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How to Have Tough Conversations at Work

Topics: Work Culture

Life is full of conflict. This is especially true at work, where you’re not always choosing your priorities or associates.

If you’re someone who would prefer to avoid giving critical feedback, the bad news is that you can only get away with that for so long before it starts to impact your career. There’s no success without risk, and most workers will have to brave tough conversations in order to achieve their goals. But the good news is that there are strategies you can employ that will make difficult talks easier on all involved.

Here’s what you need to know:

Tough conversations are a part of working life:


Challenges are an inevitable part of having a job and building a career. And, it has nothing to do with how hard-working or conscientious you are. In fact, caring a lot about what you do might even increase the likelihood of conflicts at work, since it means you’re more invested. Problems will arise, no matter your industry, or what age you are, or what level of experience and expertise you’re bring to your job. Sometimes, these challenges necessitate a tough conversation and some solid pre-planning.

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So, here are some examples of difficult conversations you might need to have at work as well as some tips for how to handle each effectively:

1. “I need to give you some feedback/criticism about your work.”

Offering a coworker constructive criticism isn’t easy. Negative feedback isn’t always received well. You need to be honest so that things improve. But, you also don’t want to be so harsh that you alienate or demoralize the person your meeting with.

Keep in mind that there is a wrong way and a right way to give feedback. You want to be as specific and clear as possible, for example. It’s best to be brief and to the point. Also, even though you’re offering some criticism, you should try to say some positive things, as well.

Be sure that your feedback is honest, too. False praise won’t do anyone any favors. Finally, be sure that you’re critiquing the work, not the person. Talk about what they do not what they’re like. It will be easier for the person receiving the critique to hear you, and make changes, if your feedback is delivered with care and consideration.

2. “I’d like you to do this thing, But I know I’m not your supervisor.”


Most organizations still have pretty tight structures and hierarchies in place these days. But, that doesn’t mean that things always line up just the way you need them to. Occasionally, you might need to ask a colleague to do something for you, or for the company, even though it really isn’t your job to do the asking.

Instead of telling your coworker what to do, be conscious to avoid making any actual demands. Instead, frame your request as a question. Or, better yet, as a favor. It’s incredible how much more helpful folks tend to be when their assistance is offered willingly rather than demanded.

Also, if you want people to step up and help you when you need it, be sure to help them when they need it. This will greatly increase the odds that someone will be willing to do the same for you when the time comes.

“Being open to helping others is a key to career success,” James Clift, CEO of VisualCV, tells Monster. “It shows that you care about the team around you.”

Clift explains that maintaining a reputation for being helpful means a lot when you ask for assistance. In this way, you’ll avoid undermining others’ confidence in your abilities.

“Having that reputation helps others be aware that if you are asking a question, it is because you want to do your job the right way, not because you are unqualified,” he continues.

You might also consider giving a couple different options for how your coworker can help you. You might ask if they could do this favor either tomorrow or sometime early next week for example. Providing a little choice raises the odds that they’ll be able to come through. Plus, it’s respectful of the other person’s time to ask for assistance in this way.

3. “You’re fired.”

Letting someone know that they’ve been terminated from their position is the quintessential difficult work conversation. At Harvard Business Review, management consultant Dick Grote offers a few tried and true tips that can help you let someone go as nicely as possible.

The most important thing is to plan this particular tough conversation well in advance. As Grote points out, “This is one time when you can’t say, ‘I’ll get back to you on that.'”

First of all, be intentional about the time you choose for the conversation. Friday afternoons, for example, can be a good time in terms of minimizing the impact of the disruption on the rest of the organization.

Second, plan out what you’re going to say carefully and thoughtfully. And, be sure to get right to the point. Warning them that you have some “bad news” at the start of your meeting can help the person you’re letting go to be more prepared.

Remember to listen carefully to what they have to say after you’ve delivered the news. This will help you respond effectively. They might feel shocked, or angry, or they might be really sad. Listening closely allows you to wrap the conversation up gracefully and in the way that’s best for the individual.

Also, be sure to cover the specifics of what happens next, such as pay, unused vacation time, references, or anything else that’s important to discuss during the meeting. It’s best to attend to these kinds of details right away in order to move forward quickly.

Finally, thank them for their contribution, shake hands and wish them well. Stand and walk to the door together. These kinds of gestures help to keep your sense of dignity intact as well as theirs.

4. “You need to stop leaning on me so much.”

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Sometimes, coworkers can become a real burden. If you’re working with someone who needs a lot of assistance, it can become a drain to your own energy and time. And, eventually your work is bound to suffer, too. It’s great to be helpful and kind at work, but you shouldn’t overdo it. It’s important for your own career, and your professional success, to learn to establish good boundaries at work. If someone is leaning on you a little too much, you might need to have a conversation with them.

It’s always a good idea to start with the simple truth. Be honest and direct about how their behavior affects you. If you don’t have time to help, simply say so. There’s absolutely nothing wrong with saying “I really don’t have time to complete my assignments and help you with this.” They should back off after such a clear statement, especially if the pattern repeats.

If the problem continues anyway, you might need to tell your coworker directly that you simply can’t help them in the way they seem to expect. It’s not personal. It’s simply that you can’t sacrifice the quality of your own work because of regularly helping them to complete theirs.

Limiting the negative impact of a needy coworker can be more difficult for people-pleasers. If you are one, you might want to take stock of how it’s helping and hurting your career. You’ll see that setting good boundaries can help you be more successful professionally. And that should help motivate you toward that end.

5. “I’m not happy here and something has to change.”

It’s essential that you address the situation if you’re not happy at work. Sometimes, this can mean talking with your boss. That’s risky, of course. If your boss is sensitive to perceived criticism or under a lot of pressure for reasons you might not grasp, your conversation could backfire. But if your dissatisfaction is threatening your productivity and making you consider leaving, it might be worth seeing if you can solve the problem — and that means talking with your manager.

Before you do so, think hard about what’s going on. What is it that you don’t like? Is there something else you’d rather be doing instead? Perhaps you just need a bit of a change. It’s natural to need to shift things around once in awhile in order to stay happy at work.

Once you’ve thought through how you’re feeling and identified some issues, make an appointment to meet with your boss. Be sure to explain that you didn’t call this meeting lightly, you’ve really thought about all of this. Then, be honest about how you’re feeling and what would help you be in a better place.

“If you’re feeling frustrated and unable to get through projects in a timely fashion because of external factors – short-staff, not enough staff support and other issues – talk to your boss,” Wendi Weiner, a career branding expert, told The Ladders. “Make sure it’s in an open fashion about your frustrations, but try to make it focused on the things you need for your boss to do to get you back to being super productive in the office. The idea is to come in with a working solution of how you can be a better employee and what tools you need to get the work done and excel in it.”

Be specific and clear. But, don’t be rigid. Offer a few different possible solutions to the problem if you can. This will give your boss some choice about how to support you which will help your request to feel less demanding.

Finally, don’t be negative, personal, or emotional during these kinds of talks. Keeping it strictly professional instead will help you get the job done.

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