Clear and effective communication is one of the most important hallmarks of a leader, but even experienced managers sometimes struggle with this when facing difficult or challenging conversations with employees. Having difficult conversations training provides the skills and tools needed to be a great leader and communicator. Helping managers become proficient in having challenging conversations in which they may bring up topics that may be emotional or difficult for employees are key concepts in the training. Leaders will learn how to approach difficult conversations with a spirit of curiosity and collaboration, while displaying empathy and support.  This training, led by Diversity Builder, Inc., will cover what challenging or difficult conversations look like, essential strategies for preparing for and navigating challenging conversations, a model to ensure success, scenarios, and crucial tools to use in follow-up after the interactions. With plentiful examples of challenging conversations, and interactive learning exercises to encourage participants to apply the training to their own experiences and employees, this class will prepare managers to reach the next level in their leadership skills. A pdf of the course outline is available upon request.

Training Goals

  • Understanding what challenging conversations are
  • Identify situations that might benefit from challenging conversations
  • Understand how to prepare for a challenging conversation
  • Recognize signs of distress during a conversation
  • Know best practices for following up after a conversation

Challenging Conversations Examples

For the purposes of this training, we are calling the conversations “challenging” instead of “difficult.”

While some conversations are demanding because the other party is angry or hostile, others will be demanding because it requires sensitivity, extra consideration of the stakes, or other reasons. What are some examples of challenging conversations? Challenging conversations are often those that leaders or managers have been avoiding. This happens for a variety of reasons, including historical baggage, potential negative consequences, or damage to the relationship with the other party. For leaders in particular, conversations that involve conflicting opinions, high stakes, and strong emotions are especially challenging.1 The training incorporates different scenarios that address the variety of challenging conversations that a manager should be prepared to tackle.

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    5 Examples of Difficult Conversations in the Workplace

    • Discussing a poor performance review with an employee
    • Moderating a disagreement between team members
    • Giving an employee disappointing news (being passed over for a promotion or leading an exciting project, for example)
    • Discussing an employee’s change in performance or behavior

    Admitting a mistake in judgment or leadership

    Difficult Conversations Book

    On the topic of challenging conversations, many people refer to the book Crucial Conversations: Tools for Talking When Stakes are High by Patterson, Grenny, McMillan, and Switzler. One of the leading books on difficult conversations is Crucial Conversations, which, in summary, discusses what makes a conversation crucial (high stakes, conflicting opinions, and strong emotions); while this training focuses more broadly on challenging but not necessarily difficult or fraught conversations. The book outlines what is a crucial conversation, effective communication techniques, including strategies for building respect and recognizing when a conflict is escalating, and a crucial conversation model.2 While it provides useful advice, it is somewhat open-ended and not specific to professional settings. However, this training focuses on challenging conversations with a focus on management in the workplace, acknowledging the unique dynamics between managers and employees. With many realistic and timely examples of how managers can approach high-stakes conversations with empathy and deliberation, participants will come away with essential tools and strategies for effective communication.

    Request a pdf training outline of Having Difficult Conversations

    [1] Kazakos-Tate, K. (n.d.) Handling challenging conversations training.
    [2] Kumar, R. (2018, February 3). Crucial conversations — tools for talking when stakes are high — a book summary. Medium.

    Communication Strategies and Preparing for Challenging Conversations

    To prepare for a challenging conversation, it’s helpful to consider the following points:

    • What is the primary issue?
    • Is the timing right?
    • What outcome is desired?
    • What is the best way to approach the conversation?

    These will ensure that an interaction is handled with deliberation, without extraneous topics or emotions clouding the issue. Considering the timing and the approach to the conversation also makes it less likely that the employee is caught off-guard or feels targeted. Managers should consider what their relationship with the employee is like. If most of the manager-employee interactions have been challenging or negative, then making an effort to build the relationship outside of work issues – for example, by team-building exercises or meals focused on getting to know one another – can reset the relationship.3

    When deciding how to approach a conversation, the Thomas-Kilmann conflict model is a useful foundation. With this model, we weigh the stakes (how important it is to achieve a goal) compared to the importance of the relationship with the other party, which determines the optimal approach to resolving a conflict.4 If a leader is highly motivated to achieve a desired goal, they might make the decision to disregard the goals of the other party, sacrificing that relationship for their own aims. However, if the leader prioritizes both the outcome and the relationship with the other party, they might choose to look for a creative solution that will satisfy everyone.

    Imagine a manager who is trying to resolve a contentious conflict between two employees. The manager should consider what outcomes they are looking for (to resolve a specific disagreement or to reset the relationship between two employees at odds?). They should think about the stakes, whether avoiding or compromising on this issue will have negative ramifications for the team, and the relationships involved. Ideally, they will work closely with the employees to find a mutually beneficial solution while maintaining an excellent relationship with both of them. This training will include scenarios like this one to help participants learn to successfully plan for challenging conversations with an eye to both employee satisfaction and managerial goals.

    How to Have a Challenging Conversation

    When beginning a challenging conversation, managers should give an employee context for the conversation by referring to a specific incident or example.5 This ensures that they understand why the conversation is necessary and what behaviors need to change. For example, if a manager has noticed a change in quality in their direct report’s work, they can describe specific examples to clarify for the employee.

    [3] Bernardo, D. (2017, May 29). You just had a difficult conversation at work. Here’s what to do next. Harvard Business Review. https://hbr.org/2017/05/you-just-had-a-difficult-conversation-at-work-heres-what-to-do-next
    [4] Cote, C. (2023, September 7). 5 strategies for conflict resolution in the workplace. Harvard Business School Online. https://online.hbs.edu/blog/post/strategies-for-conflict-resolution-in-the-workplace
    [5] Poulsen, S. (n.d.). How to have difficult conversations at work. THNK School of Leadership.

    5 Questions to Ask in a Crucial Conversation

    Maintaining a curious and humble attitude throughout the conversation is also beneficial. Asking questions is a great way to do this while building rapport with staff. The following neutral, non-judgmental questions are useful ways to learn more about the employee’s point of view.

    • What do you think about this?
    • How would you suggest we approach this?
    • Why do you think this happened?
    • What can I do to support you?

    This approach demonstrates that the leader is trying to understand rather than trying to win or dictate a solution. Setting out with a competitive attitude or trying to persuade or “win” compared to the employee will lessen trust and set up an antagonistic dynamic.6 Faced with this, an employee could choose to withdraw or dig in their heels, which won’t lead to a collaborative resolution or a good working relationship going forward.

    Overall, being empathetic (being able to see things from the employee’s perspective) and self-aware (understanding how one is coming off to the other person) are key. Listening closely to the thoughts and responses of the other person and reflecting before responding are excellent strategies. In the case of an employee with lowered quality of work, a manager might find that stress or changes in the employee’s personal or professional life could be affecting their deliverables. Recognizing the employee’s situation and working with them to find solutions instead of approaching this situation critically will set them up for success.

    Related to approaching conversations with questions and empathy, managers should understand that communication depends on more than word choice. Research demonstrates that communication depends on body language (55%) and tone of voice (38%) much more than specific words (7%).7 This can lead to misunderstandings in which a speaker’s body language is at odds with their words. For example, if an employee sees that their manager appears uncomfortable when trying to reassure them about the future of a project, the employee might come away from that conversation with concerns. Managers should therefore make an effort to ensure that their body language and tone is aligned with their words, so that their employees don’t get conflicting messages or misunderstand a conversation.

    While it can be tempting to try and resolve a conflict in one meeting, it’s sometimes beneficial to break the conversation into stages. This is especially true if either party becomes frustrated or angry. In that situation, suggest reconvening when both parties can approach the topic with level heads (which will help with finding a cooperative solution).8

    [6] Poulsen, S. (n.d.). How to have difficult conversations at work. THNK School of Leadership.
    [7] University of Texas Permian Basin.  (n.d.). How much of communication is nonverbal? https://online.utpb.edu/about-us/articles/communication/how-much-of-communication-is-nonverbal/
    [8] Poulsen, S. (n.d.). How to have difficult conversations at work. THNK School of Leadership.

    Follow-Up Strategies After a Challenging Conversation

    After navigating a challenging conversation, leaders and managers need to plan for how to follow up. Here is a list of the best follow up strategies to ensure successful difficult conversations:

    1) Confirming next steps with the employee is critical. Sending an email after the conversation is a convenient way to summarize what was discussed, outline takeaways or outcomes, and provide opportunities for further discussion.9

    2) Managers should avoid holding onto frustration or resentment after a demanding conversation. They should resolve to move past the incident and not hold it against the employee, especially if the issue is resolved.10 For example, picture a manager who has had a challenging conversation with an employee about a poor performance review. The employee was initially resistant to feedback on how to improve but ultimately came around.

    3) The manager should keep the lines of communication open with their employee and not let the incident damage their opinion of them, especially as an isolated incident.

    4) If the conflict or issue persists, managers should be proactive in addressing it with the employee. It can be tempting to avoid having a challenging conversation again, but with the tools outlined in this training, participants will be equipped to handle ongoing issues.

    While there is a learning curve to understanding how to plan for and carry out challenging conversations, Diversity Builder’s training will provide a clear and actionable roadmap for managers wanting to improve these skills. Participants will come away with renewed confidence and strong communication abilities, no matter the topic or situation.

    Resources and Further Reading on Challenging Conversations

    Interested in learning more? Take a look at the following resources cited in this article on challenging conversations, conflict resolution, and communication in general.

    Bernardo, D. (2017, May 29). You just had a difficult conversation at work. Here’s what to do next. Harvard Business Review.

    Cote, C. (2023, September 7). 5 strategies for conflict resolution in the workplace. Harvard Business School Online.

    Kazakos-Tate, K. (n.d.) Handling challenging conversations training.

    [9] Bernardo, D. (2017, May 29). You just had a difficult conversation at work. Here’s what to do next. Harvard Business Review. https://hbr.org/2017/05/you-just-had-a-difficult-conversation-at-work-heres-what-to-do-next
    [10] Poulsen, S. (n.d.). How to have difficult conversations at work. THNK School of Leadership. https://www.thnk.org/blog/difficult-conversations/