Toolbox for not avoiding hard conversations
My New Year's resolution to bring up things 30% more often.
In my interview with Osman and Adelaida last month, they shared how having hard conversations strengthened their friendship. Hard conversations don’t have to be hard – it’s basically just talking things out rather than avoiding discomfort and conflict by sweeping it under the rug. When I don’t bring up something that bothers me, it tends to build and create distance. If I can brace myself and broach the topic with my friends, we can get closer by sharing our perspectives and feelings.
In the spirit of the New Year and resolutions, I liked Danny Lavery’s challenge to “bring stuff up 30% more often.” This practice will increase my capacity to speak up when something’s not feeling right in a friendship without tipping into being 100% confrontational 100% of the time.
To aid my goal to bring up stuff 1/3 more often, I’ve collected some tools to help me bring up something sensitive with a friend:
Set the stage for the awkward conversation
“I’m a bit nervous to say this, and my goal in mentioning this is that I want to stay close to you…” (remind each other of our desired outcome)
Journal about what I’m afraid of in bringing up the issue and what positive outcomes I’m hoping for.
“I don’t know exactly what to say, but I’m going to try…” (I don’t have to have it all planned out; it’s okay to be a bit messy)
Dr Marisa Franco encourages us to hold both the positives and negatives of the friendship simultaneously, which can help your friend be less defensive. She suggests, “I know you do a lot for me, and here’s something that makes me feel a little bit hurt…”
Bring up a topic with curiosity and seek your friend’s side of the story. Slate’s Big Mood, Little Mood podcasters recommend this helpful wording (in minute 15 of the podcast): “I want to bring something up that’s been troubling me. Someone mentioned that at my wedding [they saw you do this…] I just want to know, can you tell me what happened because it really surprised me, and I just don’t quite understand.”
If things are getting off the rails in the conversation, ask for a rewind or refresh: “I’m sorry my awkwardness around this made it even more awkward between us; can we start again?”

Then what do we need?
“I really would like your honest feedback on this, and I’m ready to hear whatever you have to say.”
Ask for confidentiality, “Could I tell you about my feelings, and would you not talk to anyone else about this?”
Preface with the kind of feedback I want: “I’d like your advice on something…” OR “I’d like to rant for a minute…” OR “Could you commiserate on this with me?” OR “Can you get excited with me?”
Ask how my friend wants me to respond. “How can I best support you right now?” “Would you like advice or comfort right now?” This is also the Three Hs: “Do you want Hugs to be Heard or Helped?”
“Can I just talk to you for an hour about [something in my life]?” This has the double bonus of letting my feelings out and sharing more of myself with a friend.
Offer alternatives that nurture all
“I’m not ready to talk about that yet; could we talk about this in a few weeks after I’ve had time for my emotions to settle?”
“I don’t like Vietnamese food; how about Thai food instead?”
“I’m not up to a party tonight; can I invite myself over with a bottle of wine for some one-on-one time soon?”
When someone is grieving, and I don’t know what to do, offer concrete options: “Checking on you. Please choose from the following:”
“I’m not a big texter. Could I give you a call instead?”
“That was a hard [experience together]. Can we share each of our experiences and see how we might do this better in the future if we were to do that together again?”
Let a friend know ahead of time when I won’t be available (as I discussed in my post about being friends with people with kids)
Do you have any tips for approaching hard conversations?
Yay Friends Moment of the Month:
When my trivia team, the Droplets, successfully put these items in order of lightest to heaviest: a Starbucks short latte, a Nokia 3210 phone, 12 McDonald's chicken nuggets, and 2 tennis balls. (Answer at the bottom of the post…)
We didn’t win the trivia game, but getting that right - through some incredible teamwork - felt like a huge victory. Shout-out to my friends Clara & Rob & Wallace for hosting trivia for us!
Friend Quote of the Month:
Trivia answer: tennis balls, Nokia, chicken nuggets, latte