Remember the good old days, when you could clear up an ambiguously curt email from your boss with a stroll by her desk? Or when the anxiety of getting a dreaded “We need to chat” Slack message could be alleviated with a quick pop-in?

If only we knew how good we had it!

By this point, those of us who have moved to working from home have figured out the big stuff. Maybe your kitchen doubles as a desk now, and your pet has become a frequent surprise guest in your Zoom meetings, but nearly a year into the pandemic most of us are making it work. But there are certain things about communicating digitally that don’t always translate so easily, and of those things, experts said, is how we communicate with our bosses. And if yours wasn’t great before the age of working from home, odds are he or she hasn’t improved.

But that doesn’t mean there isn’t hope to salvage the relationship — and now, as pandemic fatigue has fully set in, may be a better time than ever, said Mollie West Duffy, a Seattle native and co-author of “No Hard Feelings,” which looks at how emotions affect our work lives.

“We know through research that we’re much more likely to read into a lack of emotion in digital communication as being negative, because we’re missing all the context cues,” West Duffy said. “So if your boss says, ‘I want to chat tomorrow’ without saying something like ‘I think you did a great job and I just have some comments,’ you’re going to assume your boss has something negative to say.”

She added that because a return to normalcy is kinda-sorta on the horizon, “we’re in a transitional moment, and we like to capitalize on transition moments because it makes having these conversations that can be awkward a little less awkward.” (However: If your relationship with your boss has veered into territory that can’t be fixed with a few conversations, it may be time to escalate — more on that later.)

Establishing how to interact

Outside the work itself, a poor relationship with one’s manager often boils down to bad communication, said Mary Abbajay, author of “Managing Up: How to Move Up, Win at Work and Succeed With Any Type of Boss.”


This was true in normal times, and is even more so now that we’re unable to read body language and other nonverbal cues that provide useful context and information when we communicate. Establishing how to interact is just as important as the actual communication itself.

“A lot of times we have conflict because we prefer different forms of communication,” Abbajay said. “You want to make sure you’re having conversations with your colleagues around how you want to communicate and what kinds of things are going to be communicated in what way.”

For example: Because home has become the office for so many of us, finding the time and space to have a conversation may not be as simple as starting up a Zoom from the kitchen table. It could mean asking a partner to watch the children, scheduling around the cooking of meals or finding a quiet room. So being flexible with how we have those conversations can alleviate a lot of misunderstanding around the substance of a chat, Abbajay said.

Maybe your boss would prefer a text over an email, or a Slack message over a video chat. But whatever the medium, knowing how to communicate can be just as important as what you’re saying.

“Make sure that you’re communicating and adapting to other people’s preferences in terms of getting their attention and time,” Abbajay said.

She agreed with West Duffy that now would be a good time to check in and have that talk, as annual reviews may be happening and the new year is a good excuse to do an evaluation about what’s working and what’s not.


“Take the time to really assess how well the virtual engagement and communication is going,” she said. “What’s working well? What are the ways we’re not communicating well?”

Managing your manager

There are many types of bad bosses, Abbajay told me a few years ago. You might have a ghost boss (someone who’s seemingly never around), a seagull (bosses who, she said, “swoop and poop” or “swoop and scoop,” meaning they “divebomb into a project” and leave a mess behind “or they dive into it and take it away from you”), or a simple “incompetent.” Of course, most managers are a combination of styles. But working remotely can add entirely new layers to those archetypes — and we may be behaving in those ways ourselves, too.

“The pandemic has turned a lot of us into ghosts,” Abbajay said. “It’s going to be up to you to help your manager learn how to manage remotely.”

Directness, West Duffy said, is often the best way to get what you need from your manager, and being proactive and naming an issue rather than hoping it will go away on its own can help give you agency in improving a bad situation.

“If you think the relationship isn’t great, chances are your boss thinks that, too,” she said. “Just naming that and saying, ‘I know it’s been difficult to communicate,’ and being on the same page during the pandemic” can clear the air and help you train your manager on how best to manage you.

Having these conversations is never easy, but going into them well prepared can help you get what you need, West Duffy said. Write down what you think the pain points are, and think through the language you want to use to discuss them. Use statements of fact, like “When you do this, it affects me this way,” and avoid ambiguity by saying, “Help me understand” the issue.


“It helps us mentally to go into these conversations not only knowing the topics, but knowing the words you’ll say,” West Duffy said.

Also keep in mind that your managers are dealing with their own stressors at home outside the job, and have compassion and empathy about the ways that may be influencing their approach to work, Abbajay said.

“You always want to assume positive intent and give a little grace,” she said. “People are stressed, and this is a very weird time.”

West Duffy added: “We don’t know” what’s going on “in someone’s personal lives, home lives, the calls they’ve just been on. We just have this one little slice, and emotions bleed into other meetings and we just don’t know. So there is a little bit of giving them the benefit of the doubt and depersonalizing it a little bit.”

When a conversation can’t fix it

Now, all that said: A stressful world is not an excuse for rude, abusive, inappropriate or otherwise beyond-the-pale behavior from a manager or a co-worker. If your boss’s behavior is beyond ghosting on an email thread or being unclear about expectations, it’s important to recognize that you have a right to a safe environment. No amount of clearing the air will fix an abusive manager.

Raising these issues with higher-ups or human resources can be tricky in a work-from-home world, so research your company’s policies and protocols.


“Escalating during a pandemic is very hard,” Abbajay said. “If you have a bully boss or a truly toxic boss, do a little research about how your HR department handles that.”

This is all the more difficult for women and members of minority groups, who are often already at a disadvantage in the workplace and who have been disproportionately affected by the pandemic. But having a clear, specific plan about how to escalate a situation and what outcome you want can help. And most important: Document everything.

“If you need to escalate, do it,” Abbajay said, “and be really clear about what you need to get out of it.”