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Advice / Succeeding at Work / Work Relationships

Your Guide to the 6 Toughest Conversations at Work

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It doesn’t matter how much you love your job or feel fulfilled by your career. You’ll still have to deal with some difficult discussions at the office. In fact, a whopping 85% of Americans say they’ve faced work-related conflicts, according to CPP Inc. research. But here’s the good news: When on-the-job differences were handled constructively, reported workers in the same study, it actually benefited the company.

So what’s holding us back from bringing up the toughest stuff when doing so has been shown to improve work conditions? “Difficult conversations are different from other conversations,” explains Holly Weeks, author of Failure to Communicate and adjunct lecturer at the Kennedy School at Harvard University. “They carry a particular emotional load—some combination of anger, confusion, embarrassment, anxiety, pain, and fear.”

Here’s how to make sure you get the outcome you want.

1. The “I’d Like a Raise” Talk

Let’s get this out of the way first. It’s one of the most common, and stressful, conversations to have with your boss.

Try: Aim to keep emotions out of this conversation. This can be hard when you’ve felt like you’ve earned a pay increase for a long time. “There’s no trick to handling conversations well despite tough emotions—only skill,” says Weeks. We know very well how to speak neutrally when we’re not emotional. The skill, says Weeks, is bringing this tone into a difficult conversation. “So commit to speaking from neutral even when you don’t feel like it,” says Weeks. It’s more likely to get you a positive response from a supervisor.

Once you’ve mastered the right tone, launch into your well-prepared argument about your proven track record, market value, and income potential.

2. The “You Tend to Fly Off the Handle Easily” Talk

In times of stress, your boss tends to get almost volatile. How do you address this with her without another outburst?

Try: Immunize yourself against this behavior that provokes you. “We need to be vulnerable to behavior for it to trigger a reaction from us,” explains Weeks. Where we’re exposed to weakness, we have three choices: react again and again, make our counterpart stop his behavior, or, best, immunize ourselves with some mind tricks to keep you calm, says Weeks.

Weeks recalls one client’s two tricks for staying calm. First, she loved thunderstorms, so when the counterpart started to shout, she pictured a huge thunderhead she had seen in Mexico, which calmed her. Second, she practiced saying, neutrally, “I can hear your points better at a lower volume.” To her surprise, this worked. The manager said to her, “Am I too loud? I’m sorry.”

It turns out that the manager was innocently offensive: Tension made her voice tighter, higher, and louder, but she couldn’t hear it herself. Because the person who had practiced spoke clearly and neutrally, the manager did not feel attacked and, in turn, was able to change her behavior.

3. The “Your Workload Expectations Are Unrealistic” Talk

Can you really have this conversation without threatening your job security?

Try: Don’t push this one under the carpet. “A difficult conversation can make the difference between the success and collapse of a valued relationship,” says Monique B. Jensen, principal of the Aviary Group, an Ontario, Canada full-service corporate consulting firm.

First, get your head in a positive frame of mind so you can have a relaxed atmosphere when you bring up your workload concerns. Next, “use open-ended questions to draw out the causes of the difficulty in this awkward situation.” For example, determine before you meet how long each task your manager asks of you realistically takes to accomplish. Then ask your boss how long she expects each item on your to-do list to take. This way, you can find out how your boss sees the workload before you come across as naive or confrontational.

4. The “Why Was I Passed Over for That Promotion?” Talk

Approaching a boss for an explanation about your job performance doesn’t have to be as stressful as you think.

Try: Use a soft approach, says Jensen. Sometimes starting a conversation that is so tied up with your sense of worth at the office can turn heated or panicked. So practice a neutral dialogue before your meeting. “Then get to the point quickly,” adds Jensen. This doesn’t have to be a long conversation when you first bring it up to your superior. In fact, it may end up being two separate conversations over time where the first one identifies your interest in a promotion. Then a subsequent conversation can be about what skills you need to improve to get that next advancement. To think: A stressful conversation has just been bypassed simply because your boss may not have even have known you wanted a promotion until now.

5. The “You’re Not Handling Your Workload Sufficiently” Talk

Here, you’re the manager, and it’s your subordinate who needs a meeting. She needs to show some improvement on the job, such as taking more initiative on new projects that fall on her desk.

Try: Aim to uphold the relationship and not ruin it. “Your reactions are your own worst enemies in difficult conversations,” says Weeks. So prepare a rough outline of what you want to say and how you predict she’ll respond. Then give her constructive direction, not just criticism, on how to do a better job. She just may come away with a better understanding of what your goals are and how to reach them.

6. The “You’re a Co-worker Who Undercuts Me” Talk

Is your colleague from another department cutting into responsibilities under your domain? Or is she part of your team, but making decisions on your behalf without your prior approval? When you have one of these co-workers in the office, it may be time to have a talk.

Try: Think like a chess player, says Weeks. She notes that this is not the same as having a strategy prepared for the problem you want to solve. Rather, it’s about having a specific way to handle the conversation because you know it will get tough. “Thinking strategically lets us see how we could move, it lets us think how our counterpart could move—even how our counterpart is likely to move.” Working from strategy—not a script—helps you anticipate problems and how to handle them. This way, it’s less likely you’ll be taken by surprise by your co-worker's response and come away with a mutual understanding that's a win-win for both of you.

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