How To Navigate Tough Conversations In The Workplace

Bad Leadership

Tackling a difficult conversation head-on is scary in any situation, and even more so at work. In fact, a study done by Harvard Business School a few years back concluded that 67% of managers are uncomfortable talking to people they manage. However, ignoring a problem that needs to be addressed can lead to more issues. Having a solution on hand will ensure you’re prepared and less likely to get flustered when the conversation goes awry. Not only will you feel better walking into your meeting, but your manager or coworker will notice that you’re serious about being proactive in addressing the issue at hand.

To help you navigate the world of tough conversations, I’m here to provide you with a guide on how to not just get through them, but make them productive, too!

Don’t wait.

Don’t wait!

If you have a problem with someone at work, don’t wait until you’re upset or angry to address it. If there’s something going on that might affect your relationship with them, speak up when the problem first arises and let them know how their behaviour makes you feel. This allows for a clear and timely discussion that can help prevent future issues from developing.


Practice what you’ll say. Whether it’s a difficult conversation or a performance review, try using some allocated time to think about how you’ll explain your point of view and ask clarifying questions. Be sure to plan what you want to say, but don’t script it, as the conversation will evolve organically.

Keep it professional.

Stay professional and don’t get personal. Whilst it may seem easier to make the conversation about you, it’s important to consider the needs of the business and your role within it also. 

Make it a conversation, not a monologue.

Turn it into a conversation. Instead of talking at the other person, ask them questions about their thoughts and feelings. This will make them feel heard, which is key to getting through your difficult conversation in a productive way.

And remember to listen genuinely. It’s easy to tune out when you’re not interested in what someone else is saying—but if you do that, then they won’t trust you to listen properly (or even care what they have to say).

Be specific.

When you’re making a request, be specific. This may sound obvious, but often lack of clarity can leave both parties unsure of the course of action. Try and have actionable points and ensure the other party finds them clear and understandable.

When presenting your case, use examples or data to back up your position. For example, if an employee has been missing deadlines recently, don’t just tell them that you’ve received 5 emails from their colleagues and they need to work harder and let their supervisor know ahead of time. Instead, have a chat with the employee and ask if they have anything happening in their lives, either at work or at home, that is impacting their work. You may discover the employee has an underlying issue they have been too nervous to discuss, and by having this difficult chat, you’ve been able to put into place solutions. 

Be empathetic.

When entering a conversation with another person, it’s important to remember that they have their own perspective and experience to contribute. As a result, your goal should be to empathise with the other person’s point of view before arguing against it or persuading them into your way of thinking. By focusing on the other person’s position and putting yourself in their shoes, you’ll be able to better understand where they’re coming from. This will also make it easier for you to ask questions that show interest in what they have to say (and thus build rapport), rather than asking questions that lead towards an argumentative tone or surface-level understanding of their position.

Asking open-ended questions is one way you can demonstrate empathy when navigating tough conversations at work. Open-ended questions require more than just “yes” or “no” answers. These types of questions help clarify what someone means by giving them an opportunity for clarification about what was said earlier on in the conversation. For example:

  • “How have the new deadlines impacted your output?”
  • “Could we discuss how this issue has affected your productivity?”
  • “Did I understand correctly?”

A good conversation is not one where you win, but one that leads to growth.

A good conversation is not one where you win, but one that leads to growth.

When you’re having a difficult conversation with someone, the goal is not to win an argument or prove your point. The goal should be to find common ground and create solutions that work for everyone involved.

When the time comes to have that difficult conversation in the workplace, it can be helpful to not only set a time aside but also make clear what will be an appropriate solution or outcome. If you don’t lay expectations out ahead of time, you may both leave the meeting disappointed with the results. Again, discussions are best when they are prepared in advance and supported with a specific plan of action.

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