Should You Have That Difficult Conversation?
A checklist to know if it's worth your time and effort?
We may feel divided right now. It’s tempting to retreat into our camps and cut each other off.
I want to offer my communication guide to help bridge the divide, help us have difficult conversations, and set boundaries.
This guide is an excerpt from my new public speaking workbook for women, Love Your Voice, that will help you rediscover your voice, empower your words, and be truly seen and heard.
Decide whether talking to this person is safe and worth your time, and use the talking point guide below to help you prepare for your conversation.
This guide does not guarantee an agreement but, hopefully, an understanding.
Is it Worth my Time?
Figure out if having this conversation is worth your time and effort:
Does speaking with this person likely improve your relationship? Yes or No.
Is this issue serious enough that you need to address it to stay true to your values? Yes or No.
Do you have enough support for this process? Can you let a friend or trusted colleague know your plan? Yes or No.
Reasons to NOT have the conversation:
Is it unsafe to speak honestly with this person? Yes or No.
Are you dealing with a toxic person? Yes or No.
Even with the best communication approach, we can not control the other person’s reactions. Use your escape parachute if the conversation is not productive. You should leave if you sense that your discussion is getting too heated.
Here are some communication red flags:
They answer your question with questions.
They deflect to other topics.
Their reaction feels dangerous.
If you fear for your safety, seek legal support and do not have this conversation alone or in person.
HOW TO PREPARE FOR YOUR CONVERSATION
Feel Your Feelings:
Most talking point checklists I researched recommend that you “manage your feelings” or leave your feelings out of the conversation entirely.
This advice misses the crucial first step: Feel your feelings before you can have a productive conversation.
Conversations go off the rails because someone has not thoroughly explored their feelings. So feel the emotions and give yourself full permission to let it all hang out before you meet. You can process your feelings by writing them down or talking them to a friend, mentor, therapist, or coach.
Writing Prompt: I feel these emotions about having this conversation…
Figure Out Your Key Purpose: Identify the essential purpose of your talk BEFORE the meeting. The Professional Mediator Adar Cohen, who works with individuals and countries in conflict, explains that we should strive for one of three outcomes: a solution, a plan, or an understanding. Decide which outcome you want and why.
Writing Prompt: My Goal for this talk is…
YOUR CONVERSATION TALKING POINTS
Step 1: Plan Your Intro
Explain why you want to have this conversation. Aim for an understanding, not necessarily a solution.
Example: “I appreciate you taking the time to meet with me. I value our friendship and want to check in with you."