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7 Uncomfortable Conversations You Hate Having With Your Boss (And How to Have Them Anyway)

Jun 20, 2017

In today’s multigenerational workforce, life tends to come at you faster than ever—and with that, diminished boundaries between you and your superiors. The way you communicate with your boss used to be a bit more polished and measured, but with the rise of social media and everyone following everyone, along with a constant stream of in-office instant message conversations and Slack chatter, it’s harder than ever to see where the lines are drawn.

But that doesn’t mean every conversation is easy.

There’s no employee handbook for dealing with your superiors, but with the right framing, these days you can talk to them about just about anything.

Here are seven uncomfortable conversations many of us will face over the course of our careers, and expert advice for powering through them.

The Problem: You Hate Their Strategy

Sometimes, leaders make bad decisions and if you sense your manager is making a damaging strategic decision, it’s okay to tell her so.

Before you bring it up, make sure you have some well-researched alternatives to the future company roadmap—and find some common ground to kick off the conversation.

“The more you can get people to nod early with small wins, the more likely they are going to keep nodding with things they may have disagreed on initially,” says Tammy Erickson, a workplace expert and executive fellow of organizational behavior at London Business School.

What to say:

“Last week, we talked about how consumer tastes are changing, and what we can do to keep up with them. You outlined one solution, but I think there are a few others worth considering. Here’s why.”

The Problem: You Hate Your Coworker

You’re not going to click with everyone in your professional life, and in most cases the best advice is to get over it.

That said, if a teammate’s behavior is so egregious that it impacts your work, or the business in general, it needs to be addressed.

First, evaluate if it’s worth making this your boss’s problem. If there’s a behavior issue, like constant deadline stretching that threatens your goals, you may try talking to the colleague directly. The same goes for social quirks—if your coworker is constantly making private, distracting phone calls, it’s probably worth having a polite conversation about the impact that’s having on the office.

If the issue isn’t reconcilable, or if talking to your colleague directly didn’t work, tap the chain of command—but be sure to have a solution in mind.

“Look at this from your boss’s perspective,” Erickson says. “You don’t want to just dump something on their lap that’s going to make their life more difficult. Give them an out.”

What to say:

“Joe and I are having a really tough time working together. We’ve talked about it directly, and weren’t able to find a solution. If there’s an opportunity, can I be assigned to a different team?”

The Problem: You Have a Major Health Issue

If a major illness is disrupting your work schedule, or if you need special accommodations, you’ll want to tell your supervisor.

Before you have that conversation, though, think about what you need from the company—whether that’s flexible work arrangements, office modifications, or otherwise.

Mental health issues like depression and anxiety may take some extra consideration. Many companies have added mental health resources to their wellness offerings in recent years, but some employees still fear repercussions (like losing out on a promotion) if they disclose a mental health condition.

“People will go out of their way to hide these things,” says David Ballard, Ph.D., assistant executive director of the American Psychological Association’s Center for Organizational Excellence. “Not only does that mean they’re not getting the treatment and support they need, but the energy it takes to hide those issues piles onto their stress.”

In these cases, Ballard advises workers to consider the nature of their relationship with their boss, as well as the culture of their organization, before bringing it up. If you think asking for special arrangements could damage you professionally, find a human resources representative who has knowledge of your health plan, or someone from an employee assistance program, to talk through your options.

For any major diagnosis, an employment lawyer can help you understand what protections you have under the Family and Medical Leave Act (FMLA) and the Americans with Disabilities Act (ADA).

What to say:

“I really love working here, but I’m suffering from a major medical problem. Here’s what my doctor recommends.”

The Problem: Things Are Bad at Home

Bad breakup? Eviction notice? You can’t exactly sever your emotions during the workday, so if a personal crisis starts to impact your professional life, you’ll probably need to tell your boss about it.

These conversations are infinitely more awkward if you’re not used to sharing personal information with your manager—think about how transparent you can afford to be before approaching them.

“The level of disclosure depends on the boss,” Ballard says. “If they’re more relationship-focused, you may be able to be completely upfront. If it’s someone who is more task-oriented, you may want to bring it up in the context of the impact it’s having on your availability, on how you’re working in the moment.”

So ... what about a hangover? If it’s manageable, you can probably just acknowledge that you’re not feeling well without going into the hairy details. If it’s not, take a sick day.

What to say:

“I’ve got a lot of personal stuff going on right now, and I know I’ll be a lot more focused if I can take a few hours to sort it out. Can I take a half-day on Tuesday?”

The Problem: You Did Something Stupid

From social media gaffes to bad business mistakes, most of us will need to do damage control at some point in our career.

If you find yourself in an embarrassing professional situation, own up to it ASAP.

“The first step is to address it right upfront, before it blows up into a bigger problem,” Ballard says. “Focus on what you’ve already done to fix it. And if it’s a really complex situation, ask to talk it through to make sure everyone is satisfied with the solution.”

What to say: “I know I screwed up. Here’s what I’m doing to remedy the situation.”

The Problem: You Need Something From Them

Every so often, you’re going to need a favor. Whether it’s a small one (an extra day to meet a deadline) or a big one (working from home every Tuesday), carefully plan out how you’re going to address it beforehand.

A little courtesy goes a long way—don’t catch your boss as he’s leaving for the day, or at the tail end of a deadline. In many cases, you’ll get a lot further if you approach it from his perspective.

“Frame it in terms of your boss’s needs, goals, and ambitions,” says Emma Seppälä, Ph.D., science director of Stanford University’s Center for Compassion and Altruism Research and Education.

What to say: As you know, I’ve been working crazy hours on the days before my deadlines. I know I would be more productive if I could work from home that day, and not have to commute to and from the office. Is this a possibility?

The Problem: You’re Not Getting Along

If you’re constantly bickering, or there’s a sense of animosity hanging over your relationship, something isn’t right.

“If your gut is telling you this relationship doesn’t feel good anymore, try to understand what might be driving it in that direction,” says Annie McKee, Ph.D. and author of the forthcoming book How to Be Happy at Work. “It takes courage, but the sooner you can sit down and begin that conversation the better.”

This will take a little introspection. Is your behavior driving the disconnect? Are you misreading the company culture? Have your deliverables slipped?

Whatever the answer, when you sit down to talk about this, make it clear that the goal is to communicate better—not assign blame.

A caveat: If all the tension is coming from your boss’s side, consider whether this person is worth building a relationship with. Nobody wants to work for a bully; it could be time to find another job, or at the very least consider a trip to human resources.

What to say: “You’ve got some big goals coming up, and I feel like I could be more supportive. What would help us communicate better?”

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