August 27, 2026 · 31 min

Welcome to the Jungle: Navigating the Cross-Functional Matrix Org

Cale flies solo in this episode and walks through a high-level version of what he calls his leadership field guide. The focus is practical leadership: how to recover stalled initiatives, develop people, handle dependencies, protect resources, adapt to change, and stay effective in the AI era. He closes by emphasizing a leadership style built on listening, judgment, and reading the room rather than forcing control.

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Cale: Hey folks, today it's going to be me. Mindy is otherwise unavailable to record today. she will be back and we've got a couple of really cool surprises that I couldn't have even thought about just a day or two ago. So I won't spoil it by saying anything else, but it's pretty good thing, that we got for our little show in the next few weeks. So anyway, this week I'm going to be sharing a bit more inside my mind when it comes to leadership thoughts and experience and what I'm doing to get some of those things out into the marketplace, where folks will find what I have to say worth paying a few dollars to know more about. So today I'm going to talk through kind of a very simple high-level version of what I call the leadership field guide. This is just an encapsulation of the things that I've taken away over the years, both from experience and from good leadership and even to this day I'm still absorbing new leadership lessons from people I work with, whether they are actually my leaders or they're just leaders in their own right or they're even peers of mine, everyone has the potential to provide good leadership if that's something that they if they something they value. Excuse me. So really what I'll do is cover each of these as the challenge that a leader faces. and then I'll give a a high-level overview or high-level takeaway of what you do as that leader to get around that challenge or to overcome that challenge that you face, That's that's a good example. All right. So now one that we run into as leaders. especially in this tech space or really any space where you've got a program or you've got something that you're responsible for it that is stalled, right, for whatever reason. So you've got leaders above you, demoralized teams below you, and there's no way for you to necessarily put your handle on why things aren't moving. And so really the takeaway that I give you here is the natural reaction is for us to run to a project plan. And say, we clearly must have a bad project plan, or we must have a lack of governance, or we must have this, or we must have that. That may very well be. but the very first thing that you need to do, and this comes from experience, the very first thing you need to do as a leader when you find yourself in this situation is have the have the guts and the courage to look at the situation calmly and coldly. and without emotion and get the clarity you need to see where the situation has gone off the rails. Don't run back to the comfort of process immediately. Right? even if you've grown up as a program manager or project manager and you've come up through the ranks, if you will, and now you're leading groups of project managers or or program managers, the answer is not even most of the time. a better project plan. It's going to be something else. It's going to be decisions that need to be made by somebody in a higher level of authority. It's going to need to be someone to look and see why we're off the strategy. You know, things of that nature. But you're not going to be able to make good decisions and lead your way, lead your team to recovery until you've taken the time and you've gotten that clarity and you have excuse me, you have what an old boss of mine called managerial courage to ask some of the tough questions. The last thing I'll say about this is you may find that one of the reasons that the initiative that you're managing is off the rails is because there's someone in a position of authority above you, or you know, in a cross-functional situation that's just flat not getting it done, or they're making the wrong decision, or they are working in some sort of counter way to what was agreed to cross functionally. And if you find yourself with that kind of situation and you can back that up. Again, that's a whole different path to recovery than it would be running back to the safety of a project plan. Okay. There's not a pithy answer to that question. those stalls happen all the time and they are complex and the answers usually match that level of complexity. This one this one is a bit more tangible, and that is how do I develop my people while I'm still focusing on myself and that team delivering results? How do we get our work done at the same time we as as a group of people and and you as a leader help grow your team's capability? And we find ourselves in situations all the time where if we are lacking time, we're lacking resources, we will sacrifice one for the other, and you well know as well as I do that that sacrifice usually comes at the experience of developing your people. Now the really the the the the quickest answer to this particular one is give your people real ownership of the things that they are responsible for. Give them real ownership of developing themselves. Okay? I I'm not saying that you make them completely responsible in every sense for their development. But at the same time, you as a leader, your job is not to necessarily literally grow your people from one stage to the other. Your job as a leader is to make it where they can take that initiative themselves and be successful if they have the drive. You move barriers out of the way. You give them opportunities to say yes to new to new things, to to new opportunities to learn. new stretch goals, things of that nature. give them those guardrails that lets them know let them know what success looks like. Right. don't let them go out there's un unprotected and and unguided and try to learn their way you know, by themselves and develop themselves. Give them guardrails, give them what success looks like. But again, at the same time you need to empower them and let them know every time you have a one on one or you have a a an annual review or you know, media review, that kind of thing. Say, hey, where are we with your development plan? what is it that I can do to help you? What it what barrier can I remove for you for you to continue to develop yourself, right? it's not your job to develop them, but it is your job to enable them to develop themselves. Okay. And that means they are the ones who are going to be making that conversation with themselves about the trade-off between getting their work done and getting themselves the next level. Okay. Again, as you know, that the you couldn't be responsible for that even if you wanted to be. All right. Managing dependencies and risks to cross-function, so cross-functional, cross-functional management, right? large programs, as most people, if you're if you're still here with me, you and you care about these sort of things, you know that these large programs depend on people and teams that you don't control, you know, those matrix organizations and versions of that. Critical path sits outside your level of authority, sits outside your team's authority, and you are responsible for getting your piece done, but you've also you're also waiting for somebody else to hand you that thing that you need to take off with yours. Right. Happens all the time in these large enterprise matrix organizations where you can't put your hand on the person's head metaphorically and drive them where you need them to be, right? So the org chart. Is the situation where your your natural inclination again is to go but to that org chart and say, I'm gonna walk the org chart and I'm gonna find this person here, and I'm gonna see where their manager is and I'm going to, you know, escalate. Okay. That is a tried and true method that does not always work. Okay. and I'm simply going to say the interesting thing about the org chart is that is not where the actual power and the levels of interest that the org chart won't tell you any of that. Not really. it will tell you who they're responsible for, it will tell you who in an HR sense. It will tell you who they report to in an HR sense, but it tells you nothing about why they do what they do. The politics, the decisions underneath, the shadow this, the, you know, the Decisions that. So I wouldn't lean on the org chart too much. Situations like this, you are better off finding yourself mapping those dependencies way ahead of time, understanding where the risks are going to be before the risk could land on you in a way that you're now stuck waiting for it to be resolved. So this is that idea of being proactive, right? And so if you find yourself with an dependency that has not been managed or understood. These are guaranteed to be the ones that become what slow you down and and stop your program from from moving forward. So the the again, the answer there, the takeaway is do that work ahead of time, risk management, right? Know what's going to bite you and and get ahead of it. it's easier said than done, I know. protecting resources while adapting to change. And what I mean by this one, this is a this is a challenge that we've all facing, we're all facing, you know, every day. the business shifts its priorities mid program. Happens all the time. Budget gets cut. You're two-thirds of the way through delivering the big thing and and budgets get cut. The timelines get cut and by a third. Whatever the case is, scope expands, and you don't get more people. And somehow you're expected to absorb some or all of those changes that happen sometimes at once or seems like it. your takeaway, your responsibility as a leader, and this one, this one is This one just takes work and takes horse trading and takes knowing where to stand on your ground and where to flex. And so what I mean by that is the discipline is knowing what you literally have to say, no, we cannot do that. Or yes and is the is the better way to say it. You say yes and if we do that, if we cut that scope, here's what happens. And you speak to downstream impact. If you cut the budget, you know, okay, fine. We are probably going to need to have to have a conversation about either the timeline or the scope. And if you get that pressure and they say you you gotta do both, you're like, let's have a realistic conversation about how that would work and what gives in in that situation. We all know that if they intend to have that iron triangle where nothing is flexible, the thing that's going to give every time is quality, right? You're absolutely going to put crap on the more on the market at that point. That's really the only that's the only out. so knowing when you have to have that painful conversation about what must be protected versus knowing when you can say, you know what, okay, all right, we can pivot. It's gonna be a little painful, but we can recover from this and we can maintain that momentum downstream. Know when to give a little, know when you have to stand your ground. and this one comes from you know that that business acumen. This one comes from knowing the organization. This one comes from knowing, you know, trends and and and that kind of thing in the group that you're a part of. to know what you are. really able to push on, right, or resist with some degree of certainty on the outcome. If you find yourself in a situation where you know that resistance is going to wind up being a political nightmare, give it some thought, right? You have to ask yourself, is that worth it? we run into this situation all the time as as leaders, whether it's thought leaders, leaders that who know the domain, you know, on top of being a people leader as well. You're like, just let me do it. You know, it's just gonna be easier for me to build that deck than it is for me to explain to you how I need that QBR information cataloged in the deck. Fine. Yeah, you may have a situation where on a a Thursday night when you're at it's nine o'clock at night and you're dashing to get that QBR done, deck done so you can get it through the cascade of pre reviews by let's say seven o'clock on Friday morning. Okay, fine. but you unless you want to be doing that every quarter from now on, every Thursday night, you're going to have to train and build up your people to help you get what you need in order to be successful for yourself. And that is going to require taking the time, g dealing with the frustration of iteration and giving them a chance to build their knowledge and become what you are now, right? You didn't come from the womb with knowledge about what the executives or leadership need in that QBR in this particular example. Every hour that you spend executing is an hour that you are not building your team and multiplying your impact by the number of people on your team. That's a trap that you're going to quickly find yourself in that is going to potentially wind up damaging your career or damaging at least your your move and your ability to succeed where you are. So again, leadership really, among other things, isn't is is not much more than multiplying the impact you have through building up your people and empowering them to get more work done. Right? When you get to that place in leadership, it's not about proving that you can do the work yourself anymore. In fact, it's literally the opposite. You have to stop doing all that work and make sure that you've built the men and women who can do that work. One of the things that you've got to do as a leader is make sure that you are standing out. in the ways that are unique and powerful to you based on the combination of things that you bring to the table as a leader, things only you can bring, whether it's the experience that you've got that the got you to where you are in previous jobs, the training, your personality, what drives you, your your frankly, your quirks, your interests, you know, all those things Coalesce and become that that catalyst for the kind of leader that you are. not let those differentiators become standed off. Don't let don't let them hit that nail that sticks up quote unquote with the hammer, right? There are things that you can provide and bring to the table because of the way you approach things and because of who you are as a leader that you really do need to protect. If they are that thing that helps you be the leader that got you to where you are, right? Don't forget the success, the pattern that got you there. several years ago prior to the pandemic. I was still sitting in the office and I had my hair down, a leader walked past my cube a few times that day doing his own things. And he topped and he said, Hey, how's it going there, Tom Petty? you know, when this person says, Hey, how you doing there, Tom Petty? that will definitely get your attention. And I kind of nervously laughed a little bit and I go, I'm doing okay, you know, so and so. And I just kind of sat and thought about that. And he came back from then on pretty much with that whole Tom Petty thing. And I went back and forth for a long time on trying to get a read on was he just being, you know, funny, trying to, you know, bond, or was he trying to send some sort of signal that I wasn't following the the pattern he expected. about two weeks or so later, after about ten more of those Tom Petty drive by, I said, I don't care. I am not going to cut my hair. I'm not going to, you know, do that that thing. I'm not doing that dance. It doesn't matter. if he's gigging me, fine. If he thinks it's funny or he's just trying to be cool, that's fine too. I just so happen to like Tom Petty, so it's like, hey, if you're gonna be, compared to anybody, you might as well be compared to one of your idols, right? So all that to say, you've got the same sort of Differentiator in your case that makes you you, double down on that, bring that to the table and leverage that as part of your toolkit. Right? Okay, we're getting toward the end here, at least of the the content that I had prepared for tonight. this one is especially relevant and is more and more relevant every single day for leaders and frankly for folks who are just in that sort of, you know. I see that I see the realm, right? the individual contributor. What is it that we are going to do to stay relevant and lead in the AI era, whether we're leading with our minds or we're leading as as people leaders or some combination of the two, whatever it happens to be. AI itself is absorbing execution work, right? Grunt work, as we might say prep work, grunt work, all that stuff, the all that, you know, upfront all that upfront planning and data gathering, you know, in like that QBR example I used earlier. that work, thank God, is being absorbed by the quote, the machine. I've I am happy about that. Right? That gives us a chance to do more strategy work and do more delivery and then spend less time building all that information and instead spend time validating it and making sure that the information we're about to present to the executives is accurate and can be defended and is painting the correct data-driven picture, you know, for example. Right? So two teams we are increasingly relying on AI and including AI as tools or additional people, if you will, every day with our team. And There are leaders out there who have not learned how to measure their productivity as leaders and measure the productivity of the teams that they are responsible for. they have not figured out how to bake in the impact of AI, both positive and negative, at least in the short term, to their productivity, right? The positives are easy to define, right? If you spend ten hours, fewer a week doing all that grunt work. those ten hours are now quote spent doing something else. Well that's fine, but what is the return on those ten hours that you're now spending doing this instead of this grunt work? How do you measure that work and what is it in service of? And can you can you document that, improve that, and bring that forward, right? That's just one kind of one example. or does this mean that your people now have more time to go take another break? You know, this this sort of thing. Productivity is not guaranteed to come just by relief of of something that is otherwise a slug, right? and if that leader is not keeping track of their value and how much their teams, their teams themselves are generating from this new situation, they are now a bottleneck either to their team's ability to compete in that market, if you will, inside that matrix organization. they are unable or or l less likely to be able to talk about the value proposition of both their work and the work of their teams when they're talking to executives about delivering against the aga against the strategy for the year, for example. And if you find yourself in that situation too long, you know the the rest of that story, which is you probably won't be working in that organization next year. you know, these days with you know layoffs and and constrained budgets and things of that nature, it's even more imperative that you are constantly seen being aware of and having the acumen and the understanding of delivering against against those those needs. I I won't say much more than that. last one, reading the room. And by the way, I'm going to take a moment here to distinguish and make sure if you're hearing the word reading the room, and you don't confuse that with leading the room or owning the room, like you'll often hear or you will hear from some leaders. And I'll draw a I'll draw a correlation to that in just a second. I do mean reading the room, right? So you walk into a situation where you're in a say at a Stereco meeting or you're in a QBR or you're just in a weekly ops review or you know biweekly ops review, whatever it happens to be, you're in a a meeting with other team members, other members of other departments, what have you, and whoever is out there talking about their their program, their status, they're saying, hey, the dashboard is green, you know, the overall department is is is hitting hitting our numbers. We're delivering against our our commits, you know, so forth and so on. But You're looking at the people. You see the chart. The chart says green, but you're looking at the people. The people are not smiling. The people are not looking at the information. They are not nodding their heads. You know, they are not energized and energetic and invested in what's being communicated by, let's say, the program manager or the director or whatever. In fact, if you listen into that person, they are just kind of you know, well, yeah, yeah, we did yeah, we're okay. We're doing fine. Well That particular vibe that you're going to get from that room should be telling you a lot. Those are signals. And those are telling you that you need to go back and do some digging on your own and find out. even if it's not your team or it's not your department or whatever, you are going to want to know what's going on underneath. You're going to want to be pressure testing why you're seeing this disconnect between what the vibe in the room and what the dashboard is saying, right? and you can flip the script around and you can have a situation of course very rarely when you see red and people are excited. the point here is is which watch rather and just make sure that you're seeing a connected through line. Okay. pay attention to the room, pay attention to the signals being given to you. Don't just focus on the green and let that be the answer and then say, we're green, cool. I don't have to pay attention anymore. Yes you do. You absolutely do. if you don't. It's just a matter of time. listen for the silences. If there is someone who is not stepping up to provide additional information or support for a contention or support for a statement made during the review of that particular program or initiative, those silences are telling a story. There's either in people are uninvested, people are afraid to say anything, either in support of or against that particular contention. or know that that's not true, and they cannot disagree with their boss in public, let's say. let's say it's the director up there presenting this this information that turns out to not be factually true. may be working off old information. They may have been misinformed. The information may have not gotten to them before they brought it in the room. Who knows? but there is a disconnect, and again, that room needs to be read and that story needs to be put together by you to get the full picture. Okay. Simple as that. Now, I mentioned toward the beginning of this one that I wanted to distinguish this between reading the room and what some folks will call leading the room or owning the room. And the reason that is relevant here is because if you have a leader who says, you know, hey, as a program manager, as a director, you've got to own that room. You've got to walk in and you've got to do this and you've got to drive That is a certain management style that I don't happen to agree with or adhere to or follow most of the time, unless it's required for reasons of say theater or to drive home a point or to get people on the ball or whatever the case may be. But that is not my go to style and that's not something I'm comfortable using. It's just not my thing. I'm not gonna walk in that room and just act like I know all Not my style. and the reason that happens is because of this bit right there about silence. If you come in the room and you're leading the room, owning the room, that sort of East Coast, you know, let's just drive. The silences don't manifest. If you cannot let the room sit and bake the way the room is supposed to, to let those silences tell that story, you are going to miss a data point. You're going to miss the fact that the dashboard says it's green, but the program is really maybe yellow or perhaps even red. And you're not going to get that signal because you're too busy driving and owning and leading, and you're not listening. I come from the school of leadership where yes, leadership is about inspiring, about empowering, listening to your people, to your bosses, to your stakeholders, to yourself, to the data. And if you are out there just driving this thing like you're selling a cell phone, So I want to kind of just kind of wrap this up with some little things that I was, you know, rec you know, recap some the things I was talk talking about. recovery, you know, as you're as you're dealing with a situation where you've got a program that you've inherited or or program that you've been driving since birth and it's off the rails. Remember, courage and clarity about the situation are the two keys, right? Find out what the real blocker is. and drive a decision based on that reality of what the blocker is, not running back to process, okay, like we talked about. Develop your people, okay. Give them the accountability and the real ownership so that they can build their skills faster, versus driving them around and telling them what to do and then sending them off to like clog training. Give them the power and the responsibility, the accountability to develop themselves and watch them flourish. Dependencies. Build those relationships that you need to know what your risks are and to know how to avoid them. And to build that dynamic, collaborative, cross-functional relationship. Put in the work and the investment before you need to cash it in, period. You're going to find if you don't that the one person that you really didn't talk to much or you didn't build a relationship with That unknown stakeholder is going to be the one who's on the critical path, and they're going to be the one that's going to be the bigger blocker, Mark my words. Be adaptable. Remember, your job as a leader is to protect the outcome, not the plan that you're running. The plan is the vehicle, the plan is the means of how you deliver. But remember, you're are responsible for the outcome. You're responsible for the ROI, getting out what we paid for, and then some, the outcome. That's your mandate. Execution. You are going to be much better at executing if you can multiply your influence and your ability to deliver by again maximizing the throughput and maximizing the efficiency and the ability of your team. That is what your job as a leader is. Your job as a leader is not to be the boss, not to be the figurehead, Your job is to make execution number one. Don't forget that you are a unique individual and everything that you do is something that only you possess. Don't try to f either adhere to some standard that's arbitrary, right? I'm not saying go out and get yourself in trouble with HR, but at the same time, have that courage. Own the what makes you powerful. Okay? That intersection, all that together is where your value comes from. AI, remember, AI requires human judgment to be successful. We are still in charge of that of that machine, if you will. It's a tool, it's a hammer, it's spackle, whatever you want to call it. it does not do work by itself without us first having started it. We need to maintain control of that agent once we turn it loose with our data. We need to have gates along the way that say I as a human I'm going to check it for validity. I as a human am to make sure that before it goes out in an email or a report or some solution is put in the marketplace, humans who know what they're doing are going to look at it. They are going to have had governance in place the entire time. the way I look at it and what I've been saying more and more in thought leadership is if we're thinking of the AI as a person, as a resource, we've already got governance in place. We've already got controls and mechanisms, if you will, that help guide humans to the right outcomes. To me the AI, if we think of it and treat it like a person, it's going to be no different. And it should, for the most part, 8020, right? It should adhere to and be and be lever governed by the same governance that we've already got in place. We shouldn't have to invent anything and we shouldn't have to let it run run wild. Lastly, as I talked about just a just a moment ago, read the room, know what needs to be said and when Know when the silence you're hearing is a signal. Know the value of what you don't hear. Know the value of being quiet and letting the data, letting the other people tell the story, let them bring the information to you. If you're not getting what you need, if the room sits there and is clearly is unproductive, of course you as a leader, you do grab the room, you guide them to where you need the outcome to be as part of that meeting, and you move on. But you don't come in like a bull in a China shop and expect success all the time. you have to let the signals get out, right, in order to be successful. All right, so if you stuck with me and you didn't miss Mindy's voice too much, I hope that you got something out of this this sort of crash course on what Kale thinks of as leadership data points, you know, in eight, eight or nine you know, slides. I'd love to do more of these kind of things and I'm sure I'll probably get better and smoother at some of the presentation pieces of it. But I really wanted you to have something to listen to and if you're watching me on LinkedIn or YouTube or or you've just worked with me in the past, this will give you more insight into who I am and how I lead and and where that all comes from. And I'm hoping that some of the things I shared with you will be things you can think about and take away and leverage in your own leadership situation. until next time, you know all I can all I have to say here is, you know, now that I know I can do this on my own without without Mindy, I may try it again. And now that you know a little bit more about how I lead and where that kind of comes from, you now have some things in in your tool belt that you maybe didn't have, you know, 35 minutes ago. Well alright, I'll see you folks next time.

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