“Woe unto she so self-righteous she gains neither wisdom nor friends.”

 Maxximillian Dafoe, Speaker, Performing Artist & Filmmaker

Is there a conversation you’ve been wanting/needing to have with someone but you haven’t felt comfortable starting the conversation because you are anxious about how your message will be received? Read on...

The best advice—maybe the most important advice—has often come to me completely unsolicited from people who saw that they knew something that could help me and knew how to present their wisdom in an empathetic friendly way.

Shoutout to everyone who has opened a difficult conversation in order to help a friend.

 

I’d like to take a moment now to thank you if you are a person who has invested in books or courses on how to communicate effectively with empathy. It’s a delicate art.

 

Especially now our interpersonal relationships are more important than ever. Increasingly people are spending more time together and—as you may have noticed—close proximity tends to highlight areas in our relationships that are in need of improvement. None of us is perfect all the time but it is nearly always possible to improve our relationships with people as we go along—IF we care to.

 

I already hear the giant sigh. I get it.

 

It can be anxiety-making to start a conversation that you anticipate might aggravate your companion, cause an argument or otherwise draw the storm clouds over head. But some of the most valuable help I’ve received has come through another person. It’s through our responsible honest interactions with people that we have access to life’s greatest assists.

 

How else would you know you had a tiny piece of paper stuck in the back of your hair if not for the kind soul who leans forward to ask if they might gently pluck it out?

 

And how grateful are you when someone shares their perspective to your benefit? I’m very grateful whenever this happens for me. Sometimes another person’s perspective is just what is needed to help a person evolve to their next level self.

 

Is there a conversation you’ve been wanting/needing to have with someone but you haven’t felt comfortable starting the conversation because you are unsure of how well it will go?

 

If this is you, read on—when you use all of these keys together, you will be leaning in with a strong foundation. To this worthwhile end, here are my keys to success for opening a conversation that your listener may find emotionally challenging to hear.

 

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Checkpoint #1 — Audible Privacy.
Make sure no one else can hear your conversation. You don’t want to embarrass your companion by announcing their business or life events to bystanders.

It can feel incredibly harsh to hear even the gentlest criticism, even if it’s constructive and positive; don’t add to the cringeyness by spilling the tea on your companion with an audience.

Art by Sébastien Conejo

Checkpoint #2 — Fun, relaxed atmosphere, neutral location.
Open your conversation in a neutral location like on a hike, or stroll around the neighborhood—yes, definitely bring the dog! Over food may seem like a good idea but in practice, it’s better to select a transitory activity during which you will start and close your topic. For example, if you want to chat to your friend, ask them to join you for a walk around the block—when the walk is over, the talk is over too. Ya dig?

 

Checkpoint #3 — A specific desired outcome designated by the conversation opener before the convo begins, which should only be to be heard and understood. You never want to insist someone give an answer or agreement right on the spot. Just ask them to think about it, and leave it there. Let them know that’s your ask (for now): for them to think about what you’ve said.

 

Checkpoint #4 — BREVITY. Be brief as possible. Close with your request. For example, “…So I want to thank you for listening – I wanted to let you know how I feel, and I’d appreciate it if you’ll think about what I’ve said.” In my experience this is the most appropriate and generous way to close. You never want to insist someone give an answer or agreement right on the spot. Just ask them to think about it, and leave it there. Let them know that’s your ask (for now): for them to think about what you’ve said. No, it’s not a mistake, I wrote it twice because it’s that important. Close by thanking them for listening and make it clear that (at present) all you’re asking is for them to consider what you’ve said. Full stop!

 

Checkpoint #5 — Be ready to move the conversation quickly to a new lighter topic. Do a toast 🥂… whatever. Release the energy of the previous topic. I can hardly stress enough how helpful it is to use the movement of your physical location as an unspoken signifier that the conversation is free to move to another topic. You literally leave the energy of the conversation behind, allowing space for your listener to process what you’ve said without any pressure from you.

❤️

Caveats…

Let me emphasize the key elements

  • PRIVACY and
  • FRIENDLY and
  • FACE-TO-FACE

 

If any of these elements is missing, wait for or cultivate the proper atmosphere. Face-to-face can be a video call but it’s important that it’s a video call and not a video of you talking at them. I know we are living in the times of social distancing and face-to-face meetings aren’t as common as they used to be, but don’t allow that to prevent  you from having intimate conversations about things that matter to you in a way that is appropriate, helpful and kind.

 

Do it right and your friend will thank you. Sometimes they won’t though—be okay with that too. They may thank you later.