Design the person you want to become.

Analog Chat Interface

James Buckhouse
2 min readNov 27, 2023


Becoming the parent, partner, or co-worker you want to be doesn’t just happen: you have to plan it, design it, and then make it happen. Strangely, the secret missing piece is often hidden in your conversations.

Ask the right questions and everything improves. If you are in a conversation with someone (especially your children) and you’re not asking interesting questions, you’re missing out.

The goal isn’t to talk, it’s to think, listen, reflect, and learn.


Try this: Instead of asking “how was school?” or “how was work?” which can be easily extinguished with a single reflexive “fine” try asking questions that engender expansive reflection. This is especially important for talking to your kids. Here are a few you can borrow and adjust. Or, if that’s too much work, just read them aloud and see what happens.

Ask the other person…

  1. How how were you resilient today? Anything happen where you had to bounce back, recover, resist, or adjust?
  2. What caught your curiosity today and how did you pursue it? What did you learn? What do you still not yet know that you might want to explore later? What else does that make you think of?
  3. How did you pursue excellence today? What did you identify as something you want to improve? How did you make progress towards getting better? What evidence or proof of improvement did you notice in your progress towards excellence? Where are you still looking for proof, but haven’t noticed any yet?
  4. What delighted you today? What secret joy or hidden beauty did you uncover?
  5. What connections did you draw today between two seemingly unrelated ideas? What happened when you put them together?
  6. When was a recent moment when you felt loved?
  7. What do you want to change about tomorrow?

These questions aren’t just for your kids. They will improve your interactions with your spouse, your team, your boss, strangers at a “networking” event, distant co-workers at the company party, and most important, they work with the person with you all the time—yourself.

Unexpected outcome

What’s wild is that when I’m struggling, hurt, worried, frustrated, agitated, or embarrassed, I ask these same questions to myself. And it nearly always helps. My own answers reassure me, because they carry me past my immediate trials towards my true, long-term hopes, concerns, gratitude, and ambition.


Try it. Slip some discarded paper out of the recycling bin, grab a pencil, and jot down answers to the questions above. I’ll bet you’ll feel better after the first one. Make it all the way to seven and you’ll feel energized, nay, almost transcendent.

Try it! Let me know if this worked for you.

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James Buckhouse

Design Partner at Sequoia, Founder of Sequoia Design Lab. Past: Twitter, Dreamworks. Guest lecturer at Stanford GSB/ & Harvard GSD