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Starting a Difficult Conversation with Any Personality Type

May 09, 2023
Enneagram Type 1, Jill Shroyer, CEO of Expedition HR about having difficult conversations on the Enneagram MBA podcast

Have you ever found yourself at a loss for how to handle a difficult conversation at work?

Whether it's frustration over having the same difficult conversation repeatedly, or not knowing how to bring it up to even start the conversation, our guest today, is going to walk us through how to start a hard conversation with any Enneagram type.

Jill Shroyer, the CEO & Lead Consultant of Expedition HR and the author of the best-selling book, Conquer Sticky Situations, is bringing her 20+ years of HR experience to this conversation, as well as all of her Type One strengths :)

In this episode, you’ll learn how to move through her 5-step formula for having difficult conversations with almost any topic - and what tweaks might need to be made based on the team member's personality style.


Jill’s approach is both effective and compassionate, so regardless of what Enneagram type you identify with, or have on your team, you’re going to leave with some very tangible scripts for having these important conversations.

Connect with Jill on Linkedin and let her know what you're taking away from this one:

 Get a copy of Jill's book, Conquer Sticky Situations:

Learn more about Jill's HR subscription model to have your own HR Director on-demand with all the support, tools, and resources, a growing team needs:


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