Your Remote Boss Doesn’t Necessarily Hate You

Your Remote Boss Doesn’t Necessarily Hate You

You have problems, I have advice. This advice isn’t sugar-coated – in fact, it’s sugar-free, and may even be a little bitter. Welcome to Tough Love.

[referenced url=”https://www.lifehacker.com.au/2017/10/why-you-shouldnt-take-your-crappy-roommate-to-small-claims-court/” thumb=”https://i.kinja-img.com/gawker-media/image/upload/t_ku-large/qk7vazgtdn4nslyybsox.jpg” title=”Why You Shouldn’t Take Your Crappy Roommate To Small Claims Court” excerpt=”You have problems, I have advice. This advice isn’t sugar-coated – in fact, it’s sugar-free, and may even be a little bitter. Welcome to Tough Love.”]

This week we have a young professional who’s having a hard time adjusting to remote management after having a more hands-on, supportive boss.

Keep in mind, I’m not a therapist or any other kind of health professional — just a guy who’s willing to tell it like it is. I simply want to give you the tools you need to enrich your damn lives. If for whatever reason you don’t like my advice, feel free to file a formal complaint here. Now then, let’s get on with it.

Hi Patrick,

I’m coming up on 26 and am still at my first job out of university. I’m not in a good place with it any more and am not sure what to do. When I first started, I had a great boss. We had a good working relationship and even better was that he believed in me and pushed me. Right from the start, he’d tell me he saw leadership potential in me. He said I had the most potential of anyone on our team. He encouraged me to speak at marketing conferences and pushed for our whole team to focus on professional development. Under him, we had a great sense of a unified team. And I felt like I was going places.

That was the first half of my time at this job. The second half has not been as pleasant. My first boss left and his replacement is all business. I have a hard time building a relationship with her… she isn’t strong in that department and also works remotely. I’ve never heard anything from her to indicate she sees “leadership potential” or anything similar in me. There is no focus on professional development. In fact, I now have to twist arms to be able to attend marketing events, webinars and so on. No one else on the team does these things any more. Our team has turned into feeling like this “marketing production line” where the focus is on pumping out as much work as we can. Team morale is low. I’m not sure if my boss can see this as she works remote. I’m also not sure if she cares.

What should I do? I can’t come out and say, “Hey boss. You’re really crappy compared to my last one.” I don’t have anyone to confide in at work. I’ve been so depressed about it lately. And yes, I’ve been applying to other positions. No interview offers yet. I would really appreciate hearing your thoughts.

Thank you,

Cross With the Boss

Hey Cross With the Boss,

It sounds like your first boss was a great leader. He was supportive, gave you guidance, and was essentially grooming you for future leadership. He was top notch, which is probably why someone else hired him. Off to bigger and better things (or maybe retirement).

To be honest, Cross, most bosses aren’t like that. Even a lot of the good bosses I’ve had in the past weren’t always pushing me to be better, giving me words of encouragement, or guiding me along the path to greatness. In fact, most people in management are just concerned with the bottom line. They’re not all kind mentors interested in helping out the next generation of whatever, they’re regular people with their own stuff to worry about. They just want you to get your stuff done so they don’t get yelled at by their own superiors. Basically, your first boss kind of ruined all future bosses for you. Your new boss isn’t a bad boss, she’s just a normal boss who wants to get stuff done in a timely manner and has no interest in pampering you. Your company, your boss, they’re not your friends, Cross. Welcome to the workforce.

A big part of the problem, however, is that you and your coworkers are experiencing what I like to call “remote work growing pains”. You see, your old boss was around to actually see your work ethic and potential first hand – something your new boss can’t do since she’s remote. All she can go off of is the results she sees at the end of the day, and the brief interactions you get with her during conference calls. That setup leaves very little opportunity for your new boss to get to know you guys, give you guidance, or grant any praise. Ever hear the phrase “out of sight, out of mind?” That’s what’s happening here, and it’s something you need to get used to. No more gold stars.

Keep in mind, though, text-based communication such as email and chat clients – which I’m sure you use – leave a lot of ambiguity. When I first started working remotely, I thought my bosses hated me because I read their emails and chats as negatively as possible in my head. When I got to know them better, I realised I was wrong, and “great” really meant “Great!”, and “it’s fine” actually meant things were fine. Chill out. Unless you’re told something is wrong, nothing is wrong.

But you’re feeling stuck, so what should you do? For one, don’t tell your boss she’s crappy (from what I can gather she’s normal). Take the initiative here and talk to your boss more. You think she’s just going to magically notice that you’re feeling blue when she’s remote? You have to communicate! Tell her that you were on a certain professional development path before your previous boss left and that you’d like to continue along that track. I mean, if you don’t tell her how would she know that stuff?

Also, connect with your coworkers. Now that your boss is remote, you guys need each other more than ever. Find a way you can all confide in each other. It will help you all get on the same page and ask for changes together if need be. And keep twisting arms to attend marketing events, webinars and what have you if that’s what you want. That’s what most people have to do in order to get that stuff. Lastly, keep applying to other positions and other companies just in case things don’t ever get better. Actually, never stop doing that. It’s how you climb in the professional world these days.


That’s it for this week. I probably didn’t make you feel all warm and fuzzy inside, but sometimes what you need is some tough love. ‘Til next time, figure things out for yourself.


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