5 Tips for Managing Your Remote Boss

August 2019

With remote work on the rise, more people are discovering that not only their team mates are spread out across the globe… but their boss is too.

Having a boss who works in a different country to you can be an unusual experience the first time around. In the corporate world this scenario is actually quite common - global corporations often have reporting lines that cross borders and timezones.

In a previous job, I had 8 hours of time difference between me and my boss. This meant that when I was leaving work, he was just getting into work!

Usually the people who have international reporting lines in a large corporation are in a mid to later stage of their career. So they generally have some experience at navigating the logistical or political challenges that may arise because of the time difference and physical separation.

Now however, it's not uncommon for someone to get a remote job early in their career or even as their first job. That can be a pretty scary prospect since there are both awesome and (potentially) challenging things about having a remote boss.

Great things about having a remote boss

  • More flexibility
  • More meritocratic
  • Less micromanagement
  • Less meetings
  • Less frequent but higher quality interactions

Some challenges you'll need to actively manage

  • Mutual trust can take longer to develop
  • Potential lack of 1-on-1 mentorship
  • Potential lack of direction / growth opportunity
  • Lack of immediate help when you need it
  • Getting your point across can be harder

With those aspects of this remote work scenario in mind, here's a few things that I wish someone had told me, the first time I had a boss who lived in a different country.

1. Share achievements often

A big part of a successfull relationship with your boss is them knowing what you've achieved. This is easy in a co-located scenario where people are sitting near each other. In a remote scenario though, wins both big and small can accidentally go unmentioned or unrecognized. Over time this can result in your boss being unaware of what a team has achieved and / or a team feeling underappreciated.

Figure out what cadence is appropriate and keep your boss in the loop regularly regarding what you've accomplished. This could be in the form of a weekly email, or even an internal blog - I've seen both of these used effectively in previous companies.

Your boss may not have the time to read each update right away, or in minute detail, but the very fact that you are taking the time to share regularly makes an important statement to your boss.

2. Don't send walls of text

If you have a problem or need to discuss something important or sensitive, avoid sending the infamous "wall of text" email.

Stewing over a problem and taking time out to articulate a long, drawn out email is never usually the best way to kick off a conversation. Your boss may not reply right away which is probably going to make you feel worse, or they might misinterpret parts of it which can lead to further complications.

The best thing to do in this situation is schedule a proper phone conversation or live video call and talk over the issue together.

3. Have regular contact by video or voice

It's important to share achievements regularly as mentioned above, but it's also important to have more general interactions regularly by video or voice. Don't let all your interactions with your boss be via email or slack - your boss needs to understand you as a person (and vice versa) and the best way to do that is to see and hear each other on a regular basis.

Weekly video or voice check ins can be used to talk about the important stuff - the company roadmap, issues / blockers you are experiencing, performance and expectations, encouragement etc. These don't have to be in real-time, you can try using asynchronous tools if timezones are making live interactions difficult.

4. Raise issues early

In a co-located working scenario it's much easier for your boss to know when something is wrong. In a remote team scenario problems can go undiscovered and unsolved for much longer as indicators are less obvious.

If you're experiencing a problem your boss can help to solve, raise the issue early and don't let it percolate - especially if you are working remotely by yourself. You risk the problem becomeing bigger if you try to deal with it alone - get in touch with your boss and ask for help, that is what they are there for.

5. Be open about your needs as an employee

When you are co-located it's easier for your boss to understand your needs and your personality type, and successful working relationships depend on this understanding.

For example some people love open-ended challenges while others much prefer a clear, agreed-upon framework to follow. Some people are motivated by public recognition while others prefer it to be private. Some people want mentorship while others want independence.

In a remote team scenario it's harder for your boss to catch on to these specific preferences as they won't be working with you side by side every day. So it's best to have an early, open conversation about what motivates you as an employee and what you need from your boss to be successful.

Jon Yongfook@yongfook

Jon is the founder of Talkshow and an experienced remote work advocate. He has built teams remotely, reported to a remote boss, worked on projects with teams in dramatically different timezones, and experienced being a company's first remote employee. He has also built and sold several startups remotely. Jon rides a motorcycle, lives out of Airbnbs and works from coworking spaces.

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