What was the last movie that you LOVED and told someone they should see?

 

By the time you’re done with a job interview you should have answers to three main questions: 1) CAN this person do the job? 2) WILL this person do the job? 3) Will this person be a good fit with the rest of the team and with our culture? This question about movies is aimed squarely at helping you with that third piece. Does this person have a similar sense of humor? Similar interests? Would they be fun to hang out with? This is important to know – especially on a small team where 1 hire could represent 25% of the company (or even more). Continue reading What was the last movie that you LOVED and told someone they should see?

If it were 100% guaranteed that you would succeed, what would you do?

 

It actually takes a minute to rewire your brain and to remove the possibility of failure and the little voice that pipes in with all the criticisms about any idea you may have. But once you can imagine that success is imminent for any endeavor you choose, it’s kind of awesome to see what surfaces. Here’s a tip: Come up with a list of four things that you would do. Two of them have to be related to your everyday life and can only affect the people in your immediate circle. The other two can be anything at all and can have any size impact, global or local (or hyper local). Continue reading If it were 100% guaranteed that you would succeed, what would you do?

Whose marriage do you most admire and why?

 

It’s not about competition with another couple. Asking your husband or wife this question is much more about identifying what inspires them and what they aspire to in your own relationship. Work through this question thoughtfully. It will make you appreciate the gift of the solid marriages that surround you and it will give you tons of ideas for how to strengthen your married life. Continue reading Whose marriage do you most admire and why?

What person would you say has had the biggest impact on your life in the shortest amount of time?

 

A deep conversation with your best friend might change your outlook on something forever. That’s great. It makes sense that a significant change would come from a relationship that big and that meaningful. But sometimes, incongruously, a very brief interaction with someone you don’t know well (or at all) can leave a lasting impression on how you see things or how you move through the world. I shared a late lunch with an elderly woman in Toulouse, France for 30 minutes and then never saw her again. I’ve thought about her regularly for the past decade. Who has impacted your life quickly but forever? Continue reading What person would you say has had the biggest impact on your life in the shortest amount of time?

Whom do you envy?

 

And what about that person or his life makes you envious? This is a brilliant question because envy is a very strong emotion and therefore a very useful marker on the path towards self knowledge. Gretchen Rubin (blogger and author who studies happiness) points out that the things that make you jealous can tell you a lot about what you want most in life. (She’s not talking about envying someone’s new laptop or watch. She mentions reading the alumni notes in her college magazine and feeling sick with envy to learn about someone’s job in writing. This is how she learned she should move her life path away from law and towards writing.) So in your life, who is it? Whom do you envy? Think seriously about it and you’ll be rewarded with a serious data point about yourself. Continue reading Whom do you envy?

What responsibilities did you have at home when you were young?

 

I’m not one to imagine that everything was better back in the day. But I DO get the sense that kids in past generations were given more responsibilities earlier on in life. And the responsibilities seemed to matter more. It wasn’t just “make your bed” or “pick up your toys” but tasks of consequence — things that, if left undone, would impact the family’s day-to-day functioning. Make sandwiches for your sisters. Or, I dunno…feed the chickens. (I just made that one up. I gotta ask my grandmas this question so I can get real answers! Go ask yours!) Continue reading What responsibilities did you have at home when you were young?

Where does most of your energy go during the week?

 

This is perhaps the most succinct and natural sounding alternative to the dreaded “What do you do?” It’s a far superior question because it opens up the range of available responses for everyone. If you’re a full-time parent, you definitely have an answer to this. If you have a 9-5 job that is not very demanding but a side hustle you’re spending every free moment on outside of work, then your answer to this question would be different than your answer for “What do you do?” If you’re retired but volunteer a lot, this question is also right in your strikezone. Seriously, now that you have this you shouldn’t ever again need to ask “What do you do?” Continue reading Where does most of your energy go during the week?

What’s one major way that you differ from the group(s) you most closely identify with?

 

Republican. Democrat. Christian. Muslim. Entrepreneur. Parent. Crossfitter. Apple devotee. Hipster. The groups we join (and stick with) do indeed signal to the outside world something about us. But you can’t ever truly know people by the boxes they check. You only really see a person when you start to understand how her unique personality does NOT line up 100% with the group identities that characterize her broadly. A Democrat who believes that life starts at conception. An entrepreneur who’s terrified of risk. A hipster who sincerely loves the new Justin Bieber album. Outside the lines is where friendships get interesting. It’s where real people live. Continue reading What’s one major way that you differ from the group(s) you most closely identify with?

What would go into a “perfect” day for you?

 

This can be a really great question but the timing matters a lot. This isn’t a great first date question because if you ask it on a first date you’ll get the response that people *think* they should be giving. Oh, well you know, I’d work out in the morning, spend time outdoors with my friends, read a novel etc etc… A first date will probably answer this like an interview question. But on a fifth or sixth date, the time and trajectory of your budding relationship allows for more authentic answers. I’d sleep in until 11am. I’d make a gigantic breakfast burrito. I’d go for a walk with my mom. (As an added bonus, the answers to this question after the fifth or sixth date will give you great ideas for the seventh and eighth dates.) Continue reading What would go into a “perfect” day for you?

Can you explain to us everything that is on your keychain right now?

 

I love this question. It’s great to kick off a meeting, but it’s also one of the best non-hokey icebreakers that I’ve seen used in group settings. It only takes each person about a minute to go through all the keys, keychains, and doodads they’ve got but you learn a lot about what people use on a daily basis, where they’ve traveled, and who’s in their lives. Plus EVERYONE’S got keys! No more human knots or trust falls or whatever. You’re welcome! Continue reading Can you explain to us everything that is on your keychain right now?

What are the 3 MOST important things that I should make happen today?

 

The most productive people I know seem to get DOZENS of things done every day. Dozens. Like 50 or 60 things, I swear! But from hard won experience I know that when I start a day with an overflowing to-do list, it rarely ends well. Probably because when I look down at a list that big I just want to start crossing things off as soon as possible. What ends up happening is that I focus on the quickly accomplished (and often less consequential) items first. And second. And third and fourth and then the day is done. Yay! My desktop is SOOO organized! On the flipside, the days are always more manageable, more satisfying, and in the end more productive if I just write down the 3 MOST important things that should happen and knock them out. Start there. End there. Anything else is extra credit. Continue reading What are the 3 MOST important things that I should make happen today?

What can I do to make you feel more confident in our future direction?

 

This struck me as an awkward question at first. It just doesn’t sound like the kind of thing that regular people ask each other. But why not? Shouldn’t it be? So often in life we have to make decisions based on imperfect or incomplete information. (It’s this way for decisions about jobs, where to live, how to save, etc, etc…) So with your partner, one of the rare times that you actually CAN have complete information about what to do in order to make him/her happier and more fulfilled, why not ask for it? Continue reading What can I do to make you feel more confident in our future direction?

How are you doing today?

 

It’s the last word in this question that makes the difference. When someone is suffering from a long-term illness like cancer, “How are you doing?” can seem like a crazy question. How am I doing? Terrible! I have cancer! By contrast, if you ask “How are you doing TODAY?” you give people the opportunity to answer honestly about the ups and downs. “Today” gives them the space to be pessimistic, optimistic, angry, grateful – the full range. Continue reading How are you doing today?

Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?

 

So this is a double-barreled question and both parts are equally important. What do your friends dream of accomplishing, or trying, or having? You need to know these things. But also, we all have roadblocks (real or perceived) that prevent us from living out our dreams. You need to know these things as well (about your friends AND about yourself). Continue reading Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?

If our family had a motto, what do you think it would be?

 

No matter what, your family has a certain vibe – a certain energy distinct from any other family on earth. What motto would capture your family’s essence? What would go underneath your house seal? Ask your siblings and see what comes up. I can tell you my family’s motto could easily be: “Send ’em home with leftovers.” Because growing up in my Filipino family, our house was often full with my parents’ friends, our counter full of food, us kids all running around or rollerblading or playing super nintendo. And you could be dang sure that if you came to our house, you’d encounter a super-abundance of food and we’d send you home with at least one plastic grocery bag full of pancit, and lumpia, and bbq and rice. I can’t tell what’s more important – the food itself or the sharing. (For a different look at this question, ask your parent instead of your sibling.)
Continue reading If our family had a motto, what do you think it would be?

Do you have a vivid memory of something you did that you were disciplined for?

 

I love hearing a good you’s-in-trouble story. And there’s a certain joy that comes over people when they recall the trouble they got themselves into. Maybe because it reminds them of a simpler time in life. Or maybe it reminds them of their family. Heck, maybe they’re just glad they survived it. Ask your grandparents this question. I guarantee it will bring a smile to their faces. And you may get to hear a story about something awesome like a 50 cent movie that was worth sneaking out for. Continue reading Do you have a vivid memory of something you did that you were disciplined for?

Can you tell me about the last team event you did together?

 

Hopefully the answer is, “Yes I can.” And ideally, the most recent team event didn’t happen 9 months ago. It’s important to see that a company is actively building up relationships and is being intentional about the organization’s culture. How does the interviewer look when she answers this question? And can you see yourself fitting in at that kind of event with that kind of group? Continue reading Can you tell me about the last team event you did together?

Tell me about a time you felt leadership was wrong (a boss, board member, professor, etc…). What did you do?

 

Disagreeing productively is a skill. And not everyone has it. When someone disagrees with leadership do they silently go along anyway? Do they silently drag their feet? Do they confront directly? Are they able to disagree in a way that brings important new perspectives into the room while not putting people on the defensive? Or do the veiled ultimatums start flying? You want a fighter. But he should know when to fight. And he should fight fair. Continue reading Tell me about a time you felt leadership was wrong (a boss, board member, professor, etc…). What did you do?