How to Start Your New Remote Job on the Right Foot

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You Got the Job–here’s how to tweak your schedule so you can enjoy your day to day.

On August 2nd I started a new job. I wasn’t expecting to change roles, but my company’s needs changed, and I had to change to meet that need. This is the nature of remote work. One day you may work as an analyst, and the next in people management. The savvy remote worker develops skills to bounce back when life (or your company) disrupts your status quo.

We can’t always control our own destiny. No one asks to have their position eliminated. But we can all develop habits that help us deal with the unexpected. A few weeks ago I talked about how to network when you don’t know anyone. This week we’ll discuss how to take control of your day to day when you start a new role.

Start with a Positive Attitude

We’ve all had bad bosses. Many of us have worked in places with a toxic culture. Or perhaps you’re in the opposite situation. Don’t let these past experiences sour your new role.

That’s easier said than done, especially if (for example) your new boss works in ways that are similar to a previous bad boss. Know your triggers. I had a terrible boss we’ll call Stan. Stan was an extrovert who needed to talk to work things out. He would repeat what other people said in meetings immediately after they said them in order to process the information. Stan was also passive-aggressive, controlling, and enjoyed calling people names.

Intellectually, I know these things have nothing to do with each other, but when I’m in a meeting with someone who is a detail-oriented auditory processor, I think of Stan. And I have to remind myself that repeating what other people say isn’t evidence of evil. It’s evidence of an auditory processor.

Trust, But Verify

If you find yourself triggered by your new boss or team, take a step back and diagnose the situation. I’ve found it helpful to ask myself a set of questions:

  1. Let’s pretend there’s a reasonable explanation for this. What could it be?
  2. Do I have concrete evidence that this person or team is mean?
  3. Could this be explained away by lack of caffeine or sleep?
  4. What did the person say when I approached them about the situation?
  5. Is there a pattern of bad behavior or is this a one off?

Give people a chance to do right by you. For all you know, someone on your team finds YOU triggering. We don’t think of ourselves as the bad guy in our own life. Remember, though, that your new team mates don’t know you. And remote workers don’t have many unplanned opportunities to see each other interact with other people. Lead with trust. We all have to make a conscious effort to demonstrate that we’re sane people. That takes time. Your reasonable response to stressful situations will show people how great you are.

Don’t Let Yesterday’s Great Ruin Today’s Good

Or perhaps you’re in the opposite situation. Perhaps your former team was great and you’re grieving their loss. This was my situation on August 1. I’d said my goodbyes to the people who were leaving, and to the people who moved to different teams. That loss was in the front of my mind during my new team’s kickoff events on August 2.

What helped, of all things, was thinking of my son. Two years ago his best friend moved away. The boys went from seeing each other every day at school to seeing each other every couple of months. My son absolutely refused to make any new friends for a year. He thought that if he was miserable long enough, he could force his friend to move back to his old home.

You and I are adults and we understand that this isn’t how the world works. But if we’re not careful, we can act as if it does. You can like your new team and your old team at the same time. Not everybody has the good fortune to work with a great team. Enjoy your memories while you work to build different ones with a new set of people.

Assume You Have Some Agency

When most people start a new job they worry about proving themselves. This is largely a healthy reaction when you’re trying to establish a good reputation.

There’s a difference, though, between trying to be a team player and putting up with unnecessary inconveniences. The remote workforce gives us an unparalleled opportunity to craft flexible schedules. Freed from the limits of geography-based offices, we can get work done in a way that lets us live fuller lives.

Don’t be too quick to give that up with your new team. You might have a strong desire to go with the flow and accept every meeting people put on your calendar and treat them as immovable. The fact is, you don’t know how sacred those meeting times are unless you ask. So ask. Assume that your boss and your team mates are reasonable people who are willing to move things around when they can.

Lead with Trust

Again, this is easier said than done. It’s my policy to lead with trust and assume the best, but it was still scary to ask my new boss if we could talk about the reoccurring meetings he was setting up with the new team. We’re following an agile model and holding daily stand up meetings. And wouldn’t you know it, those meetings were all scheduled for the time slot formerly known as my lunch break.

Now, I don’t like eating while on camera. I don’t care if anyone else does so as long as I don’t have to hear chewing. But that wasn’t the real issue. I run on my lunch break. Running outside is how I keep from feeling cut off from the rest of the world when I work from home. It’s important to me.

It’s Always No Unless You Ask

I’ll admit that I took a few days to dither about whether I would really ask the whole team to move the daily stand up just so I could go running at lunch. Once the dithering process was over, I brought it up with my boss.

As this was a potentially tricky conversation, I decided to save it for our one on one. I wanted to see his reaction when I asked to move a work thing for my running. I already knew how he liked to communicate because I asked him in our first meeting. So I sent him a quick Slack message the day before our meeting letting him know I wanted to talk about potentially moving our stand up meetings.

I explained that I block off an hour and a half in the middle of the day to finish my morning work, plan my afternoon, and then run for 30 minutes. I wasn’t sure if he chose our daily meeting slot because it was the only time that worked for most of the team, but I would like to explore shifting the time either up or down if possible.

Give your new team a chance to show who they are

Photo by rawpixel.com from Pexels

There are times in your life when you gear up to persuade people to your way of thinking, only to find out they don’t need to be persuaded. My boss picked that time because he thought it would work for everyone. He was happy to move our meeting since the time wasn’t working for me. When he brought up the issue with the rest of the team, it turns out they preferred to have the meeting earlier in the day anyway.

I found out two good things that day. First, that my boss values daytime breaks. Second, that my team is full of nice people. I would have figured these things out eventually, but I’m grateful I didn’t spend a lot of time bereft of my lunchtime run because I was too afraid to ask. Give your new team a chance to show who they are. You may also be pleasantly surprised at the result. And remember to be the sort of person who is willing to be flexible for the sake of other people’s schedules. We’re all in this remote working boat together.

Starting a new role comes with a lot of mixed feelings. Will you do a good job? Will you get on with your boss and your team? If you lead with trust, assume the best, and approach your new situation with a flexible mindset, you can craft a job that you enjoy going to day in and day out.

How to Get Ready for an In-Person Work Conference When You Work Remotely

When you work from home, getting ready for an in-person event can seem like a hassle. Keep these 3 things in mind as you get ready.

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I’m headed to New York in a few short weeks to attend a work event. Throughout the years, I’ve discovered that there are some remote-specific things to keep in mind if you rarely attend in-person events.

Go Into the Meeting With a Good Attitude

There are two primary schools of thought out there about in-person meetings. The first says that in-person meetings are mandatory if you want your remote employees to work well together. The second school of thought is that in-person meetings are unnecessary. Everything you could do in an in-person meeting you can do online. Like most things, these points of view are probably true for some people. Neither is 100% true for me.

Most days I love working from home. There is something so delightfully self-indulgent about getting to work in the quiet of my office of one. As I write this, I can hear the rushing of the wind outside, the hum of the occasional car as it goes by, and the clicking of the keyboard as I type. I need this silence regularly if I want my brain to produce stories.

I also really like seeing people in person. I can (and do) make time to connect with my colleagues throughout my work week. I have several coworkers that I consider friends even though we work in different time zones. And yet it’s often easier and quicker for me to forge those initial human connections in person.

I will suggest (with no data to back this one up) that most successful remote workers do best when they have the occasional out-of-computer work interaction. You may not feel the need to see people in person, but your coworkers may need to see you in person in order to get along with you. If you have a chance to meet your colleagues for a coffee or a workshop in person, see it for the opportunity it is. Personally, I’ve made a mental list of people I want to talk to during the conference, and I’m excited to chat with them.

Check Your Work Clothes

Very shortly after getting excited about my trip, I realized that I have no idea what people wear to work these days. The dress code at Douglas HQ is a button down shirt with a pair of old jeans and knitted socks. And while my knitted sock game is truly righteous, I suspect that I’m going to need foot ware that covers up the awesome.

I asked the internet ‘what is business casual,’ and Wikipedia said “Business casual is an ambiguously defined dress code…it entails neat yet casual attire and is generally more casual than informal (sic) attire but more formal than casual or smart casual attire,” which didn’t really help.

Other sites confirmed that a button down shirt and slacks are still fine, but how much can you trust sites that say silly things like ‘you must wear a belt’ or ‘no knitted tops?’ Does anyone else find it funny that we can get a robot to Mars but we can’t define a work style that has been around for a generation?

As far as I can see, business casual means whatever your company says it is. If you’re going to an in-person work event, you might want to check your employee handbook to see if it has any guidelines. You may also want to take a moment and think about how conservative your company culture is. And finally, take an honest look at how worn out your work clothes are. I already knew I needed to buy slacks. A search through my work tops revealed that I needed some help there, too.

Put a Face to the Name

There is nothing more awkward than showing up at a work event where people excitedly greet you…and you have no idea who they are. Ask me how I know. When you work remotely, most conversations take place via email and instant messenger. While some of these platforms give you an option to upload a picture, not all of them do. Add jet lag into the mix, and it can be very hard to remember what some of your favorite colleagues look like.

On behalf of remote employees everywhere, I ask that you please take a moment to upload a picture of yourself into your email and instant messaging platform. And please make it a recent one. My own personal rule is that I need to change my photo every 2 years. You can take a flattering picture of yourself using your smart phone. Put on a work top, stand against a wall, raise the camera slightly above eye level, and take your shot. Adding a photo gives you the moral high ground to suggest that everyone on your team do the same thing.

If you are planning a work event, ask the participants to provide a photo of themselves, and share them with the group. I work for an educational company, and the event organizer created a set of flashcards–one side has the picture, the other has the name. I absolutely love them. A quick internet search yielded several sites like this one, that lets you make your own custom flash cards if you love this idea too.

I’ll be using my flashcards every day in the two weeks leading up to the event. I might still blank out if someone greets me from across the room, but at least now I have a fighting chance.

In person events can seem like a hassle if you only work from home. For instance, you might have to buy work clothes and put on shoes. However, approach the event as an opportunity to strengthen your working relationships for years to come. If you look at it that way, it’s easier to see how the benefits in such a trip can outweigh the inconvenience. Plus you might get some nice work shirts out of the deal.

5 Things I would Have to Give Up if I Stopped Working from Home

Remote workers get to take charge of the rhythm of their days. It’s what keeps many of us working in our office of one.


Photo by rawpixel on Unsplash

Recently on Twitter, someone asked what would have to change if remote workers stopped working from home. For some reason the question really caught my attention. Here is my list of things I would have to give up if I went back to a traditional office.

#1: Singing While I Work


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Nothing helps me power through a a tedious job quite like belting out some of my favorite tunes. I’m sure I had a different coping mechanism when I worked in cubical land, but I can’t remember what it was so (probably) it was less awesome. Sadly, it wouldn’t matter how much I enjoy Lady Marmalade. No one wants to hear that in an open office.

I’ve heard of offices where you can’t listen to music at all. A friend of mine works at an office where you aren’t even allowed to wear headphones. I wouldn’t last long in a place that uses that level of micro control over its employees.

#2: The Continuous (Audible) Commentary


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I would either have to learn to be less judgmental or go back to filtering what I say. It isn’t that I talk to myself per se–I’m more like that person who watches a movie and says stuff like ‘Watch out!’ to the characters on the screen. Only, my commentary is more along the lines of ‘oh no you didn’t just try that,’ as I’m reading my email.

#3: Wearing What I Want

Sometimes, you need a top hat. Photo by the author.

The dress code at Douglas HQ is whatever I say it is. I am not one of those folks who wears pajamas all day. I usually rock a button down top and jeans, paired with fabulous hand-knitted socks. There is the occasional ‘top hat Friday.’ The added fabulousness makes up for the workout clothes I wear while I cool down from my run.

I enjoy getting dressed for work. My clothes are as comfortable as they are appropriate for my role. I can take a surprise video call at any hour of my workday without feeling like 10 pounds crammed into a five pound sack.

#4: My Office, My Rules


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I have a large medal and racing bib holder on the wall behind my office chair. My office is filled with plants, a rowdy Beta fish named Mac, and books on knitwear design, management, and running. I have a funky orange throw on my office chair. My office is full of color, pictures of my kids, and souvenirs from the places and people I have visited over the years.

My office pleases me. And I don’t have to explain to anyone why I have a pair of robots dressed like Wesley and Buttercup from the Princess Bride. I keep them out of camera range. I feel that if you have to ask, then you won’t understand the answer anyway.

#5: Enforceable Focus Time


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My entire career has been spent in roles where I am the nexus between people and processes. To put it in less lofty terms, I’m a choke point for several different departments. Back in my old office days I would voluntarily get into work at 6am on Fridays just so I could work without getting my elbow jogged every 3 minutes. I would eat lunch out so people wouldn’t drop by my cube to ask work questions while I was eating.

Now, when I want focus time, I turn off all of my notifications. If I work while eating my lunch, it’s because I chose to go running on my lunch break. My time isn’t always my own, but generally I am the boss of the rhythm of my day. All jokes about singing and top hats aside (though that stuff is totally true) THIS is why I love my remote office.

At the end of the day, working remotely allows me to be myself at work. I can indulge in my love of wacky office decorations and pop music knowing that my choices don’t impinge on anyone else’s concentration. I love the freedom to concentrate or connect with others on my own terms. It’s a lifestyle I wouldn’t willingly give up.