Know When To Fire An Employee

Episode 39

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Robert: In this episode of The Stretch Goals podcast, Scott and I are going to be talking about, is it time to fire your employee?

This is The Stretch Goals podcast, where each week, we’ll share insights and lessons learned, based on our experiences as entrepreneurs. We’ll challenge you to create ambitious goals as you start and grow your business. I’m your host, Robert Dickerson.

Scott: And I’m Scott Davis.

Robert: Scott, I wanted to talk about this week, is it time to fire your employee? Some reasons that you might tell if it’s time, if they’re not doing good work. Maybe they are doing good work. I just wanted to share an experience that I just had where I had to actually get rid of a contractor. It wasn’t necessarily because he wasn’t doing the greatest work.

I’ll just tell you the story and then you can give me your feedback, too, and share your experiences. I hired a contractor to help me with some front end development. He passed all the different tests that I put him through. I hired him. He started.

I went through and listed out exactly what I wanted done. It was pretty detailed, actually. He started out doing the work. The work he was doing, it was okay. He was getting the work done, but he wasn’t seeing the entire picture of what I was trying to do. He wasn’t testing all the different paths that needed to be. He was just doing exactly what I told him to, and nothing beyond that.

I was trying to figure out, maybe I’m doing something wrong, in terms of how I’m telling him to do something. I’m telling him exactly what to do. He wasn’t really thinking, larger term, about what actually needed to be done and what, from a customer point of view, what they were looking at, in terms of this feature.

I thought it would be interesting to talk about. I had to let him go, because it wasn’t really working out. I could tell. I want to get your insights on this. Do you think it was something where I wasn’t giving him the bigger picture? Maybe I should have given him more time? I felt like it wasn’t working when we started out. Usually, that gut instinct is right, for me. It has been in the past, at least.

Scott: Sure. A couple questions for you. Was this a side gig for him? Did he have a nine to five and he was doing this on the side?

Robert: Yeah. It was side work for him.

Scott: That was my initial take. Generally, what happens is when you’re working with somebody on a freelance basis, and they’re working on something on the side, their creative instincts, and their desire, and their passion don’t get 100% invested in to what you’re doing. They’re doing it in their spare time.

Maybe initially they liked the idea. They’re like, “Oh, man, this is great. You should try this and do this. Oh, I’m going to test this feature because it looks like it’s broken.” After a couple weeks, that starts to get old. You’re not playing video games or you’re not watching football because you’re working on this other thing that you committed to. Your interest in all that stuff start to fall. Then you only do what you’re supposed to do, which is be a C student, which is get these features done. It happens all the time.

Robert: I was going back and spending so much time fixing stuff. It got annoying. It’s like, why am I doing this? All the other people I’ve hired have been really good about making suggestions and being really interested in the work that I’m trying to do.

While we’re going to talk about employees, I think this also applies to contractors, as well as anyone you’re working with. When do you make that decision to cut them and go forward in a different direction?

Scott: Sure. This doesn’t necessarily have to be related to somebody who was doing a project on the side. Like I said in my question to you, was this a side gig thing? It happens all the time, regardless.

If you’re a full time employee, maybe you just don’t have the drive. Your idea of a job is to do what you’re asked and never go above and beyond. Those are the people that end up being bottom feeders their whole lives, or they get stuck in the middle of the pack. They never get cut during a reduction in force, but they never get promoted, because they’re not great. They hover in there. Like I said, they’re a C student.

There’s a lot of that. You’re paid to do a job. You do only your job. You don’t ever see yourself outside of that box. Not everybody is an entrepreneur, or a creative, or has a lot of initiative, like we do. This is a common problem.

It happens in every industry, not just software. It’s just a matter of who you are as a person and your character. Are you going to go above and beyond or are you just going to do what’s asked of you?

Robert: Yeah. I mean that’s the direction I wanted to take this episode is more of, your employees are doing an okay job. They’re kind of doing that, but when’s the right time to let them go, even if they’re doing the level of work you requested and they’re not going above and beyond. Maybe some ways that you can get people to get more invested and to go above and beyond.

I know we talked about this before is, that accountability and that connection with the customer, with that larger vision. In my specific instance, I felt like maybe by breaking the problem down into these small task, I wasn’t giving them the perspective of what we were trying to do, the broad vision.

They weren’t really … Even though they were contractor … When I work with employees as well. You want to get them bought in to the vision of what you’re trying to do. When you’re hiring people, you’re really selling them on that vision. You want to get them to buy in and be interested, because if you can get that buy in and interest, that’s when people go above and beyond and they understand the implications of what you’re trying to do. When they’re connecting with your customers, then they are personally involved in success or failure of your company.

Scott: Yeah. I think in your scenario, I don’t think it’s anything you did. I think it’s just the person that you were working with. I think if you can paint a picture as to what the vision of a product is, and, “Hey, go get this job done,” you’ll know you have the right person if you don’t have to give them tasks broken down in to small, minuscule chunks.

If you just say, “Here’s the runway. I’ve paved it for you. Now go fly an airline down it. Go do your job.” If you have to break it down, then you know that you’re probably not hitting the right chord with that person, at least in terms of vision.

Maybe then it’s time to have a conversation with them about a couple of things. Number one would be, “Hey, do you understand what we’re trying to build here? This is the vision. This is where we’d like to go with it. Is this something you’re passionate about?”

But, then also say, “Look. You’re getting your tasks done, but you’re only getting your tasks done. You’re not identifying other areas for improvement. You’re not identifying potential bugs that you’ve created by working on Feature A. Now you’ve broke Feature B.” Have those conversations.

That’s something that, especially with junior and mid level guys, you have to do on a regular basis anyway. Don’t forget to praise them for the stuff that they’ve done good.

To answer your question, how do you know when it’s time to fire, or let go, someone. Really, it’s if you’re not able to move forward at a pace that the company’s moving forward at and this individual’s holding you back. That’s when it’s time to move on.

Robert: That’s basically what happened with this case. I could just tell it wasn’t going to work out. I feel like when people are just starting out, you might need to give them more specific information, more detailed information. That’s how I was trying to judge. Is it just them trying to learn?

There is a runway, a learning period, where people are trying to get caught up to speed. They’re not going to be ask quick doing things, maybe, in the first couple weeks. You need to give them that time period to learn.

Then, I think you can tell pretty quickly after that whether or not they’re going to be a good fit for what you’re trying to do. In some positions, it’s okay just to do the work that you’re trying to do. In other positions, maybe more senior level people, more architects or visionaries, you need people that are going to be creative and think outside the box, where you can give them general direction.

I think those kind of people are really valuable. People that you can give general direction to. If you’re listening to this and you’re working for a company, try to find ways that you can do better at that if you want to excel within your company. Try to figure out ways that you think outside of the box and push the product forward or think in new directions, not just follow the task.

I know sometimes that can be difficult, with management and things like that. They just want you to get stuff done. But if there’s ways that you can be creative, outside the box.

For entrepreneurs and the company, if you’re a founder or you’re a manager, you want to figure out ways that you can get that creativity out of your employees and provide that general direction to them so that they can improve.

I’ve found, over time, with all the products that I worked on, is that when you provide only that general direction and really clear of what you’re trying to do, the people that I work with produce way better results than what I would do alone. The team itself produces a lot better results. I think you’ll find that that happens as well with your teams.

Scott: Yeah. I think … There’s a couple things. Number one is, if you’re a manager, or an owner, or a founder, or whatever, if your person in question is not coming to you mentioning ways to improve, or even asking about things, if they’re just doing their task and that’s it, it’s probably a pretty good indication of how well they’re invested.

If they’re not asking you about the future vision. If they’re not saying, “Hey, I saw in the code, that we could change this and it will make it more efficient,” or “it will transfer less data,” or whatever. “It won’t crash as much.”

That’s initiative. Those are the people that are going to be rock stars. If you’re okay with having somebody who just gets their task done, that’s fine, but you may, at some point, want somebody who’s going to work for you so that you’re not working as much. Like you said, you had to go and do a lot of additional work because things weren’t getting done.

The second point I wanted to make is that … You see this a lot with outsourced developers, oversees developers. You’re getting what you pay for. You’re paying as little as possible to build a product. You want it built really quick. Rule number one, the difference between the development in those types of environments is different that what you get when you hire a full time senior developer.

What happens is, yeah, you may have four or five guys somewhere in Russia, or Philippines, or India, but what happens is, they’re only doing the task that they’re asked to do. They’re not usually … If you find a good shop, they are very good, but they’re usually just doing the tasks that are assigned to them.

That creates a lot of pain points. They don’t understand the long term vision. They don’t take the initiative. That becomes very frustrating. That’s why outsourced development has such a bad rap, because all they’re expected to do is the task that you give them. That’s the same thing with a bad apple in your local development team.

Robert: Yeah. I think, if you go back and listen to [Casey’s 00:11:13] episode, where she was talking about how she was hiring her team and she was having problems, you know … When you look at those development shops that are trying to get the hours and charge, they weren’t helping her with her larger vision and how she wanted to create the product.

You really have to be careful about that. It can be a lure, almost, to say, “Oh, I can go hire this development team really cheap to get stuff done.” I’ve found in the long run you really pay for that, because you get code that’s not maintainable, you get a product that doesn’t really match your vision, so you’re always playing catch up.

If you can bring in those people that are architects that really can help you push your vision forward, then that will help you in the long term.

The other thing I wanted to mention, too, is that when people are giving you their ideas, you need to be very careful that you don’t kill that initiative by basically saying, “No, we’re not going to do that,” constantly, or making them jump through a bunch of hurdles to get things done. When I was in the corporate world, that happened to me all the time. It drains you.

After a while, you give up. You don’t want to push those ideas forward, because you know the momentum that it would take to get those things pushed forward is so great. You don’t want to go through that anymore.

You need to be mindful when your employees are mentioning ideas. I know you chatted about this in one of our previous episodes. You find outlets for them to be creative, maybe at a future date, or maybe in an alternate way, if you’re struggling with timelines. You need to make sure that outlet’s there for people to bubble up those ideas and that they’re given the freedom to work on things.

Scott: Yeah, absolutely. I think the last thing I want to say on this topic is that if you’re dealing with a contractor, watch yourself. Make sure that the agreements that have been made. If you require giving them a certain amount of notice for termination in that contract, make sure you adhere to that so that you’re not in breech.

The second thing is if it’s a full time employee, make sure that you follow the rules of whatever hiring agreement you use there. The lesson is don’t … If you’re required to give them some type of warning before they’re terminated, you better give them a warning before they’re terminated.

Make sure you follow all that. Protect yourself and your company.

Robert: Yeah, and document things and that sort of thing. You want people to succeed, I think. If you hired someone, you should try to give them the benefit of the doubt, and provide them every avenue to be successful and talk to them.

I think that’s one thing, is to bring it up sooner rather than later. A lot of times, people wait for …
They only do performance reviews every year, then everything comes out at that performance review. If you can talk to them on a consistent basis and let your thoughts known. Don’t let it boil up into this big thing.

They might not be aware that they’re not meeting expectations or whatever. If you can make that clear and really address the problems as they come up, I think you’ll find that people are able to adjust better and that you won’t have to go through, maybe, the firing process if they’re not a good fit.

Scott: Yeah, and sometimes that’s the bottom line. Sometimes, they may be doing everything that they need to do. They may even be going above and beyond, but sometimes, it’s just not a great fit, and that’s okay. You identify it, and you move on, and you find somebody who is a good fit.

Robert: Sounds good. Hopefully this was helpful. We’ll talk to you next week.

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Robert Dickerson


Robert Dickerson is the Founder and CEO of Mapout a mobile learning platform that uses video courses to educate customers and train employees. He helps companies develop and launch their products.

Scott Davis


Scott Davis is the Founder and CEO of MobX, a mobile development software agency. He has 20 years of experience developing software for Government, Finance, Sports and the Telecommunications industry.