In the last few years, I’ve had the pleasure of kicking off lots of new reporting relationships with both engineers and engineering managers. Over time, I’ve learned that getting some particular data during an initial 1:1 can be really helpful, as I can refer back to the answers as I need to give a person feedback, recognize them, and find creative ways to support them. Most of these I’ve stolen from some really amazing Etsy coworkers.

I usually keep an Evernote file for each person I manage, and the answers to these questions start that doc. This is a high-level list, but I usually add a little color to each when I’m in the room. Also: it’s never too late to ask these. Just tee them up with, “I’d like to ask you some cheesy questions to help me better-support you.”

Grumpiness

• What makes you grumpy?
• How will I know when you’re grumpy?
• How can I help you when you’re grumpy?

I flat out stole that first question from Mike Brittain. He asked me that during our first-ever 1:1 when I started at Etsy in 2013. He said he’d never asked it before. I don’t believe him; it’s SUCH a great question. “Grumpy” is shorthand for so much stuff, but it still keeps the question light and funny and easier to answer.

Feedback & Recognition

• How do you like feedback – the medium (IRC, email, in person, etc.)
• How do you like feedback – routine like in 1:1s, or as-it-happens
• How do you prefer to receive recognition? (public or private)

Have the answers to these questions WAY before you need them. Few things are harder than trying to give someone feedback; doing it in a way that you think they’ll be most able to hear it is invaluable.

Also, knowing how someone wants to receive recognition helps to ensure they’re able to enjoy the moment rather than feel really uncomfortable. For example, for a big-deal promotion, I once gave an introverted direct report a handwritten congratulatory note and a loaf of banana bread—his favorite baked good—which he chose to share with his teammates. His celebration, his terms.

Goals and Support

• What makes 1:1s the most valuable for you?
• What are your goals for this year? And for the next 3 months?
• What do you need from your manager?
• From your team? (this one is good if the 1:1 is with someone who manages people, but is typically relevant for IC’s, too)
• From your peers? (outside the team)

I often ask follow-up questions to the answers to these questions, to help me really clarify and understand.

The Wordy Question

• Human learning and growth requires the right amount of four things: new challenges, low ego, space to reflect and brainstorm, and timely and clear feedback. How are these four going for you? Is there one you need more or less of?

I only use this question if we get in the flow and it feels natural. I straight up ripped this one from the brilliant Learning and Development team at Etsy, originally created and led by Paloma Medina. Hire her if you want to make your whole life better.

The Most Important Question

• What’s your favorite baked good?

This one is CRUCIAL. I have a long document full of coworkers’ favorite baked goods. You never know when you might need to congratulate or thank somebody in a special, meaningful way. (Mine is not donuts, btw. 😉