7 Reasons Engineering Managers and Tech Leaders Get Stuck in Their Career Without Advancing

Are you stuck in middle management and struggling to figure out how you can break into the director and executive level roles within your company?

If this feels like a black box to you, then stay tuned because I'm gonna explain why you get caught in this cycle and how you can break out of it.

Hey everyone, and welcome to my channel. If you're new here. I'm Doug Howard. I'm a former director of engineering, but today I focus on helping engineering and tech leaders build the mindset, tools and strategies that you need to increase your impact, scale up in your role, and advance to the next level of your career.

And that's exactly what we're gonna focus today's episode on because I wanna walk you through the seven reasons why engineering managers and tech leaders remain stuck in your role indefinitely. I'm also gonna give you some tangible tips and tools for dealing with each one of these challenges.

But first, make sure you don't forget to hit that subscribe button so you don't miss out on future burnouts.

1 - Engineering Managers Aren't Taught Leadership Skills

The first reason boils down to one thing, capability. I'm just gonna say it like it is. You never learned the skills you need to be effective in your role as a leader. And you never gained the skills you need to advance to the next level as a leader.

Just think about it. You know what got you promoted into your first leadership position? There's a good chance it was because you were a top performing engineer. You were a top performing individual contributor or technologist or whatever field you worked in, and you were running circles around your peers and surpassed everyone and that's what got you promoted, but, I wanna change your mindset on how you look at leadership, because management is not a promotion, it's actually a career transition.

When you think about it, leading people, managing people, understanding people, this requires a completely different set of skills relative to the skills that you need to be a successful engineer. To be a successful engineer, you need technical skills, right? It's a lot of science and math and things like that.

But to be an effective leader, you need soft skills. You need to understand how to build relationships with people. It's basically a whole different skill set and we never learn these skills as engineers. No one ever teaches them to us.

When you think back to our college education, it's all technical skills. When you go a step deeper, most engineers tend to be left-brained. That's what gets us into engineering fields. And when I say left-brained, that's the logical side of your brain. That means we're more analytical, we're more logical, we're more comfortable with numbers and facts and objective analysis and things like that.

We're naturally left brained, and when we go to engineering school and when we get a technical job in engineering, it forces us to basically double down on that logical side of our brain, that left brain and it gets stronger.

Think of it like using your dominant hand. The more you use your dominant hand, the better it gets. The more coordinated it gets, the more you rely on it. And meanwhile, your non-dominant hand gets less useful. It almost, I don't wanna say atrophy, but it's less coordinated. You can't do it for as many things. It feels highly awkward and uncomfortable when you're using your left hand to do something like brush your teeth when you never do it.

That's what happens to your right brain. If you're an engineer, you're most likely naturally left-brained. But that means, you're basically overdeveloping the left brain and you're not developing the right brain unless you do it intentionally. The right brain is what's associated with creativity and soft skills and emotional intelligence and empathy and that's a key for leading people you need all of these skills, especially empathy. You need to understand other people's perspective.

A lot of times as engineers, we get moved into these positions and we never go through any type of training on how to develop these skills. It happened to me, which I'll share a little bit about my story later in this episode.

A lot of times we never get trained in these areas. If we do get trained, it's usually some type of company training that doesn't really resonate with us. 'Cause again, we're logical minded. We have a different way of thinking. We're not naturally outgoing, we're not naturally people oriented. We tend to be a little bit more reserved. We tend to be a little bit more introverted and process orientated.

The problem with mainstream leadership training programs is that, those types of programs are taught at any different company, in any different type of industry, and to any type of person, but they really don't resonate with us. We end up feeling like it's a lot of fluff. It doesn't really teach us how to actually build these skills in a way that works for us. To quantify what I mean here I'm talking about, understanding other people and h ow to communicate in a way that resonates with them and how to disarm other people's emotions so they don't get defensive. How to give constructive feedback in a way that inspires them to take action.

All these types of things, we never learn how to do these skills and it prevents us from being effective in our role as a leader. To summarize that, we are never taught how to build the skills that we need to be effective in our role.

Think about that. Imagine if you became an engineer out of college and you never built the skills you needed to be a successful engineer. How effective would you be? The same thing happens to a lot of engineers when you move into leadership roles. So you just figure it out on your own and you end up, putting band-aids on the problems instead of actually like developing these skills and figuring out how to do these things efficiently and effectively.

Now, if you are listening to me right now and you're realizing that, oh geez, maybe I didn't, Learn these skills and you're not sure where to begin. A good place to start is by signing up for my email newsletter because I provide weekly tips, tools, resources, workbooks, free masterclass trainings on all topics related to leadership, specifically in engineering and tech. It's all taught through logical frameworks and everything is based in science, and it's taught in a way that resonates with engineers and logical minded people. If you're interested in that, and if you wanna sign up for my email newsletter, I'm gonna put a link to that signup in the episode description.

2 - Engineering Managers Don't Have Enough Time

The second reason that engineering managers and technical leaders never scale up in your role or advance to the next level is because of lack of time.

You constantly feel like you're drowning in work. You can't keep up with everything. You have endless responsibilities. Your company and your boss is putting the thumb down on you to produce more and grow your team and increase your capacity. It almost feels you're at the post office, you're the postmaster general. No matter how hard the post office and the mail delivery people work, they never get caught up. They never get ahead of the mail. 'Cause the mail is always coming. It's not like you can work harder one day and there's less work to do tomorrow.

That's what it's like to be an engineering manager or a technical leader. The work never ends and the second you build capacity and increase capacity, guess what? It just gets eaten up by either more sales or more problems. So you can never really get ahead of it by just putting in more time.

It's a law of diminishing returns, and it's a trap that all engineering managers fall into. Just feeling okay, this is just a, busy period. If I put in, an extra 10 hours a week for a few weeks, I'll be able to work my way out of this. I'll be able to get the team caught up. That's a trap. Don't fall into it if you're probably already in it. If you are an engineering manager or a technical leader, that's a trap because then working 10 hours extra week becomes 15, and then 15 becomes 20, and guess what? You can do that for a week or two, but you can't do that forever. You're not gonna be as productive with that time. You're gonna burn out.

As engineers, we think of time in terms of doing, but I wanna change the way you look at time management. So you just wanna kind of start looking at how you're spending your time and just objectively looking at it like, is this adding value or not? It sounds obvious as I'm saying this, but I'll challenge you. Do you do this with your time? Do you think of time this way? Think about how you're using your time and how you're allocating your time differently.

3 - Tech Leaders and Engineering Managers are Burning Out

The third reason why engineering managers and technical leaders don't move on or scale up in their role or advance to the next level is burnout. We just got done talking about lack of time. A lot of engineering managers and technical leaders, your solution to not having enough time is just putting in more time and compromising your work-life balance. Not giving yourself the rest you need and the nutrition you need and the other things you need in your life to stay balanced and healthy.

It's insane how many engineering managers and technical leaders are burnt out. Look around your office, you'll probably notice, very high percentage of 'em are just constantly on the go. Stressed, exhausted, irritable, angry, frustrated. I was one of these managers for a while, I'm not gonna lie. There's an insanely high percentage of engineering managers and technical leaders that are experiencing burnout, and it's because it's a very demanding position. It feels like there's no end in sight, so you just keep grinding it out indefinitely and you're not giving yourself the things you need to be healthy.

I'm not gonna beat this one to death. I'm just gonna say, if you are struggling with burnout, then you should check out my burnout called Seven Ways to Recover from Burnout in Engineering. You'll actually go through a little framework to build your own recovery plan for burnout. So you definitely wanna check that burnout out if you are struggling with this. I'm gonna include an episode link in the description.

Now these first three areas we just talked about, those are all related to skills and training and resources. For example, burnout is lack of energy. Lack of time is lack of time. Time is a resource. Lack of training. But these next four are all related to support you need from other people. I wanted to make that clear distinction between the two.

4 - Tech Leaders Don't Get Enough Support From Boss and Upper Management

The fourth reason that you never scale up in your role is because you don't get enough support from your boss.

Now I wanna reframe how you look at this though, because if we say, I'm not getting enough support from my boss, then that means it's passive. That means we have no control over it. I wanna change the way you look at this. A lot of times it's because we, engineering managers and technical leaders, we never learned how to lead upward. We never learned how to manage upward. We never learned how to influence our boss. Get them to buy into our ideas and get them to give us what we need from them. This is a skill that you can learn.

But before we talk about that, I want you to think about this. How many times does your boss create issues for you that are unnecessary? Or how many times does your boss take you under their wing and actually help show you how to think of something in a different way and guide you and basically expand your perspective?

I hope you have a good boss and I hope you have a good leader. But unfortunately, in engineering more times than not, your boss is busier than you and they're not gonna be able to take you under their wing in these areas. So you're stuck scrambling to figure these things out on your own. That's why you don't really get any insights into what it takes to advance to the next level. It's a black box. It's confusing.

In many cases, your boss doesn't fully understand what you do and they'll oversimplify what you do. They'll push back on your idea. They won't approve your request for more resources. They give you an unrealistic workload.

When you don't know how to influence upward, you lose autonomy in your role. Ultimately, this creates a ton of extra work and wasted time for you because you're not doing the job the way it should be done. Instead, you're doing the job the way someone else thinks it should be done. In many cases, your boss doesn't understand what you do well enough to even be qualified to tell you the right way to do your job. So you're actually doing it way less efficiently than you should be doing it, and it's because you're stuck carrying out someone else's orders without having any say in the matter.

Back when I was an engineering manager, this happened to me all the time with my boss. He was a good guy. He had the company's best interest in mind. He just didn't know how to do what was best for the company. Our company was experiencing massive growth and when we were smaller, we didn't have that many projects in the system and it was easy to just force things through the system. You knew where everything was, so you could just go talk to John over in, the mechanical engineering division and Hey John, can you just push that project ahead of this one? All of a sudden that one would move through the system faster. We were experiencing massive growth and we were in the middle of growing pains where. Every week we were experiencing more projects and more workload than we were used to, and we were outgrowing our systems.

Our production scheduling system, wasn't really equipped to handle this. I was the engineering manager at the time and I was responsible for managing the production schedule. I had a system in place that was very clunky with, handwritten lists and post-it notes and emails and whatnot. It wasn't a great system, but we were doing the best we could with the tools we had at the time.

My point is, it was a house of cards. It was a very complex, intertwined puzzle where every project was, flowing together. I knew what everyone was working on and how to keep everyone optimally loaded, and there was a lot of things at play. My boss didn't appreciate that. He didn't understand that. He didn't understand all the things that were going on at play. He was still thinking like when we were small.

So every time we got busy and every time there was a a project that in his mind was falling behind, he would come into the engineering department and basically without including me, he would go change the workload priorities for engineers on our team. He would go tell this person to work on this project instead of this one, and then he would do, go do the same with another person. I wouldn't get updated on this either. The engineers on my team, what are they gonna do, not follow the CEO's orders, so it's a tough spot to put them in and they didn't know any better, they just assumed that they were getting the right instructions. This created huge messes for me. We didn't have the systems in place to move projects around like this and stay on top of it. Eventually I had to manage upward and confront him on this and basically get him to understand where I was coming from and get him to stop doing it.

The way I got it got him to stop doing this was by having, a short conversation with him. I basically just positioned it to him like this, I said, Hey boss, when you change around projects in the production schedule like this on me, it makes me feel like you don't respect what I'm doing, or you don't respect what goes into managing the production schedule. We don't have systems in place to move around projects easily, and I spend a lot of time each week, trying to make everything fit and work. When you change it like this on a dime, it creates a lot of issues for me. But I know you don't want to create issues for me, and I know that you have the company's best interest at heart. So can we work together on figuring out how to communicate better in these situations?

So you see, I didn't accuse him of anything. I didn't, go in there like a bat out of hell, telling him why I had a problem with this or whatnot. I just went in there saying, hey, let's work together and figuring out how to make this work better. I acknowledged his good guy identity by pointing out that, Hey, I know you're a good guy. I know you didn't mean to do this. Let's figure this out.

Now this is a skill, having these types of conversations, influencing upward, getting people to disarm their emotions, and open up to hearing what you have to say, this is a skill. I couldn't possibly do it justice in this quick episode, but my point is, without building this skill, you're gonna be stuck. You need your boss to support you in your role to be successful, you need your boss to look at you like you're ready for the next level. You need your boss to look at you and see that you're capable of everything, and if your boss doesn't support you, you know you're not gonna grow in your role and you're gonna be stuck in that position forever.

5 - Lack of Respect from Your Team

Number five is lack of respect from your team. Now, I call this the good guy complex because we think we're being a good guy, but it's actually creating issues for us. Now what do I mean by the good guy complex. You don't want to hurt your team's feelings. You don't want to be the bad guy boss. You don't want to be a jerk. You don't want to give constructive feedback that could offend the other person and get them upset you. You don't want people to get defensive with you either. You're not really comfortable with emotional confrontation either, or navigating difficult conversations.

When your team isn't performing and when your team isn't doing what you ask them to do, you end up picking up the slack for them. You end up doing the work for them, and you end up very indirectly, telling them what they need to do better. This creates a cycle where you know the problem doesn't really get fixed and the people on your team just start walking on you a little bit.

Now I'm not saying everybody. If a few people are doing this on your team, let's say you have eight direct reports and you have two or three people like this, it ends up eating a lot of your time. That work that they're not doing the right way or that's taking them longer to do, that's preventing you from growing in your role because you end up keeping that in the back of your mind.

You're thinking about, how am I gonna get this guy to do this? Can I trust this guy with this project? Can I assign this to them? Or how am I gonna explain to other people in a way that doesn't sound mean? I can't give this work to this guy because he is not qualified.

I had a direct report like this. I had a few of them earlier in my career and I didn't know how to handle it on my own. I had to learn this skill. But I had one guy, he was the nicest guy in the world. Honestly, like he'd give you the shirt off his back. He would always talk to me and ask me about personal questions about me and, my, my personal life, he knew my girlfriend's name and all these things.

He was a really nice guy, and I'll just be honest, he sucked at his job. He was terrible. He was awful. But he was so nice I didn't have the heart to have direct conversations with him about it. I didn't have the heart to basically explain to him like, look man, this isn't working. You're creating a lot of issues on the team. The team is getting really frustrated with you. I'm getting really frustrated with you. I don't trust you to do your job.

I didn't wanna be a mean guy and I didn't want to hurt his feelings. I wasn't comfortable with delivering messages like that. So what did I do? I let the problem linger for way longer than it should have. This went on for about a year, where I basically cringed every time I gave him an assignment because I wasn't sure if he'd even completed on time or how well he would do. Most of the times he was late and he made mistakes and he ended up ticking off all the senior engineers who worked on the projects downstream from him, and then they'd be running behind in their work.

All because I didn't handle these problems head on, and it was because I was not comfortable with having these second conversations the right way. Eventually I'd lose my cool, I'd get so frustrated that I'd snap on him about something or deliver a message the wrong way, which that wasn't effective either.

I'd have these moments of being the bad guy manager because I couldn't handle it. I didn't know how to explain the message in a way that got him to understand where I was coming from.

All this was just consuming my time and my energy and it was just creating a lot of problems throughout the department. Instead of fixing it, I was just managing the problem and enabling it to continue. A lot of engineering managers do this. You have this mindset of it's easier to just do it myself, it's just one time I'll fix this problem for them, or, I'll sweep this under the rug because I don't wanna hurt this person's feelings.

But honestly, this prevents you from scaling up in your role. If you want to get to the next level in your career, you need to develop this skill. You need to know how to have difficult conversations with people.

If this is something you struggle with, you should check out my burnout called How to Deal with Difficult Employees. I'll drop a link to that episode in the description.

6 - Lack of Mentorship for Engineering Managers and Tech Leaders

The sixth reason that you don't scale up in your role is because of lack of mentorship. Somewhere over the last 20 years, mentorship has gone by the wayside. In the old days, it was standard practice for new engineers to get paired with a mentor when they started in their role. Likewise, when you moved into your first leadership role, you had a leader mentor. Someone that was a higher ranking leader in your company, they would take you under their wing and teach you how to build these skills.

Maybe they'd have book clubs with you, where you'd read a leadership book together and review the takeaways and how you can put these things into action. Or, they would sign you up for a leadership training program and they would, ask you how it was going along the way and make sure it was working. They would let you shadow them in certain meetings so that you could see how they led their team.

It was a very organic but effective way at developing these leadership skills. And now companies don't do that. It's very rare where companies have mentorship training programs anymore.

A mentor is the fastest way to develop these skills. They basically show you your blind spots. They show you how to shortcut through the obstacles they faced. They help you look at things from a different angle and, give you a different perspective that you don't have. It's a close personal relationship that really just accelerates your growth in these areas. Without a mentor to show you the ropes on these things, it makes it nearly impossible because you have to figure out how to do all these things on your own. Meanwhile just retracing all the problems we've already discussed in this episode, you don't have the time for that. You don't have the energy for that. You're burnt out. You weren't formally trained in these skills. Without a mentor, it's really hard to learn the skills you need to be effective as a leader in engineering.

7 - Poor Relationships with Cross Functional Teams

The seventh and final reason that you don't scale up in your role is because you're not getting the support you need from cross-functional teams. All the engineering managers and the technical leaders I've been talking to, they tell me about how other teams just basically throw it over the wall or throw it over the fence at you.

What I mean by that is, they give you incomplete handoffs. They don't deliver stuff on time to your team. They don't match the quality and the accuracy that your team needs to do their job. So you're stuck being a detective. You're stuck searching for the common source of truth.

You're trying to find the facts and the details that you need to do your job, and you basically can't do your job. You're held up. Here's the paradox, the engineering managers like you who are watching right now, engineering managers that take pride in your work and want to do it right. Have good ethics. Have good character. You're not gonna let problems slip through the cracks.

So guess what? That responsibility now falls on you to go get it done, right? You end up absorbing more workload. You end up taking it upon yourself to get this done right, even though it's not really your responsibility to make sure other teams do their job. But this is what happens, by having good character, it's almost a punishment. What happens is instead of actually fixing the problem, you end up absorbing the problem and that's a huge problem in itself. You can see why everything we've been talking about here is intertwined. Lack of time, lack of energy, lack of support from your boss, lack of support from cross-functional teams. All these things, you're just absorbing all these things and you're absorbing all these problems from other areas and it prevents you from scaling up in your role.

The solution is, figuring out how to effectively push back on these other teams. Figuring out how to set boundaries with those teams and put the problems back where they belong. I'm not talking about not pitching in to offer help. I'm not talking about purposely letting mistakes, slide down the cracks. But leading cross-functional teams, especially when you're a manager, leading peers and influencing them, this is probably the most important skill you need.

Besides influencing upward, this is the most important skill you need to advance to the next level of your career because it shows that you know how to lead leaders. You know how to lead leaders that you don't have authority over.

So if you don't know how to lead other leaders, and if you are constantly absorbing their crap, you might think you look like the good guy. You might think you look like the hard worker who's, got the company's best interest in heart and, you know what? You might look like that, but that's not gonna get you to advance to the next level. What's really gonna get you to advance to the next level is figuring out how to push back assertively, how to set boundaries, how to put the problem where it belongs, how to build relationships with those teams so you can get them to actually want to give you what you need and to get them to want to deliver high quality work to your department.

These are learnable skills. Everything we've just talked about really boils down to a few things. One, you need to know how to influence people. You need to know how to influence and understand all types of people so you can speak their language, communicate in a way that's compelling to them, and get them to buy into your ideas and win them to your way of thinking and influence their decisions to work in your favor.

Those are skills that you can learn, but you can't do any of that unless you know how to build relationships with people. Build genuine, meaningful relationships with people because when people like you, they're more willing to help you and they're more willing to, overextend for you and they wanna see you succeed.

There's a science behind this, that's a learnable skill. And if you wanna learn how to build relationships with anybody, you should check out my YouTube episode called How to Quickly Build Relationships With Anyone. I'm gonna include a link to it in the description, and you'll also see it pop up in a second. Thanks for watching.

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