Career Advice Entrepreneurship

So You Want to Work Remote …

I have a couple of disclaimers as well as context before diving into my thoughts on working remote.

First, this post is written from a manager’s perspective, not the team member’s, particularly my own as I’ve led and grown iThemes from one person to now over 20+ since 2008. I’m focusing these thoughts and experience sharing on a situation where you (a current team member) are wanting and requesting to go from working in a dedicated office to working from home or “remote.”

Additionally, we’ve been a hybrid team from the beginning — with remote team members and in-office team members. (We currently have a 5,300 square foot office in Oklahoma City, that we call iThemes HQ.)

It’s all written in the context of a small bootstrapped company, who has been in business for 9+ years. I know a lot of companies, particular Automattic, have very progressive perspectives and expectations on remote work. But that’s not us and we don’t expect them to be us either. Every company and situation is different.

But in that context as a small team, we’ve seen what seemed like minor changes have drastic and negative effects on our team and HOW we get our work done.

We have a really really really good team who collaborates and communicates well and is extremely productive. And because our culture is very important to us … we’re very guarded and careful how we make changes to that as it’s vital to our continued success and health.

Our job and responsibility, as managers and leaders (just as your managers), is to ensure every team member, whether in our office or remote, is connected, productive and fulfilled in their job and work.

And ultimately our charge is to do what’s best for our company, team and customers and to evaluate each request situation carefully to ensure maximum success for each team member, our greater team and our company.

And yes, we’ve made mistakes and learned lessons that I want to share so you have the best chance at success.

We have a very diverse variety of team members, work, teams, and setups. They don’t and won’t work for everyone, in every situation or position.

My hope is this post will help you prepare and frame your requests in your unique position and situation and leadership, as well as prevent the problems and mistakes we’ve made and seen in the past.

The following are the things I think you, as a team member in your own organization, requesting to go remote, should be prepared for and consider as you move forward with those conversations.

Much of this also applies to in-office team members too, by the way, but there are some key things that managers do to ensure that success that often get taken for granted. For instance, we lock our office up tight. We have a doorbell that rings to our Office Manager’s office very softly. She is the distraction-cancelling protector of productivity. She knows that any time there is a disturbance or distraction in our office, we all lose.

So take it from that perspective ….

Some Thoughts and Ideas I’d Mention Upfront to You:

  • Realize remote work is NOT for everyone, every situation, or every position — Some of the most social people I know think they will be happy in a quiet home office with no regular interaction with other humans. Additionally, some job or teams may not simply be ready or right for it.
  • Know yourself, search yourself — All of this is an effort to make sure this is a win for everyone. But that starts with knowing yourself. And more importantly … WHY you’re wanting it.
  • Ask for and expect a trial evaluation period — Or even starting with one day a week. Be open, honest and transparent about how it goes. If you just give a report of all roses and no thorns, it’s liable to raise suspicion. No environment (even a dedicated office) is perfect. Far from it. Give the pros and cons, the opportunities and obstacles, the good and the bad.
  • If you’re really green, with lots to learn, this might not be the best for you — We’ve hired a number of people in our office we would never have hired remotely. Namely because they were rookies, with lots to learn and needed the mentoring and coaching that happens more easily when you can simply roll your chair over to a veteran and ask questions. Including at lunches, breaks, etc. If you’re just starting out into your career, check out my How to Be a Professional primer, before moving on. 
  • Understand that failure could mean jeopardizing your job — If it doesn’t work out, there’s a likelihood beyond requesting you come back to the office, that you’re also out of a job. And ALL  of the things I’ll mention here are to help you have the BEST chances to not just survive, but thrive, from a manager’s perspective.

Key Questions I’d Ask You:

  • What’s in it for you? I probably already know this already. But what are the benefits for you and the reason WHY you are requesting it?
  • Where specifically will you be working?
  • What is your remote setup specifically? Do you have a dedicated, private, distraction-free home/office setup?
  • Are there other people who will be in the same space during your work hours? (i.e. your home, kids, spouses, roommates, etc.)
  • How will you manage work/home/life boundaries and distractions? Goes both ways …. if you’re officing out of your house, that’s the same place you sleep.
  • What’s in it for us? The company, your teammates, your work? I ask this because most of us get what’s in it for you … but rarely think about it from the company and team’s perspective.
  • Why do you think you’re ready for this? If this isn’t crystal clear for everyone, then it becomes a rhetorical question.

The Key Dangers Of Going Remote I’d Mention To You:

These dangers are specifically in taking an otherwise great productive teammate and potentially losing or damaging all of that. These are the dangers that I’ve seen and to look out for.

  • Getting lost, disconnected, disengaged — One of the biggest complaints we’ve heard from our remote team is feeling disconnected from the team and each other. This is the toughest one for us. It’s not always anybody’s fault, just nature of the beast.
  • Getting distracted — From the laundry that needs to be done to the dogs insisting on sitting in your lap during a work call.
  • Poor communication — I’ll talk more about this, but going dark, not sharing with others what you’re doing.
  • Getting stuck and spinning your wheels — Not sharing struggles so you can get and receive help and move on to productivity.
  • Not maintaining good work/family boundaries — Not just from a work perspective of ensuring family members in your house know when you’re “working” or off, but if you’re officing out of your bedroom, for instance, when you go to bed, you can still see “work” and sometimes “worry.”
  • Not maintaining consistent work schedule or routines — I believe there are few people who can work haphazard hours and still be productive. It also rearranges the purpose of work … are you working for a team and company, or is the team and company working at your whim?
  • Not approaching it as a professional — Professionals show up, get the work done, communicate with their team … and frankly, take work as serious as it should be — the thing that allows me to buy a home, or food, or pay for my children’s college and my retirement.
  • Having the wrong mindset, attitude and approach about it — this goes back to the “What’s in it for us?” question. Make sure you deeply evaluate your attitudes and reasons for being remote.

Key Expectations and Responsibilities Of Being Remote I’d Expect:

  • It’s your job to make this a smashing success — It’s not my job either, but I want it to be a success. So make this an overwhelming and obvious win for everyone, not just you. If the promise is that it’ll enhance productivity, prove it.
  • Have a dedicated, private, consistent work space with good, reliable Internet — a comfortable private place without interruptions or distractions. We can control what happens in the office for the most part, but won’t know about them at your house or remote office. A key thing we’ve learned is setting good boundaries.
  • Good communication is non-negotiable — Going dark and off the grid does not instill trust and responsibility in your team. You should not assume anything, clarify it and overcommunicate. Like if you’re away from your computer for a time (taking a child to school, or an errand that may run long, etc), you should let everyone who relies on you, and ESPECIALLY your manager, know that you’re out. And if it’s longer than expect, talk to your manager about it first. This is even more of a priority for those positions where you are collaborating and communicating with other team members to get projects done. Don’t assume your team knows that you have ran out on a quick errand, or need to step out. I’ve heard it said — communication is oxygen for a team. It’s true. And even more so for remote teams. And conversely when you don’t communicate well it becomes distracting and damaging for everyone.
  • Availability and responsiveness is a must, especially in collaborative teams — Meaning if others rely on you to get their work done, you gotta be there and show up with them. For our team that means being Green on HipChat (the chat tool we happen to use today) and working set hours so the rest of your team knows when they can expect you, ESPECIALLY if you’re in different time zones. Additionally that goes back to other things like having access to good, reliable Internet, not being distracted by people in your remote office (i.e. caring for children or other family members or people), and establishing good boundaries.
  • Routines are everything — You may not think about it, but the structure of an office provides for many things that you will not have by default as a remote team member. One of our remote team members told me he makes sure to put on his shoes every day. For him, it’s a routine and a signal that says, “I’m at work.” Ditto for set schedules. When I first started iThemes, I was working from a home office and kept my same schedule, the one I’ve maintained for the last 9 years.
  • Traveling is disruptive and distracting — So don’t plan on it. Many people are allured by the thought of being remote so they can travel the world, or work from a hotel room off by a beach. It doesn’t work, especially if you have a very involved job, or have to take calls or attend regular meetings. I know because I’ve tried it. At best, I’m 50% productive as being in a fixed location with reliable Internet and set routines. Traveling is disruptive to routines and work, no matter how good you think you are at juggling it all. Nothing goes to plan. Flights get delayed. Time zones disrupt fixed expected schedules. And yes, you can NEVER rely on hotel or AirBnB for reliable or fast Internet, or being able to get to a coworking space in a new city. So if you want to travel the world, take your vacation or Paid-Time Off for those things and get real rest and recharging that comes from being away from work that you need.

OK, that’s it for now … I readily admit I might have missed some things and as always reserve the right to change my mind. But I hope this is helpful for you as you navigate working remote in your situation. Good luck!

6 replies on “So You Want to Work Remote …”

Absolutely spot on. I like the last part particularly. Travel is indeed distracting & doesn’t allow to be as productive as I would be if I were not traveling.
At best, I can get 25% of the work done when I am traveling, not more. Checking emails, responding to support tickets & that’s it.
In this year, the 1st week in February was the one where I got to spend one complete week at the office. For whole of January, I was traveling each & every week – for 2 days or so. That was the most disturbing part for me – to be not able to plan my year in that period. Eventually I had to plan that out in February.

Re: “Understand that failure could mean jeopardizing your job”. – I’d be wary of a manager who’s view is “if this request for remote working, which I’ve agreed to, doesn’t pan out, you’re fired”.

Dave, I’d be wary of any team member who doesn’t recognize the risks and dangers that moving from an office structure to working remote pose, as their request, doesn’t understand that.

Good post Cory.

I could add that the biggest challenge for our complete remote team of 8 is seeing what doesn’t work in the group dynamics.

Strains between team members they are easily swept under the rug or hidden to be dealt with later.

Being completely transparent in our communication (avoid DM) and sharing mistakes openly are 2 ways of fighting this.

Great points, Kim. I think it goes for every team member … good, healthy communication is key.

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