Why Some Bosses May Hate Remote Work

First, to start out, I need to make one thing abundantly clear: This piece is just a bunch of assumptions, generalizations and feelings. I’ve gathered these together after all of my own experiences. That’s why I add the most important auxiliary verb may.

I think its important to understand some of these points, however, for two reasons. First, if you’re looking to jump to remote work, it’s good to be educated about some of the pushback you might receive. Second, if you’re already remote working, your existing boss may not 100% appreciate that. It’s good to understand some of these positions so you can help rectify some of the negative feelings.

With that, let’s talk about a few of the reasons why some bosses may hate remote work.

Building Team Camaraderie is Harder

When you’re in person, it can be much easier to build team connections and relationships. It’s easy to just lean over, share a joke, ask for help, or have a quick conversation around the water cooler. There’s a significant amount of communication that is done via facial expressions and language tone. When you’re remote, this can be harder to create. There’s also the bonding forms that happen when you eat lunch together or go out for a beer after work with your peers. This is something that can be harder to build remotely.

One of the jobs of a boss is to build team unity. When given a choice, most of us will focus on our job over that of our direct reports. It’s just the hierarchy of things. So, you could argue, that by working remotely, you may be making your boss’s job harder. (We can argue a bunch that its a trade off because you can hire more people, etc, but that’s not the point here.)

But, it can be done. There needs to be more focus put on building the team. These things that happen organically in person need to be planned with a remote work force. That is to say, when you leave a team alone in person, they tend to just develop relationships. When its remote, you might find you’ve got to put a bunch more effort into building those relationships because you’re not right in their face. That being said, you’ll find that a successful boss with remote workers focuses on building that team connection.

This can come in the form of a few different ways and mixes. First, even though its remote, some companies require a yearly meet and greet and get-away. Especially if this is planned correctly, this can jump start and recharge these remote relationships. Another way to stay connected and build strong communication skills is to use video conferencing. It can be quick and easy to just message on slack or email, or to just stop at screensharing. But, the video conferencing part is important.

Over the years, I’ve had many people push back on video conferencing as they were remote workers. Tons of excuses, but I always demanded it. The benefits are great. First, we get to see non-verbal communication. This helps reduce miscommunications. Second, your boss can help identify if you’re getting stressed out and suggest remedies. You normally only notice this if you suddenly snap via text communication. Finally, when you see people regularly, there are certain chemicals that get released in your brain. This type of connection can happen over video as well, as far as I can see it. (How about some facts? Sadly I’m missing citations here.) The pushback, when it happens, I’ve stamped out with two points. One, it’s a requirement, so you need to do it. And two, if you were in the office, you’d be required to be seen. The flexibility of remote work is your own office, not the flexibility of being completely isolated. That’s not what we want.

Panic and Crunch Time

This one is highly dependent on the entire culture of the company. Sometimes certain organizations have groups of remote workers, but the entire company isn’t remote. This can be common with companies that have on-site C-suite people but remote “drones.” This can work, but it does have some disadvantages. One of them is the disconnection during panic and crunch time.

When you’re in the office, and your boss’s boss knows there’s a problem, there’s a certain level of satisfaction and comfort to be obtained by walking through a bull pen of excited, stressed or frantic workers. It’s not my place to say whether this is right, just to point out that this does happen.

When you’re in person, it’s easy for your boss to say “yes, we have a problem, but look, they’re all attending to it.” When you’re remote, unless you’re doing some sort of major communication plan and video share, that feeling may not be communicated properly. If they could be a fly on your wall, they’d know you’re working as hard as you can, throwing out solutions, batting them down, etc. But, since you’re hidden away, there’s some ambiguity there. Do the workers know how important this is? Have they dropped everything to tackle it, or are they ordering their next Mai Tai? When you’re in in person, this is easy to see.

The way to combat this is simple: develop a communication plan for this possibility before it happens. Plan out an escalation plan, and a plan and pattern for regular updates. It may not be 100% match one to one for these concerns, but at least there’s something there. It’s much easier for the boss’s boss to be ok knowing there are scheduled updates once ever 15 minutes versus not seeing anyone, and not knowing if anyone is working or cares.

Empire Builders

There’s something inspiring to look out over your kingdom, your land, and know that you built this. Again, we’d like to say these attitudes are right/wrong, but let’s just focus on the fact that they exist. Some bosses like to look over their collection of workers as the empire they’ve built.

Now, this doesn’t always have to be bad. Some bosses are inspired by the lives that they’ve been able to change. Sometimes this is from a pay raise or a promotion, other times its from knowledge, learning, and opportunity. But, looking out, they can survey their work and know that they’re building something good… no great! This is harder to do when your collection of workers is remote.

If you think you have a boss like this, it’s important to understand where this attitude is coming from. If it’s pure ego like “look at my fast car, look at my huge team,” you’re in trouble. Polish up that resume (I know, easier said than done). But it could also be that they like to see the efforts of their work. This is a much easier problem to tackle.

What they really want is to know that they’re making a difference. You can help with this by publicly thanking them through proper channels so others can see and recognize them. Another thing you might do is to share a bit more with them that you might another boss. This purposeful sharing will help offset the fact that they can’t “see” you in person. It helps them feel connected with their good work. Finally, it’s ok to even ask them: “I know it can be hard to keep an eye on everyone when we’re not there in person. What could I do better to help you stay informed?” You never know. This might get you something cool and fresh that will help you solve this problem - as well as others.

Final Thoughts

There are other reasons that some bosses may not like remote work. This is just a few ideas and ways to combat those problems. But, on the flip side, I’d say that the workforce is changing and there are many more bosses who are ok with remote work. Even if they’re ok, some of these attitudes are good things to analyze still. They might be ok, but you could go above and beyond to make the connections stronger.