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Building Your Winning Game Plan on the Court and in the Workplace [Security Sandbox Podcast]

Sam Bock

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In sports, it’s easy to define success and failure. It’s winning or losing. But in business and in tech, the lines are a little fuzzier. So how do you coach your team toward victory on the basketball court and in the (possibly remote) office?

This month’s episode of Security Sandbox features guest Kirk Arthur, Microsoft's leader of worldwide public safety and justice, and Keith Carlson, Relativity's chief technology officer, joining host Amanda Fennell to discuss the techniques that drive a great basketball team and a great business strategy.

Give it a listen to learn more about great coaching, the importance of planning and goal setting, and how to motivate your team.

Security Sandbox is all about drawing inspiration from personal passions to pursue more creative security practices. If you love the show and would like to share it with others, you can help bring it to more people by giving us a review on Apple Podcasts or your favorite app!


Amanda Fennell: Welcome to Security Sandbox! I'm Amanda Fennell, chief security officer at Relativity, where we help the legal and compliance world solve complex data problems securely—and that takes a lot of creativity! One of the best things about a sandbox is that you can try anything. This season, let's explore how curiosity and personal passions inspire stronger security. Grab your shovel, and let's dig in!

In today's episode, our sandbox hits the hardwood for a fast-break conversation on the similarities between basketball and tech—especially when it comes to building a title-winning team that gets the best out of all your contributors, not just your star performers. Joining me today is Kirk Arthur, Microsoft's leader of worldwide public safety and justice, and Keith Carlson, Relativity's chief technology officer. Both are united by their unique roles in tech and familiar passions in basketball. So let's lace them up and run the court!

Alright—I prepared for today, and I did watch the documentary, The Last Dance. I am very excited that I have plenty of things that I can say to link with security on this one with basketball. This is going to be a fun episode. We're going to jump right in from one of the biggest things that came out for me in watching basketball and all these greats that we're talking about, how they won championships and everything. I'm going to start with our guest. Kirk, what does a winning team look like structure-wise?

Kirk Arthur: I think that’s a great question and thinking, Amanda. For me, a winning team, when you think about it, there has to be a leader, right? That coach, the one that puts that together, working well with the general manager. But then you start thinking about personalities and how each fits into one another and the importance of that. Not everybody can be Michael Jordan. There has to be a Jordan, but there also has to be a supporting cast. You need your Pippen, your Rodman, you need everybody else understanding their roles and responsibilities and their capabilities. Not everyone's perfect, so if you can build a team where each weakness is offset by another person's strengths, and then you have that communication and the camaraderie that can kind of permeate across a team, for me building that environment and developing that—we see it in law enforcement, within the military organizations that are successful, we see it across sporting—it's just who you're going to go to battle with. Do you trust them to do their job, and how well do you communicate amongst each other?

AF: I communicate all the time with Keith Carlson here on the line. So, Keith, do you agree with this? Is this how you build a winning team? And you play basketball; is this the same in basketball and in technology?

Keith Carlson: There's team makeup—the personalities and the capabilities, and not everybody can be a Jordan, totally agree with that. But it's also the ability to rise to the occasion when it's the occasion and to recognize that it's the occasion. Right? That was the thing that always really amazed me about the Bulls. You'd be watching and Jordan would have 12 points in the third quarter, and they'd be down 10 points. And you're like, "Okay, they're going to go into the fourth quarter, down three, and Jordan's still going to score 30." And they would be able to take those two or three minutes’ worth of time when the other team is like, "Well, we're almost to the end of the quarter and we've got this," and they would just rise to the occasion, score the points, and put themselves in a position to win or put themselves in a position that made it very difficult for the opposition.

AF: So seizing the moment as a team, winning the quarter, rising to the occasion—all of the utmost importance for winning teams. Does this lead to a hero culture, worship situation and swarming and, "Oh, we had a P1 last night, and everybody was up for the past 47 hours and working on it, " and that leads to this mythos? Or do you think this is just a fundamental in tech?

KC: To me, yes. When you talk about leadership, there's a variety of aspects, right? You've got to have the right mix of people, but there's also situational awareness. I think that they had better situational awareness than any team that I ever remember watching or continue to watch. And so I don't know that it's necessarily about a hero or about this or that. It was that they all recognized what the important thing was at the same time. And it wasn't like they needed to have big communications or lots of meetings. It was just this sense of, now is the time that we need to do these things to put ourselves in this position.

AF: Do you think that that's a fundamental that comes from your star player—that they influence the rest of the team to rise up—or does it come from the coach or the leader? Is it a combination of both? So, Kirk, I'll ask you that one.

KA: I was going to say, I think it's a blend. You need to recruit talent, clearly, whether it's basketball or in business or anywhere. You need people to have that ethos, that work ethic, and that skill set. But then when you reference like Rodman, I don't think anybody fully appreciates how hard he works in practice and outside of playing a game. They just saw the media perception, and they made maybe some biases towards that. But as leaders, whether you're a coach—you heard Jordan talking about in the documentary how hard you knew Rodman worked, but he also knew Rodman needed to vent. There's a time when he hits a threshold and a stress level that he's got to go take some time off, right? We hear that from our leaders in the business world now. Over the last 18 months with the pandemic and how hard people can work, you need to take time off and take care of your own mental and physical wellbeing so you can be your best each and every day. So to me, it's just about recruiting the right people with the right talent, with the right work ethos that, again, complements our broader building of a team to really be rowing that boat in the same direction.

AF: What do you do in real life? What do you do in order to handle or manage or coach? If you have a Rodman on your team.

KC: You first have to identify that they have these exceptional capabilities, right? I would say in a business context... In a sport, it's 60 seconds. It's about rising to that one minute. In business, it's a little bit more broad-based because you're working with people all the time and distractions can be a little bit harder to manage, like, if I'm going to get this one good minute out of this person and then there's a distraction, it's okay. So it's a little harder in business. But it's first the recognition and then it's about taking what is really good and amplifying and being okay with letting some of the things that are a little bit more distracting have their own space and not distract everybody else. Right? It's about being able to bring the right focus to the right situation.

KA: The core of that is hiring or building a diverse team with different backgrounds and perspectives and skill sets, so you have that "better together" approach. Some people might be extroverted, and they love presenting. Other people might be terrified with presenting, but they love digging into data and helping put together material. Just understand the dynamics of that team and how best to get that out of everyone. But then also make sure, like, accolades and recognition, are load-balanced across everyone who had a stake in the overall team success. I think sometimes societal, "Oh, it's just Michael Jordan. He was amazing." No, without a supporting cast, he doesn't get his six championship rings. You have to have everybody in place.

AF: There's a quote that he said in the documentary, and it leads me to my next question. I'm going to ask both of you. He said, "It's funny. A lot of people say they'd like to be Michael Jordan for a day or for a week, but let them try to be Michael Jordan for a year; see if they like it. Let them see that it is no fun." So what kind of a coach are you? What's your coaching style? What do you draw inspiration from? How are you leading this diverse team? Keith, do you want to start with that one?

KC: Yeah, it's a great question. Diverse teams are incredibly important to make sure that you're not missing the obvious things from different perspectives. At the end of the day, it comes down to putting everybody on your team in the best possible situation to be successful. That includes coaching, including them in conversations that it's important for them to be in, and it's about identifying places where they could use a little bit more maturing and a little bit more advice and feedback and giving that to them in ways that are constructive and helpful. But it really is about, there's magic when a team comes together, and the team is more than a group of individuals. And that really comes from everybody contributing when they're at their best in the areas where they're special with what they do and leaving the things where that's not true either to coaching or to reinforcement or to other situations. It's kind of like trying to bring that magnifying glass to get everybody at their best at the right time.

KA: I agree with all those points. I think as a leader, being really in tune emotionally with your team and understanding and reading even nonverbal cues. Small things over time can become big things from personalities or perceived wrong. I think being really astute and aware of that and understanding and learning the personalities of your team, whether it's one-on-one or in group settings. Making sure that everyone has their opportunity of success—everyone's going to define success differently for themselves—and making sure you as a manager are helping them achieve that. Mentoring, giving them a clear communication path forward to achieve that. I think that's the balance, right? The really successful coaches and the really successful business leaders, they get that, and they let their people have enough rope to go be successful. They don't micromanage. You want to hire those right people to do that.

KC: Yeah, that's a really great point. The other secret to a really great team is to not over-manage because you've got to let the team develop their own personality, their own capabilities, their own opportunities to excel. And that can be the hardest challenge for a leader at times: to let the team lead as opposed to feeling this desire of, I've got an opinion, and I've got a desire, and I've got an agenda. But wait a minute. I need to stop and listen to what the team says. One of the clearest examples to me in my entire career, personally, is I got passed over for a promotion that I thought was a pretty much a slam dunk. And they hired outside.

AF: You just said slam dunk. You have to take a shot or something. You can't—

KC: [Laughs] It was a layup. Hey, I was born and raised in Indiana. Played basketball from the time I was five. I played eighteen years in city league tournaments, and I played three times a week for 25 years so you're going to get some basketball references out of me. But I got passed over for this promotion and so I wanted to know why. I went all the way up to the highest person in the organization, and they articulated it to me two or three things that I was doing that they felt like weren't really suitable to the next level. And when I asked them, all three of the items were things I could have fixed in a matter of a couple of weeks if somebody had told me, but nobody had told me. So I made a commitment to myself that, to be the best leader I could, I was always going to tell the people that worked for me the things that they could fix easily and not hold it back. That changed my career because it made me comfortable with telling people feedback that may be uncomfortable, not because I felt like I needed to confront them, but because I felt like they deserved to know the things that they should know to be able to achieve that next level. So that kind of changed my career.

KA: For me, I think those are awesome points, and it comes down to trust. Right? And that's bidirectional. Does your team trust you, and do you trust your team and have that relationship? That's where the goodness can happen.

AF: This is where I think, Keith, you and I ... we both have different leadership styles, but this is one that you and I are 100 percent aligned. I always ask that question when someone's telling me, "Well, so-and-so is doing this or there's a difficulty with this or et cetera." Do they know? Have you told them and have you said it in writing? Because everyone hears something different from a conversation, but once it's in writing, it makes it much more of a serious conversation. I always like to track everything, right, because of forensics. I'm always like, if it's not in writing, it didn't happen.

So Jordan said, "Winning has a price and leadership has a price, so I pulled on people when they didn't want to be pulled, and I challenged people when they don't want to be challenged. And I earned that right because my teammates came after me. They didn't endure the things that I endured." Do you think this is something that you feel in your role as a leader? That you definitely have this price of leadership where you have to pull on people? That they're done and they don't want to keep being pushed, but you know they can go a little further? Kirk, you're nodding—is that a yes?

KA: 100 percent. I think that's the balance of a leader and an effective leader is pulling but not too hard or too quickly. Communicating what you're trying to accomplish with them, giving them the tools and the knowledge to be successful. And when they enjoy that success, however small it might be, it builds on itself and gives them confidence going forward. Even for your Jordans of the team, pulling them back a little bit to help bring the others along and just not letting them go off in isolation or on an island just to go do their thing because they're going to do it. Again, thinking collectively for the whole team.

KC: Well, and Jordan had to grow. I mean, he dropped 63 on the Celtics in the Garden, one of the greatest playoff performances of all time. And they lost the series.

AF: Okay, that whole part of the episode was crazy. I absolutely cannot believe that situation. But he had to. You could see his face when he looked over and other people weren't there to get the ball and he was like, "Are you kidding me? Why are you not there?" Like, he just looks so frustrated because he didn't have his supporting team that he needed.

KC: Yeah, but there was something inside of him that needed to change a little bit, too, right? He needed to build some trust with his teammates. He needed to rely on them a little more. Without that learning experience, I don't think he passes off the winning shots in two championships to people that were open. He would have tried to take those shots before. He would have kept it on himself. But he learned, "I can be the dominant force on a winning team, but it's got to be a team."

KA: Yeah, I think that speaks to leadership. When you saw in that series, when Jordan was out, between Pippen and Kukoč and the final shot was going to Kukoč and how Pippen handled that. That completely eroded the leadership perspective, both internally, externally, not being that good teammate and team player. It blew up in his face when Kukoč sent the shot. That's where Jordan was so special. He backed it up, but he also understood, to your point, he doesn't pass to Steve Kerr if he doesn't trust them for that game-winning shot. He did because he did trust them.

AF: What if you have two rockstars? How do you deal with that, and how do you make sure everybody is going towards the same goal? It's easy in basketball. We know what we're trying to do. We're trying to win a championship. We're trying to win the game. We're trying to get the ball in the net. That's simplistic. How do you do that in business?

KC: Well, it ain't easy. [Laughs]

KA: From my lens, their strengths have to complement each other. If their strengths are the same, I mean, candidly, I think there's a trade on the books. You could have to trade somebody for some other assets potentially. They have to be able to work together and somebody has to be the leader. You can't have two just because you're going to get jumbled. And we've seen that time and again in the business world where you have two heads, and it doesn't it doesn't always work out. It gets confused.

AF: I guess there's this thing about the igniting the team, though, like in terms of how do you ignite them in something? Have you found any difficulty in saying, okay, this is what we're going for, and keeping the energy going? Because the longer and further you're going in that championship, the more tired people are getting, right? Potentially. I mean, this is a long road. So how do you keep the energy going? I think, Keith, for you, you get everybody together every week, right? You get the entire team together, and you all go through everything that you're working on and what your status is?

KC: Yeah, internally we run an audit-based process so that we can scale up and look at a lot of things together so that we have a common vision of what we're trying to accomplish and what we're trying to do. And yeah, I think that can generate energy and focus. But I think to keep the energy up, you have to care about what it is that you're delivering. You have to desperately want that outcome. So I think that for me, the easiest way to keep a team motivated is to spend an inordinate, disproportionate, most of your time on establishing what the result is so that everybody is really bought into the idea that that's the thing we need. If everybody really believes very clearly that that's the thing we need, that's when you find that large teams, even with a lot of diverse opinions, who are moving in a lot of different directions ... they all pull together to achieve it. This is what I like when people are in really dire situations. Like if a company is close to being bankrupt, and they have to achieve a certain market outcome or whatever the situation is. When it's clear what the outcome needs to be, and there aren't many alternatives, people rise to the occasion. And so to me, the easiest way to motivate is to make sure the thing you're trying to achieve matters, is the right thing, is important. And when it's unclear—like, I don't know if we do this or if we do that, either one is probably okay—it becomes really hard to keep people motivated and focused on delivering.

AF: Kirk, how do you keep people going?

KA: I agree with those points. For me and my team, we're geographically dispersed, and Microsoft is obviously just a highly matrixed company so we have stakeholders around the world. One is a regular cadence for me and my immediate team. It is a weekly sync just to stay aligned. Collectively we built our core business strategy and our go-to-market muscle, and we have that documented and evangelized so we don't deviate from that. And then we permeate across geographies, always iterating and massaging a little bit. But then for me it's about celebrating the successes. It's about showing up every day and working through the challenges. It's easier just to say, "Yay, we did something really good." It's harder to say, "You know what? We need to work with engineering, product groups, other entities, and escalate and bring in senior leaders to make decisions." That can be a lot of work and late days and early mornings. But doing that so it helps us be successful as a team in the field longer-term. I think just rolling up your sleeves up. We say "GSD." I won't say what the 's' is, but "get stuff done," if you know what I mean.

AF: [Laughs] This is a PG-13 podcast! I'm just kidding...

KA: [Laughs] But, you know, someone just sits on the sideline, just points and says, "Do this and do that." Like, okay, Captain Obvious, thank you. We want, at least for me, we want people in the trenches working side by side.

AF: But this is like the epitome of basketball, right? This is practice, practice, practice. You got playbooks, you run them, you run them again, and you run them again. And you keep building the muscle constantly. So we say building the muscle in tech, but it really is about sports building the actual muscle, right? You want to be ready with that memory muscle when you're going for a shot.

KA: To that point, I was reading about Mike Krzyzewski, because I think Coach K is like the standard bearer of coaching and communication. He has core practices: What you hear you forget, what you see you remember, and what you do you understand. I think that's really important—those three principles—when you think about your team and to get to the aspirational point with them.

KC: In sports, the difference between success and failure is absolutely, unequivocally clear. In business, it's not always. Like, okay, we reduced incidence. By enough? Was it a victory? I don't know. It's better, but is it clearly win versus loss? In sports, it's crystal clear. And so for me, again, there's magic to meet in metrics. If you can find the metric that, if you change it, it really does make a difference to customers, to the business, to the overhead, to the load, whatever it is ... If you can find that right metric, people will rally. And then different groups of people in different places, in different parts of the world, can think about how to measure their success or failure the same way, and I can pull everybody together. And so I think getting the right metrics really matters and clarifying what victory is and defeat is more clearly. Again, getting everybody bought into, "If we can achieve this, that's victory." You can really get a team focused on delivering because they believe. They understand. It's clear.

AF: You make these decisions off of the metrics and the direction that you're going. This ties back to Kirk. I was just going to ask the question about the coaches, like which coaches actually inspire you, which ones are drawing inspiration for you, and so on. You mentioned Coach K. I was looking and researching because, to be clear for anyone listening to this, basketball is not my passion. It is my colleague's passion, which is why Keith is here. It's Kirk's passion. And sometimes that's what happens on a team. You've got people who are passionate about something that's not your passion, but that doesn't mean you can't speak the common language and that there isn't something that correlates there. When I researched some of the coaches, I saw this one quote from Jeff Van Gundy—Coach, Knicks, Houston, I don't know, he's all over the place, like ESPN a long time. He said, "Your decisions reveal your priorities." So, Keith, with all those metrics that you're putting together, all these decisions that you make, they reveal your priorities, which for you is customer experience. You're trying to build something that people can use and enjoy and get what they need out of it and be happy about the experience and what's going on, and also get to their data faster and get to the results of what they're looking for faster. And I think that comes across. What coach do you actually draw inspiration from then?

KC: Oh, wow, what coach do I actually draw inspiration from? Look, I grew up in Indiana when Bob Knight was the coach of Indiana and was throwing chairs across the court and yelling at everybody. I went to high school with his son, Pat Knight, and anybody that knows basketball knows Bob Knight was a royal SOB. And I won't explain what that means. You can look it up. But the interesting part is, in 1975, the assistant coach at Indiana was a young guy by the name of Mike Krzyzewski, and Mike Krzyzewski played for Bob Knight at Harvard. And so Bob Knight and Mike Krzyzewski are really tightly tied together because that's where Mike played basketball in college and was an assistant. He went from Indiana to Duke at Bob Knight's success. I didn't have a ton of respect for Knight because he was really, deep down, hardcore, "I'm going to make you do it. You're going to do it my way," kind of like disciplinarian. I would say that Krzyzewski took the lessons of what good basketball was and then he added to them about like, I'm going to convince instead of force. I'm going to reinforce instead of beat the drum and beat it into you. And so I would have to say, Krzyzewski, for me, is probably the most inspirational coach in terms of being able to put the pieces together. And so, yeah, I think he's one of the coaches for me that really plans that.

AF: So I researched this one, Kirk, because I have no idea who Coach K is, but does this look like it's this coach Mike Krzyzewski for Duke? Who's Coach K?

KA: Yeah, Coach K for Duke. You got it.

AF: Okay, is this yours then? This is the one that you draw inspiration from?

KA: Yeah, I mean, I think for anybody he's at the top, right? Phil Jackson for the NBA and the way he approached the Bulls is legendary. Even Jerry Tarkanian from the Running Rebels in the late 80s. That was my favorite team of all time. But he let his players do their thing rather than put them in a box and try and control what they're going to do. That works for some teams and the structure of that team. San Antonio—right, Keith?—Popovich runs a very strict program. Rodman did not do well in that environment but others do. Robinson did, and he's a Navy guy. So it just depends on the team to mold and what you hired your group to bring on board.

AF: Alright, I'm going to draw us to a close with some thoughts I've put together. This is what I'm picking up because I always think about this from security and tech and how these all interweave. It seems like one of the big themes is planning. You need to plan your players. You need to reallocate and go in different directions in order to be a winning team. You have to decide what playbooks need to be written. You have to test often. All of this seems like just a ton of planning. That feels like the first one because that's definitely true for us in this tech industry.

The second one is situational awareness. I can't not mention that one. It's just important. Be aware of the history of where you're at, what you're doing, the aspiration, everything on the court and who's where. I think that's a big part of where we're going and how we get there quickly.

And then this third one, I don't think we could end it without saying we've got to be a good coach. It sounds like you’ve got to be in these areas. You have to make sure you continue in the areas that you're the best. Keith, you mentioned letting that shine in different areas for success for the people who have certain skill sets at the certain time that you need them. It's, you know, bringing them in, igniting the team. I like this part that you said: "You have to care about what it is you're delivering." You have to care. I use this a lot from Sharif from football. It's one thing that his coach said to him: "Kid, you got to want it. You got to want it. You got to really be wanting what it is that you're doing and care about it." So I do think that this is the three that I would probably pull together from this.

I like to always end on a quote. This one is my favorite quote from The Last Dance. It's probably the one everyone remembers, but Roy Williams on his experience with Michael Jordan, said, "Michael Jordan's the only player that could ever turn it on and off, and he never freakin' turned it off."

Gentlemen, thank you both for being here and not turning it off. You were here the whole time. You were in it to win it. You had a few layups there. We took some good shots. I appreciate both of you very much and thank you.

Thanks for digging into these topics with us today. We hope you got some valuable insights from the episode. Please share your comments, give us a rating—we'd love to hear from you!

Artwork for this series was created by Guss Tsatsakis.

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Sam Bock is a member of the marketing team at Relativity, and serves as editor of The Relativity Blog.

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