As more and more organizations are shifting away from the traditional five-day workweek it’s more important than ever to have difficult conversations at work.

How to start the conversation?

Honesty is the best policy, at least according to workplace experts and psychologists.

The shift to remote work for many knowledge workers may not have been planned—and for many of us, has accelerated feelings of burnout—but it has forced us to confront the myth that “real” work only happens in an office. Blueground’s furnished apartments in key cities worldwide have doubled as offices for quite a few of our guests in 2020 and 2021, and new guests are embracing a “work from anywhere” ethos.

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In order to have an effective remote-first workforce, company leaders, managers, and employees need to find a way to be transparent about challenges to their productivity.

The way this process plays out won’t be the same for every organization, or even every member of the same team within an organization.

Here are actionable tips leaders can use to make difficult conversations at work less awkward and get to the heart of what’s getting in the way of great work.

Business economist and clinical psychologist Dr. Merete Wedell-Wedellsborg shares how pervasive the disorientation has been in the Harvard Business Review:

“As we dug through the layers of the organization, it turned out that the feeling was widespread among other leaders and managers.

Stress incidents were on the rise, people’s emotional reactions were becoming more polarized, and there were more team defections.”

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When Emotions Run High at Work, It’s Everyone’s Problem

When she talked to leaders across a broad sampling of industries, Wedell-Wedellsborg found that people were universally stressed out at work in the second half of 2020.

“It goes by different names: ‘pandemic fatigue,’ ‘mental fog,’ ‘work/life blur,’ ‘extended vacuum,’ and an ‘endless wait,’ just to mention a few phrases I have heard leaders use.”

Work/life blur indeed. Whether we’re at home on Zoom all day or cycling between the office and a job site, our workday is happening against an every day is the same, Groundhog Day backdrop of boredom on one hand and the desperate hope for a change in the pattern on the other. Wedell-Wedellsborg points out that we need to remember that the pandemic is a marathon, not a sprint:

“Personal resilience in the second wave is a different story because it relies on psychological stamina. Psychological stamina rests on more deep-seated emotional patterns shaped by our individual needs, histories, and experiences.

Stamina is required because, frankly, the second wave is not exciting at all. People report feeling bored, disconnected and unnerved.

In contrast to the skin-deep reactions of the first wave, the second wave requires perseverance, endurance, and even defiance against the randomness, gloom, and burden of the pandemic.

“Cultivating resilience requires some emotional rewiring and calls for a different kind of appeal to team members and colleagues. The essential task is to identify your biggest challenges over the next year and then tap the psychological stamina you and your team need to get there.”

So in other words, everyone is feeling weird and burned out.

No one wants to have difficult conversations at work, but avoiding them just prolongs the damage.

When companies ignore the elephant in the room (like a global pandemic), productivity suffers across the board.

Wedell-Wedellsborg encourages C-level managers to be honest with the rank and file about challenges they’re facing and potential bumps in the road.

“Leaders need to be serious about mental wellbeing and intervene sooner rather than later. This means that your employees need more warmth and comfort than they might have prior to the pandemic.

But you can’t soothe your team with spreadsheets and plans; that takes listening and daring to stay in the hardest moments–daring to talk about doubt and discomfort—instead of skipping ahead to the next item on the agenda.”

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How to Start a Difficult Conversation

Wedell-Wedellsborg thinks the top brass should set the tone by being open.

“There are a couple of ways to approach this. One involves saying ‘I don’t know’ or sharing your own feelings of discomfort. I see an enormous difference in leaders who express their insecurities, because it goes both ways: When you dare to tell your team about the issues you struggle with, they will follow suit.”

Her advice is great for C-level employees, but what about the rest of your company? How can managers encourage their direct reports to speak up about challenges? Officevibes has put together some great do’s and don’ts for starting a difficult conversation at work:

Difficult Work Conversation Do’s

  • Do be vulnerable and open up about how you feel.
  • Do be a part of the solution and take on some action items.
  • Do check in at the end so you’re both on the same page.
  • Do think about what you’ll say and how you’ll say it.

Difficult Work Conversation Don’ts

  • Don’t start the conversation without thinking about it first.
  • Don’t let professionalism overpower humanity.
  • Don’t arrive with a to-do list or deadlines for the other person.
  • Don’t hammer at your side of the conversation.

Communicate the Purpose of the Meeting Ahead of Time

A “what are your challenges right now?” meeting might be a little bit awkward but it’s not actually a difficult work conversation.

If done right, the employee will come out of the conversation feeling that their concerns were heard and that their manager or the C-suite have also been honest about their own challenges. The invitation to this meeting should make it crystal clear that no one is in trouble.

Alison Green of Ask a Boss advises that every out of the ordinary meeting at work should come with an invitation that makes it clear whether the meeting is good news or bad news.

“In general, managers should try to let people know what a meeting will be about (so that people can prepare and also because some people get anxious otherwise), but there are times when it really doesn’t make sense to announce it ahead of time.

You often can say something like ‘I want to talk about how the X project is going” or ‘I want to talk about some concerns I have about X’ or ‘I want to make sure we’re on the same page about Y.”

For a company-wide meeting, choose a subject line like “Town Hall: Supporting Your Work-Life Balance” that makes it clear that this is not a bad news conversation. One-on-one meetings should be informal, like you’re sitting down over coffee, so don’t schedule those for 10am on a Monday.

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As we all figure out how to thrive in the new normal, Blueground is helping our guests around the world show up as their best selves.

Our thoughtfully furnished turnkey apartments have everything someone needs to get started in a new city, whether they’re working remotely or commuting into an office.

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