How to handle difficult conversations at work

Whether you’re a CEO of a Fortune 500 company or a college student working part-time at a fast-food restaurant, we’re all faced with difficult conversations in the workplace. Sometimes you’re dealing with an employee who doesn’t agree with your decision. Or maybe it’s a coworker who’s distracting you from getting your work done. Whatever it is, difficult conversations at work are inevitable.

Many of us try to avoid these types of conversations. We would rather ignore the problem in order to avoid an awkward scenario. However, this kind of behavior can lower morale and cause a toxic work environment. That’s why it’s important to face these conversations head-on and address them with confidence.

To help, here are some examples of difficult conversations at work with tips on how to handle them.

Difficult Conversations: Employee to Supervisor

Bringing up issues at work is difficult. Bringing up issues to your boss can be especially hard. From disagreeing with your boss’s decision to calling in sick, check out our tips below.

When you don’t agree with your boss’s decision

Sometimes we don’t completely agree or understand our supervisor’s decision, and that’s okay. If you feel strongly about your opinion, you should say something. Your boss will likely thank you or respect your courage to come forward. Here are some tips:

  • Keep the conversation positive.
  • Focus on results.
  • Respect the final decision.

When you’re sick

It’s okay to be sick — it happens. Don’t feel the need to apologize when explaining the situation to your boss. Here are some tips on how to handle that conversation:

  • Don’t apologize.
  • Keep it short and sweet.

When you’re overworked

Work stress is common. If you hit a breaking point and feel that there is too much on your plate, you should say something. Your honesty will help the whole team and will benefit your work in the long run. Here are some tips on how to tell your boss you’re overworked:

  • Be honest.
  • Avoid complaining.
  • Offer solutions to help.

Difficult Conversations: Supervisor to Employee

The higher your position, the more difficult conversations you’re likely to face in your work. From dealing with clashing personalities on a team to telling someone they didn’t get a promotion, here are our tips for handling difficult conversations as a supervisor.

Dealing with personality clashes

Not everyone is going to get along at work. When dealing with two people on a team who just can’t seem to get along, pull both aside privately and handle the situation as adults. Here are our tips:

  • Listen to both sides.
  • Determine the real issue.
  • Find a solution.

When an employee doesn’t meet expectations

As a manager, it is your job to make sure the people under you are performing at their best. If you notice someone who has been slacking lately, it’s important to discuss the issues in a professional manner as this can affect the rest of your team. Here are some tips on navigating that conversation:

  • Address the problem.
  • Offer ways to help.
  • Provide reassurance.

When an employee disagrees with a promotion/compensation decision

This is a common one. Whenever there are opportunities for advancement in an organization, it is natural for coworker rivalries and jealousies to arise. However, it is important to nip this is the butt right away. Here are some tips:

  • Address it right away.
  • Be empathetic.
  • Stand by your decision.

Difficult Conversations: Employee to Employee

While these conversations happen around your peers, they can still be difficult and oftentimes awkward. From telling a coworker no to asking for help, here are our tips on how to have a difficult conversation with a fellow employee.

Saying no

Many times, a coworker will ask for help on a project if they are out of town or overworked that week. However, it is not always your job to help out. If you already have too much on your plate, it’s okay to say no. Here are our tips:

  • Stay positive.
  • Offer advice.
  • Stand by your decision.

Dealing with a distracting co-worker

If your coworker distracts you to the point it is inhibiting your work, it’s time to say something. Gently pull them aside and have a genuine conversation. Here are some tips on how to handle that conversation:

  • Keep their feelings in mind.
  • Remain respectful throughout.
  • Offer to get coffee once a week instead of chatting in the office.

Asking for help

Sometimes your work week gets ahead of you, you become late on a project and you need an extra hand. It’s okay to ask for help and it is not something you should be nervous about. Here are some tips to keep in mind when reaching out to a coworker:

  • Be confident.
  • Explain in detail with what you need help on.
  • Offer to help with one of their projects in a later time.

When it comes to difficult conversations at work, communication and confidence are key. For more tips on how to handle difficult conversations at work, check out the infographic below:


Post by Sierra Skelly

Sierra Skelly is a creative writer and marketer from San Diego. She loves making personal finance and career content fun. When she isn’t writing for companies like Haven Life, you can find her reading at the beach or hiking.

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