Systems and loops - Sean Gabriel

00:00

I think it also is quite an individual journey to figure out what those kind of important leverage points are for you in your career, but to match my expectations of my current role versus a new potential role it's like, "Yeah, I could actually try to model out how that's going to work in practice." I think it is incredibly complex. The type of business that you're working in, the existing setup of the teams, structure, processes, there's so many things that go into understanding the complete system of work in a company.

00:43

How have systems helped you find your best work?

00:51

Systems... I suppose they were, I guess, a tool and a means to see a bigger picture than what was sort of immediately in front of me. You might've heard the saying that all models are wrong but some are helpful. I think if you practice a little bit fortunately just trying to draw out all the things that are around you in our environment like systems thinking, I interpret that as just a, "Hey, can I map out the world around me and try to take a guess at how things influence one another?" Almost the big benefit for me was just to try and put it down on paper and visualize, "Hey, what is the problem that I'm facing with this particular stakeholder, having a difficult conversation? Where are they coming from? What are their incentives?" It kind of traces through different places in the team or the organization you're working in.

01:52

Yeah, I think once you've kind of gone through that exercise it might show you something that you kind of sensed and knew, but take it out of your head it on put on a page can be quite illuminating. I think just practicing a little bit of systems thinking and trying to model these things is healthy, in a way, to see more clearly, even if it's wrong because just the process of trying to map it out you're like, "Oh, well, why?" That's really what it is. I think it's kind of encouraging you to ask that question like, "What is the cause of these things?" And just trying to get a deeper understanding. I feel like so often, especially when you're dealing with interpersonal things, that the emotional side takes over and it can be quite a knee-jerk reaction to how you face these challenges in your work, or you can look at the bigger picture and then actually be like, "Oh, there's some other factors at play that I might not have considered because I was just focusing on the immediate conflict."

02:50

When is an example of that? When's a time where you've used a systems way of thinking to move work or progress at Microsoft, or when's an example of that?

03:09

I think it's probably something I discovered a bit later, maybe not during my Microsoft time, although maybe the elements of it were there in the beginning. I think it's something I have studied a bit more recently since I moved over into consulting, the work I've been doing at Red Badger. The first example that comes to mind is actually a little something that Em and I did together. I know you spoke to her not too long ago. We were working together I guess on a larger program of work and there were kind of multiple teams involved, a lot of different folks, stakeholders' concerns. The shape of our team was quite challenging to figure out. If we're having a hard time getting some piece of work done, what is actually getting in the way of that? Working together, I think we just kind of applied almost a straight version of systems thinking.

04:09

We were really looking at, "Here's all the different players involved. Let's try and understand the relationships between all of them." Even starting there is quite complicated just to be like, "Are these people working together and can we see that there are signs of high trust between them, or have there been conflicts that we've detected? Can we start to understand where those things have come from?" So sort of just to see, "Here's a bunch of different players. Here's where the challenges are in those relationships. Is there bidirectional trust? Is it kind of one-way? When trust might've been broken, where did that come from?" Then we can kind of then connect the dots to something else. It's like, "Oh, there's this particular process and how things were managed. A report comes out of the blue and it doesn't have context and so it could be taken as a bit of an escalation." It's things like that where we just kind of started really from the like, "What is the system we're working with here? It's a system of people, it's a system of teams and relationships and everybody trying to collaborate on things. Okay, what are the things?" Then you just try to connect the dots of how we perceive all these things to be working, and then those are really the places for us to then go do deeper inquiry because the question comes up like, "I don't actually know how this person is working with this person. Oh, cool, maybe we should go found out."

05:30

Mm-hmm. It strikes me that you might be able to find weak spots in that system, too, that gives you the chance to in some way apply yourself more diligently. Maybe one way of thinking about it is the best work that we... The work that we pursue is often a meeting between the outside world and our own passions, and if you were able to use systems thinking you might be able to identify those needs of the world faster in some way.

06:06

Yeah. Yeah. I think that's spot on. You kind of go down the systems thinking route a little bit further just beyond kind of mapping the relationships between things and how one behavior causes another, there's some patterns that come up over and over again and these are things that are quite interesting to study and improve how a system works. One is around that idea of feedback loops where it's like that many things start to influence one another. They can do so in a constructive way or a destructive way, and so those are things where you can look to and be like, "Oh, why do we feel like we're caught in a spiral?" You might actually be able to trace out that spiral and break what could be a vicious cycle. I think the other one that you just touched on there was that idea of finding weak spots and effectively enhancing strengths would be the counterpoint to that. If you're looking at a system, you can also look for leverage points within that system where tweaking some small variable has an outsized impact on the performance of the overall system. Again, these are all kind of models so they're all going to be wrong to some degree, but they're a great place to start if you're looking for where you can focus on doing your best work.

07:18

Mm-hmm. What feedback loops have been detrimental to you in your own working journey?

07:27

Detrimental feedback loops. I would say I've probably struggled a bit more with this in a small closed system of just myself where there's a bit of a feedback loop that kind of goes on in my brain sometimes about some belief and things that I feel and how I perceive what's going on around me. Then that kind of reinforces my perception of what's happening. I'm like, "Oh, God. I'm not on top of my work or I'm not communicating effectively." But it's kind of interesting that I have a vocabulary for that now that I didn't when it was happening to me before. I mean, just to make it a little concrete, this was a bit earlier in my journey. I just had a difficult relationship with one of my first managers back when I joined Microsoft, and he was a nice guy, I don't think he had anything against me, and we were working well professionally but it came time to performance review season and I was hit with a pretty nasty surprise that he thought that I wasn't doing my best work, I was doing very poorly. In those days Microsoft had a less than cheery way of stack ranking people and so it's very much a revelation that you're like, 

09:02

“Ooh. You are looking like you're in the bottom 10% of our workforce." And it's like it's just a kind of crushing weight that comes with trying to understand and accept that feedback. And you're like, "Really? I'm like one of the worst people around here?" And so that calls me to question a lot of things that were happening, or that I was doing. And then I started to see potentially signals of it. Right? I hadn't learned the skill of managing up, for example. So like was I making visible the type of places where I was having an impact? Or even just showcasing to him places where I was struggling. I was holding a lot of that in. And so there wasn't even a feedback loop there. So there was very limited signal that he could work with. And so I think that led to him assessing that I was probably appearing to be disengaged, didn't have a ton of output.

09:56

So I can see that a lot more clearly now, but it was quite shocking to me at the time. I was like, "Wait, but I've got all these other things." But I wasn't communicating that. So I wasn't connecting the feedback loop, if that makes sense.

10:07

Mm-hmm. Yeah. It sounds like it was all internal. And I guess if your feedback loop is just a feedback loop of one, you do have way less inputs to help you grow.

10:20

Right. Right. Exactly. And then there's that bit too, where it's like if I am struggling, I should be okay with reaching out for help. It's still the hardest thing, even today, just to be willing to open up, I guess, another conduit for feedback. Because the more of those that you kind of have going in your system of how you're managing your work, I think the broader perspective you can have. And potentially the better for you. But if you're working with very limited inputs, it can be hard to see clearly the impact that you're having.

10:53

I really want to try and take this concept of systems thinking, and see if there are any areas of the, I guess, practical process of finding work that you feel it's applicable for. Have there been moments in your past when you've been practically searching for work, and adopting systems thinking has helped you? And are there any circumstances where you feel like in the future you may want to adopt systems thinking to help you?

11:26

Hmm. So you're thinking like during the actual search for a particular role?

11:32

It could be like deciding to quit.

11:35

Yeah.

11:35

It could be deciding not to quit, staying at a company. It's those change moments in your working journey.

11:46

Yeah. Yeah. I think that's actually probably a great area for people to explore for themselves, if you frame it in that context of like, "I need to make a major decision." To change or not to change is one example. It could even be a change internally, within your particular organization that you're working in. It would be good to know what you're hopping into if you can model the system you're looking for. Right? That sort of like-

12:17

Say I'm working on the engineering team, I'm thinking about transitioning over to product management as an example. It's like, okay, what is the kind of dynamic of how work is managed within the tech side of the business? Were I to come to this other side of the business, do I even understand how that system works? And how does that then connect back to the system that I know? I think it could lead to a more informed view about whether that's the kind of role that you want to take on. Because you can think about how does that ultimately get to whatever it is that kind of sparks your passion and your joy and your work. It's something that I, I suppose, without the language of systems thinking, I'd come across in my own career direction, where I've been thinking about straight out of college.

13:10

I was studying electrical engineering and computer science. I thought I was going to be programming for a living. Or I think I had some fantasies about doing like video games all day long. And just I loved growing up with them. I was like, "Hey, I could get into this industry, make these things for a living." But then I started with program management, and kind of had a nice story from the recruiter." They were like, "Oh, if you don't like it, you can go back to engineering. Just give it a try. We like people that have people skills," and kind of it stuck with me for a while. But where I am now, I suppose, in my career, becoming more of a general manager. And there's something that I kind of miss in a way about just being close to the creation of the thing. It's like that was part of my upbringing, if you like, to learn how to create these interesting services and experiences digitally out of code.

14:12

And it's like the further I progress in my career, the further away I get from that thing that originally drove me to work in the first place. And so there's something about like where I am kind of at my current level, I still have a close enough connection to a multidisciplinary team, where members of that team are the ones building the thing. And so kind of my level of abstraction in the overall system, I feel like I'm close enough to where the action is. Whereas where I to look at roles that go kind of further in a company's hierarchy, they kind of, to me, just seem another step removed from the actual creation. And I just kind of love being a part of the intricacies and the decisions that come into building something and creating something. So it's thinking about, "Am I happy at the current place that I'm at?" And then back to the idea of systems thinking, what in the system is kind of the most interesting place for me to plant my flag and be close to?

15:12

And I think I've found kind of that right balance right now, where I don't want to get too far into a management space and be so far removed from the actual making of the thing that all I'm thinking about is just business and numbers and the market. And there's elements of that in my role now. It's fine. But it's not dominating and drawing me away from the thing that I find quite interesting. I don't know if that makes sense, but it's really just about striking the right balance of like, hey, the overall system, the overall picture of how these things are built. And it's just finding the right place for myself, the right orbit to be at, within that system.

15:51

As you described it, I couldn't help feeling the benefit of systems thinking and how it takes you outside of your, I guess, immediate circumstances, and allows you to recognize the interdependencies between the things that are happening around you. And I don't know why, but when we search for work we often do completely and utterly focus on ourselves. And it is us who we're making the decision for, so I guess that's natural. But it's sometimes hard to remember that you are making this decision in a web of interdependency, that if you took a moment to understand more deeply, you are bound to then make a better decision because you have the information and the context available to you.

16:45

Yeah. Yeah, yeah, yeah. I think it's a pretty interesting realization that I also didn't get earlier in my career, that it's not just ... roles are not really interchangeable. Like a job title at one company versus another, it could be completely different. And a way to kind of visualize the difference is to think about how those organizations are structured and try to map them out. Just how are all those different teams composed? And then how do they actually go and make things, services, things for customers. Who are their customers? Just trying to map that whole thing out you see very quickly that context means everything for how these companies build their teams.

17:26

And then you go beyond that and you're like, "Okay, cool. So I found a company that's working in an interesting space, and I like the way that they're structured. I kind of buy into the system. Well, that system is quite abstract until you think about the actual people that are filling those roles." Right? And then again, how the interpersonal dynamics work with one team versus another, it kind of changes the behavior of that system entirely and your lived experience of it.

17:52

Mm-hmm. Well, you said that when you are reflecting on your system there's kind of an earth to your system,

18:02

which is that moment of creativity and the creation process, I guess, that you go through. How do you know when you're getting too far away, when your system's kind of getting too big and when you're being abstracted too far away from your original core there?

18:21

I guess the other question I'd have is like, well, but what if that core changes? Like what if actually halfway through you realize, "Hey, I don't actually want to be that close to the creation process anymore. It feels less important to me."

18:38

Yeah. Yeah. I think that's okay. Like we're human. We change, our preferences change. So if you are a moving target, well like, A- systems are not static, either. Systems change so everything is kind of a slice in time when you're kind of trying to model out how these things work. But I think figuring out my comfort level, if you like, how I manage my distance from the thing that I feel is still core to what drives meaning in my work, I think there's something around just figuring out how complex the beast is, again, by trying to map it out. If I feel like there's too many layers in the way, that could be the signal to me, that like, "Oh, I'm no longer having a real direct impact on the creation process and the thing that's being done."

19:33

But then, on the other hand, I find other things that are quite interesting and meaningful to me in my career now that I didn't have access to before. Like, for instance, becoming a manager and having the ability to coach and mentor others and kind of help them find their own path, something I really quite like doing and most people don't start their careers as managers. It's something that you kind of grow into over time and I wouldn't have known that I liked it until I had the opportunity, too. Now that I do, it's actually something that I think I also enjoy being a manager and having a team that I can help guide and nurture, in addition to being close to the work. So how I've kind of put those two together is, "Okay. I'd really love to be in a position where I have the ability to look after and manage folks who themselves are close to the creation process." That, to me, is how I manage to balance the sweet spot right now.

20:26

Yeah. It's like a node in your system has kind of spawned itself as you've gone through your journey and it's, in some way, now waiting the rest of the system, and it's being built around two pillars, in a way.

20:47

Yeah. Yeah. Yeah, yeah, yeah. It's like the second pillar only emerged, in the last five years, I'd say. Prior to that, it was just about what's the coolest thing I could work on and build with the coolest people around me?

21:00

But now, it's like, "Actually, I want to have the coolest team and the coolest set of people that can work on these things that they themselves find really cool." So there's something about like we touched on leverage a bit earlier and it's like that idea that now I think I'm in a higher leverage position to kind of spread the cool, which I think is quite interesting. It's not something that I would've predicted the first time I tried to map out how my career journey was going to go.

21:32

It must be harder having two parts of your motivation of when it comes to figuring out where you want to work next, because you'd... It's always easier to think about moving from one position to the next, if you just think about it as one specific entity, rather than the system, because it's a lot easier to just move from one system to the other.

21:54

But if you just got to try and figure out how to like, I guess... I mean, that's pretty complex when you're deciding where you want to work next. It's like, "Okay, I want to be close enough to the creation process. I want to have the freedom to manage in the way that I feel is right. I want there to be kind of an appropriate amount of layers between me and all of those things to mean that the work that I do is valuable." It's so much harder. Have you figured out how to make that any easier?

22:29

Oh, if I had the secret, I'd love to share with the world, but no. I think it's also, it's quite an individual journey to figure out what those kind of important leverage points are for you in your career. But to match my expectations of my current role versus a new potential role, it's like yeah, actually trying to model out how that's going to work in practice I think it is incredibly complex. Like the type of business that you're working in, the existing setup of the teams, structure, processes.

23:08

There's so many things that go into understanding the complete system of work in a company, which is when you think about your feedback loops to actually build that system like, what do we get? We get a few hour-long chats in an interview context where usually from the candidate side, you've only got the last five or 10 minutes to ask your own questions. Like it's very, very low bandwidth signal for trying to map out your idea of what the system is going to be like in a new organization.

23:44

So I think it is challenging and it's risky and that's probably a big part of why you get to these inflection points in your career and you're like, "Well, I want to make that jump." You could almost think yourself out of it, in a way, if you're like trying to get a complete perfect view of the world and then it's actually like, that's probably not possible, especially from the outside.

24:07

So what are the kind of critical paths, like the most sticky parts within that system that I need to understand? Those would be the areas that I would want to question everybody that I'm meeting from the other side, the actors in that system be like, how does this thing work? Like, how do you actually get feedback from your customers? How are employees talking about the management structure and are they getting good feedback on their own career performance and how they want to grow? It's like, what are the things that are important to them?

24:40

You have time to ask a few targeted questions, I would be looking for the ones that would really influence my view of how their system works so I can construct that mental model of if I were in that system, is that how I'd want to work, too? If the answer's no, then it's probably not the right place for me.

24:59

Before we came on, we're briefly talking about humility and vulnerability and how that can help us find our best work. As we've spoken about systems, it almost seems like a similar way of saying the same thing, which is, if you are thinking about a system you are inherently then not thinking about yourself. You're putting yourself second and you're embracing everything else around you in the same way that if you're being vulnerable, or if you're showing humility, you're putting yourself second to recognize, I guess, the circumstances around you. Is it fair to make that comparison, do you think, and what benefit has being vulnerable and having humility had for you?

26:03

That's a good one. I'd say it's fair to a degree on the basis that we are ourselves, I suppose, inherently biased and have our blind spots. So we're, as individuals, only ever going to have our imperfect view of how the system works.

26:28

The truth is probably it's not even anything you or I could see together and it's something that like collectively everyone needs to weigh in on. Even then, it's just a model and all models are imperfect.

26:39

But I think you're right. The exercise itself does allow for some mental discipline to like extract yourself out of the equation and be like, "Okay, it's not just my impact, but all those things around me and how they interact with each other." I think there is a kind of built-in humility to that because the underlying assumption is not that all

27:03

interactions are brokered through me. There's so many other things in the complex system that have nothing to do with me. And, yes, I'm not the center of the universe in this equation. I'm certainly the hero of my own story, the hero of my own career, and all that. But I'm one piece of a much larger entity, an organism, if you like, which is this team or this place where I want to go work.

27:26

So I think to the second half of your question around where has that kind of humility served me well in my career, I think I've tried to learn that skill about when you initially get mad at something to instead try to get curious because it's not to say that we're not going to have our moments of frustration or have the emotion come by, but we can challenge ourselves to step out of that moment and think, "That really pissed me off. Why am I about that?" And then that question prompts you to think about the bigger picture.

28:12

You kind of step away from the emotion that you're feeling, kind of looking into yourself in a way, and you're like, "Huh, I've felt a certain way, why do I feel that way?" And then you can kind of wind back to, I think a level of systems thinking to say, "Oh, it's because of this thing that happened. That really frustrated me." That's something that happens quite often because we have a broken process around this. You can start to then channel that kind of initial reaction into some sort of positive change, which I think is a much more constructive way of dealing with the initial frustration than just taking it to the pub and having a moment with your coworkers and saying like, "This is crap."

28:55

Yeah, there's a time and a space for that, but if you want to prevent these things from happening frequently, if you want to continuously improve the environment around you, then it does help to see the environment clearly using a systems map as a way to understand where those things are coming from.

29:19

When does systems thinking start to border on spiritual because in some ways, like you said, it's an organism, you're seeing this way more broadly than just me as an individual.

29:42

Yeah. We could go down that rabbit hole, like what is this experience that we're all living in, right? The universe is just one enormous system. And we think we know some bits of it that are governed by physics and chemistry and the scientific branches and whatnot. There's some things we can't explain. What is the thing that drives the things that we can't explain? Religion has an answer. Science is looking for an answer. There are many ways to think about... Well, if we want to get a complete view of everything, that's probably not possible without making some giant assumptions about how things work that are beyond our way of seeing things.

30:28

So I think, yeah, there's a spirituality in that where if you can't come up with a clear view, then you're going to have to make a leap of faith. I suppose that's kind of at the universal, the massive, massive level of everything that we possibly know. If you bring it back down to kind of the work that we're doing, there's certainly going to be parts of the system you can't see. So you'll have to make your best assumption about how things are working there too. There's a kind of leap in faith in that. I think in the context of what we were discussing earlier around looking for new opportunities and trying to find a new role, you're going to make a leap of faith about some parts of that system that you don't fully understand.

31:09

You'll probably look for signals elsewhere, like in how that company or people in it, what they'll say about it, or how it's positioned in the public space. Going through and thinking about how the different processes that you know in your own organization might work in that organization. You're not going to have that full detailed list before you take the role, so you're going to have to take the guess based on everything else you can see. So yeah, do you need to keep the faith? I think you do. You have to be brave and hope and pray to an extent that when you're making that big move, you're like, "Well, I hope most of these things are going to work out the way I want compared to the ones that don't." And yeah, trusting that you're making the right decision.

31:58

Thanks for sharing your insights, Sean. And I really hadn't thought about finding work... I hadn't realized it was so dependent on the systems around us and that's really an insight for me because it is so tempting to see it as an individual journey that we need to kind of go into ourselves on. And whilst that's important to a certain degree, it's also really important to recognize where you fit in the system that you're in.

32:43

Yeah. I think so. I think it's also something that seems to be the trend of the modern age too. If you think about the way work used to be back in the industrial era, for example, the systems were a lot simpler in one sense where it was actually the type of input that you put into the system was quite commoditized and replaceable. Now, so much work is kind of moved up into the knowledge space. So much of it is dependent on people interacting with each other. So these things are just infinitely more complex than they used to be.

33:20

So I think you're really onto it there that even if you were a team of one in a company of one, you yourself are participating in a market and a system which is so vastly complicated that it's really hard to separate the environment around you from the individual experience that you're having. So I think if you're just focusing on the individual, you probably have a slightly incomplete view of the world, regardless of how big the team is in your immediate space. Everything is interconnected now, right?

34:00

Yeah. I'm going to try and balance both a bit better than I was before. And thanks so much for sharing it, Sean. Loves it.

34:12

Yeah. My pleasure.

34:13

Thanks, man.

34:14

All right.

34:14

Take it easy.