Manage Time. Live Intentionally, with Travis Ensley

26 Jun Manage Time. Live Intentionally, with Travis Ensley

My guest is Travis Ensley. Travis is one of my best friends on the planet. This guy, over the past 20 years has been a successful leader within the tech industry. He’s worked with startups all the way to fortune 500 companies.

I can say that he’s successful because the companies he’s helped have been wildly successful. But I can also say that because I’ve gotten to know many of the people that he has led. And they love working for and with him. Here’s the thing, as you’ll see, Travis has this kind of no-nonsense Ron Swanson quality to him, so I’m guessing that he’s already bristling at my accolades, but I’m going to go further.

He’s been successful in business, but I can also tell you he’s successful in life, too. He’s an awesome husband and dad, and I’m also grateful to say that he is an “bonus uncle” to my boys, and that means the world to me.

We talk about a lot of subjects, but today we’re going to dive into the subject and focus on one area of expertise that Travis is just incredible at, and that is establishing systems to manage your time, your
tasks, and your priorities. He is a black belt level genius at this. And I benefit from his wisdom on this front weekly, so I wanted to get him on DREAM THINK DO, so you can benefit from it, too.

INTERVIEW:

So pour yourself a cup of coffee and let’s get to this. Travis. Welcome to DREAM THINK DO, buddy.

I’m honored to be here. Thank you.

Absolutely. So, we’re going to talk about systems and strategies. I mean, you use technology, but your brain works in this way. There’s been a couple of questions I’ve been dying to ask you as a long-time friend. I assume I know the answers to this, but before we dive into the specifics, I want to start a little bit more in your brain. How about that for being scary? So, I wanted to ask you. You’re one of the most organized systems oriented people that I know. But have you always been that way? Like, were you that way in junior high and high school?

There’s very little chance my mom will listen to this. So I will say yes.

I’ve got your mom on speed dial. I’ll check right now.

I was one of those kids who would open the bag of Skittles and organize them by color because it made sense for me to do it that way because I wanted to know exactly what I was doing. I’ll tell you that my room was not very clean when I was young, but after high school, I went into the Navy, into service, and they beat that out of me. And so, coupled with that, I like to say that I’m just this side of obsessive-compulsive disorder.

The healthy side of it, right? The healthy side.

Yes, the healthy side of it. With my experience in the service, the very regimented leadership they gave solidified the kind of lifestyle that I choose to lead that way.

Absolutely. I wondered if that experience just kind of ground that into you for the first time, or whether that was bringing out natural tendencies. But I assumed it was bringing out those natural tendencies.

It allowed me to understand why I thought that way. I think it encouraged that behavior. It showed me a lot of interesting ways to do it, too.

But it’s also interesting to think about how the world of technology that can support systems for helping navigate our time and our task has evolved so much. I’ve seen you experiment with different things, try different things, so that was something that I was looking forward to diving into with you. I think sometimes technology can be a benefit, but I think sometimes technology, with all of the options, can also start to bungle that up a little bit.

I think in a lot of cases it comes down to discipline. I think technology, in general, can be a huge distraction. It’s designed to be that way. Hey, it’s a cool thing, or this is the next widget or the next flashy thing that’s going to come up, and so everybody has great ideas. In this day and age, it’s very easy to take those ideas and translate that into an app or a product. But it’s a saturated market. You have to find the ones that work the best for you.

It is important to find a way that works the way your mind works. It’s good to have a process then find a product that supports that, rather than having a product drive a process for you that you’re not comfortable with. And I think that’s a key component of that.

I wanted to talk about the process before we started talking about technology. Technology can change, but I know you’ve got a core set of principles and process that you rely on, first and foremost. So what are those core principals when it comes to managing your time and your priorities, your tasks, all of that? What do you think of first? What’s the filter that you use to start to make those decisions?

I guess it comes down to priorities. I think you have personal ones, you have professional ones, and I’ve never been a big proponent of this “work-life balance.” I think it’s all one thing. So when it comes to management of time and task and things like that, the priorities are going to change every day, based on what that day holds. If it’s a really busy work day, then sometimes I’m going to give a little bit more time to the work thing. If there’s a busy life thing going on, then that gets the priority. And so that’s just spending a little time understanding what the priorities are at the time, at the moment, and putting them in the right order and then doing them.

So being able to say the work-life balance can go out the window. Thinking about it all as a whole, as opposed to dividing it up, that helps to guide you.

Yes, exactly.

That’s awesome. So, let’s talk about that. You’re in the tech world; you’re in leadership, executive level, so there’s always plenty going on at work. I would imagine that if you’re not careful, especially if you’re not keeping an eye on both life and work, it can be easy to always default to work. What are some of those things that you’ve found helpful to check yourself, to make sure that you’re staying on track as far as those life priorities as well as work priorities?

I think efficiency is a really important component of being organized. When it comes to separating and understanding what the right thing to do is when often it comes to, how easily can I do both. Which ones support the priority? I like to start my day with here’s what I know about today and outline. Here are some of the personal things that need my attention and I can fit them at these points. And then here are some of the professional things, and then leave a little bit of time for flexibility there. Trying to understand the big picture, and being intentional about dedicating some time right off the bat, first thing. I’m an early riser, and so I get the opportunity to engage my brain. I also have a lengthy commute on occasion, so I can spend time thinking about that, and coming into the day prepared for at least what I want to happen.

Do you tend to organize your day mostly the morning of? Some people swear by doing it the night before, some people swear by doing it the morning of. Where do you land on that? Is it usually mostly mornings of, when you’re planning out the day?

I love consistency. I use calendar apps. Google Calendar is one of the most important things that I use, to make sure that I look at it at the end of the day, saying hey, this is what tomorrow’s going to bring. I try to be as consistent as possible. And that’s not just for me; it’s also for the people that I serve as a leader. Because they also need consistency.

More broadly, I try to schedule the heavy lifting work Tuesday through Thursday and leave Monday and Friday more flexible. Trying to keep things as consistent and predictable as possible is very helpful from an efficiency perspective.

So, some of that you’re doing as far as blocking it out, being able to say meetings are going to mostly fall on Tuesday, Wednesday, Thursday, and then Mondays and Fridays can be travel. But it can also be those catching up days. I love that you can get into a rhythm. Your team can probably get into that rhythm as well.

Yes. Those are the things that I can control. There are some things you can’t but is obvious. People invite you to things. But for the most part, everybody wakes up on Monday morning like, oh man, it’s Monday morning. I need the sharpest pencil in the box first thing, so I’ll front-load my week with a bunch of really hard important things to learn or do or think about. My approach is to sort of ease into the week, being intentional about that; having a few one-on-ones, or a planning meeting or something like that, to get yourself started. Likewise, on Fridays, to be honest, I mean, let’s everybody be honest, Fridays are not the most collaboratively productive day of the week.

Right.

People are starting to check out if they were checked in at all. Friday afternoon, three o’clock, it’s a ghost town. So take advantage of that. You can try to change that, but more so I think it’s important to take advantage of that. I often work from my home office on Fridays as basically an admin day. Start the day that way and get through those things, and then take a little bit of time at the end of the day to plan for next week.

That’s awesome. I know that Dan Pink has a new book out that’s all about time management and priority management, and he talks about that. Optimize the tasks to the time of day, to the time of the week. Don’t try to do certain things in that first two hours of Monday morning. Be able to say, alright. Know when your optimum windows are for certain types of activities and try to schedule as much as you can to those things.

Some people swear by their to-do lists. I’m a to-do list hybrid kind of person. But they swear by their to-do lists to manage their day. You’ve got tasks that you’re managing, but you also have a large team of people that you oversee, that you influence, impact, which also influences your day as well. What systems do you use to efficiently manage tasks?

I love to-do lists. For two reasons. One is that, as you said, it’s efficient. And two, it’s great to get things out of your head. I get taskable things from many directions. I get them from my own people, so people who were asking me to do things for them. I get them from my management, and I get them from my peers, and so they’re coming all over, from lots of places. And so what I’ve found, for me, is to aggregate them, to one place and just work from that one place.

And that one place is called Trello. Trello is a basic web-based system. It’s also free, which is good for non-enterprise products. On Trello, I put things into categories. I have an “idea” category. I have “my boss” category, items to discuss or inform him on. I have a “to communicate” category, which are things that my team or my peers should know. “Tasks,” which is the to-do list thing, and then, of course, “in-progress,” which is things that have started. That’s where a lot of the delegation happens because as we all know, if you can’t do, then you lead.

And then the most important one is the “done” column. There’s nothing more rewarding and satisfying than dragging something from “in-progress,” or from a “communication” thing to the “done” column. At the end of the week, I archive that whole thing. Okay, new week. I have that itch to scratch every week. I need to at least find out that I was successful and productive in some way.

There’s just nothing like a bunch of to-dos checked off the list, whether that’s on a legal pad or whether that’s using Trello. I know you’ve got a system for this, and I want to ask you about it. But I think one of the challenges that happen with to-do lists is that people will start to have multiple to-do lists, right? And they start it, it’s a good thing, but then all of a sudden, these lists start to get so robust and maybe in some places so that it always starts to work against them.

How do you decide what’s going to get your focus each day? How do you keep track to be able to say, these are the things I’m going to focus on today?

Trello is an aggregate, so I get a lot of my tasking and just communication stuff from various forms. There are one-on-ones where I take notes, Of course, email. Whatever the source or context, Trello has a card feature. So I put tasks on these cards. I put a priority on things. My priority levels are do-now, do-soon, or do-eventually. They’re color coded. Trello has a great feature to remind you at a certain time to have something done, and I’ll usually have that on there. At the end of the day, I look at my Trello board, and I see things that were done, and maybe I need to change that status of that priority tag. Maybe it goes from a soon to a now, and that’s the next day.

But doing that in real time, I think a lot of people get a lot of lists because they usually get inundated with information, and it’s very easy to do when it’s coming at you at every possible direction.

So when you get some information, do something immediately with it. You can ignore it. That’s a thing. You can say, this doesn’t matter to me. So I’m just going to get rid of it. Be intentional about categorizing the things that matter and those that don’t. And be honest with it. That takes practice. It takes years to get a good system going.

I think being intentional about when it comes in and doing something with it immediately, keeps you from having to go back and do it later. And so, even if deleting it is the thing you do, or just deciding to ignore it or pushing it off for another day, that’s still something. And then you can focus on the things that matter that are in front of you.

What I love about this system, is that the core system of those different categories of tasks, and the prioritization of those tasks, and then being able to say alright, and having it all in one place. Especially at the end of the week, to be able to say, alright, these are the things that I got done, these are the things that need to be done next week. And to be able to have that satisfaction and the clarity. That can make all the difference.

Now, do you encourage others to adapt to this system? Do you get people all on board doing the same thing? Or do you find that it’s just important to do your own thing and work it out as you go?

Everybody has their own system. They gravitate to the way that they work, as long as it’s an efficient way for them, and they’re getting the work done, that’s great. I happen to use Trello – and I was introduced to it by a peer. I wasn’t interested at first, but then I geeked out on it.

But really at the end of the day, the communication component, managing all of these tasks is important. However, you go about getting it done. Ensuring that everybody is on the same page with what’s being done, what’s not being done, what status those things are, that’s really the important part. The rest of these are just tools to get to that.

I love it. So let’s change gears a little bit. I want to talk a little bit about your day-to-day, as well. A lot of people say, don’t have your email open all the time. Check it once or twice a day. At the same time, we live in a world where people need information. They need to be able to reach you. Especially with the teams that you lead. How do you do it? Especially in regards to people reaching out.

One thing I’ve done is to shut off notifications. That way I’m not interrupted every second. Email, frankly, is the new snail mail. If you want my attention right away, there are three others ways to get my attention immediately. So email is very much a documentation of something, and you can get to it when you get to it. So I’m intentional about checking that on occasion. But when it comes to immediate, time-sensitive things, text or Slack or whatever IM platform you are using.

That’s where I usually get in more trouble because you’ll start a conversation. Usually, it’s in a group, and that group will start talking about a topic. And if you think, wow, this is a really important thing, I probably need to be paying attention to, and whatever I was doing at the time that that conversation started is at risk of not getting back to until that conversation is over.

That’s where the flexibility comes in to play. I can be as regimented as I want to be, and I like to try to be as regimented as I can be for an efficiency perspective. But being rigid doesn’t work. Not all the time. Having a framework works. Adhering rigidly to that framework is probably irresponsible.

And so that’s where communication is. Especially in this day and age. Communication happens. Whether you choose to be part of it or not is a really important thing you have to decide.

So basically, if it’s HipChat, if it’s Slack, you’ll engage in those, especially as you’re able, throughout the day, as opposed to just cording them off the certain times of day?

Right. In software, things happen. Things break. People need attention for a lot of reasons. So that’s part of my responsibility. In a small company, in the smaller companies that I’ve had, especially the young ones that are growing quickly and time sensitivity is a lot more important for the revenue, the success of the company. Those boundaries get extended into the evening sometimes. In larger companies, or mid-sized companies, where some of those patterns have been established, then you can put some boundaries a little bit closer to what I consider a standard work day.

I appreciate that. I appreciate the transparency. Switching gears a bit, how would you say, as far as just keeping yourself mentally sharp and on task – how do you find yourself doing your best, staying sharp?

It is debatable whether I do or not. On my tombstone, the only thing I want it to say is, he was intentional. That’s one of the things that I have a lot of value for. Especially as I get a little bit older, my kids are getting a bit older now. So the more responsibility that I have, either in leadership or home or anywhere – I take that responsibility seriously, and so I want to make good decisions. So I’m trying to mitigate as many opportunities for bad decisions. Being tired at three o’clock in the afternoon, I am not going to make as good of a decision as I would have at eight o’clock in the morning.

So I plan my day that way. If I have to have an important meeting or an important one-on-one, it happens in the morning. It doesn’t happen in the afternoon because they’re not going to get the best Travis that they can get because I know who I am and what I do. I got to bed at like 9:30.

Right. Because you also get up in the hour that has a four in it, so yeah. I’m with you. I think that is important, though.

22-year-old Travis would be woefully disappointed in my sleeping patterns now. I get a solid eight hours. At least a solid six and a half and some change. I like to be intentional about that. I like to make sure that I’m restful. And that means not just sleep, but it also means, I start my day in my car. I’ll listen to Audible. I have an Audible subscription. I’ll listen to professional development books in the morning, on my into work. It gets my mind started, and I can start thinking about stuff. But on the way home, it’s fiction. And it’s not exciting fiction. It’s lame science fiction stories or boring podcasts just because I need to wind down a little bit. I want to get my mind back into a state that I can be available to my family when I get home. I think that’s probably as important. Even now, screens after eight o’clock; I’ve been reading all this stuff about blue light, and I’m cognizant of that. I’m bad at it. But at least I know I’m doing something not good for me right now.

But I’m trying to be mindful about rest. It’s more than just sleep. It’s clearing your mind. I use all my vacation time. For the American workforce, going on vacation isn’t something that people see as an important thing. But I have been very intentional over the last couple of years. I plan at least a week [inaudible 00:35:13] that I have the opportunity to do that. That may not always be the case. But taking the time, and even if it’s a staycation or a small camping trip, or some weekend with a friend, doing something. To disconnect for just a little bit so you can rekindle all of the excitement that got you in that position, to begin with. And then you go back happy. That’s what keeps you going. Once it becomes super hard to do that, that’s when you need to be paying attention to what’s really going on.

I can remember even a conversation we had about that very subject. That you realized, as a leader, that you needed to take that vacation time, not only just for yourself but to set the example for your team. Because you started to look around and say, why isn’t anybody taking their vacation time? So for you to be able to say, hey, I’ve got to lead by example on this, you wound up giving a gift to your team as well, to do that same thing.

Okay, so we’ve been talking about how we apply this in the work side of the equation, but I know you’re not a work/life balance guy, but a life guy, right? And you’ve got work and life, and it’s all one big thing. How have you applied some of this at home? You’ve got a busy home life, as well. What are some of the things that you’ve tried to apply and maybe where have you also given yourself permission to not apply these things?

Sure. Well, as organized as I am, my wife makes me look like an infant in this category. She is by far; she’s our chief operating officer at our house.

You married up; there’s no doubt.

In a multitude of ways, absolutely. She does a lot of stuff. I’m the boss at work, and I come home, and I ask her what needs to be done. Now, we’ve used Trello. We have home projects. Whether it be a basement thing, or a bathroom remodels, or buying our couch. Those things can get documented. We have Google Docs. We have spreadsheets. We do our budget in a spreadsheet. So a lot of that stuff still kind of happens in that same way. She’s an IT professional, as well, and so she understands that, and she has to stay organized at her work. So we use a lot of those concepts. I would say that the intentional and the rigidity of those frameworks are probably not as important at home because instead of employees, I have children. I was blessed with two daughters, and so I am one man in the house. And so the thing that is frustrating about that is they have their own lives!

So I found that a very loose framework at home, using a lot of the same tools but a little bit less rigor around that, is pretty good.

I’m a big fan of the Ensleys. Awhile back I talked with your older daughter. She told me how she quit something. I said, well, why did you quit it? And she said, it’s like dad said, you don’t half-ass two things, you whole-ass one thing. I said, Yes, that is awesome.

But I do know that some of this it might sound very task oriented, budgets and spreadsheets and all of that, but you also use this to dream together a little bit, too. How do you guys do that?

One of my favorite things to do, and certainly one of my wife’s favorite things to do, is to plan vacations and to look at places to go and things that we can do there, and we can map out. Sometimes it only gets to be just a plan, we never actually do it. But sometimes we do. We had an opportunity to go to the UK last year, and that was a long dream coming. It was something that we had documents for and lists and things. For me, I got to buy things that I needed to buy, and that’s fun to do for me. It’s exciting to be able to fantasize about going somewhere or doing something together, and then to be able to visualize some of that and see it all come together.

Well, I know you guys were very intentional about keeping that in the dreaming category, saying these are some of the things we could do and experience and all of that, but let’s make sure we’re not just making a big to-do list. You maximized the opportunity, but had a whole lot of fun, too. I love that you guys do that. And I see you doing it on so many fronts.

I always try to ask, as I wrap this thing up, what’s one last word of wisdom as we’re wrapping up this conversation?

There are so many little nuggets. I guess one phrase that comes to mind that I find myself saying all the time, whether it be home or at work: “well done is better than well said.” We can plan all we want. We can make lists all me want, but if you don’t do those things, it’s really all for nothing. So making sure that you do the things that you say you’re going to do and it’s not just a bunch of lists and papers and processes. It is the accomplishment.

Absolutely. Couldn’t agree more, man. I love how you do it. So thank you for being a part of DREAM THINK DO.

Hey, it was my pleasure. And now you can stop harassing me about it.

Alright, well thank you, Travis, I appreciate it.

And DREAM THINK DO-ers, I hope you enjoyed this episode, as well.

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