Six questions for better conversations

I was in the car the other day with my husband, driving up to a fancy event with some quite established folks in their careers. We knew about each person, their prestige, their work, and their reputations. So I also knew that the default American question “What do you do?” wouldn’t suffice for the dinner party.

We started brainstorming a list of questions to ask people instead, and I jotted them down to remember for later. Asking people better questions is a great way into a more interesting conversation. Here’s some of what we came up with:

What puzzles are you currently working on?

I love talking to people about what they are learning, and what their process is while they are discovering, building, and grappling with a project.

What have you recently figured out? Any fun “Aha” moments in your life recently?

This one is about that feeling of unlocking something. For me, I’ve recently found a good pool and a swim routine, and I’m constantly thinking about how to adjust and iterate on my routines to garner a better day. Each little piece of the puzzle I put together is fun for me to think about.

What are you excited about right now?

This opens the door for people to tell you about their work or their hobbies—whatever lights them up. And even if the answer is, “You know, nothing—I’m in the doldrums right now,” that still gives space to go deeper in the conversation.

What did you do last weekend?

We’re obsessed with what people do during the week, and what they do for work. Flip it on its head and ask people about their weekend and their leisure activities.

Who are you learning from right now?

I like seeing who people are connected to, and who is teaching them, and what they’re learning. I’m always studying different people’s work, and I find that this is a good way to get into people’s research, thinking, and reading, without asking the question “Read any good books lately?”

What’s something that’s not obvious about you right away?

I ask this question in my Mastermind applications, and it’s a wonderful way to go beneath the surface and see who people are. It’s always a fun one, because often the answers aren’t obvious right away—and it’s really cool to hear the answers!

Going deeper: ask three questions

I’ve written about this elsewhere, but after the first question, instead of flipping back to you, ask another question, and another one. It’s the third question with someone else that’s usually at the heart of the subject and gets into the good, juicy conversation. My favorite follow-up questions are:

Tell me more about … 

What was that like for you?

What about you? What questions do you love asking people?

Screw the fairytales

In my twenties, I was on track to fulfill all the obligations of being a woman in this society: engaged to be married, great job, graduate degree education, wanted to have kids. Society was happy for me, and that ring on my finger was the icing on the cake. The problem? I didn’t like the job, and I was wildly uncertain about the prospect of getting married, even though I’d said yes to the proposal. Then, over the span of a year, I lost my rib (it was taken out of my body through emergency surgery), I lost my fiancé, and I found myself in completely new territory. What happens after the fairy-tale ending? In most books, my engagement would have been the happily-ever-after. Here, I had a new lease on life, and finally, slowly, started listening to myself and what I wanted, instead.Read the article

How you move through the day

There are many ways to go about a day. It’s not always as important what gets done as it is *how* I am showing up, and *who I’m being* in the process of all the doing and non-doing that I’m engaged in. In my mastermind circles, we call this “ways of being.” We work through three major phases and processes in our work together, which I describe in this post. Read the article

July Book List

July was a busy reading month. I was focused on recording and prepping interviews for my upcoming maternity leave, and with all the extra interviews scheduled, I had quite a list of books I needed to read to prepare! Here’s the complete list of books I read over the last month: one of them, Overwhelmed, is one of the best books I’ve read so far all year. Read the article

What will teach you more?

Instead of trying to make the best possible decision based on an estimated guess of an outcome, it’s important to remember that we can’t control the outcomes. (If we could, then planning, marketing, and making would be far more boring and predictable.) Instead, I like to ask this question in order to make decisions in the face of uncertainty and unpredictability.Read the article

Join me! Live podcast show in New York City — Thursday, August 9th

Friends! I’m joining the host, best-selling author, and founder of Unmistakeable Media for an intimate evening podcast recording of the Unmistakeable Creative Show. We’ll be taping live in New York City on Thursday, August 9th, after work. Join us. Tickets are sold in advance and are first-come, first-served, with an intimate venue and a limited audience size. Yes, I’ll be staying up late and waddling my big pregnant belly to a stage downtown to talk about startups, parenting, philosophy, and systems. Srini Rao is the bestselling author of Unmistakable: Why Only Is Better Than Best, and will be leading the discussion.Read the article

How to Do A Quarterly Review

One of my favorite practices as a business owner is to do a quarterly review and reflection. Each quarter I set OKR’s, or measurable goals, and reflect on the progress made in the last quarter. A quarter is a perfect amount of time to set a goal and make progress on it, and it’s a great interval to catch yourself if you’re not making any forward progress, either. For the last several years of my life, quarters have been the backbone of part of my planning process. Here’s what OKRs are, how they work, and my system for quarterly review.Read the article

How My Kid Teaches Me About Leadership

The learning curve of building a new human from scratch and re-wiring yourself as a parent and a functioning adult comes with plenty of challenges. Yet it also feels strangely familiar: like the long days of marathon training, or like the late nights studying to get your MBA on the side of your full-time gig. Here’s how parenting rewires us as leaders.Read the article

The Word You Keep Using

Our subconscious has a way of winding itself into our writing, if we’re paying attention. This practice always startles me, by reminding me of something that was sideways and not quite at the surface.Read the article

Three Things To Grow Rich In (That Aren’t Money)

Wealth can be created across more areas than just financially. Sure, monetary wealth can be a beautiful thing, and I’ve got aims to grow wealthy in money. But there’s three areas that are more important to me for wealth than just money. Read the article