The nature of work has changed so much just in the past 20 years. Let alone the past 60! Asking this question about grandparents’ jobs is definitely like stepping into a time machine. (As an aside, did you know that before alarm clocks, there was a job called a “knocker-upper”? You paid a person to knock on your window at the hour you specified. Crazy! Continue reading What was your first job? What was your favorite job?
All posts by Carlo
What are you looking forward to most in life right now?
Not rocket science. This one is just a solid question that could open up discussion about things happening at work, church, with family, friends, vacation… Continue reading What are you looking forward to most in life right now?
How do we make sure that it’s possible for this new idea to fail?
You want the idea to succeed, of course. But you have to make sure that you know what metrics on what criteria qualify as a failure. Eric Ries says it best:
“Unfortunately, if the plan is to see what happens, a team is guaranteed to succeed – at seeing what happens – but won’t necessarily gain validated learning. This is one of the most important lessons of the scientific method: if you cannot fail, you cannot learn.” Continue reading How do we make sure that it’s possible for this new idea to fail?
What does your spouse think of this person? (Not a question for your Cofounder, but rather about your Cofounder)
A startup cofounder is someone you’re going to spend A TON of time with. Before you go into business together, your significant other should meet the potential cofounder. It’s best if your S.O. also vibes with this person. And your S.O., who knows you very well, might be able to spot signs of future friction that you may be blind to because of your enthusiasm about the startup idea. Continue reading What does your spouse think of this person? (Not a question for your Cofounder, but rather about your Cofounder)
What is everything you can do with a brick?
Before you start answering this question, get a pen, a few sheets of paper, and a smartphone (or other way of timekeeping.) Give yourself 5 minutes to invent as many uses for a brick as you can. And go! Don’t self-censor much at all. Any use of a brick goes onto your list. As the uses get more and more unorthodox (a veggie masher! a laptop stand!) you’ll be moving your mode of thinking “outside the box.” After 5 minutes answering this question, go back to the activity you were stuck on. You’ll have new eyes for the problem. Continue reading What is everything you can do with a brick?
How could referring your business make your client’s life better?
For those of you who are hesitant to ask existing clients to refer friends/colleagues to your service, it becomes much easier if you yourself have a clear understanding of how your business improves people’s lives. Once you can articulate this benefit and you internalize it, asking for referrals isn’t slimy; it becomes a way to serve more. Continue reading How could referring your business make your client’s life better?
Why is this position open? Is it a new position or a replacement for someone?
No tricks to this question. It’s just straight up good to know if this position was created because the company is growing/evolving or if the position already existed but was vacated (in that case, was the previous person promoted? Moved to a different part of the business? Fired? Quit?) Continue reading Why is this position open? Is it a new position or a replacement for someone?
What is the toughest decision you had to make in the last year? How did you make it? Please walk me through your process.
The particular situation and eventual decision don’t matter here. It’s the process that’s most telling. Insist that the interviewee literally walk you through the process step by step. Are they more analytical? Did they write out pros and cons on a piece of paper? Are they more emotional? Did they have confidence in a gut feeling and go with it? Are they more relational? Did they call up a trusted mentor? Did they own the ultimate decision? And are they able to communicate all of this lucidly to you? Love this question. Continue reading What is the toughest decision you had to make in the last year? How did you make it? Please walk me through your process.
Did you have a stuffed animal or favorite toy growing up? Do you still have it?
This is a good one for team building because you see a different side of your colleagues than what they normally bring to work. And answering this question requires just a smidge of vulnerability, which is a great thing for everyone to practice. Growing up I had a stuffed rabbit named “Huggy.” I still have him. Brought him when I moved across the country even. I’m 31. Feel a little funny telling you that but… you know, whatever. See, now you know that about me! Continue reading Did you have a stuffed animal or favorite toy growing up? Do you still have it?
How will I know when it’s enough?
Ads tell us the dumbest shit. “Buy this car with the heated seats and it will make you happy!” “If you’re uneasy, it might be because everyone you meet can tell that your clothes are from 6 months ago.” “Why be like yourself when you can try to be like the rich people on this reality show we invented?” Gaaah, I’m getting all nuts just writing about it now. The happiest people I know can answer with above average clarity this one question: “How do you know when it’s all enough?” Enough money. Enough stuff. Enough recognition. Answering this question for yourself is difficulty level 1000 because it involves values and priorities and our personality baggage. But it’s crucial that we try. Continue reading How will I know when it’s enough?
What was special about the first time you hung out with mom/dad?
For me, one of the most humbling and crazy parts of growing up has been slowly, fully realizing that parents are just people. Yup. Just people who were born a couple decades earlier and made babies. Our parents are (and have been) just trying to figure things out like everybody in our own generation is trying to do. Questions like this one open a door onto that generous place where we can really get to know the people under the “mom” and “dad” hats. Continue reading What was special about the first time you hung out with mom/dad?
If [name] wasn’t your name, what would you want your name to be?
I’ve gotta come clean – I’ve got about as much insight as the next random person about what will or won’t work with a teenager. I can see this question working with some of the teenagers in my life but it all depends on the relationship you have with them. (And it depends on the day you ask…) Give this one a try, though. It’s hypothetical enough to be fun and allows people to reinvent themselves a little bit which is what adolescence is all about. Let us know how it goes! Continue reading If [name] wasn’t your name, what would you want your name to be?
Which one of your teachers would survive a zombie apocalypse? Why?
Everyone loves a good zombie apocalypse! And your kid certainly has opinions about all her teachers. Combine the two and you can get some great insights into which personalities, teaching styles, and subjects your little one likes or dislikes. Continue reading Which one of your teachers would survive a zombie apocalypse? Why?
What about our current life do you think would most surprise your 10-year-old self?
Life trajectories are beautiful and often unpredictable. It’s fun to learn about what your partner thought adult life would be like. You can appreciate the good surprises together. And for the sadness-tinged surprises (because that happens too – “I never thought I’d live so far away from my family,” or “I was sure I would have traveled abroad by now”) this question can help you start planning something special and memorable: a surprise visit home or that trip abroad after you’ve saved up for it. Continue reading What about our current life do you think would most surprise your 10-year-old self?
I’m not familiar with that. Could you fill me in?
It happens in all kinds of situations. Someone assumes you’re familiar with a term (or concept / organization / person / thing) that you don’t actually know about. “I was talking to her at SoCap when…” “I think their run rate is $400k but the more important thing is…” “We asked our boys not to use YikYak but what’s hard is…” In these situations it’s super easy to just let the reference pass. Nobody wants to look like they’re not in the know. But it’s actually pretty powerful to get eye contact and interject with some form of “Wait, what is that?” Admit you don’t know and be the kind of person who learns quickly from there. That’s more effective (and impressive) than being a know-it-all (or posturing that you are). Continue reading I’m not familiar with that. Could you fill me in?
What $100 (or less) purchase has most positively impacted your life in the last year?
This question gives you such a cool angle on someone’s day-to-day life. Learning about what small-ish purchase has changed someone’s life can tell you a lot about hobbies, routines, frustrations, splurges, all kinds of things! Plus, you might get some really good ideas for your own next life-improving purchase. Continue reading What $100 (or less) purchase has most positively impacted your life in the last year?
What personal habit are you proudest of?
It might seem like a stretch to lead right out with this question so you can always just say, “Out of habit I’d normally ask what you do but instead can I ask you something different?” Then asking about personal habits opens the door to any number of answers: Playing the guitar a bit every night. Checking in with parents once a week. Flossing. All kinds! I promise it’s not as awkward to ask this as it might seem! Continue reading What personal habit are you proudest of?
If we could collaborate on any project together, what would you want it to be? (Could be a business, a rock band, an artistic creation…)
No matter how much you’ve fought and still fight with your siblings, brothers and sisters are a blessing. Nobody knows you and your story the way they do. Kick around some ideas of things you might collaborate on. If the answers are goofy, you’ll have a good laugh. If the answers are exciting, then remember me when you’re the new Jackson 5. (Don’t remember me if you’re the next Kardashians, though. I’m not taking the fall for that shit.) Continue reading If we could collaborate on any project together, what would you want it to be? (Could be a business, a rock band, an artistic creation…)
What kinds of clothes, hobbies, slang terms were popular when you were a teenager?
Come on? Does this one really need any explanation? Is it ever a bad time to hear your grandparents explain “keen” or “swell” or talk about the first time they saw a bikini? (Heads up: We’ll all be old someday soon so make sure you’re taking notes about cat memes and Gagnam style so you can explain it all in 2070.) Continue reading What kinds of clothes, hobbies, slang terms were popular when you were a teenager?
What is something that you’re really bad at?
Simple, disarming, and likely to lead to a fun conversation. Just make sure that you sympathize instead of mock. And make sure that you share something you’re really bad at, too. Continue reading What is something that you’re really bad at?