Important Conversations Guide and Practice Sheet

Challenging conversations are an inevitable part of an individual’s personal and professional life. They are essential to cultivating productive relationships. While there are many types of challenging or important professional conversations, there are some common guidelines that will help you navigate the preparation and initiation of challenging conversations. Use this practice sheet to think through and prepare for different types of difficult conversations that might come up in professional life.

Potential Conflict Dynamics

  • Influential person
  • Supervisor
  • Coworker
  • Family, friends, or partner
  • Professor
  • Team member
  • Asymmetrical “power” dynamic
  • Misunderstanding Change
  • Vulnerability
  • Conflicting goals or needs
  • Different values
  • Making a mistake

Prepare

The key to navigating challenging conversations is preparing for the conversation. A good place to start is gauging your self-awareness regarding the particular conversation. Next, is empathizing with the individual you want to engage in conversation.

Self-Awareness Reflection

  1. Identify the topic/issue you want to address.
  2. What are your emotions and why? Be responsible for how you feel and understand why you feel that way. Common emotions could be discomfort, intimidation or anxiousness.
  3. What are your concerns about the cause or potential outcome?
  4. What assumptions about the situation or individual do you have?
  5. What is your relationship with this individual, and how can you be of service to the other person?
  6. Why is this important to you?
  7. What is your ideal outcome?

Self-Awareness Reflection Brainstorm











Empathize with the Individual

Prepare for the conversation by doing your research on the work and perspective of the individual you are connecting with.

  1. Why are you connecting with this individual?
    • What about their experiences, skillset, or education background do you find interesting?
    • What would you like their perspective on?
    • Why do you find their perspective valuable?
  2. How will you utilize their time wisely?
  3. How do you engage with their current work?
  4. What is the right place, time or format to have this conversation
  5. What questions will you ask the individual?

Research on the Work and Perspective of the Individual You are Connecting With











Sample Conversation Templates

Opening: positive statement “something they would want to hear”

Middle: “However, something they don’t want to hear”

Potential solutions and corrections (What do you think statement)

End: “Something they want to hear”

Opening: Thank you, why this individual’s perspective is valuable. Your objective.

Middle:

  • Compelling questions
  • Listen
  • Finding common ground, demonstrating vulnerability
  • Compelling questions

End: Gratitude, follow-up with results in the future

Practice