A tip for having better conversations

Up for today: a few of the questions I can’t stop thinking about.

A few weeks ago in the MMD Book Club, we chatted with Kelly Corrigan about her memoir Tell Me More: Stories About the 12 Hardest Things I’m Learning to Say.

I loved this book, have read it twice already, and included it in yesterday’s blog post about great books that celebrate the power of female friendships, because my favorite moments in the book were about Kelly’s relationship with her friend Liz.

In Tell Me More, Kelly relates the story of their friendship: how they went from being social friends to being intimate friends, the kind who truly could talk about anything. (I’m sure Anne Shirley would have a different phrase to capture their relationship.)

I’ve talked to so many women, both in Book Club and in real life, who read Tell Me More and come away from it thinking, I wish I could be a friend like that, or, I wish I could HAVE a friend like that.

But it takes bravery, and a heck of a lot of relational savvy, to get to that place. When it comes to friendship, how do you bridge the gap between What are you doing this weekend? and feeling truly understood by another? How do you build a relationship where you can talk about anything—including the things that aren’t considered fit for polite conversation?

This is the question so many women wanted to hear Kelly answer. And so I asked her: What are the baby steps in getting from here to there, from a shallow relationship to an intimate one?

Her answer: Ask better questions.

In Kelly’s words, “It’s helpful in a tactical sense to have better questions in your back pocket for your daily interactions.”

Sounds easy enough. But what does that look like?

*****     *****     *****

The process begins with one core assumption, according to Kelly. “Everyone is starving for intimacy,” she says. “Everybody would like to be in a more intimate conversation than the one they’re having. You have to believe that first.”

That belief gives you the nerve to say something different. So that even at cocktail parties, Kelly has come to ask a different kind of question.

Not How are you?, but What are you working on this week?

Not Are you going to work out today?, but What’s driving you crazy right now?

Not Are you going to that party tonight?, but Who are you worrying about this week?

We may want better, yet our default mode is often to participate in the superficiality that drives everyone all so crazy. It doesn’t have to be that way. According to Kelly, “it’s very easy with a slightly different question to fall into something more interesting and more revealing.”

If you ask a slightly different and slightly better question, that might yield a different and more meaningful conversation.

And while you’re at it, Kelly advises that, when you’re talking with friends, or potential friends, you let it hang out a little bit. “You don’t want to be running around town like a TMI machine,” she says, “but reveal a little bit.”

Kelly pointed out that when you tell someone your life is amazing (or even pretty good) right now, that’s great for you, but it’s death to a conversation.

Instead, make a point to open up a little bit, and share the stuff that’s not so great. As Kelly says, “When you include the thorns of your own experience, you have something to talk about.”

Does it seem to you like everyone is starving for intimacy? What conversational openers do YOU carry around in your pocket? Please share your favorites, plus your thoughts on Tell Me More, in comments.  

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  1. Ginger says:

    Loved our conversation in the book club about this. I think about this book at least once a week (probably when I’m dreading a situation when I know I’m walking into small talk potential).

    I try my best to never ask someone “how’s work?” but instead, “what’s keeping you busy these days?” That way, they can answer with work, if that’s the thing they’re thinking of, and are passionate about. But, they can also talk about their family, a great book they can’t put down, a trip they’re planning. Whatever someone is busy about, it’s usually important to them. So much more interesting.

    • Tracey says:

      I love your question, “what’s keeping you busy these days?” I’m a stay at home mom and I dread the question “what do you do for work?” because although I don’t work outside the home, there are lots of things keeping me busy these days!

    • Michelle says:

      Ginger, I’m not sure if you also realize the blessing of this question (which I LOVE) is it does not presuppose someone works outside the home. The standard small talk opener of ‘what do you do’ is my absolute least favorite as I find it the least important aspect of most people. I hope your idea catches on Ginger!

    • Ruthie says:

      Yes! I love the question, “What’s keeping you busy these days?” I heard that suggestion somewhere else recently, and whenever I remember to use it, it gets great results. Like Tracey, I’m a homemaker and mom (though not as needed in the “Mom Dept.” these days), and I, too, appreciate how it avoids the “Do you work?” question, which I had taken to answering with a light-hearted, “Yes, although I’m not GAINFULLY employed.” “What’s keeping you busy?” sets people up to give insights into their passions and frustrations, leading to much better conversations.

  2. Nicole says:

    Just want to let you know what an excellent friend you are to so many. You have the gift of making great conversation with your guests on WSIRN and you ask wonderful questions. You make the world a more beautiful place, via your blog (such a pretty website), your books, and your podcast. I didn’t even know I had a “reading life,” and you have enhanced it immensely. I look forward to hearing your friendly voice every Tuesday. Happy Valentine’s Day!

  3. Sandy says:

    Just last night I was sitting with another mom from our youth group, waiting for our kids. She asked me if I’d had a good week. When I responded that I had she asked, “What made your week good?” I loved this question. I not only felt like she really cared about my answer, but it moved me beyond pat answers.

  4. Leslie says:

    This is a topic I have struggled with for years. Although I’m not superficial, I often ask superficial questions. I’m nervous about getting too close maybe because I’ve been hurt by people whom I thought were my friend. Being a military spouse, we have moved often so making the acquaintance friends is easy, but becoming intimately acquainted is VERY hard. I will say, thanks to my IRL book club I have made more intimate friends. I think our love of reading brings us together in more intimate ways. I have not read the Corrigan book, but reading your blog makes me want to pick it up AND try harder at becoming and HAVING a better friend.

    • Lindsay says:

      I can really relate to this – I’m an expat and have had this experience multiple times of being hurt when someone who I thought i could really let go with later made it known that we were more of acquaintances. When moving around your hungrier for friends and security which makes the pain worse. What I’ve started doing to protect myself, is being really direct with people and asking questions like “I’d like to start to share more personal things with you as I consider you a Friend and would love to have more candid conversations, what do you think?”. Or, with other more direct people who maybe will be terrified by that question (men, often),just “I think we should be friends, what do you think?”. It sounds awkward and it kind of is to be honest but someone who wants that relationship with you will be thrilled you asked and happy to agree! Someone who reacts awkwardly would have been someone who would have hurt you later if you weren’t more clear.

  5. Michelle Wilson says:

    I think about this book all the time. I am naturally gregarious and the idea of a party or social gathering is always appealing unless I’m tired. I know how important it is to me to feel ‘seen’ that I know others must feel the same way. So even though I am kind of adept at small talk, I have made it a priority to ask those other kind of questions and man, oh, man have I had some amazing conversations with people. They just light up. No one has said ‘none of your business or why do you ask’. If you are going to take the time to ask the questions then you have to take the time to listen because in most cases, it is going to be much more than …great, and you.

  6. Anna B. says:

    What a relatable post and comments! I haven’t read the book (it’s on my TBR now) but I’ve heard of the “better questions” idea on podcasts previously. I came across an article “36 questions that lead to love” from the New York Times a while back https://www.nytimes.com/2015/01/11/fashion/no-37-big-wedding-or-small.html. Don’t let the “lead to love” part stop you – I’ve used these questions with colleagues, at networking events, and with new friends. Some of my favourites:
    – would you like to be famous? if yes, then for what?
    – what has inspired you lately? (people reveal all sorts of secret passions when prompted with this one!)
    – if you could invite anyone in the world – dead or alive – for dinner, who would it be?

    Also, asking people how they met their spouse or partner always leads to a fascinating conversation – whether you’re asking your boss or new friend.

    • Kerry says:

      Thank you so much for that link!! This was a timely post for me and the comments are, as usual amazing!! I like MMD conversation opener of “What is saving your life right now” I think that is a fun question.

  7. Alicia says:

    I look forward to reading this book. Sometimes it’s hard to transition into thoughtful questions and answers because people (and I) expect the usual “safe” ones we’re all used to. It takes a second to actually think about how to answer! I’ll work on not being afraid of that second pause and use some of these great questions. I can see how they’d make people light up.

  8. Carol B. says:

    This is a great post. Closer friendships are something I crave in my life. I’m finding that when I open up a little bit, I become a project to “fix”. That is not what I am looking for. How do you know someone is safe to let the wall down a little bit with?

    • Tammy Botham says:

      Knowing when to let your walls down is extremely hard. I tend to pay attention to how someone talks about other people in their life. If they are gossipy or negative or if they share personal stuff of someone else’s, I take that as an indication they will do the same to me. Additionally, I make efforts to not exhibit those behaviors for that very reason.

  9. Sarah says:

    This is a fascinating topic and I love the interesting questions that have been listed so far – I’d love to encourage people to keep them coming as I’d love to compile a list for myself to reference from time to time! I like the idea of reconnecting with an old friend by saying What have you been up to lately that’s been exciting for you?” Vs “How have you been?”

  10. Ali says:

    I remembered this at a networking event last Friday. An acquaintance said that euthanasia is the new abortion. I’m thinking: WTF?? But I said, “Tell me more.” Heard about a grandfather who had escaped capture by the Nazis, joined the resistance, sailed over to America to build a new life. And now, at 94, has decided that his time has come. Definitely not a surface-level conversation!

  11. Rebecca Primis says:

    This post and the comments ring so true for me! One of my favorite things to ask is “What are you excited about this week or this month?” For my colleagues, the variant of this question is “What project are you most excited to be working on right now?” It’s easy to get caught up in conversations about being busy and overwhelmed, so I like questions that encourage one to take a step back and look for joyful, positive things to share.

  12. EL says:

    Rebecca, loved your last comment! I too like to keep things positive instead of focusing on the negative or at the least give the conversation a chance to be positive instead of complaining and negative.

  13. What a great approach! And I think it’s a perfect parallel to the philosophies around the power of vulnerability that have become really popular over the last few years. I personally hate the question “what do you do?” and I make a point of never asking it – I usually try “what brings you here?” or “what’s your day been like?”. Thanks so much for sharing, lots to think about!

  14. Claudia Resta says:

    Just finished Kelly’s book and will begin it again next week. There was so much to absorb, and so much I know I missed! It was wonderfully relatable, and I eagerly anticipate reading her other works!

  15. Elizabeth says:

    The last couple of years, I have really been craving deeper and more authentic connections, so thank you for the ideas. But I also still like asking, or being asked, “what do you do?”, I’m just curious about how others make their living,it’s such a major part of our lives, good or bad. (And of course, SAHM is a totally legit occupation, and just as interesting to me).

  16. Ronda says:

    I love this and loved the book too! My go to question for getting more is what was the most interesting/fun thing you have done lately? It can get some wild answers and sometimes I get some really good book recommendations from those conversations. I’m so glad for some other suggestions here as well as I think it is something we have to practice as it is easy to fall into the small talk patterns even if we don’t enjoy it.

  17. Amber says:

    Brilliant. I especially love assuming people want more intimacy than it seems like they do. That affirms my intuition and that alone is so helpful! Thank you for this important post. We all need deeper relationships in our lives.

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