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These Are the 10 Most Difficult Conversations to Have in the Workplace — And How to Handle Them It's tempting to put hard discussions off, but procrastinating can make things worse.

By Amanda Breen Edited by Jessica Thomas

Sometimes, navigating the workplace requires hard conversations — whether it's asking for a raise, delivering bad news or owning a mistake.

It can be tempting to put off those difficult discussions, and many people do. A survey from VitalSmarts revealed that more than 80% of workers are hiding from at least one uncomfortable conversation.

But not confronting workplace issues head-on will only hold you back.

Tension in the workplace can actually be a good thing, Liane Davey, psychologist and author of The Good Fight: Use Productive Conflict to Get Your Team and Organization Back on Track, told CNN — if it's productive and not left to fester.

Related: Dreading an Upcoming 'Difficult' Conversation? Here Are 10 Tips That Can Help.

HR solutions company Remote analyzed Google search data to determine the top 10 most difficult conversations in the workplace.

Check out the full list below — and read on for advice from Remote's VP of people Nadia Vatalidis on how to approach the trickiest subjects.

  1. How to ask for a pay raise
  2. How to tell your boss you're sick
  3. How to give negative feedback
  4. What to say on your first day of work
  5. How to report unfair treatment
  6. What to say to someone leaving a job
  7. How to report bullying at work
  8. How to talk to your boss about burnout
  9. What to say to an employee who is leaving
  10. What to say when you've made a mistake at work

These difficult conversations will come up, Vatalidis says, but there are ways to make them a little easier.

"All team members should be encouraged to proactively address problems, rather than avoid the conversation and prolong an issue," Vatalidis explains. "Leaders should strive to create a work environment that fosters open communication and honesty so when they are needed, these types of conversations don't feel so hard."

Vatalidis suggests managers establish regular 1:1 meetings with direct reports to help keep those lines of communication open.

Related: The Value of Having Difficult Conversations in the Workplace

For employers and employees alike, Remote recommends keeping these five tips in mind to make those hard discussions more manageable:

  1. Don't wait. The "perfect" time to have a conversation usually doesn't exist.
  2. Be prepared. For example, if you're asking for a raise, know how much you want and be able to explain why you deserve one.
  3. Know your talking points. Sharing these with all conversation participants in advance ensures everyone is on the same page.
  4. Remain professional. Don't let your emotions get the best of you.
  5. Collaborate on a solution. Brainstorming a way forward together will end the discussion on a positive note.
Amanda Breen

Entrepreneur Staff

Senior Features Writer

Amanda Breen is a senior features writer at Entrepreneur.com. She is a graduate of Barnard College and received an MFA in writing at Columbia University, where she was a news fellow for the School of the Arts.

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