better in the future.

Stephen Matini: Executive roles, those people are the ones who are supposed to make strategic decisions, and yet a good idea may come from anywhere. People that are closest to the issue, most likely they're going to see what's happening. Based on your experience, how would you say that an organization could transition from a model of having people on top being the strategic one, to having everyone in that conversation?

Jessy Hsieh: When you're saying the people on top of losing their identity, could you clarify what you mean by that?

Stephen Matini: I mean the C-suite.

Jessy Hsieh: Each organization is going to be different. But I do think though that in terms of strategic leadership, in order to generate the best possible ideas you want to have a lot of observations. In your organization how can we include all of these ideas so that we can be sure that we are at least having the broadest set, the broadest ideas? Then you amplify those ideas that are generated.

In terms of strategic leadership, it is part of their identity to ensure that all the voices are heard or at least they're generating as many ideas that they can. Then, how do we raise that to the power of 10? A lot of times people who are in those positions of power, they come from the assumption that they have the best ideas. They've gone up the ranks, they assume that they might have. It's the people who are in leadership come from that thought that will never be falsely certain.

They’ve risen up the ranks mostly because they now have experience in seeing all the different as many perspectives as I can, even from like multiple functions, multiple perspective, being able to see from different vantage points the organization, then they can operate at the strategic level. A strategist, C-suite, really being able to have this thinking, what are those things that we can move as one?

Strategy hopefully is really allows multiple functions in organization areas of interest in an organization, multiple people, to be able to move as one organism. At the C-suite level, their identity is not in the title, but their identities really should be in their experience, to see that they can never know it at all, and then also to utilize that experience to help marshal, and bring an organization to be able to move disparate parts as one organism is strategic leadership I think.

Stephen Matini: People have amazing ideas, and actually what they found tremendously frustrating is the fact that often times their voices are not fully heard.

Jessy Hsieh: Yeah, for sure.

Stephen Matini: And those are missing opportunities for innovation, for creativity, and for being more strategic.

Jessy Hsieh: Often times, I think that back to the order of operations, real leadership is empowering, that’s the exponent. Seeing what you have in these parentheses in your organization. What currently exists. People, their ideas, each person's experience and then empowering. That's the exponent. Empowering people who work in your organization to speak their ideas, to feel heard, empowering to give them voice.

Giving them voice often times just asking them, what do you think about this? Give us examples of what is your day to day? What do you think would improve this? That is really just empowering them, before you go outside, you know, to find what other people are doing. Data is quantitative and qualitative. It's not about how much, it's about how. How many ideas do people come up with? How are you empowering people to feel heard, to speak their ideas, so that you can ensure that you are gaining the broadest range, broadest variety, and also the deepest?

There are many excellent consultants, who bring forth the best ideas, that their experience from seeing across organizations will lead to the best practices. But each organization has such a depth of knowledge that is all kind of within individual minds. How do you get empower those, that diversity, that depth of knowledge, those depth of experience? And bring that and empower people to speak their ideas is critical.

Stephen Matini: All the choices that you made in your life that brought you here, you know, you told me about your mom, your parents ... what is the contribution that you hope to give through your work in strategy?

Jessy Hsieh: Oh ...

Stephen Matini: That’s deep!


Jessy Hsieh: That’s really deep. I think for me teaching is the closest that I feel that I can experience infinity, because every little minute that I spend with students, it's just the starting point of a seed that can germinate into infinite different possibilities. What I really hope to contribute is that the students that I interact with, they can see that there nothing is a foregone conclusion, that there is no such thing as the right way. There's no such thing as the one way, that if we are thinking about in terms of that, then we are robbing ourselves of the opportunity to experience the possibility and the infinite possibility of the future. I love teaching. I wanted to get better at this because I it's the closest I've experienced to infinity.

Stephen Matini: There's a word that I don't think we have said in this conversation, but I think it's probably it could be a synonym of infinity, which is freedom. The national strategy for you is so much connected to choosing. You know, for me choosing is about freedom. Choosing is the biggest freedom that you can possibly have. And so the last question for you is this. When you feel like crap, when you're having like a really difficult moment, for whatever the reason, is there any specific choice, or something you do to get out of the funk that somehow, you notice, works well for you?

Jessy Hsieh: The title of this whole podcast Pity Party Over. I just love that. Okay, I just, I just love it in so many different ways. So for me, I would actually say that translating things to action, something that you can do is an initiation of freedom, it’s an initiation of choice, and it's also a way to get out of the pity party if you will, right, like the funk.

For me, for me, I always feel the most free when I think of things in a different way, so I will give it exam. I recently turned 40. So leading up to this, a lot of my friends were like, oh by the time you're 40 we should have this, we should have a, b and c, we should have, you know, accumulated in some sort of thing. It always seemed like an end point, like 40 just seemed like some sort of endpoint.

No, screw this, you know, this is just the beginning. So freedom to me is reframing certain situations in a way that makes us feel that we have agency in our life. I want to start a movement, I'm gonna call it my F. F. Y. F. F. It's the start of my 41st year of 40-first. For example, my first time having a dirty Martini, which I've never had, which I love. The first time eating mutton. My first time, my first mammogram that I had, it was also during ... My first time, what else did we do? What else they did? This is the anti bucket list.

I don't care what everyone else has done. This is my first, my first time seeing my friend's new daughter. My first time doing a 2000 piece puzzle. It's a movement to reframe how we're seeing things that are expected to be the end, or the mark of an end of something, and really it's part of the first of a new beginning. What can I see differently? Instead of thinking things are coming to the end or things that I'm losing out, or things that I don't have, constantly going with that mindset. What are the first things that you, you are doing for the first time? You are thinking for the first time, that you are feeling for the first time? Those first. Pity party over, how do I get out of the funk? Freedom is refraining. It's a mindset to look at what currently exists in a new or different way, that puts your own stamp on it.

This decade. My mom was diagnosed with cancer when she was 45 And she died when she was 50. All of us, if there's anything that we learned from the pandemic, is that there is no certainty about what's going to happen in the next moment. For me switching that from like, oh gosh, you know, what am I going to do to like? Okay, what is it that I can do right now? What is it that's new for me right now? What are those things that I want right now? There's no such thing as a plan. You come to life with a plan, you're going to be sorely disappointed

Stephen Matini: Miss Jessie, you are a precious gift.

Jessy Hsieh: Oh Stephen ...!

Stephen Matini: Thank you for doing this with me. We should do this again.

Jessy Hsieh: Yeah, absolutely.

Stephen Matini: Thank you for listening to this episode of Pity Party Over.

In the episode Jessy points out strategy as a confluence of choices and chances, things you can control and things you cannot control.

A good strategy questions all certainties and assumptions with a curious, open, and flexible attitude. Strategy is not a rigid plan based on dangerous false assumptions, but the smallest set of choices that optimally guide or force other choices. Understanding the context of those choices is also critical.

For individuals, teams and organizations, choosing well requires awareness or why we do what we do. Purpose drives results, and results tell us how things might be able to work better in the future.

The best strategic ideas require leveraging different points of view by listening to your people and giving them a voice. Strategy is about choosing, and choosing is the freedom to reframe challenges to make us feel we have agency in our personal and professional lives.

If you are interested in developing your strategic thinking, you can contact me via email, LinkedIn or Twitter, or sign up before a 60-minute complimentary Live Session. Please check the episode's notes for information.

If you enjoy this content, please subscribe to the Pity Party Over podcast available on Amazon Music, Apple Podcast, Google Podcasts, Spotify and many podcast platforms and apps.

I invite you to browse our leadership and managerial development programs at dot. ALYGN is spelled A L Y G N . company.

Be happy, be well, and until we connect again, thank you for listening.

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