Module 5 Briefing Sheet

Managing Difficult Conversations,
and Influencing Stakeholders

Click the appropriate title below to download:

The focus of this Module is on how to manage difficult conversations. For in-house counsel, difficult conversations arise in a variety of contexts: while providing risk-mitigation advice to business-side clients on a development proposal or opportunity; in handling employee relations issues with employees and managers; during the course of internal investigations; during negotiations on a deal or dispute settlement; etc. While several of the pre-reads talk in terms of “negotiation,” Rob Wilkinson urges you to pay attention to the insights they provide on “peeking behind the curtain” to understand and navigate the difficult conversations that arise in that context. Similar to the Relational Awareness Module from Module 2 on Emotional Intelligence and Interpersonal Communication, Module 5 will provide a framework for unpacking and managing difficult conversations, and influencing the stakeholders who may be part of them.


Optional materials: Rob Wilkinson has been developing a series of Case Studies of leaders who demonstrate mastery in handing difficult conversations and influencing stakeholders in a range of different settings. He thought you might be interested to see how universal these principles are. If you want to read one or more of them, you will have to license the content. The link to the study and the fee to license it is noted next to the title.


  • Read the Leading with Intentionality - The 4P Framework for Strategic Leadership paper and listen to all four episodes of The 4P Framework for Strategic Leadership podcast series.
  • Read the following:
    • The excerpt from the Difficult Conversations book
    • Enhancing Your Effectiveness as a Negotiator
    • Errors in Social Judgment
    • Negotiating with Emotion
  • View the video How Do You Handle Emotions?
  • Think about examples of what your most difficult conversations are: at home, at work, with superiors, colleagues, direct reports, external clients, etc. What is difficult about these conversations, concretely?
  • Recall and write out a recent workplace conversation that was difficult for you. Using two columns (I said – They said), write a brief verbatim “script” of the actual conversation (not what you “wish” you had said!). Try for a minimum of 8-10 lines of the actual conversation. NOTE: Be ready to discuss this conversation during the Module.
  • Think about a current or upcoming conflict you personally are managing or will need to manage. NOTE: Be ready to discuss and analyze it during the Module.


  • What strategies to you use when you need to engage with someone who deeply disagrees with you? How do you typically respond (verbally and/or behaviorally) when you are engaged in a difficult conversation?
  • What role does process management play in your ability to achieve results as a leader? How explicit are you personally in thinking through your own process choices as you engage with colleagues, groups and team members?
  • In what ways do you imagine emotions playing a role in your job? What might be some consequences to avoiding the human and emotional impacts on people as a leader? What are some of the barriers to dealing with emotions effectively?
  • What signals do you think you send to people around you, either explicitly or implicitly, that indicate what you value, prioritize and care about? How would you define your own identity as a person and as a professional?

COHORT MEETING (Meet to discuss the following BEFORE Classroom Session)

  • Check in and share any additional learning from the previous session.
  • Have a brief discussion about your leadership development plan:
    • What did you commit to start and stop doing? Are you doing it? How is it making a difference?
    • Did you create an accountability circle? How are you using them?
    • What action step do you need to take next on your Development Plan?
  • Share your “recent difficult workplace conversation” and your insights regarding:
    • Your skills to manage the conversation effectively.
    • Your self-awareness of your behaviors and impact on the conversation.
    • Your impact on the person involved.
  • Share any additional insights from the pre-work.


  • To reflect on and test one’s assumptions about the most effective ways to communicate with others to get the desired results
  • To decipher the underlying structure of every difficult conversation and to interpret the significance of what is said — and what is not
  • To manage conflict effectively as it arises, and see conflict not as a liability, but as a catalyst to creativity
  • To understand the role and importance of process management in influencing stakeholders.
  • To recognize and address strong emotions before they lead to communication breakdowns that cause stress and damage relationships
  • To reflect on the messages you intentionally and unintentionally project in the immediate and dispersed environments within which you work.

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