Episode 223 Transcript:

0:00:00 Ramona Shaw: This episode is all about the connection between playing chess and operating well in the workplace when it comes to strategic skills, big picture thinking, as well as office politics. I have a very special guest with me today to talk about all these things. So let’s dive in.

0:00:17 Ramona Shaw: Here’s the how do you successfully transition.

0:00:19 Ramona Shaw: Into your first official leadership role, build.

0:00:22 Ramona Shaw: The confidence and competence to lead your team successfully, and establish yourself as a respected and trusted leader across the organization? That’s the question, and this show provides the answers.

0:00:34 Ramona Shaw: Welcome to this episode of The Manage Track podcast. I did say in the intro that I have a special guest with me today. This is Shawn Stewart. He’s an engineering leader, but he’s also an avid and really good chess player. And every once in a while, when we talk about work stuff, he does bring up chess analogies, and I find them really intriguing, and I think you will, too. So I invited him on the podcast to talk about chess and leadership.

0:01:00 Ramona Shaw: Welcome, John.

0:01:01 Shawn Stewart: Ramona. Thank you for having me. I’m really excited. Two of my favorite subjects, leadership, specifically around engineering and also playing chess. And, yeah, I’ve seen a lot of patterns between the two, and it’s helped me to grow as a leader, and it’s something that I use as a teaching tool with a lot of the folks on my team.

0:01:19 Ramona Shaw: You’re really good at using analogies to make a point, and I know that one of them is usually airplanes. The other one is chess. How did you get into chess? And what fascinates you about, do we call it a sport? Yeah, I guess so.

0:01:31 Shawn Stewart: It’s a bit of a mental sport, and for folks that know me, I play a lot of chess. I play about ten to 20 games per day, usually a lot of 1 minute, three minute games. It’s a way to keep my mind sharp. But the way I got into chess was almost by accident. I did so during college. A lot of my friends were playing. I hated to lose, and so I would learn to play effectively so I could win and I could have bragging rights.

0:01:58 Shawn Stewart: But eventually, along the way, I started to understand a deeper beauty in the game that I started to connect with a lot of things in life, including work.

0:02:08 Ramona Shaw: Okay, so, speaking of. And I’m going to piggyback right off what you said with how you noticed the connection between how you operate as a leader in an organization to chess. What is one of your favorite analogies when it comes to leadership and. And chess?

0:02:22 Shawn Stewart: Yeah, there are a few things that, you know, most chess players, they learn how to move the pieces effectively, like some of the basic rules of the game, which doesn’t really distinguish chess a lot from checkers, with that basic understanding. But as you develop and grow in the game, you start to realize that there’s a bit of an orchestration that happens at a deeper level, and it happens in a very dynamic way.

0:02:49 Shawn Stewart: The way I relate that to life is we all start off with an ambition or an aspiration about where we would like to go with all of the best laid plans that we have. There’s a lot of dynamic changes that are happening in the environment that influences some of those early decisions in our plans, and we have to adjust to them. For some people, this becomes a big obstacle, and for others of us, we understand this to be the dynamic nature of the environment to begin with.

0:03:19 Shawn Stewart: And so that adaptation ends up becoming a bit of a superpower. And that’s what I’ve learned through chess, that the adaption of the changing environment is something that we can actually use to our benefit if we can anticipate it and use it.

0:03:34 Ramona Shaw: So what I find that you do all the time is constantly reassessing what the situation is and what the dynamics are versus what some of us will do. And what I definitely notice about myself every once in a while where I get stuck into a certain assumption. This is what I think the plan is. And I don’t reevaluate quickly enough to be able to show up as my best self. And that is one of the things that I find really interesting when it comes to growing as a leader. And hence why we’re talking about this, because the further up that you go in your career, the more these type of things like adaptability and more that we’re going to talk about here matter early on in the career, before you’re stepping into a leadership role, a lot of it is about your expertise and demonstrating technical skill and the ability to execute and problem solve. And then as you grow, we start to incorporate a lot more leadership skills and they start to dominate your performance.

0:04:35 Ramona Shaw: And then in order to further go up and play the game at a higher level, adaptability and more of those things are increasingly important. And I think it’s a hard skill to learn technical skills. We go to school and we learn from others, but those kind of skills, they’re self taught. Some of us are naturally gifted, but some have to because they kind of learn the hard way through mistakes. Let’s talk about learning those skills, and then I’d love to hear what else that you learned through chess that you think is really important at that higher level.

0:05:06 Ramona Shaw: But learning those skills, other than learning through chess, how do you help others in your organization, within your team, develop leadership skills on that level?

0:05:14 Shawn Stewart: How many times have we all found ourselves in a situation where we’ve assessed a problem or an opportunity, and we create a plan and we start to execute, and then things change, and as those things change, we react to it in a negative way. It’s almost as if the change itself became an obstacle and we start working, unblocking ourselves from this obstacle, because we’d really like to get back to the hypothetical plan that we created in the first place.

0:05:46 Shawn Stewart: You think about all of the energy that you spend to unblock what’s actually happening in reality, to get back to the place that we constructed in our mind, and we never quite get there right. And it’s very frustrating. And I think that’s the challenge a lot of us face. Instead, the way a chess player really thinks about their moves and their situations that they’re going to end up in. They’re actually thinking about all of the permutations, the possibilities of environments that they will end up in into the future, and they accept them.

0:06:21 Shawn Stewart: I could make a move, but the conditions of the environment could create a bunch of different scenarios that I’m going to have to respond to, and I simply accept them and I create plans around how I will respond to them. So in those cases, you’re really not looking at the change as something that’s inhibiting you. It’s something that you’re actually planning for. So a lot of times when I talk to members of my team, the problems always sound like I had a plan.

0:06:52 Shawn Stewart: I agreed with a group of stakeholders or peers about moving in a direction, and we’re not going where we ended up to be. But there isn’t a lot of assessing the current situation or the different permutations of future situations and understanding, even voicing and accounting for the different ways that we could end up into the future so that we can be okay with it. And so really just helping folks see that in a way that doesn’t feel like it’s interfering with the work.

0:07:28 Shawn Stewart: But just as a natural reaction of making a move, folks start to become a lot more comfortable with the changes that happen down the road.

0:07:36 Ramona Shaw: When one thing that I would assume, so correct me if I’m wrong, but I assume that if you as a leader, look at the change and you have a positive outlook on that, and you’re looking specifically for opportunities to leverage that change and to adapt to it quickly, that through the way that you engage in conversations and through the questions that you ask, this mindset is almost passed on to other people where they start to adapt and start to think the same way versus if you’re looking at change or changing dynamics or relationships as issues, then other people start to see it that way, too.

0:08:12 Shawn Stewart: Yeah, 100%. And I’d go a bit further even, and I categorize it in terms of short term goals versus long term goals. We have fixated on a specific point, and I think that’s really important. We should all have a North Star and the direction that we’re heading in, we shouldn’t deviate from that. That’s clear. But along the path of getting to that primary objective, those short term goals are really those opportunities that pop up that initially seem like obstacles over optimizing for identifying the short term goals before you’ve started ends up becoming an excellent way to waste a lot of time and drive up costs and in fact, in some cases distract you from your long term objective.

0:08:59 Shawn Stewart: I encourage folks to look at short term goals as opportunistic serendipity, for lack of a better term, on the pathway to a long term goal. When I’m continuously assessing the changes that are happening within my environment, and part of achieving these goals is really expecting that failure will happen, but not in the sense of I tried to do something and I didn’t accomplish it more in terms of a learning exercise.

0:09:29 Shawn Stewart: I attempted something without clear knowledge of whether it would work or nothing. And so what I learned is where the alternative pathways actually are versus the paths that I took that didn’t really lead me in a direction that would take me back to my north star.

0:09:48 Ramona Shaw: And so what I’m picking up from that is anticipating the failures, too, so that when these things happen or you miscalculated the patterns at that point, you’re not going to feel like the person needs to reprimand it in a way or you’re not going to make them feel this way. But instead of, you’re really looking at it as a way to reassess and reevaluate and go back and look at where did we go wrong? And speaking of that, I know that you do this with games where you would go back, or even when I see you watch, like, YouTube, I don’t even know what they’re called, where they, like, debrief a game and they would go back to plays that they made way in advance, that then ends up.

0:10:27 Shawn Stewart: Yeah, they’ll replay old games from great chess players and do commentary on it. It’s a lot of fun. For some folks, I think it’s a sleeping aid, but for me, it’s, it’s a ton of fun.

0:10:37 Ramona Shaw: But then through that, they’re not looking at who is to blame and whose fault it was. They’re really looking at where did that person miss the moment or the opportunity? And the opponent started to take the hand and lead the game and, you know, where did all that happen? And it’s very analytical. There’s no blame involved. It’s all about learning and growing. And if I imagine you’re in a situation with a project or initiative or even sort of interpersonal dynamics, where we would all go back and look at, where did we miss the mark? Where did we miss an opportunity, and how can we learn from that? That turns into a very different conversation.

0:11:12 Shawn Stewart: Yeah, totally. And I think the insight for me, when I look at that, let’s classify that in the bucket of pattern recognition. The thing about pattern recognition is there’s a lot of bias that we’re not maybe aware of. That’s in pattern recognition. Sometimes we recognize patterns because we’re biased to the pattern. And I think what makes great chess players, great chess players, is that they understand that and then they look beyond those biases to look for additional signal elsewhere. Like, they deliberately do this.

0:11:46 Shawn Stewart: So it’s sort of like, yeah, I found the four positions that I anticipate happening, but is there maybe a fifth and a six that I’m not looking for? And this becomes a discipline that folks work on. If we can do the same in our daily management of our teams and our projects, I think it’ll lead to significantly better outcomes. An example of this in practice is if my teams come to me with an idea or a plan or project plan, I might ask questions like, what happens if your assumptions are incorrect?

0:12:24 Shawn Stewart: What happens if we fail or don’t achieve the goal that we’re looking for in perhaps a few of these milestones that we have set up, what are the alternative pathways? And so what it does is it allows us to really think through a plan that’s not just comprehensive, but a plan that really accounts for the things that maybe we’re not aware of despite our bias. And once we play these plans forward, regardless of what happens, even the things that we might consider failure, and we only consider them failure because we haven’t appropriately planned.

0:12:59 Shawn Stewart: Once that quote unquote failure, which is really just a planned deviation, happens, we already have a ton of tools in the tool belt to address for it. And we take that learning forward and becomes a much better part of the execution process.

0:13:14 Ramona Shaw: So those are all little ways that you weave it into team management. What are some other things that you’ve learned through chess that you’re now applying and you’re recognizing that allows you to operate at this higher level? Think more strategically, be more adaptable, or play better into office politics?

0:13:32 Shawn Stewart: Yeah, I think there are plenty, but I’ll pick two that are really useful for me. The first one is taking initiative. Chess is a turn by turn game where each player makes a move and then the next player has to make another move. A lot of what we do at work is very much like that. We make a move and then we wait to see what happens from the environment or the other players on the board, and then we have to respond to it.

0:13:59 Shawn Stewart: So taking initiative, being the first person to make the move and knowing that the other moves happen as a result of my first move is extremely important. So this is something that I employ on a day to day basis. It’s something that I teach folks within my teams to always identify opportunities to take initiative. The second thing is understanding that a chess game happens across three phases. There’s the opening, where you’re really looking to establish yourself, take initiative and put yourself in a very strong position.

0:14:35 Shawn Stewart: There’s the middle game, which you’re dealing with a lot of conflict. Things get really dense in the game. There’s a lot of moving pieces and you have to manage it. And this is what effectively tells you, determines whether you’re going to have a successful third part of the game, the endgame. And the endgame ends up becoming a very strong tactical, strategic, even positional game, where you have very few pieces, you’re close to the end.

0:15:08 Shawn Stewart: Every single move is critical, and you have to make sure that you’re making the right move. But you can’t get to the end game until you’ve established yourself well in the opening, until you can manage all of the chaos that’s happening in the middle game. And with the anticipation that I will eventually get to the end game. So how do I get there in the best possible position? Because when I get to the end game, I’m going to have a lot less choices and opportunities to make mistakes.

0:15:36 Shawn Stewart: So I bring those forward. In all of my conversations with folks, I speak through, you know, asking questions and qualifying decisions that folks have made throughout the process. But the framework I use in my mind is definitely chess based.

0:15:49 Ramona Shaw: It’s fun that you said the best possible way that to get through the middle part, and I thought many of us want to just get there the fastest. And I think that is the pitfall, or we feel drained or frustrated through that middle part where it’s chaotic, where we have opposition, where we have to go, the informal behind the scenes conversations that need to take place in order to get buy in from people to really leverage their perspectives as well, and when we think that is sort of the annoying part of the process versus seeing it as a natural part of the three phases that will allow you to successfully position yourself for that endgame, that completely changes the mindset that we have during that time period.

0:16:33 Ramona Shaw: So when people say to me, I don’t like office politics, or I don’t like that this takes so long, or that I have to get sign on and I have to talk to people before the meeting and after the meeting, it’s a mindset issue, right. You would look at that as, wait a second, these are all opportunities for me to position myself strategically to have a good endgame in place.

0:16:53 Shawn Stewart: Yeah, that’s absolutely right. And I would say if your thinking throughout those three phases is, how do I get through this as quickly as possible? The fact of the matter is your opponent’s not thinking that way, and it’s to your detriment to move that quickly. Patience is very, very important as well as initiative. Initiative does not mean speed for the sake of speed. Initiative means identifying the best possible position and getting there first.

0:17:24 Shawn Stewart: That’s a very critical thing to understand. The middle game, when things get really, really dense is really a game of tactics where you’re really trying to assess who has the stamina, the fortitude to stick through the difficult part to get to the end. And so at that point, it’s actually recommended that you deliberately slow down and wait and plot and plan in order to get through it. The folks that really try to rush to that end up finding themselves in a suboptimal losing endgame position.

0:18:02 Shawn Stewart: And yeah, that’s definitely a key point. Work doesn’t always have to feel like two armies at war over a chessboard, for sure, but there’s a lot we can learn from it, because at the end of the day, great teams are teams that win, that overcome adversity. And I think those are the key things that we learn from using this analogy of chess and applying it to the workplace.

0:18:25 Ramona Shaw: Love it. Is there anything that we haven’t yet touched on that you’ve learned through chess? And you think it’s important for leaders to keep in mind as they are learning and growing with their strategic thinking and planning skills? And all of that.

0:18:38 Shawn Stewart: Well, I’m. I’m talking with Ramona today, and one of the great things about chess is that you can promote smaller pieces to become queens. And the more queens you have on your board, the more powerful you are. So I would encourage folks out there, get as many queens on your board, open up your diversity hiring. I think it’s a big part of it. So that’s a little plug I’m putting in because I think diversity is a really important part of building teams, at least in my world.

0:19:04 Ramona Shaw: Shawn, thank you so much for joining the conversation and talking about chess as an analogy and as a way to think about how to operate at that higher level. One of the things that I definitely recognize speaking with leaders across the ranks is at every new level, there are new skills that become more important than they were before and then their skills that we’ve developed and honed, but they start to become less important and only really marginally contribute to that next level performance.

0:19:34 Ramona Shaw: And when it comes to working well with changes, adapting, communicating effectively across the organization, thinking strategically, and playing those pieces well to set yourself up for the endgame, those are things that will become increasingly important as you grow in your leadership role. So thank you for the conversation, John. I appreciate you being on. I hope this wasn’t the last time. So we’ll have Shawn back on the podcast in the interim.

0:19:59 Ramona Shaw: Have a great week, and we will be back with another episode of The Manager Track podcast next week. Bye for now. If you enjoyed this episode, then check out two other awesome resources to help you become a leader people love to work with. This includes my best selling book, the confident and competent new manager, which you can find on Amazon or@ramonashaw.com book and a free training on how to successfully lead as a new manager. You can check it out@ramonashaw.com masterclass these resources and a couple more you’ll find in the show notes down below.