The Happy Engineer Podcast

168: What Every Engineer Ought to Know About Middle Management with Jason Gallaugher | VP of Engineering

Do you need a roadmap into, or OUT of, engineering middle management? You’re not alone.

These are some of the toughest jobs in your career, in some ways harder than being Vice President.

So listen now for how to win as an engineering manager!!

In this episode, meet former Vice President of Engineering at VidYard and Principal Founder of ThreeNorth Consulting, Jason Gallaugher.

If you want to succeed in middle management, you must understand how to get leverage. You must change your approach. You must block the imposter voice and unsustainable work that leads to burnout.

Jason has spent over 20 years in engineering and technology, where his journey has taken him across scrappy startups, large companies and rocket ships.

His curiosity and energy have pushed him into roles ranging from software developer, product manager, P/L leader, all the way up to technology executive.

And he understands that being a manager can be the hardest job of them all.

Now, Jason is primarily a coach and advisor to executive teams. His energy comes from his love of people + technology, and using his skills to help technology organizations become High Leverage..

So press play and let’s chat… it’s time for YOU to master middle management!

Ready for more? Join us in a live workshop for deeper training, career coaching 1:1, and an amazing community!  HAPPY HOUR Workshop Live with Zach!


The Happy Engineer Podcast

WATCH EPISODE 168: Engineer to Manager – Overcoming Challenges in Middle Management



LISTEN TO EPISODE 168:  What Every Engineer Ought to Know About Middle Management with Jason Gallaugher

Previous Episode 167: You Don’t Have to Be John Maxwell to Be a Great Leader


The Top 3 Principles for Mastering Middle Management

In this episode of The Happy Engineer Podcast, Jason Gallaugher and I delve into the challenges and opportunities for engineers navigating middle management and executive roles.

Here are the top three insights:

1. Embrace Uncertainty: Transitioning from technical systems to human systems requires a shift in mindset. Embracing ambiguity and widening your aperture to see possibilities are crucial for career progression.

2. Letting Go: Delegating tasks and responsibilities can be emotionally challenging but essential for career growth. Understanding leverage and power dynamics helps identify high-leverage tasks.

3. Purpose Over Prestige: Pursuing management roles solely for the title or money may lead to dissatisfaction. Finding fulfillment and energy in your work should drive your career decisions.

To go deeper and build an action plan around these points and why all this matters, listen to this entire conversation.


Jason has spent over 20 years in tech, and his journey has taken him across scrappy startups, large companies and rocket ships. His curiosity and energy have pushed him into roles as a software developer, product manager, P/L leader, technology executive and coach/advisor. Jason’s energy comes from his love of people + technology, and using his skills to grow and lead amazing organizations



Please note the full transcript is 90-95% accuracy. Reference the podcast audio to confirm exact quotations.

[00:00:00] Zach White: Happy engineer. You’re going to be glad you’re here today. I’m super excited for this one, Jason, man. It’s been good to chat before we hit record, get to know you and welcome to the happy engineer podcast. I appreciate you making time to be here, man. 

[00:00:13] Jason Gallaugher: Right on. Thank you, Zach. Looking forward to chatting.

Expand to Read Full Transcript

[00:00:15] Everybody that knows me knows that talking is something I really enjoy. So, uh, yeah, happy to do it here. 

[00:00:21] Zach White: That’s a, that’s a good thing. Everybody who knows me knows I like to talk. You’re in the right place then Jason. And what I’d love to. with a question that comes up to me over and over and over as a coach for engineering managers and leaders.

[00:00:40] And it’s this tension when we get to, especially mid career, but maybe we even feel it as a junior engineer, but especially that engineering manager. Band of our careers where we ask ourselves, hmm, do I want, and do I have what it takes to push this career thing to the next level, to get into executive roles, be a director, be a VP of engineering, maybe go lead a startup.

[00:01:07] Or is this really where I need to stop? Because I got a family now I’ve got the mortgage. Now I barely have time to keep up with my job as it is. I’m already putting in. Nights and weekends on occasion, if not all the time and gosh, Jason, I see the VP on my org. And I don’t want that life like, Whoa, that just, that just looks awful.

[00:01:30] And so we get trapped in this place and wondering, how do I even assess or make a decision about what to do? And you’ve successfully and really in an amazing way done this VP role. I’d love to hear more about it, but if you were coaching me, I’m the engineering manager, like, Hey, Jason, what should I do here?

[00:01:47] Tell me about that point of decision and how you think about, uh, What it means to push on and up versus stay where you’re at, or even backtrack. How do you frame it? How do you think about that? 

[00:02:02] Jason Gallaugher: Yeah. such a great question and something you battle all the time, any of us in the leadership positions battle.

[00:02:07] And I think that you know, the perceived inscrutability of what everyone in an executive role is doing or what goes on day to day, What I’ve observed is a lot of folks, either on my teams or in my orgs, or people that kind of see my titles and what I’ve done, have a much, much huger conception of what is going on than, than I do, or what’s actually happening.

[00:02:27] And I think there’s an analog to this. One of the best books I ever read when I was a new manager, was Behind Closed Doors by Esther Derby and Joanna Rothman. you know, the premise of that book is that, as an individual contributor, as a developer, it’s not obvious what your leaders are doing, and if you become one, what the heck do I do now?

[00:02:47] Especially if there’s no sort of like rational onboarding for becoming a manager. 

[00:02:50] Zach White: So 

[00:02:51] Jason Gallaugher: if you sort of apply that idea to, higher levels, I’ve been a manager for a while. I’ve picked up a couple of teams. it’s sort of important to that the level of abstraction increases. there’s other systems and other levers and other things you’re thinking about in other ways.

[00:03:07] Obviously, you’re benefiting from some added experience in some ways. 

[00:03:10] Zach White: Sure. 

[00:03:11] Jason Gallaugher: But it’s doable. So I think the first thing is just understanding and, we all have that imposter voice that always speaks to us all the time. the first step is blocking that out and sort of reassuring yourself that it’s not that far a leap.

[00:03:26] This isn’t. somebody like me does not get in these positions because, you know, we’re that much further ahead of anybody else or, you know, circumstances were great. We, we sometimes had sponsors or mentors that really helped us along the way. and we had opportunities that came our way that we took on, but.

[00:03:45] Beyond that, there wasn’t some sort of special thing that, tagged us as ideal executives. 

[00:03:50] Zach White: Jason’s IQ is not a one 80. You’re not some special, from birth born to be a VP person. You’re just another great engineer who took a role and went for it. 

[00:04:01] Jason Gallaugher: Yeah. Just like leaders are not born. And I strongly believe that as well.

[00:04:05] And I think anyone that is a manager right now can sort of put their hand up and go, yeah, I totally agree with that. Executives are not born 

[00:04:12] Zach White: with it, not born with it. So let’s talk about this discrepancy between what a frontline manager. Leading one or two teams and honestly hustling every day just to keep up with this player coach role that they’re caught in versus what is actually happening at that VP level and why the difference.

[00:04:32] So Jason, if you were to go back to before you had any experience and exposure behind the closed doors of an executive position, do you remember what you thought it was all about back then versus what it is? And can you describe some of those differences? 

[00:04:49] Jason Gallaugher: I thought, my goodness, like these are people that have a vast amount of experience compared to me.

[00:04:56] Sometimes true, definitely more experienced as, as a pattern. Um, that they also had to be, have a hand in every decision that, you know, it was something where if I’m, Put it a different way. If I’m struggling with time management already as a manager and I extrapolate that to, five X, seven X higher headcount or responsibility, it’s inconceivable.

[00:05:21] It’s like, I’m already tapping myself out 18 hours a day doing what I do right now in a very limited sense. And, you know, if I extend that to an organization, that’s like a hundred people, it just doesn’t work out. So I think. It’s sort of understanding the fact that, and this is one of the key skills that a manager can have that I think helps with these things is learning how to delegate and it’s like delegation to the next degree in terms of I can’t get involved in everything.

[00:05:47] I can’t possibly do all of those things. So how do I set up a system around me that make sure that I could trust what’s going on and trust is a word that’s going to pop up a lot in our conversation, I think, but. it’s about setting up a system that allows you to spend time on those things.

[00:06:02] So it’s like, you know, I’ve had those conversations coaching wise as well a lot, which is it almost feels like in that transition or in that conversation about how to step up in levels, or in some cases, it’s founders. Or technical co founders that are looking to move up to a higher level of abstraction along with the business rather than look for a promotion in a bigger company in a, in a management role.

[00:06:21] But it’s, yeah, it’s about putting yourself out of a job to a certain extent, which is like, do I have the people around me that can take on some of these things? What decisions can I maybe, get done 80 percent as well as I could do them given, given what I know? But what would I do with that added time?

[00:06:36] Well I’d probably go look out different horizons, right? 

[00:06:41] Zach White: For sure. This distinction that’s super important between our tendency to extrapolate our current activities and behaviors and workload and The drivers of workload, which is team size in many cases at that front line, or even senior manager, you know, M2 type roles.

[00:07:03] And, and you just say, gosh, so if that team underneath me was 5X the size, my God, how could I ever keep up? and that’s really not the case anymore. It’s not an extrapolation of the same activities. We are doing different things. Can you describe for yourself, what was the, what was like the most important switch in your understanding of the, the behaviors that create value as a VP versus the behaviors that create value as a manager and, and how you had to change or develop yourself as a leader.

[00:07:39] You mentioned delegation and trust some of these ideas, but could you really get specific, like what’s the, what’s the difference in the value creation at the two levels? 

[00:07:49] Jason Gallaugher: it’s about leverage. what are the things given this chair and the chair holds power?

[00:07:55] I mean, you can’t ignore power dynamics in an organization, but it’s, what are the things that I am uniquely positioned to accomplish where I sit right now? And that’s universal to any, any role. And it really helps with these delegation conversations, because the answer is, I’m not sure, or I think there’s probably four other people inside my team or inside my organization or my company that can probably do these things.

[00:08:16] What is your perspective? And what are you most uniquely able to do? And for a manager, it might be that you know the system, the software system you’re working on, the part of the infrastructure, the part of the, you know, DevOps or developer experience flows that you’re looking at. I understand those better than anybody.

[00:08:34] Therefore, I should keep my activities in things that are high leverage and improving that broader system. And if it’s something that’s kind of down towards, smaller items or items that used to be fun, because sometimes you run into that tension as well, or things that make you feel good. but ultimately the thing that’s always in the background with this is back to this little notion of delegation or giving up ownership is that to get to those higher level activities, you’re typically giving up something and there’s anxiety around, will it get done?

[00:09:03] Can I do these new things? What happens if I give them up? And there’s all of this sort of emotional baggage that’s attached to moving around in the system like this because you never You know, you’re never sure 

[00:09:15] Zach White: Delegating 

[00:09:16] Jason Gallaugher: something or moving yourself into more high leverage tasks in the part of the system you’re looking at or as an executive as part of the entire system all of Engineering in different areas like that You end up being silent or trusting in a lot of different areas that you weren’t silent or trusting in before 

[00:09:32] Zach White: Yeah, 

[00:09:33] Jason Gallaugher: so and that creates a lot of emotional tension, which is like i’m accountable to that, but i’m not actually doing it Oh my gosh, what do I do now with that?

[00:09:42] So yeah, 

[00:09:43] Zach White: not just with what you said there, it’s also sometimes the thing that you got recognized for being great at that, then you must let go. And I remember for me, that was one of the hardest parts when I became a senior manager at Whirlpool Corporation, you know, leading these projects and engineering teams, it was, Like, Oh, wait a minute.

[00:10:03] My favorite parts of my last job and the things that I’m known for and best at in the company right now are no longer a part of my job description that was really hard to let go. And as much as I thought that I. Quote unquote, mastered that in my career days, Jason, now I’m facing it again in building my own business.

[00:10:25] It’s like hiring people for my company now and saying, Oh, like that, that aspect of the coaching I really love. And that’s what, that’s why people join our programs. no one else could do it as well as I can. Right. Which is the same lie that I believed back as a manager and it pops right back in as a CEO and founder.

[00:10:45] These are. easy to talk about consciously, but there’s something emotional, something subconscious behind it that often keeps us holding on to it longer than, than we should. And so if you were going to say

[00:11:01] What’s the thing that causes people to take the risk? They take the leap, they go to director, they go to VP and then they flame out gloriously. There’s the, you know, the burnout stories or the nights and weekends, their families, their divorces, all this stuff. Where do they miss the mark in making the jump that you think leads to those negative outcomes?

[00:11:22] Jason Gallaugher: I think it’s the allure of the title and the allure of, of the perceived prestige and real prestige, honestly, that comes with these types of roles. And I think it’s the same sort of, again, there’s a lot of kind of fractal scales here that we talked about within organizations and tying it back to the same decision between do I remain as an individual contributor or do I take the leap into a manager.

[00:11:43] there’s a lot of reasons people might become a manager for the wrong reasons. Hey, it’s the only path to advancement I perceive in my company right now. It’s the only path to more money or, you know, because there aren’t two different paths in a fairly well developed engineering pathway in that organization.

[00:11:57] Sometimes they have three pathways, including the kind of a fellow pathway and other things. But if you think about that, I’ve already made the decision. I want to be a people leader. I really love what I’m doing right now. why would I jump ahead? And, and, you know, in terms of my own experience, it was because, you know, yes, there was a title attached to it.

[00:12:13] But the first time I walked into a P a VP, not a PM title done that a few times to a VP title, you know, it was because the, the problem set and the challenge was highly interesting. It was kind of moving from a purely technical role to running a technical business as a P& L leader. And that That was sort of enough of a safe jump for me to think like, okay, I’m pretty good at this type of system and I can jump into this other type of system.

[00:12:36] And that seems like a reasonable set of challenges. And I’ve got some people around me that I trust. And that seems like a great opportunity. It’s going to take me somewhere. it’s like, okay, I’m, I’m being offered this title and it’s really, really awesome.

[00:12:50] And it’s sort of shortcutting all of the other thoughts that you should probably have, which is like, is this right for me right now? Is this the right company right now? Is this the right circumstances? Do I have a support structure around me to help this? Do I have a sponsor in place? Because, I mean, let’s not discount the benefit of having a sponsor and a mentor and other leaders around you that can help you.

[00:13:10] So it’s sort of, Um, to me. Yeah, it’s getting caught up and sort of like, I can’t believe I’m being asked. I’m so honored and I’m so excited and happy that I’m going to be holding that title finally and forgetting to ask all of those other questions that you would ask if you were being hired by another company, if you were being brought in somewhere else.

[00:13:27] So to me, that’s the biggest thing and getting in there and realizing the support structure. The mandate, it wasn’t what you believed it to be. And that sort of realization of that gap existing is just too much. It’s just like, okay, I don’t see a path to succeed here. Is it going to step back into what I thought I was really good at before?

[00:13:45] And you know, that’s, that’s where it lands. 

[00:13:48] Zach White: I’m just going to be direct about this, Jason, you tell me if you agree or disagree, but the reason to move up being just about the money is one of the most dangerous and I think false, reasons it, it looks good on the surface, but it’s really ineffective and unsustainable to have a career that you’re going to love because, 

[00:14:11] you don’t actually want money, everybody thinks they want money. And, I get that, but we don’t really want money. And, and the Ray, I tell my clients say, Hey, look, Jason, if I could give you a billion dollars, it’s going to be yours, but it’s in a bank account. And you can’t actually spend it or use it.

[00:14:29] It’s just yours. You have to just keep it and look at it. You’ve got to put it on the shelf. And there it’s like, nobody like that’s stupid, right? You can, you don’t want the money. You want what the money is. Can bring you, you want what the money does for your life. And you got to get really clear about why you want money because money itself is not the thing.

[00:14:48] And a lot of people haven’t done the deeper digging around, they just know more money is the next thing. And that’s fine. I don’t, it’s not a judgment. I think it’s awesome to go after great income and great rewards, get paid for the value you create. But if it’s just about money, almost every time, you know, within short order, you’re going to find yourself.

[00:15:09] Burning out and frustrated and not actually well suited to the role and to the work. Would you agree with that? Or do you have a different lens on the money? I 

[00:15:18] Jason Gallaugher: I can tell you from that, right, like my own experience that, you know, there’s always another mountain to climb, right? Uh, I remember these phases of my career, even the first few years in the industry as a junior programmer, uh, just being excited that bug fixes.

[00:15:33] That I had committed or going out to like a reasonable number of people and commercially ship product. Like I thought that was the coolest thing in the history of the world. that happens all the time now. And you just don’t even think about it. And every so often I found there was another sort of mountain I wanted to climb.

[00:15:47] If I can just stick with this for another year, I’m a leader in this industry and I can stay in this industry as a leader, and if I can do this, Oh, I can, I can lead at scale. That’s great. I can lead at scale. And you know, through that. You know, the comp numbers go up and everyone again should be demand fair compensation and know what their market value is, but yeah, it’s just, there’s always another mountain to climb, you know, once you reach, where you are, it’s, it’s, it’s important to think about why you’re doing it and are you getting energy from, the system you’re working on and the work you’re doing and the environment that you’re in.

[00:16:19] you know, ambition is cool. Everyone should feel that they should feel energy around the thing they’re building or the team they’re leading or where they think they can go next but, you know, honestly, I think it’s just, you know, are you getting energy from it or not?

[00:16:30] And if you’re not ultimately, yeah, that’s, that’s not going to be sustainable or you’ll try to make it sustainable. And there’s a cost to that, one that’s insidious as well, that sneaks up on you. it’s important to be compensated fairly but, you know, that, that can’t be everything.

[00:16:45] So 

[00:16:46] Zach White: Jason, that, that first line, that manager role is, is actually one of the toughest jobs of your entire career.

[00:16:53] And I was wondering if. You could reflect back really quick. First of all, do you, you know, is that true? How do you think about the difficulty or complexity of different roles you’ve held in proportion, right? To our experience at the time and the challenge at the time and those sorts of things.

[00:17:08] Um, and maybe any specific story or moment that stands out to you as to why you feel that way. 

[00:17:13] Jason Gallaugher: Yeah, I think, that middle management function, whether they’re called team leads or software development managers or whatever it looks like, take the brunt of a lot of things in the organization, they’re a nexus for a lot of different activities that are going on.

[00:17:27] And, you know, somebody like a VP engineering, like me, yes, we’re naturally a nexus for the activities of the organization, but the system set up. With all these other leaders in it, and ideally ones that we’ve hired or brought on or developed or trust that make life a lot easier, but in that first role, and I think back to, some of my first experiences as a leader,

[00:17:46] you are accountable yourself to the technical work that’s happening. You’re in every PR, you’re in every architectural decision. You’re expected to be a technical. Star at the same time, you’re responsible for. Managing people, which is completely new or at least something that, you know, you’re still working on a lot of the toolkit for how do I develop people?

[00:18:09] in an environment where in a lot of cases, if you were just promoted into that role, they were your friends and peers six months ago and people you hung out with all the time, you shared everything with, and now everything’s kind of changed a little bit. So again, there’s emotional load and everything.

[00:18:24] And there’s a lot of emotional load around that, which is. I’m trying to do everything all at once, and I’m also trying to be the central focal point of every communication, especially in big companies. And that was my experience in places like Blackberry, where, when it was at scale 10 years ago,

[00:18:40] you’re expected to be the representative of that team to all of these other actors within the organization. So it’s just a lot. And if you look around, there aren’t that many people to delegate that to. And, there’s not a lot of people asking you to, to take something over for you, right?

[00:18:58] They’re not asking to help in a sense. They’re all worried about their own mandate. yeah, I think that’s true. It’s a really tough job. it’s middle management. Middle implies, all of these communication paths where you sit inside the graph of communications in the organization is like so huge as far as communication and the number of, possibilities as far as what you’re trying to manage.

[00:19:19] So, you know, it’s sort of this contradiction that happens where it’s like kind of the hardest job cognitively, in my view, just where it is in the system and how it works. and people are typically. Yeah. Um, a lot of companies are really great as far as like having intentional development plans for people.

[00:19:36] yeah. And it gets easier. And that’s the other thing too, that’s huge is it’s like as your skills grow and as the system moves around you and as you learn to set up these, these delegation points and people you trust and life actually gets easier if you let it, but it’s that one moment where you’re sort of, holding everything together yourself or at least a perception that you are.

[00:19:56] Yes. It is massively stressful. So yeah, that’s the first place I look at a lot of organizations. If I’m, consulting or if I’m, starting a full time gig, it’s fine. The team leads find the SDMs and talk to them and find out what’s up because ultimately they’re in the middle of everything.

[00:20:12] And you can diagnose a lot of things really quickly and just supporting them. Talk about leverage points. 

[00:20:17] Zach White: yeah, for sure. I think, I really like that. Well said. And that’s why that particular band of the organization is my primary focus for all of the work that we do with Oasis of Courage. And yeah, we help people in all kinds of engineering roles at all levels, but I’m really passionate about this middle band because of the things you said and the range of Preparation and training and support and help that’s provided is so incredibly broad, Jason.

[00:20:44] I know you’ve probably seen it and experienced it, but everything from, 20 percent of your time is in training and it’s really robust. And you never have to look for more than a few minutes to find the resource or the tool you need all the way to, I’ve had a client. she was an amazing.

[00:21:00] Individual contributor got her manager promotion. She was just weeks into that role when she onboarded to our coaching program. And our first few conversations, it was like, what’s a manager? What do I even do? What is, what is my job? It’s like, wow. Like they didn’t even go so far as to explain. What’s the expected results that you’re going to drive and what are the ways that the managers in our organization operate?

[00:21:26] And what is the toolkit that we use to lead? And how do you do performance reviews? Like none of it was explained. They just gave her this manager title and said, go, wow. This is so there’s a lot of experiences being had and you can understand why people get challenged and confused about, Hmm, do I really want to take this at an even higher level than where I’m at?

[00:21:49] So Jason, let’s do this. I kind of want to go off script and let you maybe call it a choose your own adventure here for just a moment, because as we’ve been talking, three or four topics have surfaced that I would love to just dig deeper on with you, but I I don’t think we’re gonna have time to do all of them and something else exciting may come up as we’re chatting.

[00:22:10] So I’m curious for you. Knowing what’s had the biggest impact in your own engineering career and the things you’re passionate about in the industry now, one was the idea of blocking the imposter syndrome voice. One was this idea of power dynamics in the organization and sponsorship and the importance of that.

[00:22:32] And how do we learn what’s going on there and how to create that. And the third was this idea of emotional health and sustainable Lives in leadership roles and then creating that kind of culture for our teams. All of these are awesome topics. What’s calling your name first, Jason, where do you think we should go?

[00:22:54] Jason Gallaugher: I can go anywhere, surprised me. I think I’m cool with that. 

[00:22:57] Zach White: Okay. Okay. Let’s, let’s touch on power dynamics then for just a moment. Yeah. And then we’ll come back to the others because I think as engineers, Because we live in a systems mindset, logical, analytical view of the world, oftentimes black and white, some of these things are either a bit hard to understand, or frankly, we just don’t want to Even believe that it’s happening.

[00:23:20] It’s like, I should just get rewarded for the value and the merit of my own work and forget this whole power dynamics thing. So when you say power dynamics and then sponsorship as a maybe subset of that whole world, what is it? How do we get to know what’s happening in our own org and what do we need to do?

[00:23:41] Jason Gallaugher: Yeah. And this is where I think it’s a huge transition point for those of us that are in quote unquote engineering careers or technical domains, because we’re all system thinkers. And that’s, that’s really cool. And the systems we work with, cause there’s a whole lot of different types of systems. The ones we work with, Despite the fact that they’re frustrating a lot, they’re generally deterministic.

[00:24:02] They’re just sometimes linear, but often we can see stuff in software systems that are gremlins or however you might want to talk about it. But, there are systems by which the feedback loop is actually really tight. it either compiles or it doesn’t, or the PR passes or it doesn’t, or the fix works or it doesn’t when we test it.

[00:24:19] Like you’re getting immediate. Gratification from the work you’re doing, you leave, most days, hopefully, or you’re not too frustrated by the problems you’re facing, but there’s sort of this transition point involved with all of this is, is like the human systems, which are actually.

[00:24:35] Equally is important, but you don’t start perceiving that until you get a handle on the technical systems. You start working through the hierarchy in a certain way. this is, this is relevant for staff engineers, principal engineers. there’s a lot of folks that need to do things like influence or figure out how to progress through the organization, find sponsors, find people to work through this and this notion that, yeah, there are differences in power in the organization.

[00:25:00] So that’s the biggest, yeah. Sort of general point is that how to get comfortable with the human system and it’s it’s non linear It’s non deterministic. It’s chaotic. It’s inherently chaotic. You’ve got a lot of people You know subject to their own psychology in the organization. there’s no there’s no proofs.

[00:25:19] There’s no there’s a lot of guidelines Any system for that side of the business or for the human system, that’s too prescriptive is going to fail just because you can’t predict inherently what people are going to do. So, understanding then how to deal with that system is just a massive level up, especially when you’re looking at, okay, I’m pretty good at this.

[00:25:38] I’m good at this as a scale of my own team. How is this relevant to the rest of the organization and how do I progress my team? How do I progress myself? Soit gets into very social, strategies for me. I’m an extrovert. I got shoved into a lot of meetings cause I wanted to go to them early in my career, which sort of set the stage for this, but these are not.

[00:25:57] These activities are more difficult for some people than others, and that’s okay. And I think a lot of us might feel, even those of us that are extroverts, that we just don’t have the chops to do it, or we’re out of our class, we’re speaking to people that, starting to light up those conversations, like who are my, and this is something that pops up a lot.

[00:26:14] Like if you’re, if you’re a manager in an organization, who are my equivalents across other roles in the company? Who are those people that work in, you know, go to market team sales, marketing, uh, lots of excuses to work with them and really understand what they’re doing, but ask them what they’re up to ask them what they’re doing.

[00:26:32] and ask those questions of everyone else in the organization, find excuses in a sense to have those conversations and that’s not just across, but it’s up as well. in some organizations back to even topics like management training, a lot of organizations and a lot of leaders, especially executive leaders are really good at having things like one on ones and they’re good about not making them status meetings, but actually like, how do I help you get to this next point that you want to get to in your career?

[00:26:59] Have I asked you about your goal yet? If that hasn’t happened already, It’s okay to ask. It’s okay to listen. It’s okay to realize, too, that, despite the fact they’re being a power differential with titles. You can still ask those questions. You can still demand those things for yourself in a way that’s reasonable or comfortable to you.

[00:27:17] But, we’ve moved from a place of sort of like very linear proofs in a sense, in sort of the technical systems we work with to something that’s incredibly ambiguous to us. So I think as far as like traversing through the organization, it’s about building relationships now. and sometimes it’s just about the discipline to go like, I’m going to talk to two people this week.

[00:27:36] Random in my organization. or now we’re remote. We used to be in person. Haven’t talked to this person in a long time. Let’s just reach out. And it’s not with an end in mind, necessarily. You’ve got your goal in the back of your head, but it’s this notion of opening up possibility. This is how you deal with these types of ambiguous systems, just be ready for a possibility when it arrives.

[00:27:55] And the only way you can do that is initiate as many trials in a sense within the, The system as you possibly can, you’re testing things out. You’re having conversations. You don’t know if this conversation you’re having now in three months will have this other effect, which is like, Hey, I was in this other meeting with a bunch of senior people.

[00:28:11] I remember that you told me about this thing three months ago. Are you interested in this type of opportunity? Or would you like to learn about this? and it’s about setting these things up and putting these possibilities in motion. But again, this is all language and concepts that are really, really different than like the best way.

[00:28:26] No. Yeah. Keeping possibility open these are all kind of good architectural concepts as well. good organizational concepts, but it’s, I think an underserved area that people believe they need to have this like powder down, they need to have, We 

[00:28:40] Zach White: spend our whole early career stage coming out of college and then learning how to predict Y equals F of X for some really complex thing or this project management thinking, I want to know step one, step two, step three, step four.

[00:28:53] That’s going to cover the next six months of development. And here’s the whole plan. And I know how this step builds to this step builds to this milestone. And then you come over here and to your point, Jason’s like, all you need to do is go have the conversation. Nobody knows what’s going to happen after that conversation yet.

[00:29:10] It’s like, we can’t plan the next six months worth of. Social dynamics that are going to show up in the organization. It’s just willingness to say, okay, I know I need to connect and go ask this question or reach out about X topic or get to know these people without a determined, guaranteed outcome. And, and I can’t build the project plan of social intelligence, you know, for the rest of my career.

[00:29:35] I think that’s a hard shift for people. Cause you spend so much time learning how to connect all the dots between here and the finish line in your engineering work. And then you come over into this career building, emotional intelligence, social intelligence world. And it’s like, wait a minute, none of these dots connect, Jason.

[00:29:53] What the hell? You know, but, but that’s, that’s just how it is. And you gotta be willing to take that next step into the unknown. I like that open to possibility and widen the aperture, like just let’s just see what’s 

[00:30:03] Jason Gallaugher: possible. And fight the fear in a sense. Right. And I think the final point around that is that the people higher than you in the hierarchy that have more power.

[00:30:12] Are not as scary as you’re letting them be. And there’s a lot of manifestations of that fear, right? I’ve had situations too, where like, I know myself, I’m pretty driven and direct, but I, I’m pretty friendly. I’m very fairly personal, but you’ll say things like, okay, every Friday, you know, I’m setting aside three hours for office hours.

[00:30:32] And I would love to talk to literally anybody. Tell me about your hobbies, tell me what you’re working on, rant at me for two of those hours. Like I am up for it. it’s all good. And then You know, a lot of times it’s cricket. You’re sitting there with your gigantic title going, why? Why won’t anybody come talk to me?

[00:30:50] I don’t want to play this off as some sort of, a lonely thing or anything like that. But I think that’s like a barrier that, people don’t realize is as low as it actually is that these people are actually willing to talk. They were in your seat a little while ago, probably a shorter amount of time than you think there is.

[00:31:07] And they actually want to hear from you. And it’s not perceived as climbing. It’s not perceived as. This sort of like negative, ambitious sentiment that I think a lot of us program into our brains as well. And somehow this is bad. go talk to them. They’re actually willing to do that.

[00:31:22] It’s not going to offend anyone. And you know what? And if it does offend somebody or you do get treated rudely, then that’s actually signal for maybe some other aspects of the system you probably need to be looking at, which is that doesn’t happen everywhere. Leaders shouldn’t talk to you from that place.

[00:31:39] Right. So yeah, human systems and. Fighting the fear and engaging with it and you know what good things tend to happen from that 

[00:31:48] Zach White: I love the fighting the fear in my company my coaching organization Jason this oasis of courage for that exact reason Yeah, do not see technical acumen as the barrier to our career growth in any case It’s always these pieces now, of course, we need the experience in the technical acumen as well But I think For engineers, that’s the easy part.

[00:32:07] Everybody loves to go learn a new skill and develop on a new area. All right. So if we go all the way back to the start of the chat, here’s Zach White. I was, I’ve came for your coaching, Jason. I needed your help today. Should I move up the org chart or should I not? I’m convinced I want to move up. I want to do this.

[00:32:23] but I don’t have that sponsor. Like you mentioned, and I’m willing to face the fear and go have the conversation, et cetera. But I, I don’t really know what I’m asking for. Can you just describe if you were saying, Hey, if you don’t have that level of sponsorship in your organization right now, and you’re going to go make an ask, what is it that you’re actually asking for?

[00:32:48] How does that conversation go? Could you provide some really tactical, even though like what kind of words you would recommend using, or if there’s anything to avoid In having a sponsorship conversation. 

[00:32:59] Jason Gallaugher: the ones that have been in that have been really effective, have been ones where people are just asking questions, back to our point around the behind the closed doors, the drawn curtain, tell me about what you’re looking at.

[00:33:11] you know, one of my favorite questions for interviews and anything else, like what’s keeping you up at night right now, you know, tell me a little bit about your world. You know, it could even be like a tactical problem. You’re looking for help with. So I think that’s the biggest thing through all of those sort of conversational starters.

[00:33:26] I mentioned, which is just. It’s okay to ask for help back to the fear thing. I think this is another huge area, which is, I think we have a whole group of. Folks in our industry that are going through their day to day. Not asking anyone for help when they actually know they need it. So I think that’s the biggest thing is it’s okay to ask people regardless of how you perceive their power in the hierarchy, just ask for help.

[00:33:51] And maybe it’s not help about like, Hey, I’d love to make VP in the next two years. 

[00:33:55] Zach White: Yeah. 

[00:33:55] Jason Gallaugher: It’s like, okay, maybe it’ll happen. Maybe it won’t. Like these jobs don’t pop up all the time. And that’s not sort of a very, again, deterministic thing you can think about, but it’s a reasonable goal to have to say, I want to work at that level of scale, but it’s more about, Reverse engineering, visibility for what your team is doing.

[00:34:12] Opportunities that are smaller than might arise, 1 of the things you get really good at as an executive is marketing yourself and marketing the work your teams are doing to a broader audience. And this is the impact we had. Here’s how to tell that story. Ask for help with that.

[00:34:25] It’s like, I think my team did a really good job. Maybe I, you work within the organization, this person’s in charge of, or there’s somebody else inside the organization, you know, can you help me tell the story here? I’m not asking for anything more. I just like for help to tell my own story.

[00:34:39] you know, the worst thing that can happen there is that, Oh, well, there’s probably some other things you have to think about, or there’s some new perspectives, or maybe the story isn’t as great as we thought it was, but that’s okay. and that’s a huge thing, but ultimately. You’re just looking to kick off some level of relationship, on safe ground.

[00:34:55] And again, asking for help is one of the most powerful ways to, to kick that off, especially in that type of hierarchy. back to my previous point, if you’re greeted with, I don’t have time, I don’t know who you are. I’m not really interested. That’s signal. That’s okay. There’s maybe other people you can talk to.

[00:35:11] Um, and you know, it’s just as a final bonus sort of thing. The people that are the best storytellers in the organization are usually right beside you. They’re the product managers. In the R& D organization, right? Go find them. Go ask them how you can work together to tell the story of the organization or the team in a better way.

[00:35:25] If. this other sponsor didn’t seem to respond well. So yeah, ask for help. Just ask for help. And it’s okay. 

[00:35:31] Zach White: That’s a whole nother episode we need to have on storytelling and product management, because I know a lot of engineers want to get into that space or are in that space and that’s a key thing.

[00:35:41] Amazing. Well, Jason. If someone wants to explore deeper, the topics we didn’t get to touch today, imposter syndrome, or, sustainable, emotional, healthy leadership and organizations and how to create that culture, or just consider. Hey, like, where are you working? I want to be a part of whatever you’re doing, Jason.

[00:35:59] Where can people find you and get to know more about your career, your life, and your future from here? 

[00:36:04] Jason Gallaugher: you know, thinking through my writing and a lot of other areas right now, but the safe place to learn all of these things is by LinkedIn profile. Uh, watch the spelling of my last name, obviously.

[00:36:13] so look that up on, on the podcast title, but, uh, that’s the best place you can look right now. And, as far as what I do, I engage with companies both as a advisor, but, also looking for full time gigs So looking for my big stuff and my journey. So yeah. Open to have conversations.

[00:36:28] Zach White: Jan, early January, 2024, as we’re recording this. So if someone’s listening in the distant future, who knows where, Jason is making an impact these days, but yeah, if you need his advice, through three North call and make it happen. And for sure, if you, need Jason to come lead your team, I’m sure for the right opportunity, any of us can be persuaded.

[00:36:47] So amazing. Well, Jason, this has been awesome. There’s so much to learn from, from you and you know, as well as anyone I’ve ever had on the show. As an engineer, as a coach and advisor yourself, questions lead, answers follow. And we all want really great answers in our career and in our life. So we need to ask really, really great questions.

[00:37:12] So for you, what would be the question that you would lead the happy engineer with coming out of this conversation? 

[00:37:19] Jason Gallaugher: we covered a lot, but I think the biggest one I have when people come to me and ask these things, is. Where in the last couple of years did you find yourself having the most energy?

[00:37:29] The most, you know, because happiness can take on a lot of forms, positive sentiment can take on a lot of forms, but for me, I tend to orient the conversation on energy. If you’re in a one on one, it’s usually the most indicative question and people think for a little while and they tell you about something that happened last year.

[00:37:44] It’s usually a qualifier for me to say it could be anything as small as you want. And you know what, if you want to reach outside of quote unquote work, Let’s do that too. Cause I just want to learn about that. So I think that’s, that’s the biggest thing. What was the, what was that time the last little while that made you the most excited and let’s start riffing off that moment if you hadn’t thought about it.

[00:38:03] Cause it’s easy to get buried in, you know, your stresses and forget about those moments. And that’s usually a kickoff to a great conversation in my experience. 

[00:38:14] Zach White: So good. Well, you talk about signal. That’s a really powerful signal in your own life. Where in the last couple of years have you found yourself?

[00:38:22] With the greatest level of energy. And I’ll tell you, Jason, I, I coach this to every single engineer I meet. It’s not about time. It’s about energy. That is the X factor to your life and to your results. So amazing. So, so good, Jason, thank you again for being here, making time for the podcast and to share your wisdom and, uh, look forward to connecting again down the road, man.

[00:38:43] Jason Gallaugher: That was amazing, Zach. Thank you so much. 

[00:38:45] Zach White: Yeah. Cheers.