Direct Connect Forum: Difficult Conversations

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Post By Anna Thiele, Deliberate Directions Leadership Strategist

Anna focuses on writing website content and hosting a “Leadership, No Homework” book club. Anna received her Bachelor of Arts in Communication, with a certificate in Leadership and Human Resources, from Boise State University. In her spare time, Anna enjoys rock climbing, traveling, music, and the Enneagram.

Everyone has difficult conversations. Some of the time they are a surprise and other times we thankfully have time to prepare for them. Douglas Stone, in writing Difficult Conversations, sheds light on a few techniques that we can use in any situation. He also shares about three hidden conversations that happen inside every conversation. These insights and strategies are sure to aid you in your next conversation, difficult or not.

Douglas Stone starts by clarifying the three conversations we have within every conversation. These act as barriers to seeing the other person as a person, making it impossible to hear their concerns and impossible to come to a resolution.

Afterwards he provides a step-by-step strategy for getting through our own barriers in order to have that conversation.


Watch the video below and then download the ‘notes page’ to work through an activity to help clarify your understanding of the event, so you can have clarity on what is difficult about the conversation.

It Didn’t Start Out Being Difficult…

From our live event, August 24th, 2022, Tiffany Williams, Owner of Progress LLC, shared a story about her recent difficult conversation. 

In a networking/peer group, Tiffany shared her elevator pitch for her company. From my understanding, Progress LLC organizes office and personal spaces, specifically for those who have OCD. When Tiffany shared that to the group, one member shared their frustration with Tiffany’s commitment to help those with OCD. That frustration being that OCD shouldn’t be called out as something that needs to be fixed, they are people too. Tiffany had no idea that she would be involved in a difficult conversation that day and hadn’t had any previous conversations with this person. She wondered if in the future this topic of learning could be applied in the moment or would it always need to be a separate, one-on-one, conversation?

So, that’s the question; if you accelerate in the five strategies for having a difficult conversation, master the 3-part assertion statement, and recognize in that moment you have a conflict- can you resolve it right then and there?


Difficult Conversations Script

Download to learn more about Difficult Conversations

Difficult Conversations in Action

Fill out this worksheet to explore how you’re applying your learnings from Difficult Conversations.

I'm Allison Dunn,

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