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The 4 Most Difficult Conversations You’ll Have in Your Career

U.S. News & World Report U.S. News & World Report 7/11/2015 Alison Green

A faceless man and a faceless woman with mouths open wide sharing a speech bubble.: When you tell your boss you're quitting, keep your statement short and direct. © (Getty Images) When you tell your boss you're quitting, keep your statement short and direct. One of the most stressful parts of work life is figuring out how to say something tough, unpleasant or awkward to a colleague. Most of us aren't fond of difficult conversations in any setting, but doing it at work can be doubly challenging, because we fear for our professional reputations and relationships. 

Here are four of the most difficult conversations you may need to have in your career and the secrets to making them go smoothly.

1. "I'm quitting." This one might sound easy, and many people fantasize about the day they walk out of a bad job or a poorly managed workplace. But when it comes down to actually doing it, those same people often find it surprisingly hard to let their bosses know that they're leaving. People often feel regret about leaving something familiar, even when they weren't that happy there, and it can be tougher than expected to say the words "I'm quitting." That's especially true when you did like the job and your manager and are moving on for reasons that have little to do with them.

How to approach it: The key to resigning gracefully is to keep it short and direct. For example: "I've really appreciated my time here, but I've made the difficult decision to move on, and my last day will be November 17." And know that it's normal to feel some regret; bringing any period of your life to a close can be bittersweet.

2. "I'm firing you." Ask any manager, and you'll hear that firing an employee is one of the hardest things he or she ever has to do. Even when the employee has been given every chance to succeed, it's natural to feel terrible about taking someone's job away.

However, taking action when someone isn't working out is one of a manager's most basic and crucial responsibilities and can't be shirked. (Unfortunately, managers far too frequently err on the side of not letting people go when they should, typically because they want to avoid the tough conversations it will entail.

How to approach it: In most cases, a firing should be the final installment of an ongoing conversation. The employee shouldn't be blindsided, because you've already told the person about the problems and what needs to change; warned her if her progress isn't what it needs to be; and explicitly said that her job will be in jeopardy if you don't see specific changes. If you handle it that way, then when the actual firing conversation happens, it's an expected next step – not a surprise. It's still going to be hard, but it's far better than firing a shocked employee who didn't see it coming and had no idea that your concerns were serious.

3. "Stop harassing me." You'll be lucky if you go your whole career without encountering sexual harassment, racist remarks or other inappropriate behavior from a co-worker. Federal law requires employers to address sexual harassment or behavior that creates a hostile workplace based on race, religion, sex, national origin, age (if you're over 40) or disability, so you're very much entitled to tell offenders to knock it off – and to report them to your company if they don't. But knowing that the law is on your side doesn't necessarily make it easy to speak up.

How to approach it: First, know that if you're not comfortable saying something directly, you can go straight to your company's human resources department, which will have a legal obligation to address the situation. However, if you're willing to say something to the offender on your own, that can be a more efficient and direct method of getting the behavior to stop. (And when you go to HR, they may encourage you to do that if you haven't already.)

The key is to clearly state that the behavior is unwelcome and that you want it to stop. For example: "Please stop asking me out. I've told you that I'm not interested, and I need you to stop asking." Or: "I don't want to hear that kind of comment. Please don't say those things around me."

4. "I made a big mistake." Everyone makes mistakes at work, but if the mess-up is large enough, your job or reputation might be on the line. Coming clean can feel like putting your career at risk, but you'll look far worse if you don't say anything and it comes out later. Professionally, it's much worse to be someone who makes mistakes and doesn't own up to them.

How to approach it: Be as straightforward as possible, as soon as possible. Make it clear that you understand the seriousness of the mistake and that you're mortified that it happened. Explain briefly and without defensiveness where you went wrong and what steps you're taking to avoid it ever happening again. You might find that this approach makes your manager much less worried than she'd be if you didn't approach it this way.

Or, yes, it's possible that you'll have a lot of work to do to regain your boss's trust. In the worst-case scenario, she may have real doubts about your fit for the role. But, as tough as that would be, it's better to talk about that explicitly than to have it happening below the surface without talking openly about it. 

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