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How to manage difficult conversations at work

March 22, 2022
Written by Michelle Kuly

Difficult conversations – whether you’re late on a deadline or didn’t feel comfortable asking for help when you needed it – this kind of exchange is essential to the workplace. We all miss the mark and make mistakes. But when it goes left unchecked, these issues can fester and degrade your work’s effectiveness. 

These days, the change of pace in the workplace requires welcoming lots of trial and error, setting the expectation that things won't always go how we want, and showing a willingness to learn and adapt. Increasingly, knowing how to navigate tough conversations on any project is essential – having the tools to get through them will get you to the other side more quickly.

Here are 6 ways to help you prepare for the talk, navigate the right words to say and manage your discussion as smoothly as possible.

1. Prep yourself.

You don’t need to write a script, but it is helpful to think about what you would like to say beforehand. Hone in on the root of your problem and write down three things you would like to accomplish in your meeting. Staying focused will help keep your discussion from going in an unexpected direction.

2. Make tough convos a regular occurrence.

Create space on your agenda to check in on what didn’t go well in weekly check-ins with team members. In meetings, use the Rose/Bud/Thorn technique: highlight something that is working well, discuss an idea or area of opportunity you have not explored and talk about something that isn’t working. Work through the solutions together.

3. Consider how the other person is feeling.

If you notice they are upset, take a minute to pause and let them collect their thoughts. Consider their communication style and lead with empathy and compassion to show that you care.

4. Focus on implications, not the "facts" of what happened."

Facts feel subjective these days! People often rely on "but that wasn't my intention..." which can make discussions more divisive. Instead, focus on the consequences of what happened – a project was delayed, there was a loss of trust, someone felt they didn’t have clear direction. Then, work together on how to mitigate these issues in the future.

5. Leave space to hear from the "other."

It's likely there was a reason things went sideways. In addition to focusing on the implications, focus on what conditions led to the issue and ways to mitigate against them in future. Give people the opportunity to say, "I didn't have enough time so I felt rushed and cut corners. Next time it would be helpful if..."

6. Learn from the discussion.

Reflect on your difficult conversation afterward and think about what worked and what didn’t. In Harvard Business Review’s article How to Handle Difficult Conversations at Work, Holly Weeks, author of Failure to Communicate, said, “Handling a difficult conversation well is not just a skill, it is an act of courage.”

Extra resources

How To Handle Difficult Conversations At Work
Digital Body Language: How to build Trust and Connection, No Matter the Distance
Failure to Communicate: How Conversations Go Wrong and What You Can Do to Right Them


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