How to navigate challenging conversations at work

By Pam Penner, Owner, Facilitating Solutions

Imagine an employee who reports to you has not been meeting their deadlines. You have noticed they spend a lot of time socializing, and they have also expressed frustration that they are not getting the promotions they feel they deserve. You haven’t talked to them about these issues yet, because you know they will react emotionally. Reluctantly, you set up a time for their performance review.

To ensure the conversation is productive, you know you will need to be prepared for their reaction and that it will be important to maintain your professionalism. However, you are unsure even how to start preparing for this challenging discussion.

To begin, it is important to realize the root causes of problematic behavior vary: Difficult behaviour may be the result of a person being emotional, resistant, or behaving badly. We can’t control the behaviours of others, but can control our own actions. To do so, we need to reflect. What are our reactions to a difficult person or situation, and what are the reasons we react the way we do? What can we do differently to ensure a productive conversation that enables change in a way that is respectful and inclusive?

In our hypothetical example, some specific questions that would be useful to answer before holding the conversation would be:

  • How do I address problematic behaviour with this employee?
  • How do I set up the environment for this challenging conversation?
  • How do I start the conversation?
  • How can I tell them their behaviour is problematic without causing conflict?
  • How do I manage my reaction and theirs?

Having clear answers to those questions in advance of the discussion will allow for a productive discussion and help you, your employee, and the organization move forward and improve.

Broadly speaking, learning how to deal with the reactions of others and to manage your own feelings are essential for a productive workplace. Doing so will not only help in the context of a difficult conversation with an employee, but also with co-workers, clients, or managers.   

Further Learning

Attending the seminar, Navigating Challenging Conversations – Giving and Receiving Feedback will help you discover techniques for assertively, respectfully, and accurately describing behaviours you find difficult. It will also give you the tools you need to request a change and help you prepare for and conduct difficult conversations in a productive and collaborative manner.

Once you’ve completed Navigating Challenging Conversations – Giving and Receiving Feedback, you will be able to:

  • Identify your own attitudes and beliefs about giving and receiving feedback
  • Recognize the ideal praise-to-criticism ratio
  • Outline the benefits of feedback – what do you want and what do others want?
  • Describe the elements of giving constructive feedback including designing an environment conducive to having difficult conversations
  • Describe the elements of receiving feedback
  • Prepare for a difficult conversation, including using a model for communicating assertively and respectfully
  • Use language to effectively describe the problematic behaviour (or for when giving praise) in an assertive yet compassionate manner
  • Demonstrate effective listening skills – how to support the shift in behaviour
  • Set limits and disengage when feedback is unconstructive
  • Manage self when giving and receiving feedback

If you want to learn more hands-on conflict management strategies, also consider Pam’s, Introduction to Conflict Resolution on February 3 & 4, 2022, and Communicating Under Pressure coming in fall 2022.


Headshot of Pam PennerPam Penner

Pam has worked in the field of conflict resolution and relationship building for over 20 years. She holds a Master’s degree in Conflict Analysis and Management and is a certified coach with both the International Coaching Federation (ICF) and Coaches Training Institute. She also works at the Justice Institute of B.C. as an instructor and coach helping students develop their skills.