How to Deal with Difficult Employee as a New Manager | Advice for Engineering Leaders

When you're a new manager, handling a difficult senior direct report can be very intimidating, especially when they have way more experience and expertise than you.

But there's a really simple way to change the dynamic of your relationship with them, and I'm gonna show you how.

Stay tuned.

Hey everyone, I'm Doug Howard, and welcome back to my channel. If you're an engineering leader looking to enhance your leadership skills, then you're in the right place because in today's episode, I'm gonna teach you the most efficient and effective way for you to find common ground with a difficult senior level direct report.

But before I get too far, make sure you hit that subscribe button and make sure you ring the notification bell too, because I wanna make sure that you don't miss any valuable insights on how you can increase your impact as an engineering leader. 

The longer you're a manager, the more likely it is that you're gonna have an extremely difficult employee to deal with and dealing with someone who has more experience than you is a whole different animal.

Why Are Difficult Direct Reports so Difficult?

But before you can fix the problem. You need to understand why people act difficult towards you in the first place. Sure, there are some people who are extremely difficult to deal with no matter what, but in most cases people aren't difficult. They're just different, and that's where it usually begins.

You see, it could be any number of things. Maybe they think differently than you, or maybe they have a different set of ideals or core values, or maybe your way of doing something is just creating issues for them and you don't realize it. I could give you 1000 different scenarios, but the point is, when you feel like someone is being difficult with you, the situation typically stems from different perspectives.

Now, this might sound painfully obvious, but the reason I'm pointing this out is that usually the problem starts from something very small and barely noticeable, but then it escalates over time. It could start as a minor difference of opinion, but then grow into something bigger, and eventually it alters the other person's perception of you which makes them believe that they are even more different than you, and it puts up an even bigger wall for you to climb over when you're trying to bridge that gap. 

How I Dealt With a Difficult Employee as a New Manager

This happened to me shortly after I became an engineering manager. One of my direct reports was a senior engineer with over 30 years of experience. Meanwhile, I hadn't even turned 30 years old yet.

I'm not gonna lie. Managing a person with that level of knowledge and experience was pretty intimidating at first. And it didn't help when he'd aggressively pushed back on me every time I reviewed and red marked one of his projects.

Instead of spending 10 minutes to pick up my requested changes, he'd spend at least an hour writing out lengthy, cynical notes next to each one of my red mark comments. All of them were always explaining why he was right and why I was wrong. 

From there, I had to take the time to read his comments, then go back and forth to gain consensus with him before wrapping up the project. This was becoming a major time suck and something had to change. I couldn't let this go on. 

Needless to say he was testing my patience, and if you feel like you struggle with patience in these scenarios, you should check out my episode called Three Powerful Techniques That Will Improve Your Patience and Focus. I'll leave a link in the description. 

Figure Out Why Your Direct Report is Acting Difficult

But getting back to my story, I was considering giving him direct orders with clear consequences, but I felt like that would only make the situation worse given that he wasn't really handling my directions very well so far. I couldn't afford to lose this employee either. So I didn't wanna tick him off.

So I had to figure out a way to make this work. So instead of, you know, bulldozing him, I took a step back and considered his perspective as a senior level employee. 

I thought, well, if I were him, I probably wouldn't enjoy my work being challenged by a rookie manager who's half my age. In fact, it would probably make me feel like this person doesn't really recognize my seniority or appreciate my expertise or understand the unique value that I'm bringing to a table, and that would be pretty insulting if I were in his shoes. I'm not gonna lie. 

When Dealing with an Employee who Wants to Run the Show, Lead with Appreciation

So now that I understood the problem and why he was acting defensively, I could take a different approach in resolving it. Instead of emailing him the red marks on his next project, I scheduled a meeting for him to review the project with me. 

Here's how I approached him in the meeting. I told him, Hey, I appreciate all the feedback you've been giving me on the drawing checkprints, over the last few weeks. I've been learning a lot from you, and I wanna use this meeting to help me get on the same page with you so that we can get your projects moving through the system smoothly with minimal design changes.

I led the conversation this way to let him know that I appreciated his expertise and to show him that I wanted to understand his perspective. So I walked through each of the red marks on the drawing just like this. I was saying phrases like, can you help me understand why you did X, Y, Z this way? I probably would've done X, Y, Z this way, but can you show me why that wouldn't work? I'm sure you already considered this, but why isn't X, Y, Z done this way instead?

Now, when we went through each of those scenarios, sometimes his way was correct and other times my way was correct. Most times both of us were correct and it was simply a matter of personal preference, but instead of playing an egotistical game of tug of war, we were working together now. We were gaining mutual understanding and we were building rapport with each other. 

This Was The Solution to My Difficult Direct Report

I did this with him one time, but here's the most interesting part. Our relationship permanently changed for the better after this conversation. He stopped aggressively pushing back on things, and he became even more open to receiving my constructive feedback. Whenever there was a disagreement, he calmly explained his rationale. Then we worked together to figure it out and we'd learn from each other in the process. 

This was the first time that I intentionally used soft skills and empathy over hard skills and logic to influence the situation to work in my favor as a manager. But after seeing the impact that this approach had on saving time, energy, and stress, I was hooked. I started looking for more ways to use influence to my advantage on a daily basis. 

My Advice for Dealing with Difficult Employees as a New Manager

But if you're struggling with a senior level direct report, here's my advice to you.

Start by challenging yourself to understand their perspective. It's very easy for us to assume that they're wrong and that you are in the right, but don't look at it that way. Before you approach them challenge yourself to view the situation in their eyes and consider how you would feel if you were in their shoes.

When you do eventually approach them, do it with the genuine intention of trying to understand their perspective and understand where they're coming from. Don't try to correct them and don't try to explain why their way is wrong or why your way is right. Just focus on having a curious mindset towards learning why they see things differently than you.

You can show them this by asking questions like, how do you think this should be done? Or, what do you think is the right way to do this? Start by asking their opinion. 

Then when you want to interject your opinions and your ideas, do it in the form of a question. Ask questions like, do you think this would work too? Do you feel like this is a good option? Would you be okay with doing it this way? Doing this in the form of a question is so important because you're keeping the communication line open instead of drawing a line in the sand, which ultimately prevents you from having any chance of influencing the person.

If you want them to change something they're doing, propose it as a question and propose it as a temporary trial period. Definitely don't make it sound permanent. You wanna make them feel like they can always go back to the old way, because a lot of times, senior level employees are stuck in their ways and they're not automatically open to new ways of thinking. So you want to make it feel like it doesn't have to be permanent on the front end when you're trying to open them up to it. 

You can do this by saying phrases like, I'd like to try it this way on the next three projects, and if it doesn't work, we can go back to doing it the old way, would you be okay with that? When you do it this way, now it's an agreement that both of you are working on together. 

If you wanna learn how to take this further, you should check out my episode called How to Quickly Build Relationships with Anyone. 

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