You don’t even have to be planning a birthday dinner to ask this question! The point is that people always like to be helpful so it’s good to frame the question in a way that gives someone an opportunity to solve a problem for you. And everyone has restaurants they like. There are also lots of good follow-up questions that can come after you start talking restaurants. “When did you last eat there?” “What’s best on the menu?” “What was the occasion that brought you there most recently?” All of these will lead to more authentic connection that the rehearsed answers to “What do you do?”
Continue reading I’m planning a birthday dinner. Any great recommendations?
All posts by Carlo
If you could have picked any place in the birth order for yourself, what would you have picked? Why?
Maybe your sister would’ve wanted to be the oldest by 5 years. Maybe your brother would’ve wanted to still be the youngest but not by the 8 years that actually separated him from the rest of the pack. Hearing the “why’s” behind the choices will put you into your siblings’ shoes. You’ll get a glimpse of what your family looks like from their perspective. (And perspective is always a good thing!) Continue reading If you could have picked any place in the birth order for yourself, what would you have picked? Why?
Can you tell me about your wedding? Where was it? How many people were there? Did you dance? Did you eat?
This question has a not-so-hidden agenda. It’s pulling double duty. First off, this is a beautiful thing to talk about with your grandparent. It just is. 100% worth it. But secondly, for anyone who is planning their wedding or is going to in the future, these questions are a MUCH NEEDED dose of reality check. Today, the wedding industry machinery is a crazy thing. It’s completely out of hand. They make it seem like you absolutely must serve a full meal, and dance, and take pictures, and have wedding favors, and host a brunch the next day, and, And, AND… Or else guests will be horrified and feel embarrassed for you. Ppshhh! B.S. As humans we all do compare ourselves to what we see around us. Comparing is inevitable. But fine – if you’re going to compare your wedding to something, why not compare it to your grandparent’s wedding? Odds are it was simple, and sacred, and amazing. Find out the details. Honor that tradition. And if tiered cakes and drone shots and goodness-knows-what-else don’t feel like you, screw it. Do what Nana did. Serve punch and pie and be in love for 50 years. That woman is kickass and you know it. Continue reading Can you tell me about your wedding? Where was it? How many people were there? Did you dance? Did you eat?
If you couldn’t live here in [City], where would you choose to live instead?
NYC? Boulder? Madrid? City of choice can tell you a lot about a person and their hopes for the future. This question is a door. You might get to know what kind of setting energizes a person. You might learn about family members and the importance of proximity. You might discuss what’s not to like about the city you’re in at that moment. This question feels very approachable while still offering depth. Continue reading If you couldn’t live here in [City], where would you choose to live instead?
If you could only work for one hour each day, what would you do?
Your doctor has told you that if you work a minute more than one hour each day, your heart will explode. This is how Tim Ferriss sets up the question. So what would you do? This is a thought exercise…but also not. I tried this for two days over the summer. How did I spend my one hour of work? 15 minutes high level email. 5 minutes nit-picky email. 30 minutes working on new resources for my language learning business. 10 minutes updating my Workflowy to-do lists and planning out what should happen the next day. (The last 10 minutes was the real revelation for me. I’ve only got 60 minutes before my heart explodes and 10 of them go to planning and to-do’s? What the hell? Turns out having a well-defined to-do list for the next day is CRUCIAL for me.) What does your 1 hour look like? What does that tell you about your (and your colleagues’) “normal” 8+ hour workday? Continue reading If you could only work for one hour each day, what would you do?
Who’s someone you want to impress? Would you let that person do a 1:1 with your co-founder?
Here’s another question that’s not for your potential co-founder but about her. What kind of gut feeling do you get when you imagine your potential co-founder meeting 1-on-1 with an investor? An important journalist? Your longtime trusted mentor? You might feel awesome. Or you might have some reservations (this could be the case with a technical co-founder, for example). But either way it’s something you should think about as your founding team and first hires come together. Continue reading Who’s someone you want to impress? Would you let that person do a 1:1 with your co-founder?
What’s the next right thing?
Maybe you’re like me. If I’m not sure what new project I should focus on or what next strategic business move to make, sometimes I can get bogged down in trying to plan too far into the future. I can obsess about the details – details that will probably change soon anyway. I can lose a whole day in planning contingencies. In those times, it always helps me get moving again to ask simply: “What’s the next right thing?” That’s all you can ever really do anyway. The next right thing.
Continue reading What’s the next right thing?
Are we making our product better? How do we know?
Eric Ries asks this one-two punch of all the startup teams he meets with. To the first question, without fail everyone says yes. To the second question, that’s where the rationalizing starts. Ries cautions against making up a story that links recent product changes to cherry-picked positive metrics. (“Well, more people added themselves to our mailing list this month. Probably that means the new homepage pictures are working.”) Instead, he makes the case for “innovation accounting” which you can read all about in Chpt 7 of The Lean Startup. Continue reading Are we making our product better? How do we know?
What gets you most excited about the company’s future?
Your interviewer should have a convincing and authentic answer to this question. And they should light up a bit when they give it. That is the most important thing. The possible answers could be as varied as “upcoming growth” or “continuing to serve our devoted customers.” But if there’s no answer (or only a forced one), then beware! Continue reading What gets you most excited about the company’s future?
What were you doing the last time you looked at a clock and realized you had lost all track of time?
This state is known as “flow” — a concept popularized by psychologist Mihaly Csikszentmihalyi (yeah, I have no idea how to pronounce that either). A person in “flow” engages in an activity while “fully immersed in a feeling of energized focus.” Joyful. Productive. In the moment. Anyone worth hiring goes to this place often. And it’s extremely valuable for you as the boss to know what kind of activity and what kind of setting puts a potential new hire into this state of working. You’ll know if the person’s temperament and interests make her a good fit for your company and your culture. Continue reading What were you doing the last time you looked at a clock and realized you had lost all track of time?
What is the best gift you’ve ever given someone?
To me, “best” doesn’t mean it was the most expensive gift or that you had to camp outside a store for 3 days to buy it. Maybe you didn’t have to buy it at all. A great gift is great because it’s something you chose very specifically. It was the perfect thing (or action) for that exact person at exactly the right time and he/she just LOVED it. In that sense, what’s the “best” gift you’ve ever given? Continue reading What is the best gift you’ve ever given someone?
Is it true? Is it necessary? Is it kind?
This is a 3-part test that you can use any time you’re debating whether you should bite your tongue or give someone a piece of your mind. Ask these three questions in this order. If what you’re about to say fails one of the tests, there’s no need even to continue on to the next part. A peaceful heart. A clear conscience. A predisposition to kindness. You get a lot from these 3 questions. Continue reading Is it true? Is it necessary? Is it kind?
How did you end up in your career? What are your most and least favorite things about it?
For some people, there was a particular moment or interaction when they knew what career field they’d want to enter. For others, they ended up where they are gradually after a series of “one-thing-led-to-another’s”. Some folks felt pressure from family. Others were pressured by financial concerns. The reasons why are all over the place. Do you know your parents’ reasons? Continue reading How did you end up in your career? What are your most and least favorite things about it?
How old is “old”?
There’s a higher chance of your teenager answering this question if only because he gets to call you old. I’ve seen this question lead to some very interesting discussions. I think it’s because you as a parent are being intentionally vulnerable in asking it. And from your teenager’s perspective, if the adults in the world are growing old, then that means the teenagers are growing up. Grown up is how he wants to feel. Continue reading How old is “old”?
What was your favorite part of lunch?
Let’s not make things more difficult than they need to be! Cut straight to lunch – regularly a highlight of the school day. As with all good questions, this one can’t be answered with a yes-no. You’re guaranteed to get some info about friends, jokes, topics of conversation, etc. Continue reading What was your favorite part of lunch?
If you were by yourself for the entire day tomorrow and could do anything you wanted, how would you spend the day?
“Put on your own mask before assisting others. Oxygen is flowing even if the bag does not inflate.”
We’ve all heard this. And we all know what it means in terms of day-to-day self-care even when you’re not on an airplane. But it’s often very difficult to actually take a mental health day or even carve out an hour or two each week for reflection, exercise, meditation, creative writing, pleasure reading, etc. Ask your partner this question and you’ll know what the O2-starved part of her wants most right now. This is important information. And even if you can’t arrange an entire day unplugged, you can probably knock out bills/bathing kids/doing dishes to give your partner 1 hour to journal and think. It might not be a whole, full day but…oxygen IS flowing even if the bag doesn’t inflate, right? Continue reading If you were by yourself for the entire day tomorrow and could do anything you wanted, how would you spend the day?
What are your bottlenecks?
Tons of bosses struggle with relinquishing control. They don’t delegate enough. They won’t fully cut loose a colleague so he can take the project and run. They insist on giving final approval when they’re already 99% sure that the thing was done well. I’ve been both a boss and an employee. As a boss I’ve been guilty of all these things – mostly because I didn’t realize I was doing them and slowing everything down. Asking this question helps an employee “manage up” with his boss. Once a boss sees the bottlenecks clearly, she can more easily take action to delegate them away. Continue reading What are your bottlenecks?
What advice would you give yourself from 10 years ago?
We all have nuggets of wisdom that we learned the hard way. Why not share the learnings with each other? Plus opening up about mistakes and regrets always deepens a friendship. Continue reading What advice would you give yourself from 10 years ago?
Do you have any trips coming up?
I’m not a fan of filler conversations about the weather. It’s the quintessential surface-level small talk. But that conversation is also kind of unavoidable sometimes. It just happens. When it does, this question is an awesome bridge to more interesting stuff! “It sure has been cold lately.” “Yeah, you said it. I wish I had vacation plans somewhere warm. Do you have any trips coming up?” Boom. From there you can talk about memorable vacations, recommendations, that time you attempted snowboarding… Continue reading Do you have any trips coming up?
What do you appreciate most about how we were raised?
Comparing notes is healthy. And it doesn’t take long for this question to inspire funny stories between you and your siblings. Your childhood might have been pretty idyllic or kinda dysfunctional but either way there will be something about it to appreciate. (Appreciating like this also has a way of putting you in charge of your own future.) Continue reading What do you appreciate most about how we were raised?