WIN Society Summit 2023
September 20 - 22
The Ritz-Carlton Chicago
Chicago, IL

Tough Talk: How to Engage in Difficult Conversations



Program Agenda

  • Wednesday September 20, 2023
  • Thursday September 21, 2023
  • Friday September 22, 2023
6:30p - 9:00p

Welcome Reception and Dinner

8:00a - 9:00a

Group Breakfast

9:00a - 9:30a

Welcome and Introductions

Felice Wagner and Steering Committee Members

9:30a - 10:15a

Opening Discussion: What is “Tough Talk”?

Mary Kaczmarek, facilitator

Members will convene in small groups to discuss tough talk, i.e., difficult conversations that we tend to fear or avoid because of the potential for negative fallout and damaged relationships.
10:15a - 10:45a

What the Awful Roy Family of the Succession Series Can Teach Us About Difficult Conversations

Using examples from the acclaimed HBO series, Succession, Mary will provide an overview of the worst communication habits exhibited by the hateful Roys.

10:45a - 11:30a

Small Group Discussions and Provide Feedback to the Larger Group: Normalizing Difficult Conversations to Lead to Better Work-Related Outcomes

11:45a - 12:00p

Refreshment Break

12:00p - 12:30p

Large Group – Lightning Round Discussion: What Did You Learn from Your Small Group Sessions?

12:30p - 1:15p


with client panel participants as guests

1:15p - 2:30p

Client Panel Discussion

Felice Wagner, Executive Director

Chicago-based women in-house counsel will discuss issues related to achieving their career success, current priorities, and their respective strategies for managing difficult business conversations.


Adjourn Programming for Day One

6:30p - 10:00p

Group Dinner at TBD Location

8:00a - 8:45a

Group Breakfast

8:45a - 9:30a

Ask and Give Ritual

Mary Kaczmarek, facilitator

In the large group, each participant will submit an “ask” for a professional favor, support, or assistance, as well as a “give” she can offer to address another’s request.

9:30a - 10:15a

Group Discussion: Themes from Day One on Normalizing Difficult Conversations

10:15a - 10:30a

Refreshment Break

10:30a - 11:45a

Rounds of Role Plays Featuring Best Practices for Having Difficult Conversations

11:45a - 12:00p

Large Group Debrief

12:00p - 12:15p

Closing Comments and Adjourn

Felice Wagner and Steering Committee Members