The Most Difficult Conversations You Have Ever Had At Work

Author

Rose Pastore

November 27, 2014

This week at Fast Company, we’ve been talking about challenging conversations, from “Your performance sucks” to “Hey boss, I’m pregnant.” We learned the common mistakes managers make when delivering bad news, and what to do when a coworker has a meltdown in the office.

We hoped to find stories of people navigating stressful topics with courage and compassion, so we asked our Facebook followers: “What’s the most difficult conversation you’ve ever had with a boss, employee, or coworker?” Some of our favorite responses, collected below, are examples of how to approach emotionally charged discussions with strength, tact, kindness, and integrity.

On A Smelly Coworker

“Talked to an employee about body odor. In a private meeting in my office I said I wanted to ‘check in with him to see how everything is going.’ When a few minutes of conversation had passed I said, ‘there’s a difficult subject we need to discuss. It’s come to my attention that there is an unpleasant odor from you and your office. What do you think is going on?'” —Dara Wass Barwick

On Being Vulnerable

“It was difficult but the best thing I ever did. Breaking down in my bosses’ office and telling them that I had PTSD. They built a support network like you wouldn’t believe. Helped me learn the power of my story and gave me room to create something amazing, using the skills the military gave me and transferring them to the entrepreneurial education world. Ever since that moment they challenged me to get help, and since then I have been nothing but successful after two deployments to Iraq.” —Jeremy Boeh

On Brutal Honesty

“My bosses were owners for forty years. I had to tell them ‘what got them here, won’t get them there.’ Meaning they grew it to a $10 million dollar company in 10 years, but that was 30 years ago. It was time to let new blood get them to their $100 million dollar goal. I was fired. They are now an $8 million dollar company.” —Demian Ross

On Fessing Up

“I owned up to my boss and my colleagues what I failed to do as my accountability, which could cost my company millions of dollars. After I told the truth, I took actions to correct the mistake and the company was able to get the money that could have been lost. It was really tough because I had to give up my worry about my reputation and also I could be fired. However I felt more powerful after I came clean because I no longer had anything to hide.” —Wendy Koh

On Discovering An Affair

“Explaining to my married boss and one of my coworkers that I found out about their affair because of the instant messages that were left stored on my ‘new computer.’ Not good.” —Gaylene Macdonald Hemsworth

On Showing Compassion

“I had a conversation with an employee who had a few issues mentally. OCD, possible bipolar disorder, and quite a few social issues. For me, it was difficult because I had such a great amount of experience in dealing with various mental health issues. I never wanted to sound belittling, judgmental, or mean. Tone was important, and compassion. There were several conversations, and he thanked me most every time. I never wanted to make him feel alienated, even though most employees and customers treated him poorly. It taught me patience.” —Lisa Ruhappynow Marie

Related: Is It Ever Okay To Cry At Work?

On Too Much Information

“The company owner told me of a coworker in another department who would be laid off before the employee knew. Of course, I didn’t need to know that. In same conversation, owner let me know he trusted ‘absolutely no one’ and ‘everyone is a liar.’ Very tough to swallow about colleague’s dwindling job and to hear owner’s lack of faith in the staff, me included.” —John Martin

On Finally Speaking Up

“Telling my business partner and husband of 16 years that ‘I’m not coming in anymore, I’ve had enough and want my turn now.’ Still feeling guilty.” —Justine Luo

On Exposing Corruption

“My hardest conversation was when a federal judge offered me a bribe. Fortunately, my experience as an investigator prepared me for such things. I knew this judge also kept a loaded pistol under his robe, to intimidate any complaining clericals. I left, and immediately reported the incident to our inspector general. I was later invited to accompany the criminal investigator team when they raided the court, and took down the judge.” —Bruce Waltuck

On Making A Hard Choice

“I decided to close down my own company and take a job. I was the boss/employee/coworker. The discussion was with myself. It was tough. Having to lay myself off.” —Jim Seybert

What’s the most challenging conversation you’ve ever had at the office? Tell us in the comments below.

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