How to prepare for difficult conversations - Andrew Shirman

1. How to Prepare for Difficult
Conversations
So that People Will Listen
By Andrew Shirman, November 5th, 2016

2. Quick Intro
• Born and raised Chicago, Illinois
• Taught in Yunnan for 2 years with Teach For China
• Founded NGO Education In Sight and social
enterprise Mantra

3. Quick Group Intro
• What’s your name?
• Where are you from?
• What made you interested in joining the session today?

4. Why should we care about preparing for difficult conversations?

5. Today’s Goal
Learn the 8 guidelines of positive communication to craft the opening to a difficult
conversation we may need to have in our lives.

6. The 8 Guidelines for Positive Communication

7. 1) Keep It Simple
Make your message short, on topic, and resist bringing in other aspects or
even old wounds

8. 2) Be Positive
Reflect on what you admire in this person or what they do well. Also, if
possible, frame what you want positively. E.g. – “Clean up your clothes” vs.
“Don’t leave your clothes everywhere”
1) Keep It Simple

9. 3) Be Firm
Remember why you wanted to start this conversation and seek to find a
solution that will satisfy your needs
1) Keep It Simple
2) Be Positive

10. 4) Be Specific
Address specific behaviors or issues. The more specific, and clear, the more
likely you are to compel them.
1) Keep It Simple
2) Be Positive
3) Be Firm

11. 5) Label Your Feelings
Sharing how the situation makes you feel (stressed, afraid, resentful, etc.) is a
powerful way to break down the barriers in conversation
1) Keep It Simple
2) Be Positive
3) Be Firm
4) Be Specific

12. 6) Take Responsibility
Even if it’s small, accept your role in this situation. “I know I have….”
1) Keep It Simple
2) Be Positive
3) Be Firm
4) Be Specific
5) Label Your Feelings

13. 7) Empathize
Put yourself in there shoes, even just saying “I know you might feel…”. Let
them know you hear them and can see things from their perspective.
1) Keep It Simple
2) Be Positive
3) Be Firm
4) Be Specific
5) Label Your Feelings
6) Take Responsibility

14. 8) Offer To Help
You’re making a request of them. Show them you are willing to work to
achieve the solution too, and that you are still ready to support them.
1) Keep It Simple
2) Be Positive
3) Be Firm
4) Be Specific
5) Label Your Feelings
6) Take Responsibility
7) Empathize

15. Our 8 Guidelines
1) Keep It Simple
2) Be Positive
3) Be Firm
4) Be Specific
5) Label Your Feelings
6) Take Responsibility
7) Empathize
8) Offer To Help

16. Discussion Part 1
Using the 8 Guidelines, work through the below scenario with a partner to craft a short
paragraph that would help you address this issue.
Your roommate of more than a year has always been a little messy. However, since he has
his girlfriend broke up last month, things have reached a new level. It’s gotten to a point
where you need to move his things and clean up his mess just to get around the
apartment. One night, when you’re both relaxing after work, and are in good moods, you
decide to bring this up.
1) Keep It Simple
2) Be Positive
3) Be Firm
4) Be Specific
5) Label Your Feelings
6) Take Responsibility
7) Empathize
8) Offer To Help

17. Open Discussion
1) Which of the guidelines do you think you would find the most challenging? Why?
2) Besides these guidelines, do you have any other recommendations?
3) What advice would you give to a friend who was about to have a difficult conversation?

18. One Action
Commit to using these strategies in your next difficult conversation. If you already know
what your next difficult conversation will be, identify it, then use our guidelines to map how
you might start to address the issue. If uncomfortable doing so here, feel free to use a
hypothetical situation below.
1) Keep It Simple
2) Be Positive
3) Be Firm
4) Be Specific
5) Label Your Feelings
6) Take Responsibility
7) Empathize
8) Offer To Help
Hypotheticals
• Difficulty in a relationship with a partner
• Work politics
• Concern over a family member’s behavior
• Living mate conflicts
• Leadership/management struggles

19. Thank You
• Let Abe, myself, or the group know if these techniques prove useful
• Global Shaper Dinners – every other Thursday evening (next one Nov. 10)
• You guys were amazing today!
• Brunch anyone?