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6 Difficult Work Conversations and How to Handle Them

Business person having an bright idea light bulb conceptWhether you are the CEO of a Fortune 500 company or the manager at a fast-food restaurant, having difficult conversations at work is inevitable. You know when you have to talk to someone about how they keep showing up 45 minutes late or someone else because they keep taking personal calls at their desk? We’ve all been there.

Communication in the workplace cannot be understated. And when it comes to handling difficult conversations at work, proper communication is key. These types of conversations can be awkward and unpleasant, but below are some tips to keep in mind the next time you have to face a difficult conversation at work.


Tips for Handling Tough Work Conversations

Everyone’s defenses are high when these conversations roll around so it’s key you keep your cool and have a plan when they do. Here are a couple of tips to help.

  1. Don’t avoid the conversation: The longer you wait, the harder the conversation becomes.
  2. Have a purpose: Hone in on the problem right away.
  3. Be confident: Take initiative and get to your point quickly.
  4. Be open to the other person’s perspective: This will help you solve the current problem together and may even help your relationship in the long-term.
  5. Use “I” statements: Starting your conversation with “I” instead of “You” promotes positive communication and avoids putdowns.
  6. Stick to the facts: Be clear about what happened and take responsibility for your part in the situation.
  7. Come up with a solution: Find a solution together and come up with a game plan moving forward.
  8. Follow up: Within the next week, follow up with the other person to make sure they are doing okay.

6 Types of Difficult Work Conversations and How to Handle Them

From asking a coworker for help to addressing personality clashes between teammates, below are eight difficult conversations with actionable tips on how to handle them.


Employee to Supervisor


1. When You Feel Overworked 

Sometimes we get to our desk on Monday and a wave of anxiety runs through us. It’s okay to feel overwhelmed at work. If you have too much to do, be honest with your boss so you can come up with a game plan together to ease the stress. You will be doing yourself and your team a huge favor. Here are some tips:

● Be honest

● Avoid complaining

● Offer solutions to help


2. When you don’t agree with your boss

Disagreeing with someone is tough—especially when that someone is your boss. If you feel strongly about your opinion, you should speak your mind. With that being said, make sure to do it in a respectful and non-condescending way. Odds are your boss will appreciate your confidence and will respect you even more for speaking up as long as you handle it appropriately. You could be doing him or her a huge favor. Here are some tips:

● Keep the conversation positive

● Focus on results

● Respect the final decision


Supervisor to Employee


3. Addressing personality clashes with teammates 

Not everyone is going to get along in the workplace. If you are faced with two personalities on a team who just can’t seem to work out their differences on their own, it’s time to step in and address the problem. Here are some tips for handling that situation:

● Listen to both sides

● Determine the real issue

● Find a solution together


4. When an employee disagrees with promotion decisions

It’s natural for competition and jealousy to arise when promotion opportunities are present. If you catch employees being disrespectful or gossiping about a recent promotion decision, it’s important to stop the chatter right away. Here’s how:

● Address the issue ASAP

● Be empathetic

● Stand by your decision


Employee to Employee


5. Asking for help

It’s okay to ask for help. A lot of times employees will avoid this because they don’t want to seem incompetent. However, reaching out for help is not something to be ashamed of. It’s smart and will likely help you in the long run. Here are some tips on asking for help:

● Be honest with what you can handle

● Give thorough instructions

● Offer help on future projects


6. Saying no

On the other hand, sometimes a coworker will ask for your help on a project you simply don’t have time for. If you already have a lot on your plate, it’s okay to say no. Here are some tips on how to do that:

● Be respectful

● Tell them about your current workload

● Offer help in the future




About the Author: Tom Anderson is the editorial director at Haven Life. He is an award-winning journalist whose work has appeared in, Kiplinger's Personal Finance, Money, Monocle and Wired.

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