How to Work From Home Without Hurting Your Career – An Interview with Bobby Dewrell

I sat down in the studio (virtually – Bobby lives hundreds of miles away) with Bobby Dewrell.

Bobby is a terrific leader, and has spent the last 15 years as a remote worker.  Experienced as a team member and as a leader of remote teams, I asked Bobby some questions about how to maximize effectiveness, and I think you’re going to like what he has to say.

Want more about Bobby?  Head over to BobbyDewrell.com 

Interested in his Killer 1-1 template?

(I call it the “Career Creating” 1-1 template)

Download it here

And… Want to stay in the loop about Remote Work?  Get on the email list: http://TomCooper.us/workfromhome and I’ll send you the Top 5 Mistakes You’re Making on Video Calls

Transcript

Tom Cooper 0:00
Becoming a geek leader. Welcome to the becoming a geek leader podcast. My name is Tom Cooper. As a geek, I’m on a mission to figure out better ways to lead others at work and at home. Through the becoming a geek leader podcast, I’m sharing what I’m learning, so I can help make you more effective at leading people to ready.

Bobby Dewrell 0:24
Hi, it’s Tom Cooper. I’m glad you’ve joined me for today’s podcast. Joining me in the studio today is Bobby Rael. He and I met working on a software project. It’s been a few years back. Now, Bobby’s probably gave me this stuff to read, I don’t know. But he’s a technical expert focusing on technology initiatives, process design and solving business problems. Today we’re hoping to learn some key lessons from a successful leader who spent the last 15 years working from home rhythm 15 years so yeah,

no, believe it or not. But and and that doesn’t include unemployed time.

So you know, that I think I think one of the biggest benefits of of working from home is you always know you’re the smartest person in the room.

Tom Cooper 1:06
So why not wait? Sometimes I see your dog coming. Yeah.

Bobby Dewrell 1:10
True. True, true. So you’ve been doing remote work for a long time. And I’ve got a bunch of questions for you. I wanted to talk about two different kinds of things. One, I want to talk about what it’s like to be an employee. And then the other is I’d like to ask you a little bit about what what’s it like to lead a team when you’re the leader, and you’re not in the room with folks? so sure. Um, so as a remote employee, what’s one thing your boss has done that really helped you?

Um, you know, I think the most important thing that a boss can do to help you when you’re remote, is it’s an extension of trust, and it’s making sure that they stay in contact with you. one on ones become very important. regular check ins, just reach out, you know, how’s things going? Just a quick touch base, by whatever communication I mean, it doesn’t matter if it’s if it’s great. Like email, if it’s, you know, if you have some communication like a Slack channel or Google Hangouts or you know, any of those messenger type things that you would use, you know, just a quick reach out, making sure things are there, making sure you’re getting what, what you need from, from a company culture perspective.

So, um, one of the things I’ve seen, though, is that it’s so easy to kind of to fall back to facts only to Jesse looking at it, you know, what’s, what’s the status of x, because that’s fine. I’m so guilty of that I that I’m so task oriented. I’m like, where are we on x? You know, and, but, but how is that harmful?

it’s harmful, because I know some of it, too has to deal with the type of person and you know, there’s, there’s definitely been and not to get ahead of myself. But you know, when I’ve led teams before, you have some of those people that that’s all they want to talk about right in. And so if that’s all your employee wants to talk about, you know, certainly don’t spend a lot of time trying to get out what’s going on with the wife and the kids. But most people, when you’re a remote employee, you’re not getting that water cooler conversation, right? You’re not getting those, those little off the cuff conversations that are going on, in so you start to feel detached. So that’s the problem with what’s the status of x, because you don’t feel a part of the culture anymore. You feel like you’re worth only one thing. So it’s it’s important to, to take extra time when you want to find the status of something, you know, don’t be disingenuous. I mean, there’s, there’s quick times when Hey, Tom, all I’ve got time to do right now is ask, what is the status of this I got something big going on? really find some time to loop back around. When you’re in the one on one meetings, maybe schedule an extra five minutes to let them talk about what’s happening in their life or cool things or their kids done? You know, any any little thing like that? Mm hmm.

Tom Cooper 3:58
That’s great. I think it’s helpful to have Think about that. And then so as a remote employee, what’s something that’s gone wrong?

Bobby Dewrell 4:07
Wow, okay. Well I in what terms having having done it, having done it for so many years I can I can think of the time I was having landscaping done and the landscapers absolutely cut the copper wire coming into the house and I had no connectivity for two days while I waited for the cable company to show back up Yeah, that was that was unplanned vacation time is what that was

Tom Cooper 4:36
Oh, no, I’m thinking I’m thinking more from a communication or or team connection perspective what could go wrong in that regard?

Bobby Dewrell 4:43
So you know, um, and as as as you know, me well enough Tom, I’m one too often put my foot in my mouth. So I can think of one story that that probably answers not only what went wrong, but what what went really well. Think back I was, I was early in my work from home career. So I was one of the few people working remotely, actually in a different state from most of the rest of the team. And I’m sitting around and it’s just before a holiday, and everybody starts posting everything and our comp channels and everywhere else and sending these pictures of this wonderful holiday party that they had. Right that it was they’re having this this great little holiday party and everybody getting together and it was free food and it was all this and so you know, Bobby being Bobby right, I dropped in a snarky comment about must be nice to be one of the loved ones that live close by thanks for all of us, you know, out here in the nether regions. No sooner I promise you it was maybe half an hour after I made that comment. Got a few laughs You know, everybody it was said tongue in cheek. It really really was. Um, it was maybe within a half hour that That the the FedEx was at my door with an envelope. And it was it was from the head of our group. And it was a 15 or $20 gift card. Yeah, Amex gift card for me to go out and have a lunch. So yeah, so So again, probably one of the greatest things right and essentially what it was is they had figured out how much it cost per person to throw the party. Sure. And what they did for all of us remote is they they sucked up the cost of shipping it to us, but they got us a gift card for exactly that and send it out. So that you know, I mean, yeah, we weren’t sitting with everyone and having the camaraderie. But we were we were at least able to get the free lunch. Yeah, we had right. That’s right. We had been thought about

Tom Cooper 6:49
Yeah.

What’s something you had to change about the way you worked in order to make it work to be at work at home guy

Bobby Dewrell 6:56
Wow. Um,

That’s a good question. Because it’s, it’s been so long and I’ve worked this way for so long. You know, I think one of the first things that I had to realize is that I had to set my own boundaries. Um, because it’s it, you know, I’ve always been one to hop in and go until the job is done. Right. And, you know, it’s not uncommon to work a little extra hours but, but what I found is without anyone interrupting me right in and maybe there’s a nicer way to say it, but without that, that that office environment right where you have the the drive bys, right, the person pops in to say hello or whatever, and they end up in that side conversation. You know, I would work from the time I woke up until almost the time I went to bed. Wow. And we’re constantly in straight in Take a break and, you know, maybe get something to eat. And you know it if I had to learn how to force myself to take some of those breaks, I actually had to learn to force myself to try to take some time and reach out to other either remote employees or internal employees and, and do the virtual drive bys what I call it right just the Hey, you got a sec, let’s chat about something right and in in take some time to have a personal conversation.

Tom Cooper 8:32
But a good point. And I appreciate that tip because it is easy to kind of get heads down especially if we have work to do that requires us to be thinking and process work where you know, we can easily get all the data and get in that and just not be present with other people. And so would you schedule something like that to put it on your calendar or how do you manage it?

Bobby Dewrell 8:53
No, I you know, I don’t in I have from time to time if it if it comes out if it’s somebody haven’t caught up in a while, you know, I might reach out and say, Hey, can we grab 30 minutes? You know, one day? Yeah, you know, that’s, that’s no different than you would say, Man, Tom, I haven’t seen you about let’s grab lunch today, right or something like that. I’ve actually done some of those conversations over lunch. You know, video conferencing has has really changed a lot. And actually, it’s, it’s funny that I’m going to be a little tangential here. But I’ve noticed an impact from video conferencing that that I hadn’t seen before. And you know, I’m a I’m a pacer. So when before I had all kinds of wireless headsets, I would burn through two or three a day, right? Because I was it was just constantly Yeah, it was we were constantly on phone calls or whatever. But I could put that on and I could walk around the house and I could walk and think and talk and it was funny. I put a pedometer on myself and realize that got nearly two 10 miles one day and never walk outside. Yeah. Oh,

so.

So with the advent of video conferencing now everybody’s Well, I want to see you I want to see your face I want to talk to you like we’re there. Well, that’s great. I can’t carry the entire computer around with me all the time. Right so so now all that said, I mean, I saw you can

Tom Cooper 10:20
literally Yesterday I saw that there was a video that went live. Somebody had taken their video display their video camera with them into the bathroom. Oh, yeah.

Bobby Dewrell 10:28
Oh, I saw that too. Yeah. Yeah, I yeah, I was I was religious about checking you on the phone. Anyway, so yeah, so now you know, it’s it’s it’s significantly more sedentary. So it’s kind of a give or take, right. It’s, it’s great to be able to, to see and talk to the person and judge all those you know, facial expressions, all those things that I miss. But at the same token, it it it locks us into a single location. So, you know, I think a developing tip that I have and a theory that I’m working on, I actually, actually recently, you know, kind of made a statement that hey, I’m going to start taking some of these video calls from my phone off camera. Right so that I can walk around. I can kind of look at stuff I can stretch my legs still in the house, right still, it’s still here working,

Tom Cooper 11:24
What you need is a hover drone.

Bobby Dewrell 11:26
Exactly.

We’re just two years out.

Tom Cooper 11:31
Yeah, exactly. So, so what have you seen bosses forget to do that kind of hits a remote worker hard.

Bobby Dewrell 11:38
Um, again, it all comes back to communication. It’s, it’s the forgetting to include, right? And I can’t tell you how many times I’ve seen it. You know, four or five people are there in the office. Hey, we’re gonna call a quick huddle. They call a quick huddle. They make an audible when something And the next thing you know, it’s two days later and you’re like, I didn’t know anything about that. Oh, well, I told everybody on Tuesday. Well, I didn’t hear. Oh, yeah. Yeah. So it’s the, you know, it’s the it’s the keeping in mind that someone’s present and, you know, it’s, it’s kind of a two edged thing. The other side that I’ve seen too, that is, hey, they forget to include me in in these one off conversations. But that doesn’t suddenly mean cc me on every email, right. Like, I you know, I think we’ve gotten in a bad habit with when we when we work together in a location, I can just forward you an email and get up and walk over. Hey, Tom, I just sent you an email. I want you to check this out. Um, you know that? Well, you know, I guess this is just a separate pet peeve. But you know, a huge pet peeve of mine is to get an email from somebody that says FYI, And then there’s like 14 email chains right below it. string of emails. And I’m like, Well, I don’t know which part is for my information,

Tom Cooper 13:09
right? Apparently, all

Bobby Dewrell 13:10
of it. So let me let me scroll all the way to the bottom and start reading about the kinson yerba and get up to where it got back on to work. And what do you want me to see?

Tom Cooper 13:20
Right? Oh, my goodness, look at some really good stuff. I don’t want to shift gears and talk about being the leader of remote team because you’ve played that role to kind of facilitate and organize that kind of stuff. So the first thing is, is it possible, you know, we got this new thing. We’re all trying to figure out how do we work remote? How do we manage that and some of us have been doing it a bunch, but for a lot of folks, this is brand brand new, is it even possible for a coat for a remote team to work as well as a co located team?

Bobby Dewrell 13:44
Absolutely, absolutely. I had a team of five direct reports probably about 25 people in all. I think two maybe three of us worked in the same boat. Okay, um, for the most part, we were all all remote. And across time zones, we were from Eastern to Pacific Time Zone and actually IPT India. So, we were. So yeah, across all those time zones, we were still able to get together. Um, honestly, I think, you know, 100% remote team can sometimes be better than a hybrid team. Right? Because you don’t, you’re not forgetting one way or the other. Okay. So when when you’re 100% remote, it becomes I won’t say communication becomes more formal, but it becomes a more deliberate act. Okay, right. And when it becomes a more deliberate act, then you’re you’re starting to include people in and hey, do I need to tell this guy to or right Wait, that was just You know, Tom and I talk and I need to let you know, this guy No, too. So, so I think it, you know, it works really, really well. And in, you know, in my opinion I, and of course it’s me in you know, I always think I’m the best ever but I think we were, we were probably one of the highest functioning teams in the organization. I think we were, we were very, very effective. So it’s my routine.

Tom Cooper 15:28
Alright, so you mentioned that being more kind of intentional about some of that communication. So how do you communicate differently than if you were co located? What What do you do if you’re co located is different from you know, you’re saying, Okay, I got to take this model, it’s working when I’m co located. I got to find a way to do similar things when they’re remote. What are you doing?

Bobby Dewrell 15:47
I so you know, for me when I say intentional, I don’t think I’m I’m communicating any differently. I think it’s a matter of I’ve got to be intentional. remembering it, right? I’m kind of a very visual person. So if I see you, I’m going to say, Hey, how you doing in chat? And if I don’t see you, you know, all of a sudden I realize, Oh, yeah, all of a sudden, I realize it’s been a month and I haven’t talked to you. Right? So you’ve got to be intentional in trying to make sure that you’re reaching out to people. So what I made sure that I did you know, I used an old formula of one on ones and we had one on ones every week. And every week, the way my one on one went, is, you know, we had five minutes just to catch up. what’s what’s going on? Anything that you want, right, the next 10 minutes were for me, for me to give you everything that was going on, right? Like hey, these are the things I need you to work on. This is what I need you to get done. The next 10 minutes or for you To say, here’s what I need help with. Right? Hey, you gave me this task last week. Yeah, I don’t have that, you know, oh, hey, I want to start working on this. I’ve got that. So, so that 20 minutes in the middle was specifically about work. The five minutes at front was anything in the world. Okay. Tell me, tell me about your kids baseball game. Tell me about the trip you just took with your wife. Tell me about the vacation. You’re planning? Right? Anything like that. And then the very last five minutes, we’re okay. Let’s talk about your goals. Right? So we had 20 minutes in the center that we were always talking tactically, hey, I need you to do this, this, this and this. Right. And yeah, you would ask questions. I mean, it’s not. When I say the 10 minutes or for me, it doesn’t mean that I was just talking. But if we were time bound, hey, I need you to do these three or four things, right asking questions. Now you’re going to give me updates on a couple of things I gave you last week or maybe we talk a little more about one of these things you asked for clarity. And then we finish up talking about your goals.

Tom Cooper 18:03
Okay? Now when you say talking about goals was that was that like, your tactical goals or your career goals or what it you know, like I gotta stop I gotta get on this quarter or stuff I got to get done this year where I want to go, what I want to be when I grow up?

Bobby Dewrell 18:17
Yeah, it was more more related goals in terms of annual compensation and bonus and review, right? So what are the bigger things now? Because once a quarter, we would have a longer meeting and do a quarterly review. And then we would talk about it but those were kind of those weekly incremental updates. of, you know, hey, is something veering left on you veering right? Um, you know, I, I laugh I don’t think I ever gave a negative review to someone that went, man that caught me off guard. Yeah,

Tom Cooper 18:55
remember one time I had an employee who was used to getting A’s and I gave him B, and he was really not happy about not getting an A. And I said to him, Well, let me ask you first is anything I said to you in the review, not factual? And he said, “No, it’s all factually accurate.” “Second, is there anything that we just went over that you’ve not heard from me before today? No, I’ve heard that.”

I did my job.

Bobby Dewrell 19:25
But you know, what’s wrong with a B? It’s not an A.

Tom Cooper 19:28
Apparently, apparently. Oh, my goodness. Well, I think it’s, I think Let me ask you one more question. And that’s what is frustrating about leading a team remotely.

Bobby Dewrell 19:41
Um, to me, the most frustrating thing is, is we didn’t get to really have any of those real bonding moments. When you when you work together, you know, you can you can plan a night. Hey, let’s let’s go. Spend 30 minutes and grab a beer, right? Or, let’s let’s plan to go bowling here or I would see some of the other teams that would do picnics, right or, or some of these other you know, little things kind of during the day, right that that was just a way to to bond, um, you know, like just the the goofy stuff where they would all go down together in not goofy but but the stuff where they would all go down together in you know read read books at school right at to kids so they’d split up different classrooms going and get back or or they would do the back to school school supply stuff or they would put together care packages or you know, those things that that don’t have anything to do with work. Yep. But it’s a way to bond and hang out with Yeah, that’s, that’s the important thing. So you know, if you can find a way You know, I’m gonna say it again to be intentional about that, you know, let’s face it if if you’re running all remote, you’re, you’re saving money on, on offices on equipment and all kinds of infrastructure. You know, I’m not saying don’t take that savings but I’m saying take some of that annual spend and put it back to invest in the employees in a in a one or two day event like that where you can bring everyone together and and have that opportunity.

Tom Cooper 21:35
So most of what we’ve talked about in this conversation today has been kind of evergreen it would be relevant six months ago or two years from now. I want to turn a corner for just a second and talk right this minute about, you know, we’re in the middle of this Coronavirus thing in the US and worldwide really, I mean, and now everything is is topsy turvy, and so a lot of folks are Jumping into this remote work thing for the first time, or they’re having to do it at scale that they’ve never done it before. I was talking to a group last night and they said, all of a sudden we realized our desktop refresh was irrelevant, right? We we’ve been, you know, calling Dell to try and buy a bunch of laptops and you know, Dells, not shipping one off laptops to anybody right now. I trigger like mad for the companies that are desperate. So, so but we’re in this in this zone right now. So if you were just starting out, you’ve never done remote work stuff before. What are the one or two things that you think man, I got to make sure I get this right if I’m gonna make this work.

Bobby Dewrell 22:37
So I would say that one of the very first lessons that that I learned and that I think still holds true today, although I will say video conferencing probably helps with it a little bit. Don’t lose your routine. Right now. If you’re going into the office, you get up in the morning, you get a shower, maybe or maybe you took it The night before, right you know but but you brush your hair you brush your teeth ladies put on makeup, right? Yeah, you put you put on clothes and you go to work. Okay? Do the same thing. Don’t Don’t lose that routine. I can tell you I remember early on, right? Hey, I’m just gonna check one thing real quick, right and it’s so easy. So I’m just gonna check this one thing real quick and then all of a sudden it’s three o’clock in the afternoon you’re going man Something smells really bad. And you realize it’s you. Right? So so if I had to give him one tip take a shower. Ah, good. A second. Yeah, the second

Tom Cooper 23:39
all right teenagers. Right.

Bobby Dewrell 23:43
The second big tip in you know there’s there’s a lot of ways that you can do this, but find dedicated space. And you know what, yeah, we don’t all live in in multi bedroom. You know homes. Some of us might be in efficiency apartments or Whatever I, I don’t care if it’s a corner, right, fine. Find some space, that when I walk into this space, I’m at work. Yeah. And when I walk out of that space, I’m not at work. So I find some consistent space.

Tom Cooper 24:19
That’s a really good one. I remember when I was my first house wasn’t very big. And so I had a spot a corner of the family room that I could use for workspace, and then, you know, it was like, Hey, get out of here. I gotta get I gotta get work done. And then the next house, we had to have that, and I actually hit me this really massive bedroom, and I ended up with a desk, a huge desk in my bedroom. And it was, you know, that was hard, because Am I here to sleep? Or am I here to work, you know, and then, you know, of course, the view behind me was my bed. Right? The other side of that, but yeah, I can see that. That’s a that’s a really good tip. Well,

Bobby Dewrell 24:52
well, it could be and I just I am sorry, I know you’re probably getting ready to wrap but, but it could be on that Sunday. Yeah, but it could be on that too. You know, think about this. If it’s not that it’s the dedicated space that you’re always going to work in. Right? So, so maybe maybe it is, you know, maybe, maybe you’re an architect, maybe you’re a school teacher, maybe you’re something where you’ve got to spread out, right? Yep. Still take the time every night, to collapse it down and move it to that dedicated space. Think about this, you you’re driving to work or you were driving to work or before now, right. So you, you know, the average American has a 20 minute commute. Okay, right. And, you know, maybe maybe you’re listening and you’re going well, I live in a small town. It was five minutes. I don’t care. So you had five minutes. You had some portion of your day that you were getting into a car driving to another building. That’s right. And, and I would argue during that time, you’re, you’re getting out you’re putting down you know, briefcase backpack, you’re pulling out coffee, I’m a coffee right boop boop boop You know, there was some amount of time that was set up in prep, you don’t lose that. Don’t lose that you need that time. And it’s it’s nothing more than to go through the mental process of separating home and work. Otherwise you’ll you’ll you’ll go crazy. There’s there’s a reason why priests in the Catholic church were vestments, right? It’s so they can they can change they can take that off there the weight of those things sit in that in that ritual for so so

Tom Cooper 26:31
I’m a mindset thing is what you’re talking about.

Bobby Dewrell 26:34
I’m a big fan of ritual right when it when it comes to things like that. So

Tom Cooper 26:38
well, that’s terrific. Thanks for that. I appreciate you making the time for us to talk about that. And thanks for being here to talk about this. This is a big challenge that people are facing and the the one thing that I heard on that call last night we had a few dozen senior execs on the call talking about the challenges they’re facing. And and what they said is man was tough to remember we’re in this together and we’re having all the same challenges. We’re trying to work on this. And you know that human connection components important. But also, we got to find a new normal. And so I wanted to get together with you and go through some of this stuff. Because I know that this is this is content that’s going to really help people. So thanks for making the time to do that. Appreciate it. Oh, sure. Sure thing, enjoyed it. And we’d love to do it again. It’s it’s a lot of fun. It’s a few things that I can declare to be a 15 year expert on.

Bobby Dewrell 27:26
Terrific. Thanks. Thanks, Tom.

Tom Cooper 27:30
It’s Tom, thanks for listening to the podcast. And if working from home is something that’s important to you, if you find yourself doing that a lot now, where you’re going to be doing it more in the future. I’d love to have you stay in the loop on this topic. I’m going to be publishing a bunch on this over the next few months. And so what I want you to do is is go to Tom cooper.us slash work from home Tom cooper.us slash work from home and what you can do is get in the loop and also I’ll send you my five minutes biggest mistakes you’re making on your video conference calls tip sheet. So head on over to Tom cooper.us slash work from home and I’ll talk to you again soon. This is Tom Cooper. Thanks for listening. Be sure to join me next time for another episode of becoming a geek leader. Join me in my mission of discovering better ways to lead others at work and at home.

Transcribed by https://otter.ai