How to have a difficult conversation at work

Think back to the best places you’ve ever worked. What do they all have in common? Sure, they might have had a fridge stocked full of energy drinks or a ping pong table, but we’re also willing to bet they rocked at communication. The best workplaces are those that foster a culture of honesty and adaptability— and know how to have a difficult conversation at work.


So whether you’re a small business owner, a first-time manager, or just new to HR, here’s everything you need to know to navigate those difficult conversations and come out of them stronger than ever.


1. Plan, don’t script

You don’t want to sound rehearsed. But before the meeting, it can be helpful to jot down the main points you want to discuss, and use it as a way to guide the conversation. This will make the meeting more productive, and lessen the chance of your getting swept up in emotion.


2. Acknowledge your coworker’s perspective

Before heading into the meeting, take some time to think about how you arrived at this conversation— from the other party's viewpoint. What do they feel happened? Can you understand why they’re upset?


3. Establish a safe space

When employees fear repercussions— losing their job, being reprimanded, or even social isolation— they’re much less likely to be open about their feelings. Create a safe space by managing your reactions to their feedback. Resist the urge to be defensive.


4. Admit you’re uncomfortable

Your coworker is not looking forward to this. One way to diffuse the tension in a difficult conversation at work is to acknowledge that you’re nervous too. It affirms that you’re in this situation together, and you will work together to find a way through.


5. Practice workplace empathy

You’re just two people trying their best.





6. Listen, listen, listen

The quickest way to escalate a difficult conversation at work is to talk over your team mate. Give them space to tell you what’s on their mind. Work hard to concentrate on what they’re saying rather than just thinking about what you’re going to say next.


7. Provide specific feedback

The subject matter might be difficult, but dancing around the critique or talking in metaphors leaves room for further confusion and misinterpretation. Use as many concrete examples as possible to root your feedback in reality.


8. Leave room for consideration

Not every pause has to be awkward. When your coworker is finished speaking, take a moment to reflect before responding.


9. Collaborate on a solution

Leave this conversation with a clear plan forward. Treat this part like you would any other meeting and work together to create action items before you leave. This ensures you’re on the same page, and both feel that your time has been productive.


10. Recap the meeting

Summarizing each other’s perspective before you leave the meeting is helpful for building empathy as you move back into your day-to-day working relationship. It signals that you understand and respect each other’s experiences.


Difficult conversations at work are not for the faint of heart. But nurturing relationships is just part of the job.


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