Grumpiness
- What makes you grumpy?
- How will I know when you’re grumpy?
- How can I help you when you’re grumpy?
“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?
- What’s your favorite way to treat yourself?
(I updated this question when I wrote Resilient Management. It’s important to be sensitive to the fact that folks may not want to talk about food, and many people just don’t treat themselves with food anyway. The heart of this question is really about knowing how to acknowledge your teammates in the way that they prefer!)
This one is CRUCIAL. I have a long document full of coworkers’ favorite ways that they reward themselves (e.g. a margarita, a massage at their favorite spa, a sushi dinner, a day off). You never know when you might need to congratulate or thank somebody in a special, meaningful way.