How to have a tough conversation with your boss during a pandemic

One of the more complicated byproducts of living and working through a pandemic is the utter loss of spontaneity. When everyone works in the same space, it’s a lot easier to casually have conversations that might otherwise seem awkward or urgent. When you’re all working from home though, it can be a bit more complicated to raise important issues, much less mull over them for a while- or revisit if things become awkward. That said, there are some conversations that are too important to postpone.

It’s new to everyone

Before you work yourself up about approaching your manager, when you’re all working virtually, “It’s helpful to remember that this is new for everybody and there are no experts when it comes to how to negotiate work in a pandemic,” said Samara Bay, speech and dialect coach and host of the Permission to Speak podcast. That gives all of us a little wiggle room in our approach. 

The success of your team depends on it

Feeling awkward probably isn’t reason enough to postpone having the big talk, here’s why. If something doesn’t work on your end, it’s entirely possible that it’s messing up the flow of your entire department. Even worse, if you don’t mention it, someone else might.

Stay in touch with your manager

Even if you’re not great at checking in regularly, now is a good start to ease into the habit. “Don’t forget the purpose of your manager,” said HR expert Samantha Friedman, SVP of People Strategy at Vettery. “They are not there to be a babysitter or gatekeeper of some sorts, rather, they are responsible for the success of the team and the individuals that make up that team.”  It’s also important to remember that they’re there as a resource and to support your growth. Friedman reminds us “Just because we’re remote and thankful to have a job in a time of high unemployment, does not mean we hit pause on our professional development.” Besides, “This is as good a time as ever to take advantage of them as a resource.”

Issues to discuss right now

As companies prepare to return to work, Friedman said that it’s important for employees and managers to re-establish their communication and working styles. “Whether you’re continuing to work remotely, returning to work at the same time, or on different rotating cycles, it’s important to take the time to revisit or reform your working relationship.” That might include figuring out if the frequency of touching base or even figuring out the medium for meetings or how the team will connect in the future. 

It’s not just business

We can be so focused on doing a great job that we often forget that our bosses or supervisor have to be tuned into our personal concerns as well. “Employees should remember that their manager has a duty to support their professional development but also their personal wellbeing,” explained Friedman. 

You might also want to consider whether “this time of global crisis has loosened any of the rules around your work’s culture, especially around the separation between public and private life,” Bay said. She also advised asking yourself if there’s an opportunity to say something “that feels a little more private as you ask for what you need? Not necessarily the whole story about why you need what you need but dare yourself to be just a bit more revealing than you might have been before all this and own it.” Bay also said to realize that “your boss may very well be grateful for the honesty, too.” 

Sooner is better than later

If you have concerns about returning to work, for whatever reason, Friedman said to “make sure to have that conversation sooner than later and set expectations. That way you and your manager have ample time to determine how to accommodate your concerns and determine the best path moving forward.”  

Try for face time

If you’re not sure how to broach the subject with your boss, keep in mind that video conferencing is probably the way to go. “For any meeting with your manager, whether it’s sensitive or not, I always suggest a face-to-face meeting using video conferencing software if in-person is not possible, Friedman said. Depending on your relationship with your manager, you can then decide if you need to set up an additional time to meet virtually, or if you’re comfortable that you’ve covered all of your topics of concern. 

Give them some advance warning

Don’t randomly drop important concerns into your regular catch up calls. “If you are taking the time to prepare for a meeting, it’s usually in your best interest to let your manager take time to prepare as well,” recommends Friedman. While you’re at it, “Consider emailing them to say that you have put time on their calendar to discuss your concerns regarding X and can adjust the timing based on their availability. That way, your manager can come to the meeting prepared and you can engage in a more productive conversation.” 

Be prepared

Even if you’re great on the fly, you’re best off preparing an agenda. “It is always in an employee’s best interest to come to meetings prepared, no matter who it’s with or what it’s for,” Friedman said. If you don’t get a lot of face time with your manager, Friedman said that it’s even more important to know what you want to say and how you’re going to say it. “When coming to your manager with a concern, you want to be able to explain the concern from a high-level, provide context into the situation, and talk through a few potential solutions that either you or your manager could assist with.” Besides, “Taking a solutions-oriented approach and offering potential practical ways for you to work through your concern shows your manager that you’re committed and typically leads to better results.” 

And be prepared to be disappointed at times

So, what happens if you hate your boss’s response? Can you ask for a redo? “If you go into a meeting with a very specific desired outcome, you are more likely to be disappointed,” Friedman said. She added that “Like most relationships, the one between manager and employee will involve some give and take and it’s important to have that awareness when going into the conversation.” Since there will probably be negotiation and back and forth, Friedman advised preparing yourself “to make your points and rebuttals that much stronger.” More than that, even if you don’t like your boss’s response, that doesn’t mean the conversation is over. “It’s important to understand what the concerns the manager and/or the business may have so you can properly prepare and address them when you come back to the table to negotiate. Continue to maintain a solutions-oriented approach and provide additional context or research to support your argument while addressing their concerns.”

At the end of the day, it’s important to keep communicating with your supervisor or manager to remind them just what a valued member of the team you are.