Do You Trust Your Employees?

Episode 38

Find us on Twitter @The_Scott_Davis or @RobDickersonJr


Robert: In this episode of the Stretch Goals Podcast, Scott and I are going to be talking about trusting your employee and do you trust them? This is the Stretch Goals Podcast, where each week we 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: I’m Scott Davis.

Robert: This week’s episode I wanted to talk about do you trust your employees, because I think a lot of times, founders, managers, when you hire someone, you choose them and hire them because you think they can get the work done. Then, you do things like you go micromanage them. You cut out benefits like working from home because you want to see what they’re doing all the time and so you’re not fully trusting that employee, even though you hired them to do the job.

I’ve seen this a lot in the corporate world and also as a founder, when I’m hiring people, I want to hire people that I can trust and ask the right questions and bring them on and trust that they can get the job done and not be following along behind them and let them work from anywhere. Right? Because my business is distributed and people work from everywhere and so I’m not going to be around them all the time to know what they’re doing. I’m putting trust in them that they’re getting the work done. I want to talk about that a little bit.

Scott: Yeah. It makes a lot of sense. I’ve always had this policy, even when I worked in the corporate world, and I’ve extended it to what I do now. If you’re getting your work done, I’m not going to be bother you. You can work 20 hours a week and I’ll pay you for 40 as long as you’re getting your work done, but if you’re not, I expect you to work 60 to get the work done.

That’s the thing. I’ll let you do whatever you want. I’ll let you work however you want, but I’m going to give you a set of tasks that you’re going to agree should be completed and I expect them to be done. I’m not going to micromanage you, but if the trust is broken and you’re not getting those things done, then I’m going to be asking you a lot of questions. I don’t want to have to do that.

Robert: Yeah, because it takes a lot of time. Right? I mean, I don’t have time to go hire someone and then follow behind them and make sure they’re getting things done. I think you have to set the accountability of talking to the person and say, “Here’s what I expect you to do, the expectations.” Then, be able to have a way to measure that. Right?

In software, we can look at the code. We can look at their output. In other jobs you can do something similar. Figure out how you’re going to measure that output, how you can tell if they’re getting stuff done and use that ability to measure to give them feedback, to make sure that they’re doing their work, so that way they can work from anywhere. You can look at the quality. You can look at what they’re doing and making sure they’re getting things done.

Scott: Right. The key there is, if you let people work how they want to work, they’re going to probably do a better job than if you’re confining them to some preconceived set of rules and notions about how they should be doing their job so let them do it their own way. You’re probably going to get a lot better output out of them.

Robert: Yeah. I mean, they’re going to be more productive. I mean, everyone works best at different times and different locations and that’s the thing I really like about remote work because for me, at night sometimes, I’m more productive. During the day I’ll go work out because at certain times I can tell that I’m not going to be as productive. Everyone’s different, right, and so to try to force people into a box, to work at a specific time. I mean, within a corporate job, sometimes you have to do that. You have to be there at a certain time, but if people need to work at night or something, give them that flexibility to get the job done when they see fit and when it fits within their schedule.

Scott: Yeah. I agree. I mean, when Marissa Myer from Yahoo, Marissa Mayer, however you say it, when she publicly, a couple of years ago said, “Yahoo will not allow anymore remote working.” I mean, in my head, I was like, “Well, that’s the end of Yahoo.” Right, because you’ve took the flexibility of life away. Now, you’re working a 9 to 5, actually you’re probably working a 7 to 8, 7 AM to 8 PM, in Silicon Valley because that’s how the hustle is, but now you can’t go get your flat tire fixed. You can’t take your kid to the doctor because you’re at the office all day. You can’t even run to the bank to deposit your check if you don’t have direct deposit.

I mean, that’s the kind of thing, that structure, prevents you from doing and it creates more stress for you. Giving people flexibility, maybe they don’t work from home all day, but at least give them the flexibility, go home in the afternoon, run an appointment, and then work the rest of the day from home. It’s more effective. More efficient.

Robert: Yeah. I mean, more and more people are looking at that work life balance in how they choose a company. They’re looking to balance their life and get things done when they need to. More companies are moving to this remote work force, where people can work from anywhere. I think trust is becoming even more important now than maybe it was before, when everyone was in a central location and you’re able to watch them and figure out what they’re doing and manage them. I mean, you just have to have a higher level of trust in the people you hire and you have to ask the right questions.

I know we talked about this in a previous episode, asking the right questions, bringing on people and maybe doing test projects or something like that to figure out if they’re the right fit. Then, once you identify that, to set that accountability so that they can get the work done.

Scott: Yeah. I mean, have you ever had any issues with people on Upwork not doing what they committed to?

Robert: No, not really because I make sure at the beginning and I set those expectations of what I expect them to get done. I try to bring a level of transparency, especially when people are just starting out working with me. I just hired another guy the other day to help me with some stuff. I’m just trying to set those expectations out front of sending me the stuff you’re working on, checking [inaudible 00:05:37] more often so I can see what they’re doing, at least to start out. Then, when I get a better feel about how they work, how long it takes them to do things, then I just let people run, man, because that’s what I hired them to do. I don’t have time to sit there and micromanage them.

The thing I’ve found about hiring people, especially contractors and people off of Upwork, is that you don’t need a whole lot of hours. In a corporate job, a lot of times you might be there for eight hours, but you’re not doing eight hours of productive work. Right? Maybe you’re doing four to maybe six hours of productive work and everything else is meetings and talking and who knows what else goes on?

When I hire people doing contracting and they can really focus, say, for four hours on a day on a specific task, it’s amazing how much stuff they get done because then they’re thinking about the work that they need to get done during their off hours. Right? They’re able to think and plan and figure out what they want to do. Right? If they come across a problem, they have that time to think as opposed to just sitting there trying to hammer away at the problem.

It’s similar as if you have a problem one day at work and you come back the next day in the morning and you solve it immediately. Right? It’s those extra hours that are just wasted trying to figure stuff out. You can be really productive when you sit down and focus and take away all the fluff and the other things that maybe come with being in a corporate environment.

Scott: Yeah and I hate meeting for meeting’s sake. It’s one of the dumbest things. Let’s just have a regular meeting. No. Let’s get rid of the regular meeting unless you really need to meet. I agree. If you can work from home or work in an environment where you can focus, that four hours is going to equate to eight hours of somebody else who’s under an environment where they’re not comfortable. I agree. It’s all about giving them the flexibility to do what’s most comfortable to them and get the most efficiency out of their work.

Robert: Yeah. It’s the whole multitasking aspect too. If you can remove that aspect and just have people focus on a specific task, and a lot of times that comes down to management to make sure that you’re not giving them too many different tasks, that they’re really able to focus on a specific thing. Then, get that done. Then, move on to the next thing. Right? If you start throwing all these different things and changing what they need to do in the middle of it, that’s just going to make things take even longer.

Scott: Absolutely.

Robert: I mean, the moral of the story is you got to put more trust in employees and you got to hire the right people. I think that’s the start of it. Hire the right people. Then, put your trust in them. Set that accountability. Set the way that you can figure out if they’re getting the work done and you’ll be amazed at the productivity people will have when you give them that freedom and that flexibility.

Scott: Absolutely. We’re living examples of it Rob. I mean, we get things done and we do it in our own way and we’re super efficient at what we do. Guys, don’t forget to check us out on SoundCloud, iTunes, and now on YouTube and check us out on social media as well.

Robert: See you next week.

Scott: Thanks for listening to this episode of the Stretch Goals Podcast. You can access the show notes for this episode and listen to other episodes by heading over to

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Each week we'll share insights and lessons learned to help you create ambitious goals for your business.

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.