Examples of Difficult Conversations at Work

Regardless of whether you want to have certain conversations at work or not, you will have them. It’s just part of working. Whether you’re the boss of your own business or whether you’re an employee or contractor, sometimes these types of conversation happen and sometimes they’re super-hard.

1. Pay Raise Issues – Some employers will never give you a pay raise unless you ask for it. Some companies have policies in place where you get a raise the same time of year as everyone else, during your performance review. For others, you must ask.

This is a very difficult conversation to have, but you must have it. Set an appointment, take with you examples of your successes, and bring a number with you a little higher than you think you can get. This is an expected event in the workplace, so rest assured that your boss is expecting it.

2. Feedback for Poor Performance – It can be very difficult to be the boss sometimes, especially when you need to give an employee feedback for poor performance. The best way to approach this is to tell them a couple things they’re doing right, and then talk to them about the things they’re doing wrong. But don’t just say what they’re doing wrong; tell them how they can fix it and set deadlines.

3. Letting Someone Go Due to Performance – Having to fire someone is never something you go into lightly. If you’ve already given them a warning and tried to help them fix their performance issues but it’s just not happening, it’s time to have the talk to let them go. Usually, they’ll have to go that day, so you need to be ready for the fall-out and ready for them to be upset about it. Try to be non-judgmental but firm.

4. Letting Someone Go Due to Layoffs – This type of difficult conversation at work is harder than a lot of the others, because it’s not the employee’s fault. Write up letters of recommendation, and try to give them a decent severance package if you can. Even try to locate other positions for them elsewhere when appropriate. Be gentle, explain the situation, let them know you’re going to give them a knock-out reference, and then let them go.

5. Inappropriate Colleague Behavior – If you have a problem with a colleague who acts inappropriately at work, try talking to them about it first. If that doesn’t work, contact HR or your supervisor depending upon company guidelines. It’s never easy to do this, but it can be best for the health of the entire team. Perhaps the inappropriate colleague may even learn a lesson and become a better person for it.

6. Asking for a Promotion – It can be difficult to work up the courage to ask for a promotion at work. But, if you have the credentials, the experience, and have proven yourself and there is an opening, then you should do it. Gather all your proof, set up an appointment to talk to the right person, and you may be surprised at the answer.

7. Issues Related to Sexual Harassment – This is probably one of the most difficult to deal with. Most of the time it is a male supervisor or colleague doing the sexual harassing, and it can be hard for a woman to complain. But the best action to take is to let the person know that you find their behavior unacceptable, and that if it happens again you will file a formal complaint and then follow through.

8. Power Challenges – Often there is a lot of workplace drama in relation to power challenges. This can be a difficult one. If you work in a team environment and someone in the group is often challenging you to the point of being rude, it’s best to try to have an informal conversation with them first. Then if that doesn’t work, bring in your supervisor or HR.

These conversations are difficult to have at work, but they are conversations you must have nonetheless. Do not put them off when they arise, because most of the time taking no action is either permission for someone to act poorly or permission for you to never get a raise. You’ll feel better once the conversation is over if you act with integrity, honesty, and empathy.