Skip to main content


Allie Ryan

Published on

March 9, 2023


agency life, Communication, HR, thought leadership

Workplace conflict is generally not anyone’s favorite part of their job.

It’s safe to say when you are performing well, the business is performing well, your direct report is performing well, your people are happy, and your company culture is strong that things are easier and more preferable. But it’s not realistic for things to be going well all of the time, which often results in difficult situations and tough conversations, including for professional leaders.

While having to deliver a hard message can feel daunting, and there may be a period of discomfort, in most instances these difficult workplace conversations leave everyone with a more constructive outcome. People may leave feeling more supported, with more direction, feeling more included, and happier in the end. And perhaps most importantly, nothing will change if what is not working is not addressed.

Despite knowing that a tough conversation needs to happen, people often avoid them. I am guilty of this too. Anxiety creeps in. We find reasons not to have the conversation. What if I hurt this person’s feelings? What if they are a high performer? What if they are more senior to you? What if it wasn’t that big of a deal?

In those moments, it’s important to ask yourself: who does it help if you avoid difficult conversations at work? Spoiler alert: no one. The behavior won’t change. And you will remain frustrated with them. It doesn’t do anyone good to keep quiet.

yellow old fashion phone on yellow background

Related Article: S2E01: Communicating With Empathy

Below are 10 tips to help you feel more confident and ready to dive in.

Be prepared

Before initiating a challenging conversation, do your research. Know the facts of what happened. Consider different perspectives. Think about the different questions or responses that may come from the person so you can be prepared with answers.

Know your audience

Similarly, consider what you know about this person. How do they like to hear feedback? Think about timing and setting. Would this person want a calendar invite in advance to prepare or a more spontaneous call? When possible, have the conversation in person and out of the office when appropriate. Never have a difficult conversation via chat or in a group setting.

Assume the best

People want to do well. No one shows up to work hoping to make a mistake or to have poor performance. Unless you have reason to believe otherwise, give the person the benefit of the doubt.

Come with an open mind

Every story has more than one version. Each person’s experience is valid. There can be more than one truth. Consider what your own blind spots may be and don’t jump to conclusions before the conversation starts.

Lead with empathy

Remember that we are all human and that mistakes happen. Think about how you would want to be treated if you were on the receiving end of the conversation. Acknowledge that it may be an uncomfortable conversation or difficult discussion.

Be objective

Stick to what you know to be true. If you are unsure, ask. Avoid placing “intent” on behavior. Saying “you missed your deadline” is much better than saying “you’ve been slacking.”

Be clear

Be clearer than you think necessary. Tell the person what you did see/hear and what you want to see/hear instead. You can even write it out like that. You did X, I need Y.

Seek to understand

There is usually a reason behind poor performance, for example. It could be lack of skills. It could be lack of proper technology. It could be family care pressures. It could be health concerns. Understanding the root cause will help you and your employee game plan a powerful action plan.

Determine next steps

What does this person need to be successful? How can you support this person? There should be clear, actionable takeaways on how the person can do better.

Follow up

Send a written recap of what was discussed and the next steps for everyone involved. This allows everyone the ability to refer back to what was discussed. Do what you said you would do.

four white chairs at a table in a yellow room

Related Article: S1E06: Being a Leader in 2022 & Beyond

Remember, no one is equipped to handle every kind of situation. Use the resources around you and seek advice from trusted mentors. Reach out to your human resources team to talk through your plan.

You may not say or do everything ‘correctly’ when addressing something that is not working well. But some action is almost always better than inaction.

Having difficult conversations at work are teaching moments for all of us. It means we are learning and growing and a lot of good comes from that alone.

Not reaching a positive outcome when having tough conversations with team members? Get in touch with our human resources team for more insights!

Get in touch