The Top Delegation Challenges Engineering Managers and Tech Leaders Face (and How to Overcome Them)

The biggest reason engineering managers and tech leaders never scale up in your role or advance to the next level of your career is for one main reason, and it's because you never learned how to effectively delegate.

This is the key to creating more impact from your time as well as literally creating more time. If you wanna learn how to develop this critical skill.

Stay tuned.

Hey everyone, and welcome to my YouTube channel. If you're new here. I want to quickly introduce myself. My name is Doug Howard and I'm a leadership coach for engineers in tech and in engineering. What I really specialize in is, helping you guys increase your impact by teaching you soft skills and helping you combine EQ with IQ.

I don't wanna waste any time. So today's episode we're gonna talk about tips on how to improve at delegating, and I'm also gonna talk about the main challenges that prevent you from delegating in your role, along with how to overcome them. I wanna start by explaining why delegation is a critical skill that every leader needs to master.

Why Delegation is a Critical Skill Every Leader Needs to Master

The first main reason why it's so important is because of career advancement. So many engineering managers and technical leaders reach out to me, DMing me, or commenting on the YouTube channel episodes, and they ask me, how do you break out of middle management and how do you advance to the next level in your career?

They don't understand, what this relationship is between not being able to effectively delegate and then being trapped in this cycle where you don't have enough time to get everything done. What they're not realizing is if you don't delegate, you're not really a manager. No matter what your title is, you're just a glorified individual contributor because all you're doing is really taking on more tasks and you're not empowering anybody on your team.

Career Advancement Doesn't Happen without Delegation

The reason I'm explaining all this is because in order for you to advance your career to the next level, you need to prove your ability to the higher ups on how good you are at creating more impact from the people on your team. Optimizing your people on the team. When you're an individual contributor, it's all about optimizing systems and processes and how you complete tasks.

But when you move into the higher level role, it's not so much about task performance, it's about how do you get your people to perform. How do you optimize them, and how do you manage your time? But it's not, how do you block time off to get more done with your time? It's how do you reallocate your time and your resources to get more impact from everyone that is in your influence radius.

I'm not just talking about delegating to your team, but I'm also talking about delegating upward and delegating cross-functionally, and offloading tasks. But before I get into the hows, I just wanna emphasize that, delegation is a critical skill that you need to advance to the next level in your career. If you don't develop this skill, you're gonna stay stuck in middle management forever. It's gonna be really hard for you to create that time that you need to keep investing in your personal growth, to get more done. To focus on contributing at the higher level, thinking about strategic initiatives like growing your team and how you're gonna increase your capacity.

Time Management vs Multiplying Your Time

Now that leads me to the second reason why delegation is critical to your success as an engineering leader, and that's because you need to be able to delegate to be an effective time manager, to be in control of your time. Every engineering manager I meet always tells me I don't have enough time.

And I'll be honest, it's true. You don't have enough time. We're all locked with the same 24 hours in a day. That's no secret. Engineering managers have a ridiculous amount of responsibilities, and they range all over the place. 

You wear a million hats. You need to support your team and you have strategic planning initiatives. You have to develop the people on your team. You're usually tasked with, staying on the cutting edge of innovative technologies and automation. Then also you're expected to provide support to cross-functional teams, like sales and manufacturing and answering questions for them.

You're pulled in a lot of different directions and everyone thinks, their priorities are asap. They need your help now. And it's more important then what you're working on, at least that's how they feel. So they're just constantly in your ear. Your inbox is always flooded. You don't have enough time to get everything done.

One of the main ways to gain time back is through delegating. You wanna start by delegating routine tasks and lower priority activities, because this frees your time up to focus on high impact tasks that contribute directly to your team's success. You're gaining time back through efficiency and innovation. 

Delegating tasks, allows you as a manager to tap into more diverse perspectives on your team. When you don't delegate, you are doing things just the way you know how to do it. You're getting a very localized opinion. You're not getting the best solutions. You're just going with your way. Don't get me wrong, your way might be great. But usually when you delegate something to someone else, you find out that they have a better way of doing it. You just didn't give 'em a chance to explore and to learn. I just wanna connect delegation with this idea of diversity. You're pulling more opinions in, you're pulling more ideas in. Usually that leads to a better solution or a better means and methods versus the way that things are currently being done. 

As I'm talking about that, I want you to just think about back to when you were an individual contributor. What was the most frustrating part of being an individual contributor? It was when you'd go to your boss and ask, why do we do something this way? And then they'd tell you, because that's the way we've always done it. And they wouldn't explain to you the why behind the process. They would just tell you to do it this way. You hated that when you were an individual contributor. So don't be guilty of being that type of manager now that you're in the role. 

This is why we fall into as trap. We fall into as trap because that's the way we're led when we are in the individual contributor seat. We don't really know any other way unless we're taught how to do these things differently, as a leader when we get into the role. 

Moving on, when you delegate, you get better at utilizing the skills of everyone on your team too. You gotta know your team really well. Know what their strengths and their weaknesses are, as well as their interests. Where are they looking to grow and where are they capable of growing? When you're crystal clear on these things, then you shouldn't be afraid to delegate because you're gonna create more efficiencies by getting the right tasks in the right people's hands.

What I mean by that is, we all have a diverse set of strengths and weaknesses, and some people are better at other things. Some people enjoy doing things that you hate, right? So don't be afraid to delegate just because you think that's a mundane task. Someone else might actually enjoy that task or they might find it, a relief to have something that's a little bit more monotonous. We're all different. We're all wired differently. Don't take it as a given that, everyone looks at these tasks the same way that you do.

The other part of this when you're delegating is that you're giving the team an opportunity to feel like they're stepping up and they're contributing more. They're getting a chance to showcase their unique skills. You're not just gaining your own time back, but you're creating a more positive morale for other people on the team because they feel like they can take ownership of something. They feel like they can contribute to something more. 

Just like you want to contribute to something more at a higher level. You wanna take on more responsibilities for your boss. There's a circular thing going on here. It's a collective, always try to remember what were your thoughts when you were in that individual contributor role and, did you want more responsibilities? Were you frustrated because your boss wasn't giving you more responsibilities? Put yourself back in that old you's shoes, if that makes sense. The old you's shoes say that three times fast. 

The other part of this with efficiencies and time management, by delegating, you're reducing burnout. Where I'm going with this is, if you're burned out or if people on your team are burned out, you're not producing at your best. You might be putting 10 hours a day in, but how productive is that time really, how much results and output are you getting from that time? If you're burned out, if your team's burned out, you're not doing anyone favors by putting in more hours. Your work gets sloppy and you're making more mistakes. We all are guilty of this too. The more behind we get, the more we think we need to put in more time. That's where delegation comes in, again.

By distributing tasks, you can prevent burnout amongst yourself and amongst your team because you're reallocating the work where it belongs. You're making the workload more manageable, which improves job satisfaction and just overall mental wellbeing for you and everyone. 

Developing Your Team, Reducing Risks, and Creating Scalability 

The third area of why delegation is so critical for engineering leaders and tech managers is because you need to develop your team. That's your number one job. When you really take a step back to think about it, as a manager, your job is to develop your team. The more your team grows individually and collectively, the more you're gonna grow and the more you're gonna advance and the higher you're gonna go. Like I said before at the beginning with career advancement, the higher ups, they're looking for the people that know how to optimize people. They're looking for the people that know how to get the most out of people, how to get more impact out of people. 

You should keep this at the front of your mind as a leader at all times. Am I developing my team? If I'm not, that means you need to take a step back and figure out what things can I delegate as a tool for developing my team. Because when you're delegating tasks to your team, it basically creates opportunities for them to stretch their skills and for them to learn new things. They enjoy taking on more responsibilities and all of this leads to personal and professional growth for them, which is essential for retaining the top talent and building a strong team.

This is something that's a big challenge throughout engineering right now is employee retention and losing your top performers because there's a big shortage of engineers right now. There's just not enough engineers to fill these roles. So you're seeing a lot more companies get more competitive with trying to poach your people and lure them away with higher salary benefit packages that your company maybe can't match right now.

Where I'm going with this is by making sure you're delegating, the people on your team, you're making them feel engaged and you're letting them know that you're trusting them. You're investing in their personal and professional growth, which a lot of times that's more important to people than money. That's going to make sure that your top performers are staying put versus looking somewhere else to go.

When you're doing this and you're making sure that your team feels engaged and like they're growing, that improves your team's continuity, which in turn improves your team's scalability. When you're delegating, you're making sure that knowledge isn't concentrated in a single place, which a lot of times, it's you.

Delegation basically guarantees that knowledge isn't concentrated with a single person. This happens all the time at engineering companies, and it happened at a lot of the companies I worked for where there's a specific person who knows how to do a specific thing and they're the only person that knows how to do it. Then it's basically just tribal knowledge.

The longer that goes on, the harder it is to capture that knowledge. What happens if that person leaves or retires or becomes disgruntled and doesn't wanna share that information. You lose it. There's no documentation or anything. But by delegating responsibilities out, you're spreading that knowledge and you're also lifting it. If it's something you're delegated or if you're having a senior on your team, delegate their knowledge to a junior, the way that current person does, it might be a great way of doing it, but there's always ways to make things better. By passing that down to someone else, you're basically getting the best ideas involved. 

The main point I wanna make about all this, if you're an engineer, spreading the knowledge like this, it reduces your risk, by involving multiple team members in various aspects of a project or process. It makes your team more resilient to risks. Sometimes there's these things that are beyond your control. So you never want to be, limited by a critical point of people. Obviously people can leave and quit. But the other part of this is what if upper management tells you that they're restructuring your team? They're gonna take these people away and move 'em to a different role. You don't want to have one person that's the only person that knows how to do this. 'cause that'll handcuff you, that'll handcuff your team's growth and your growth.

Why Engineering Managers and Tech Leaders Struggle with Delegation

Now these are the reasons why delegation is critical to your success if you're an engineering manager or a technical leader. But a lot of times, we struggle with delegation and it's for several reasons. And you can't really fix the problem if you don't know what the cause of the problem is. I wanna just go through some of the main reasons why we struggle with this, and these are the most common reasons why that I've encountered over my career and with all the engineering managers and technical leaders that I've managed and worked with in a client-based relationship.

#1 - Lack of Training on Delegation

The first reason is quite simply lack of training. Delegation is a skill and just like any skill, it needs to be learned and developed and practiced. If you don't learn it, you won't just automatically get better at it. 

A lot of engineering managers, struggle with this. Your manager didn't do delegation well, so you never learned how to do it well. Then when you get into a manager role, you don't do it well. And then the next person who, who replaces your role, who that you train to replace you, they don't learn it well. There's this kind of cyclical effect of engineering leaders don't naturally learn soft skills like delegation. So they don't teach these skills to their team.

What happens from there is when you're in a manager role, you don't have confidence in your ability to delegate. Just think about this for a second. A lot of the times what's holding you back is you're just not sure if this is something you should delegate or not. You're not sure if you feel comfortable with telling this person, Hey, I want you to take this thing on. It's because you've just never learned this skill. 

#2 - Catch 22 - Not Enough Time to Delegate

The second big challenge is lack of time. This is one that all engineering managers can relate to. It's ironic that one of the reasons that managers resist delegation is because they feel like they don't have enough time to train or oversee their team members when they're trying to delegate.

I just wanna point out that, this is a short term mindset. This is a short-sighted way of thinking, and it prevents you from realizing the long-term benefits of delegation. What happens is, you get into this cycle where you feel like there's not enough time to delegate this task. There's not enough time to invest in my skills. There's not enough time for this, there's not enough time for that, and then all of a sudden that becomes such a habitual way of thinking where you just default to saying, I don't have enough time for this. You stop to consider if this is something you can actually delegate.

This lack of time trap, and don't get me wrong, that's a limiting belief. I know you're busy and I know you have a ton of responsibilities, you don't need me to remind you of that, but you can always make time for the things that are important. You should always make time for the things that'll have more impact on you.

#3 - Wearing Multiple Hats and Task Switching Hinders Delegation

The next main challenge is task switching. Now, let me explain what I mean by this. When you move from a technical role into a leadership position, this means that you're juggling a wide range of responsibilities. As a manager, you might find it challenging to delegate because you believe it's quicker for you to just complete the task yourself, and it's quicker for you to do that than to explain it to someone else.

I hear this from all engineering managers. It's just faster if I do it myself. You're right, in the short term today, in this moment, it is faster for you to do it for yourself. When you think this way, nothing will change, because that means, oh, I always have to do this in order for it to get done. That just means that all you're gonna do is absorb more work. As you grow and as your team grows, as and as capacity grows, you're not gonna grow in your role because you're basically creating a handcuff on yourself. I need to do this every time it comes up because that person is incapable of it.

Now as we continue going through this list, you're gonna notice that a lot of these areas I'm talking about require going outside of your comfort zone. If this is something you struggle with, I want you to check out my episode called How to Get Comfortable with Going Outside of Your Comfort Zone.

#4 - Shifting From Technical Expertise to Leadership Mindset

Moving on, the number four reason why most engineering managers struggle with delegation is because of technical expertise. What I mean by this is, engineering managers and technical leaders, you get promoted into your positions because of your strong technical skills.

You were most likely a top performer back when you were an individual contributor. However, when you transition into managerial roles, you end up finding it difficult to switch from the hands-on technical tasks to entrusting other people to do it the way that they like to do it and still get it done.

This is a tough mindset shift that you have to make because as an individual contributor, yeah, you want to be a doer. You want to be a person that's capable of doing all these things. Then when you get into this leadership role, you all of a sudden feel like, you're not as valuable to the team if you don't know how to do these things, or you're not contributing as much if you're not physically doing the task.

I'm just curious, can you relate to this as you're watching this? If you can relate to this, give this episode a like, or let me know in the comments if you can relate to this. 

I know that this is something I struggled with. After I moved into a manager role, I had been working in the industry for five-ish years at this point, and I was a top performer as an individual contributor, and I had all my own systems that I made. I had my own templates for things. I had my own Excel spreadsheets, I had my own formulas. I had my own behind the scenes systems. We were a very small tribal knowledge company, but then we were growing and when I started hiring more people on board, a lot of them were coming directly out of college and they were more comfortable with newer technologies than I was. 

I had this, reluctancy to allow them to do it their way because I wasn't really clear on how that technology worked. I was more comfortable with doing these things by hand, doing hand calcs and whatnot and doing my analysis that way. I didn't really trust the software, so I had a tough time delegating these things to these younger guys who just came aboard right outta college because, it was basically like a foreign object to me. I really had a negative impact on them upfront. 'cause I tried making them do it my way. 

I tried taking them out of their natural habitat and learning how to do something that they had never done before. They really struggled with that. They didn't know how to do it my way and it didn't really come natural to them. Finally I realized that I hired these guys to increase the capacity in the department. I hired these guys to take work off my plate, and if they're not naturally figuring out how to do it my way, then maybe I should reconsider how we're doing things.

This is a tough mindset shift to make because as engineers, we have confidence in our methods and our means. We stand by our way of doing things. But as a leader, it's a little bit different. It's not about your way, it's about the outcome. It doesn't need to be done the way you do it, as long as you get to the right outcome that you're trying to achieve. That's a little mindset shift you wanna make.

#5 - The Perfectionism Paradox

Now this leads me to number five, which is perfectionism and I haven't met an engineering manager or technical leader who isn't guilty of this. We have these high standards that we hold ourselves to, and then in turn, we end up holding everyone to these standards, no matter how unrealistic these standards are

It's a good thing when you're an individual contributor because you wanna make sure you're paying attention to the details, and you're not missing anything and you're dotting all the i's and crossing all the T's. When you're an individual contributor, you'd rather err on the side of perfectionism versus sloppiness. 

But when you get to be a leader, perfectionism can really hold you back because it's really subjective. Are you being a perfectionist in the sense that things need to be done for a quality and accuracy perspective? 'Cause that's important. But on the other hand, are you being a perfectionist because you just want to see things done your way? There's a huge difference between those two.

If you're an engineer who struggles with perfectionism, I challenge you to take a step back and just think about are there other ways that are acceptable for this work to be done? Instead of just assuming it needs to be done this way and this person can't do it this way, take a step back and consider, are there other ways to do this? Are these ways, okay? Are these ways good enough?

#6 - Trusting Your Team to Do Things a Different Way

Number six is trust issues. Do you trust your team? Delegation and delegating tasks, this requires trusting your team members' abilities and trusting them to take risks. Letting them know that you trust them to take a chance and, fail. 

As far as why you struggle with this, if you're an engineering manager, is feeling like you don't have the confidence in your team's skills, or you have a fear that it won't be done the right way or completed to your satisfaction. A lot of times, we don't like relinquishing control.

Don't get me wrong, you can't just delegate things blindly. You can't delegate things to people who you don't trust. But if you are not trusting someone on your team to delegate a task to, consider, do you not trust them because they haven't earned your trust? Or do you not trust them because you haven't given them a chance to earn your trust? Those are two different things. 

Another thing I wanna point out there is, you can't expect perfection right away when you're delegating something. Maybe you gave someone a chance one time and they didn't hit the ball outta the park. They didn't hit a home run. They struck out, that's on you too. That doesn't mean that they're incapable. It just means maybe you gave them too big of a task upfront, or maybe you didn't give them clear enough instructions. I want you to take ownership of these things instead of blaming on the other person. 

The thing I wanna point out here is this is why it's really important to build close relationships with your team so that you have a good understanding of what their personal strengths are and their weaknesses and their interests. You need to trust your team and show them that you trust them and make them feel like you trust them. That trust will be returned to you as well.

#7 - Weak Communication Skills Prevent Clear Expectations

The seventh reason why engineering managers struggle with this is communication issues. Effective delegation requires clear communication about expectations, timelines, and outcomes, processes, boundaries to stay within all this stuff. You need to be a good communicator.

If you struggle with communication skills or if you don't trust your ability to communicate clear expectations to other people, it's gonna make you hesitant to delegate out of fear that you won't be communicating clearly and that your message won't be received accurately. 

If this is something that you struggle with, you should definitely check out my episode called How to Make Sure People Listen and Understand You, because I give you a framework for how to do this technique called empathic listening, where you make sure that your message is received and heard, and it gives you a chance to clarify that through roundtrip communication. So definitely check that out.

#8 - Tech Leaders Worry ABout Relinquishing Control

Moving on to the number eight reason why engineering managers and technical leaders struggle with delegation is control concerns. I think you might be sensing a theme here, right? Like I said earlier, some managers just struggle with relinquishing control.

As engineers, a lot of times we are creatures of comfort. We like knowns, we don't like variables, we don't like unknown variables, and we don't like risks. By relinquishing that control and handing something over to someone, it makes us feel very uncomfortable. We feel uncomfortable with not being directly involved in every aspect of our projects.

We fear that we're gonna be losing influence over our ability to jump in and fix something when it goes wrong. We're afraid that something's just not gonna work or it's gonna become unfixable or it's gonna have a irreversible consequence.

But if you want to grow in your role as a leader, and if you want to grow in your team, you have to get over this fear because the only way you're gonna grow in your role is by learning how to be comfortable with relinquishing control in certain areas. You want to do it in gradual steps. You don't want to just, toss it over the fence, blindly. I'm not proposing that, but I'm just saying you have to figure out, what are safe initial risks that make you comfortable with it first? What are smaller steps you can take first that are in route to delegating the bigger task you're trying to delegate?

#9 - Engineering Managers Don't Want to Be Perceived as Dumping on Their Team

Moving on to number nine, fear of rejection. 

Now this is a big one, believe it or not. I'm curious if you can relate to this. Some managers worry that by delegating a task, you're essentially passing the buck and letting it roll downhill. You're worried that your team is gonna perceive you as basically ducking your responsibilities and dumping it on them. 

I made this mistake all the time when I was a manager. When I first became a manager, I should say, I hated it when I got dumped on. There's a difference between dumping and delegating, but I hated it when, someone gave something to me with unclear responsibilities and unrealistic timelines.

Somewhere along the way I associated that with delegation, which are two different things. Delegation is teaching and coaching and creating safe bounds and empowering someone else to develop skills. Dumping is just throwing something over the fence at someone without really giving realistic expectations.

I didn't distinguish the difference between the two when I first became a manager. I had this, reluctancy to be the bad guy. I didn't want to be the manager that was dumping on my team. I wanted to be the good guy manager that was relatable and that supported my team and took on, more challenges for them and, protected them from the drama and the BS work. That was my identity as a manager. My intentions were coming from a place of wanting to support my team, but, when I did this, all of a sudden I didn't have enough time to actually support my team because I was constantly putting out fires and I was absorbing my more workload. It was preventing me from actually doing what I wanted to do.

I became a manager because I loved developing people. I loved growing my team. I loved, working with my people and empowering them. All of a sudden I wasn't doing that 'cause I was just absorbing their problems. Then they put me in this unique situation where, all the problems in the company were coming at me from every direction. My team was pushing it up to me because I created that relationship. My boss was dumping it down on me and then cross-functionally, other teams were dumping it on me too. Because if other departments were slowing up my team, I would just end up fixing it because I didn't trust the other cross-functional teams to fix these problems.

Where I'm going with this is, no one wants to be a bad guy. No one wants to be a jerk. But at the same time, you gotta be careful because if you end up absorbing other people's problems, you can't really ever do your job effectively. You're actually hurting your team more than you're helping them.

#10 - Personal Recognition

The 10th and final reason why managers struggle with delegation is because of personal recognition. 

Now, I don't think this is a challenge for too many managers, at least I hope not. It wasn't a challenge for me, but I have picked up on this from some people I've been talking with. The idea that when you are an individual contributor, it's pretty clear what your role is in the project. You accomplish this aspect of the project and your technical skills are seen and you basically get that acknowledgement from other people. When you're in a managerial role, and if you are delegating, then all of a sudden it's not crystal clear what your contribution was anymore.

You get worried that you're gonna be perceived as irrelevant by the company. You're worried that the company isn't gonna see the value you're bringing to the table. It slows you down from offloading tasks because you still want to feel important. You wanna feel like you're bringing value. You wanna feel like you're irreplaceable in a sense.

It's okay to have these feelings. I'm not dismissing that, but you gotta be comfortable with making this mindset shift from doing to delegating. The company will see that you're having a bigger impact on your people by offloading these things. The directors, the executives, they're looking for people that aren't doers. They're looking for people that get more out of people, so they'll recognize these things. Try to get over that mindset block there. 

These are the 10 biggest challenges that prevent engineering managers and tech leaders from scaling up in their role and it's all related to delegation. 

To overcome these challenges, you should focus on proactively developing your delegation skills because this is a skill that you can learn and get stronger at. You wanna do this by building trust within your teams. Consciously recognizing the long-term benefits of empowering your team members to take on more responsibilities. Delegation isn't just about offloading tasks. It's a critical leadership skill for fostering growth and collaboration and innovation.

You need this skill to advance to the next level of your career too. If you're realizing that you need to improve in this area, but you're not sure where to begin, you should watch my episode called How to Embrace Delegation.​

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