The Learning Leader Show With Ryan Hawk - 262: Keith Yamashita - The Keys To Great Execution (Oprah, Starbucks, Steve Jobs)

Episode Date: June 17, 2018

The Learning Leader Show With Ryan Hawk #262: Keith Yamashita - The Keys To Great Execution (Oprah, Starbucks, Steve Jobs) Keith Yamashita  has led SYPartners for the past two decades, a practice that collaborates with CEOs and their leadership teams to build great companies and organizations. He's worked with leaders at Apple, eBay, IBM, General Electric, Johnson & Johnson, Facebook, Nike, Starbucks, and Target Corporation, among others. SYPartners has been recognized by The Wall Street Journal, Fast Company, and Fortune for its unique, human-centered approach, applied to both business and social challenges. Earlier in Keith's career, he was the chief writer for Steve Jobs.  The Learning Leader Show Action Step - "Build a daily contemplative practice to create mind-fitness." Show Notes: Sustaining excellence: The ability to envision a future that doesn't currently exist -- Make it a reality Optimistic Creative A diverse background Authentic communicator Daring and bold People Keith has worked with who have sustained excellence: Oprah Winfrey - magnetic personality, she can envision the future we want. She constantly re imagines herself. She has a strong creative core. She has a sense of deep creativity. Howard Schultz - He's always restless, reinvents regularly. He's earned 9,000% return on investors money How do you respond when Oprah calls you for help? "We are always on the outer edge of incompetence.  We take on projects that we don't know the answer to.  And then figure it out.  We respond to those calls with deep humility." Why choose Keith and SYPartners? "If a leader wants to try something new... We help them experiment." Starbucks: Closed 8,000 stores for racial bias training. Keith and team helped them build new habits SYPartners origin story: "Our goal has never been to be famous, our goal is to be impactful" 25 years ago with "three partners and $912 in my checking account" Started as a communications firm --> Strategy --> Innovation --> Culture --> Transformation There are 200 employees now "We fight for greatness. We help leaders choose a more daring path" "Everything is set with intentions" --> "Set your intentions and be very open to the universe" How do you respond to skeptics? "When I started I had $912 in my checking account.  I had to borrow money for rent." Only you know what's inside of you.  "Your skepticism needs to be inward, not outward." "If greatness is your choice, it's not made in big leaps, it's made in daily focus." "Micro actions add up" How to make the leap from individual contributor to manager? Leadfully.com has been helpful What was it like working for Steve Jobs? "I showed up with writing samples. He said they were awful. He was testing me to see if I believed in my work.  It was the worst interview of my life... However, I got the job." "He's the toughest boss I ever had.  But I learned more from him than anyone I've worked for." Steve was gifted in seeing what people were capable of and he was willing to push. He knew how to motivate you to your capacity The danger in mimicking Steve's behavior? "People try to mimic the behavior, but they don't have his intentions." Mimicking the behavior without the intentions is a recipe for disaster. Execution and implementation: Mind-fitness - Creativity in moments that matter. Be connected to others in a calm way. Ideas are just ideas. "You can train your mind to be present in this moment."  Don't judge others. "Build a daily contemplative process." Build a daily creative practice - Read, write, take notes, be awake, alive, aware. Get a folder, cut out articles, pictures. Create inspiration.  Recall past events. Understand what moment you're in - What's happening? Develop keen awareness to the moments Why books are the greatest investment ever (my thoughts) Use the "Get To Know You Document"  

If you work on the mind fitness part, spend time to calm your brain, spend time to be present, spend time to be aware, spend time to notice, spend time to reflect. These things in the end do not require huge investments in time in order to radically change how creative you are and how much you can rise to each moment that matters. This episode is brought to by Gusto. Gusto is making payroll benefits in HR easy for small businesses. Modern technology does the heavy lifting, so it's easy to get things right. PCMag and fit small business have called Gusto the best payroll for small businesses. Gusto saves you time. 72% of customers spend less than five minutes to run payroll.

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That's G-U-S-T-O-com slash leader. Welcome to the Learning Leader Show. I am Ryan Hawk. Thanks so much for being here. We are hosting a live in-person workshop here in Ohio in the fall. We'd love to have you on developing personal excellence as a leader. We're taking the best of the best what I've learned over the past four years and putting everything we have into this two-day workshop.

We'd love to have you. For dates and availability, go to Ryanhawk. That's Ryanhawk.me. That's Ryanhawk. dot me for dates and availability to our workshops. It's going to be great. Now on tonight's featured leader, it's with Keith Yamashita for the past two decades. He's worked alongside CEOs and their leadership teams to define and then attaining greatness for their institutions. He's worked with leaders at Apple, Starbucks, IBM, GE, Johnson Johnson, eBay, Nike, Gap, and the Coca-Cola

Company, among others, when leaders at the best companies in the world need guidance. They call Keith and his company at S.Y. Partners. A few of the topics we got into what it's been like to work with Oprah Winfrey. And then advice on how to implement and execute. We got to this near the end, but it was one of my favorite parts and one of my favorite answers to this question I've ever received. And then making the leap from individual contributor to managers. Keith has done this and he's helped many others do it as well. Then he shares on its experiences as Steve Jobs, chief writer, and what type of boss Steve was and what he learned. Incredible.

Ladies and gentlemen, this one's so good with Keith Yamashita. All right, Keith, excited to have you here on The Learning Leader Show. Welcome. Thanks, Ryan. I've really been looking forward to this based upon your story and the people you've worked with. The people you've helped and your business at S.Y. Partners, it's fascinating to be. So I'm excited to jump in, but real quick to get us going. As I mentioned, you have worked with some of the greatest leaders in history, truly,

I mean, which is amazing to say. So that's why I feel this is a great opportunity. And I'm curious from your perspective, what are some of the common themes or common characteristics you found in leaders who sustain excellence? Ryan, it's so fascinating. I was thinking about this this morning. And I think the thing that the leaders we have worked with do better than any other leaders out, that I've seen is that they're able to envision a world or a future that doesn't yet exist and then use everything in their might, everything in their power, everything in their capability

to make it a reality. So it's this ability to envision a world that is not true yet and then do the hard work to make it true. And there's kind of commonalities that come after that. So if you're about creating this new future, their sense of optimism, their sense deep. They're sense deep capability and creativity, their ability to harness diversity, you know, create these cultures of welcoming, they're authentic communicators. But it's kind of these things. We tend to work with leaders who are very daring. They're not leaders who are there to perpetuate the status quo. We tend to work with leaders who really boldly want to take their organizations to the future. Who are some of the first ones that come to mind when you hear that phrase

sustaining excellence. You know, it's such a broad list of people we've been fortunate to work with. You know, we've worked with Ginny Remedy at IBM as she tries to turn IBM to a new era. Bobby Coddick at Activision, Kevin Johnson, the CEO at Starbucks, Bernard Tyson at Kaiser. But, you know, two leaders who really come to mind for me, we've had the good graces of working with Oprah Winfrey. And, you know, Oprah has this magnetic power to a. envision a future she's trying to create, a future where we're all seen, a future where we're

all heard, a future where we have the power in our lives to create the lives we want. And she's constantly reimagining herself, her companies, not just her company, but she's involved with many companies. And she's a leader that has this kind of strong creative core. And it's something that's quite admirable because I think that the part in leadership that is going to be most valued in the future is this sense of deep creativity, this imagination of the heart and mind to create something new in the world, often assembled by things that are in the present, but reassembled or reimagined in a way that's really pretty profound. So Oprah's definitely one person that I think of when I think of sustained excellence. And another is one of the four

founders at Starbucks, Howard Schultz. You know, he has, he joined the company. 40 years ago, he has been deeply engaged in every aspect of it. He does not hold its, in any era, its current performance as precious. He's always restless and reinvents the brand. Ryan, you know, he came back about 10 years ago, 12 years ago to retake the helm of Starbucks. And he's remade so much of that company using creativity, using this great connection to his people. He's so much. She calls them partners. And over that time, has had a 9,000% return on Starbucks stock. So it's the great cultural work he does, but it relates in really sustained performance. So when someone like Howard Schultz or Oprah calls you, have you just built up enough of a resume and enough of your own sustained excellence to where you say, yeah, I could help somebody like that. I could help Oprah.

Because to me, I would be thinking in a lot of the regular type people who are listening say, I'm confident what I can do. I prepare. I'll get ready. But how in the world am I going to help Oprah Winfrey? I mean, what are you thinking when you get calls from people like Howard Schultz or Oprah Winfrey or in the past Steve's jobs? What's your mindset around that? Rarely do they call directly.

We're almost always called by people they know. But my first response is always one of really deep humility. We call as white partners affectionately a firm that is always at its outer edge of incompetence. I mean, we get invited to work on these with leaders on the work that's most valuable to them and as beyond their own capability of something they've done before. So I think the first thing is deep humility. Almost every call that comes in or a call that we're connected to, my first thought is always like, wow, are we actually capable of doing this? And that seems really hard to do.

So almost none of them start with a cocky approach at all. It's actually quite the opposite. But in humility, I think we all try to take a step back and say what's ever true about what these leaders stand for, what is that? the deepest character of their organization. What is the purpose and mission then drives them? And then what's the best way to unleash this deep transformation that wants to be born? And I think if you approach that work with a lot of humility, you end up seeing the path forward.

And I think part of the way that we really try to work is not, it's with courage and bravery, but not a lot of bravado. We tend to be a pretty quiet company in that regard. Why do you, why do people either call S.Y partners and call you specifically or why are people referred to work with you? You know, it's interesting. I think maybe largely because of the internet, maybe because of information traveling faster, almost all leaders and organizations are privy to the same information, right? So the data about what makes a company tick, you know, there's so many quote-unquote best practices out there. The kinds of calls we get are because a leader wants to try something, remedy something, attack something, envision something that puts them in new territory or on new ground.

And where they themselves are going to be experimenting and trying things that they haven't done before. So the kinds of relationships we end up building are with those kind of like-hearted and like-minded leaders. And therefore, the things that we get asked to work on are fairly unusual. They're not necessarily standard projects. There are very few projects that we work on repeat in the same way. They may have themes that repeat, but the actual work is quite different every time. And one of those projects recently has definitely been in the news. So Starbucks shut down 8,000 stores in the United States.

And S.Y Partners was the, you guys led the design team for their racial bias training. And it sounds like from, by the way, a pre-call with Lisa on your team. And she is phenomenal. I give her huge, just one of the best pre-calls I've ever had. She was fantastic. but I would imagine that this work you did with Starbucks in a time of when they were going through some negative things was full of lessons for modern leaders. So I'd love for you to tell me about that. Yeah, there's so many ways we could dissect this story.

So let's try a couple different ways. So 8,000 stores, 175 Starbucks team members. They closed each of those stores for four. hours of deep conversation about racial bias, racism, structural bias, or how the country or structures we live in pass on bias generation by generation, often unintendedly. I think it's the largest business conversation on implicit bias and structural bias in business that I've seen that has happened all at once. And let me tell you a little bit about the Genesis.

This has been well covered in the news, but for the listeners who maybe had a busy week otherwise, about a month ago, Starbucks had a really, really tough incident in one of their Philadelphia stores where two men came in to meet a third friend of theirs to have a business meeting. And at that time, Starbucks had a policy that said that a customer was defined as someone who was going to buy something in a given sitting. and that policy encourages Starbucks partners or Starbucks team members to graciously ask people if they would like to buy something. And unintentionally, if you don't buy something, you kind of get on this list of someone who the team gently ushers out the door. These two men who were black men in Philadelphia were there to have a meeting, but they hadn't bought anything yet. and the team in the store asked them to leave, and then when they didn't leave, the police were called, and these men were taken out of the store.

And so the genesis of this day was this, you know, as a Kevin Johnson, the CEO of Starbucks, this reprehensible event in their Philly store was the trigger for this gathering of 8,000, stores and 175,000 members. What's interesting is we all have implicit bias. We are all the result of the society we live in. And though we often think that we treat others with the same amount of respect and attention, if you study each of our actions, that's not actually true. We're not nearly as virtuous as our hearts tell us that we should be. And so this gavis,

on this day was to teach people that once you see your own implicit bias, you can actually pause in a situation and choose to show up as your better self. When you understand structural race or bias at play, you can help the institution be more enlightened in the policy it sets and how we work in our mindsets. And so it was this four-hour deep conversation about all of that. and most importantly is tied to 12 months, you know, 12 more modules, 12 more conversations, all of which can build new habits and new rituals of belonging. So it was a very intense month leading up into the store closure. And, you know, we really drew on neuroscience.

We really drew on many different experts from Starbucks team. We drew on many different experts about how to create harmonious communities. And I think Starbucks is courageous and brave to take on this topic and really make their company one of every single person feeling heard and respected and uplifted. And that's really the task at hand. And so when this happens, did they immediately call you and say, Keith, it's time to we need some help? Well, how did that come about? You know, we're we have been a partner at Starbucks over the last 12 years. and we have worked with them on some of their deepest aspects of transformation,

much what Howard set out to do 12 years ago and continues to this day. So as this was unfolding, we were in conversation, and we really raised our hand to help because we believe that Starbucks intentions are good ones. And this incident in Philadelphia does not represent the Starbucks that we know they want to be. And so we were in conversation with their CEO, Kevin, and obviously Howard Shultz, their founder. And that it unfolded from there. It was really an act of caring about that future that brought us all together. Yep.

So I would imagine there are some listeners, too, because this is something I talked with Lisa about that. You're a very charismatic guy. You can get up on stage and do a great job. You help people when you're in the room with this hummus. approach, but you're not world famous, even though maybe you should be. Maybe that's because you don't want to be or you haven't, you haven't put any effort into that. Or like, as you said, you guys approach it with humility and you kind of stay in the background

and you're quiet. But I'm curious about the origin story of S.Y partners. What were you doing before you started it? Why did you start it? What was your, like, how, how have things changed since you started? I mean, there's a lot of questions there, but really it's just what, what was going on leading up to because I find people and I certainly am are fascinated about when somebody makes a big move, an inflection point in their life.

What causes people to do that? Because there are a lot of people listening who are thinking about things like this. Maybe they have a side hustle or, you know, I've gone through this personally too. So they're really thinking about it or maybe they envision this for their future, but they don't have it all really mapped out yet. and maybe hearing from you about where you were, what you were doing, who you were working with, and then wait, I'm going to do my own, start my own business, and now the business is huge. But I'm curious to go through your origin story.

Yeah. Wow. Well, first off, I'll pick up on a strand. Our goal as a company has never been to be famous. Our goal as a company has been to have an impact. And so actually we keep a pretty low profile because out of respect to the leaders and companies we work with because it's really about them. It's not about us. That given, I'll tell you a little bit about the origin of SY partners.

And I wish I could tell you, since we're a transformation company and we believe in whole self and we believe in the power of intention, I wish I could say that the founding of SIP was all of those things, that it had great vision in it and it had amazing intention. And it was well thought through. And I think in reality, it was a simple company with no stated plan, no stated strategy, and no intention particularly. So what we do for living versus our origins maybe don't match at all, or maybe there's a story that you're saying, which is wonderful things can come out of humble beginnings. But basically, we started the company 25 years ago. there were three partners at that time, Diane Harwood, Robert Stone, and myself,

who all in some way had an association with Apple. And our origins go back to Apple, and we can talk about that later if you have interest in that. And at that time, I was working for a firm in San Francisco, and I'm super happy in my job and role, and I was working on the launch of Saturn, the Car Company. and one of my would become business partners, Robert, said, well, why don't we found a company? And we could work on all sorts of things that communicate about companies that are trying to do good in the world.

And I was like, Robert, I don't know why I need to leave the job I have. I have a pretty great job and get to do really wonderful things. And he said, yeah, but wouldn't it be fun to do that's kind of entrepreneurly and on your own? And I said, well, maybe, I don't know. I was a maybe kind of cautious 27-year-old. And our third partner, Diane, said, you know, let's just do it. And so we started this company with no particular plan.

Our first work was with Apple and with Levi Strauss and a number of Bay Area companies. And it was more about how to talk about a company. It was more about communications. And then over the years, in order to be a good communicator about a company, you actually have to understand it, strategies. So we added much deeper strategic capability to the firm. And then it was like, well, if you're really about strategy, you have to be able to innovate and create new things.

So we added other disciplines to be able to do, you know, daring new innovations, new products, new ways of working, new culture. And then that then evolves to, well, every great company has to transform over time. And that kind of explains the company we are today. It's about 200 of us between two offices. a combination of really creative-oriented people with all sorts of different backgrounds in business design and psychology,

in neuroscience, in design, in storytelling, in poetry. We've really tried to assemble a very diverse core of people who all are about kind of term we use fighting for greatness, meaning in a world that too often settles for less. We help leaders choose the more daring path and the more unusual path in terms of the positive impact they can make in the world. So that's our origin story. I wish it were more thoughtful and intentional. It's been very, very organic. Every time we get asked to do something that we do not know how to do, we raise our hand and get into it.

And it's through that, as I said before, always being at the outer edge of our incompetence. That the firm has gotten started. So you kind of listen to what your clients or potential clients are asking you for, even if you don't fully have the answer, but you're willing to figure it out as you go? Yeah, I mean, I think it's two beautiful things come together. So we are very big into this notion of intention. It's something we actually have learned from working with Oprah. Winfrey. It's everything set an intention. What do you hear for? What do you trying to achieve? What matters to the world? What matters to you? And so you'll hear often at SIP this phrase, be careful

what you wish for because we will put intentions out there. Oh, I wish we can make a better contribution in the conversation about race. Oh, I wish we could make better education possible for students around the globe. Oh, I wish for a healthy version of this that would be a better societal citizen. So we often will voice these things at S.Y.P. Not in a mystical way, in a humble way. And often that is met with interest, connection, clients, collaborators that appear sometimes seemingly out of nowhere.

And it's always been those two things that have driven us. Set an intention and then just be very open to the signals of the universe. And I will tell you it has become very reassuring that when those two things align, and for us they align often now, that's where the best work is. So I guess maybe for people who are really passionate about your show, it's what intention do you have? What unvoiced thing is harbored in your heart or in your intellect that wants to be unleashed and let out? And then how can you be the most open to hearing those signals from the universe? Because they're there.

And they reach you. And that's how new opportunity happens. So, Keith, I need to play the role of devil's advocate or skeptic. Okay. So there are people listening who are absolutely saying, it doesn't sound like Keith has, it sounds like his journey has been pretty smooth. He went from Apple. You know, you were the chief writer for Steve Jobs, which we can get to

a second. And then you started this company and you immediately had customers and it was great. And there's somebody listening now who is in middle management who has a decent to below average job, meaning that they think it's okay and they like some parts of it, but they don't like other parts of it. But they say, Keith, I have a mortgage and I have two cars and I have three kids and I have a lot of expenses. And I would love to have my intention. and my passion unleashed on the world. I would love to. But I also have a life to live and bills to pay and a high fixed monthly cost, meaning

family house mortgage, all that stuff. So what do you, how do you respond to somebody who would, who's thinking that right now as you, as you said what you said? Maybe three, three quick responses, Ryan. One is when I started S.Y partners, I had $912 in the bank. almost no savings. I could not make the down payment on the first rent for our 300 square foot office, I mean, tiny, tiny office.

And I had to borrow from my partners to even make my first payment on our lease. So my first response is, I hear you, I'm with you, I'm there, I have a mortgage, all the same things. second thing I'll say is only you know what's inside in your own capability and capacity. And I accept skepticism from those who when they look inside say, I have nothing else I aspire to and nothing else to give and nothing else untapped. And I hear that skepticism and I get it. But if you have an idea you know that needs to be born, something that you know you know, you want to pursue, a talent that you know to bring forward, really that skepticism has to be placed inward, not outward. We have a statement here. We mean it lovingly. Greatness is a choice.

And how much we limit or delimit ourselves depends on that choice. And there have been no shortage of hardships at S-Y partners. We've run out of cash. We've gone through downturns. We had the dot-com collapse around us in San Francisco. We've lost major clients. We've messed up on assignments. So I don't want to pretend that our path has always been upward. There have definitely been moments that have gone down. And my third point is if greatness is a choice,

it's not actually made in profound leaps. At least that's not the way I experience. in my own company. It's in the daily choices we make about where we focus our intention, where we focus our intention, and how we use our time. So if you're sitting there skeptical, as you are rightfully given the choice, it's what do you do with the time you have today and tomorrow? And it's in that daily choice, small choices, really, micro choices.

that progress is made. The, and Shane Snow's book, Dream Team's recent guest, and that's, I read, read about you. Shane, yes. I've talked to Shane a lot about his relationship with you and you guys talking. And that's why I reached out. That's why it's just a side tangent. That's why it's great to read books. And when you read books, you learn about guys like you, Keith, and then we are able to have this conversation that I wouldn't have known if I wouldn't have read that book.

But anyway, you say in that book that micro-action. add up. And I'm a huge believer in this and the compound effect and the day to day actions and the James Clear, one percent better every single day, the aggregation of marginal gains, the brick by brick of building the house, right, the compound effect, Aaron Hardy, all of those things I found too. I get a lot of questions now like how are we able to have the show go so well and to have it become now my full-time work at doing this show and speaking and consulting and helping other leaders. And it's that right there, Keith.

I think that's the key is the day after day after day and the consistency. You know every Sunday night at 7 o'clock, this show will ship 100%. And I am dedicated. Not only that, but it will ship with quality. So I've got to find great people and have good conversations. But that takes a lot of time and effort. Right. Leading up to this conversation, they've probably invested 15 to 20 hours

of work to understand your story, to have that long conversation with Lisa, to do all the work. And I know you've done the same thing because we care about putting out quality work day after day after day. You know, Ryan, it's interesting. The genesis of this conversation we've been having about microactions goes deep into the same conversation about diversity and inclusion and welcoming. So, you know, earlier in the conversation, we talked about, you know, leaders that have really sustained excellence are ones that are able to harness.

the diversities around them. And where this term came from was there's a pretty prevalent meme out there about microaggressions, the small, irritating things that we do that exclude others. And this can be certainly about race, but there are all sorts of methods of exclusion. And when we were really thinking about microaggressions, we were like, well, what is the countervailing force to a microaggression? So whether you exclude someone because of their gender, their age, their rank, their title, their country of origin, their language, the color of their skin, their sexual orientation, their gender expression, whatever you are excluding someone on,

and that's called a microaggression, what is the countervailing force? And we just started to say, well, actually, they're micro choices, micro-actions. And these are the daily efforts of inclusion that matter. Who you talk to first, who's in your social network, who you say hello to in the hall, who you invite to a meeting,

who you choose to lend advice to, who you choose to seek advice from, how you spend your time, with whom you spend your time. Each of these are tiny, tiny little choices, tiny little decisions. But if we shift them to be more inclusive,

the way I say it is there will be a hundred of these choices that naturally come your way today. You don't even have to do anything out of the ordinary. They will find you. And in that moment, how will you choose? It turns out that once you start thinking in a micro-action way, meaning be much more intentional about your daily choices, that is also the path to so much progress, achievement, satisfaction, impact in the world, exactly as you say it.

Our businesses, our lives are actually rarely made on a singular decision or singular act. They are often made through tiny, tiny little actions that happen and unfold every single week and month. You know, I just came to mind, Keith. One of the things that I would imagine happened as you guys grew and now you have 200 people, Was there a moment that you had to shift from just being a creative and someone who is doing the work to someone who actually is a manager and leading other people within your business? Yes. I mean, what you figure out pretty early is a business depends on its ideas, but it survives based on its cash flow. and when you approach payroll and you're going to miss it, this becomes really quite pungently important to you.

It really casts off this smell that you're like, we are not going to make payroll. We need to do something about it. Let me continue the story of S.YP because very early on, one of my fellow Apple alumni joined the firm, a woman named Susan Schumann. and very early on joined us, Y, partners, and 20 years hence, is our CEO. And Susan and I struck a partnership, which is, I would say my strength as a human being is

in the generative, creative energy required for these new ideas. And Susan also has that incredible capability, but she is also an amazing systems thinker, a really great operator, a really great leader. And it pretty much became clear seven, eight years into my company that if that's why partners was going to become our company, I would need to have deep partners that we worked with side by side. And Susan has really been my partner in this endeavor for the last 20 years. And we lead the company together. She's a much better manager than I am. And I have come to terms with that's a joyful thing and not something I should be shamed.

by and we lead it together daily. What makes her better than you as a manager? Oh, wow. She is thoughtful. She's decisive. She is not afraid of tough love. And within that tough love is a heart of gold. And I think that she is just much more decisive as a leader than I am. I tend to be sometimes overly thoughtful and slow to act. She is deeply thoughtful instantly and quicker to act. And so we make a lovely duo. And duoship is one of our key philosophies about leadership itself. And we talk about that more if you want. So anyway, so as I've grown as a leader,

as Susan has grown as leader, and most importantly, how we've worked as a duo to lead the firm, you realize that our leadership is about bringing out each leader's what we call superpower, what you're gifted, what your masteries are, what the thing is that you're great at. And then really look to others to fill out your repertoire, that it is not possible to be a complete leader. It's that you need to be a collaborative leader and together be complete. What about that person who's making the jump from individual contributor in any type of role? I have a sales background, but any type of creative role and you're going from, okay, now you were the one and you're now leading a team of 12, let's say.

And this is a jump that I think is the biggest jump in any career, even bigger than the jump going from manager to VP of leading leaders, I found I've made both of those jumps and I made a lot more mistakes during the first one than the second one, even though I've made mistakes during both for certain. But I'm curious, what advice, if you're talking to someone earlier in their career and they're either on the verge of making that leap, because a lot of those people are listening, but you're making that leap or you've made the leap nine months ago and you realize, man, I've really, I think I've messed some things up. What advice do you give to that person based on your experience? as well as the people you've worked with.

I think the first thing to realize is it's a whole different set of masteries required, meaning just because you're a gifted individual contributor doesn't automatically make you a wonderful and brilliant manager. If you want to lead fully in the way that you are, as brilliant as you are as you are as you were an individual contributor, if you want to do that as a leader, you actually have to work on it. Early at the top of the show, we talked about these traits, optimism, authentic communication, creativity, ability to harness diversity. We find that above and beyond task management, which is certainly an important role as you become a first-time manager,

it is these traits that really make you a brilliant manager. About five years ago, we set out to chart this and actually created an offering called leadfully.com that has all of these things explored. It helps new leaders, young leaders, first-time leaders, assess where they are on their scale of optimism, authentic communication, creativity, on and on, kind of these key traits. And then it helps you build those traits day by day. Again, it's all in this microactions and daily behaviors that this work really happens. What's the site?

Is it still live? It's still live. Yes, absolutely. It's called Lead Fully, L-E-A-D-Fully. f-u-l-l-y-com. And there we have a number of articles, very pragmatic articles about what you can do day-to-day. We have a great assessment there that you can kind of measure what your capability is like as a first-time leader.

And then also authentic advice that you can kind of go into that helps you do the daily, daily task of leading. Interesting. Okay, cool. That is really helpful. So one of the other cool parts of your story is the fact that you go on your LinkedIn bio and for a number of years, you were the chief writer for Steve Jobs, 1989, 1990. I know you have a history with him doing more than just writing, but I'm curious, how did that come about and what was it like being the chief writer for Steve Jobs? Well, so I'll first clarify, I was the chief and only writer.

So I want to be humble about this. I'll tell you my genesis of working for Steve. So my very first job out of school was to work at Apple. And again, this theme of in a zone outside of my competence. It was a job I worked in the education marketing group. And anyway, I got a call from Steve's chief brand and marketing officer. who said Steve would like to meet you and please bring copies of your work. And I went in, you know, very young leader, you know, was maybe 23, 24, very, very young.

And I get this call to come see Steve Jobs. Now, you have to remember Steve was 34 at the time. So, you know, we, he was in between his two eras at Apple. And I had the worst interview of my life. I showed my work. And he's like, oh, that's terrible. And I said that, like, right away. This is awful.

And, you know, like, why are you here? And I said, well, your team invited me to be here. So I don't really have to be here. And he's like, well, show me something else. I showed him something else. It's like, oh, that's even worse. Like, I don't even know how you got in the door. And I was like, well, you opened the door.

I'm not interviewing here for my benefit. I was asked to come. Anyway, probably the worst interview in my life. I mean, it was a horrific interview. Just everything I said was countered with a skeptical question. Everything that I brought up was really cross-examined. I later learned that this is a common Steve practice, which is he's really trying to figure out what you believe in, what you're willing to fight for, what you think is important, and how well you can do under pressure. and a couple weeks later, Steve extended an offer to come and be a writer at next and to work with him on his writings.

And also to work with the team as they launched a next set of computers. And toughest boss I've ever had by far, most brilliant boss I've ever had, learned more in the time I work for him than pretty much the rest of my career. all of his intensity that is rumored is true, and also his great gift of finding what's extraordinary in each person he works with is also true. It was probably the toughest part of his life from a business success standpoint. It was between his two eras at Apple.

And what it taught me is in those darkest days where Next had very few sales and a lot of skeptics, the power of vision, the power of extreme creativity, the intensity required to build something new, that things can always be better, that bringing up your objection to the quality of something

is your vital job. All of these things were things Steve taught all of us, and I was very much a beneficiary of. Do you think, though, I found that he's a creative genius, but that abrasive approach, I, it's tough. I just, I always go back and forth because I'm a huge Apple fan and I love the Stanford speech and there's a lot of great things. But if somebody, like, did you question, well, wait a second, why would I work for somebody who treats me this way?

Why would I work for someone who says this is horrible and awful and it was a terrible? Didn't, didn't you question like, well, who does he think he is? Why do, why would I want to work with him? I didn't, I didn't at all question who he thinks he is because he, by that point, was already extraordinary accomplished. Okay. So this work gave him a bunch

a lot of credibility. Yeah, well, huge. I mean, builder of Apple. But what I can say is Steve was gifted in many,

many dimensions, but two above all else. One was the dimension of seeing people and their capability fully. And he absolutely knew how to motivate

based on what he saw in you. And it's an incredible thing to watch. It's an incredible thing to feel when you're on the receiving end of it. His ability to see you and see what capacity you have that even you do not let know you have is this deep, incredible gift. I think what you term abrasiveness, I would term as he had just this deep obsession about things being done right. Meaning if we are going to bother at all, Let us do this in a way that honors the quality of the task.

And he was just insistent that each of us live up to what we said we wanted to contribute. And his criticism, his sharp critique often came off of what you yourself had told him you were trying to achieve. It wasn't so much you've failed, Keith. it was more the sense that you have not lived up to your own hopes and expectations. So those two things I take away from my time with him. I mean, they're still deep in my own practice as a leader. Was your writing bad, though?

Did you think it was it not up to your standards? I mean, I would assume if you gave him writing samples, it was the best you had. I was 24. So it truly wasn't good enough. It was the best I can do with what I had from where I was. And the thing is that he sees you, and I think great leaders do this.

They see you not just in the present tense. They see you three years from now, five years from now, ten years from now. And part of their moment with you is about transferring that hope they have about you in the future. I'm incredibly indebted to Steve for that. Because you guys, that wasn't the only work you did together, correct? We worked on and off from that point forward. And I'm still a very big fan of Apple, though Steve has passed. It's a company that I still deeply respect, and we've done a fair amount of work at Apple.

In his honor and also in the honor of the people who work there, you know, they've done a remarkable job. What about those who try to mimic him but don't have the creative genius? aspect to their personality. I think of Elizabeth Holmes at Theranos. I don't know if you've worked with them. I've never met Elizabeth. It's hard for me to say much about her because I've never met her. Okay. You know, what I can't say is obviously he's one of the most written about leaders and I would be silly to think that I had some insight that hasn't already been well covered by others. But what I can say is when people try to imitate his actions, without the depth of understanding about trying to get things right in the world, trying to make a dent in the

universe, and really to do that, seeing you fully and deeply, not just in your present tense, but in the future. I think when you try to mimic the behaviors without those two core intentions, you really miss the whole point. The point is his insistence, all of us as leaders have a disappointment that our vision of the future and our reality of today don't match. What you do with that heartache is the difference between getting it right and getting it wrong. He had very little filters on the heartache. He would share it. He was incredibly sensitive human being. For me, I have many of the

same panches. I channel it in a different way. That's more appropriate to my style. But his style was extraordinary for him. I sound nostalgic. He was very formative in my early career and sticks with me to this day. I love it. I could talk about that forever, so I appreciate you to dive it into it. Keith, I think we mentioned during some of the pre-call that one of the areas that I love to focus on is the implementation and execution of ideas. of what we've learned.

I think a lot of people listening to the show are very good about seeking knowledge, going to conferences, taking detailed notes. But where it really matters is when it comes the time to actually execute and implement on the ideas. And I'm really curious because you guys are masterful creatives and you help help the best of the best. What about the part where it's the daily and regular execution on the ideas? What are some of the ideas of your thoughts around execution? Yeah, you know, so maybe similar to your other guests you've had and maybe different than some of your guests you've had is I think there are

three things that really matter to me in execution. One is something I call mind fitness, creativity and how to harness previous experiences you've had. We'll come back to that in a minute. And then being able to employ them in moments that matter. So when we think of execution, we often think of execution as kind of a laborious to-do list that never ends. And that execution is merely implementing it. And I find that that's actually the wrong mental model

for the adaptive, agile, and constantly changing world that we live in. And what is most important as a starting point is what I call mind fitness. So our mind, our ability to be centered, our ability to not think selfishly, but instead be connected to others, our ability to see things from a calm way, our ability to see that ideas are just ideas. They are not us. They are things our mind has created and we can study them just like everything else in the world. I know some of your other leaders you've interviewed have worked with the Dalai Lama and our firm has been lucky enough to do so as well.

And this whole notion that you can train your mind to be present for this moment is one of the great gifts that you can do as a leader if you want to improve your execution. Your ability to be present, your ability to not have to judge others, your ability to connect with others

with a sense of belonging, your ability to not waste time cross-labeling each other, denigrating each other, all confidence ability of having a fit mind to do so. So my first thing is build a daily contemplative practice. Meditate, pause before you go into the meeting. When you go into a meeting, one thing leaders can do is spend two minutes in silence, whole team, eyes closed, eyes open,

just saying let's clear out what happened in the previous meeting. Let's just get it out of our heads so we can be present for what we have to talk to now. So daily mind fitness practice. Second, build a daily creative practice. What do I mean by daily creative practice? So you talk about your audience being voracious readers and careful note takers. That's a big part of a daily creative practice. It's about being alive, awake, and aware of what's going on with you. Clip the article, mark it on the web, save that Instagram entry. That book, underline the passage, rip it out, put it in a folder. One thing I tell new leaders to do is literally get a standard manila folder

and then start cutting out articles, pages, pieces, photos, things that inspire you and create this great backlog of inspiration. Because what creativity is is, in fact, rarely a spontaneous burst in the moment. What it is is recalling something that has inspired you in the past and applying it to the moment that you're in. So create a daily, created practice. And then the third thing I recommend for execution is really to understand what moment you are in, moments that matter. Are we in a looking at the world through a new lens moment? Are we in a, oh, wow, we've discovered an aha moment. Are we in a moment where we need to rewrite the narrative about what we're doing, what matters? Are we in a moment

where we have to make a tough decision? Are we in a moment where we have to integrate our work into some bigger system, the failure in execution is often the failure to recognize what moment you're in, to not be aware of what moment you're in. And so, you know, we have this whole budding curricula about really recognizing moments to be absolutely certain, you know, so far we've identified 13 major moments that leaders are in when they need to execute. and really ensuring that you understand the context of the situation you're in ups your effectiveness and execution. Whoa, that was great.

Maybe it's too much. That was really good. No, I was just going through my hands hurting from basically writing what you said word for it. But I think that part is a big deal to me. And I wasn't sure what you're going to say. And I love it, especially the, we learn in moments. of reflection. And too many people, and I'm definitely,

have messed this up a lot, but too many people go from meeting to meeting to meeting to meeting to meeting with zero reflection. Or they, quote, don't have time to read books, which obviously is false for 100% of the human beings on this planet. So I don't have enough time to breathe. I'm sorry.

Exactly. You know, so I just think... Iseration is the oxygen on which we all survive. Right. Well, I was a guest on a podcast recently, and we talked about reading and it came up, and that actually was said, and I said, think about this when it comes to books, okay? And sorry for the quick tangent, but it's really important to me. When it comes to books, you have geniuses that are investing years of their life to reflect,

to write, to edit, to put the best of the best that they have in their mind at that time for years and put that in the form of a book, you could click and pay 15 bucks on Amazon, have it immediately downloaded on your iPad or your Kindle and read the best of the best of what they have. We are so lucky. We are so lucky to be able to do this. I just think you have to think at books from a foundational level that I have all these incredible virtual mentors. I'm lucky to get to talk. to a lot of them too, but even if you're not lucky enough to talk to them, you still can know exactly what they're thinking in the moments they wrote those books. And so that's why that the contemplative process is so critical of blocking out time every day to think, to reflect, to grow, to learn, like that is critical. And it seems to be a commonality. Yeah, this notion that our mind fitness unleashes our creativity, which allows us to show up in moments that manner. In order to challenge the status quo, in order to innovate, in order to execute with quality, it's this mind fitness creativity moments that matter.

And if you work on the mind fitness part, spend time to calm your brain, spend time to be present, spend time to be aware, spend time to notice, spend time to reflect. these things in the end do not require huge investments of time in order to radically change how creative you are and how much you can rise to each moment that matters. And I think this is something in a super busy, super, you know, social media streaming day. We have cut off our ability to reflect. And it's actually in that reflection that our future success lies. Keith, this stuff's awesome, man. Thank you so much for being here. I absolutely would love to continue our dialogue as we both progress.

It's been inspiring for me and really great. I'm appreciative of your time, your investment. Where would you send my listeners to learn more about you online? Oh, wow. I think you can, whether than learn about me, I think it might be better to learn about our applied ideas. So leadfully.com, L-E-A-D-F-U-L-L-Y dot com,

has great advice to do young or old, let's not be ages here, leaders and managers. You could also go to a website called unstuck.com where you can really go after the microbehaviors of being stuck, should not be shameful. Great people get stuck all the time. There are little techniques you can do, microactions you can take.

You can master all of that at unstuck.com. And then if you want to learn more about S. Y partners as a firm, please, please tune in at SYPartners.com. Perfect. Leadfully.com, unstuck.com.

SYPartners.com. Hey, Keith, thanks again for being here. I look forward to the next one, man. Ryan, it was a delight. Thank you. Bye-bye. Thanks, fan. Wow, that one was so helpful, and I love the conversation with Keith, especially

the part near the end when we talked about implementation and execution. My hand truly was hurting from taking so many notes. This was a really useful conversation. I hope you enjoyed it. If you did, I would love it if you would write to review, subscribe, and rate the show in iTunes, Apple Podcasts. That's write a thoughtful review. Rate the show. Hopefully five stars. and subscribe in iTunes, Apple Podcasts, it really helps spread the message all over the world. And thank you so much for getting the opportunity to continue to do what I love most, have these fascinating conversations with incredible ears, and your support helps me do this. Thank you so much. I will see you next week. Can't wait.

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