What’s the name of the lady who cleans this building?

 

The CEO of Charles Schwab, Walt Bettinger, tells a story of the only test he ever failed in college. He was trying to maintain a perfect 4.0 GPA but his business strategy professor gave a 1-question final that caught him off guard. In Walt’s words:

“…the professor said: ‘I’ve taught you everything I can teach you about business in the last 10 weeks, but the most important message, the most important question, is this: What’s the name of the lady who cleans this building?’

That had a powerful impact. It was the only test I ever failed, and I got the ‘B’ I deserved.

Her name was Dottie, and I didn’t know Dottie. I’d seen her, but I’d never taken the time to ask her name. I’ve tried to know every Dottie I’ve worked with ever since. You should never lose sight of people who do the real work.”

This is a great story. I wish the sentiment were actually visible in the financial industry broadly. But even if we don’t see it there, we can still put this into practice in our own lives. Scooping ice cream, waiting tables, going door-to-door for a non-profit… I’ve done those things and to this day I remember the people who were authentic and kind. If it was you, thank you! Continue reading What’s the name of the lady who cleans this building?

When it comes to the actual skillset of being a friend, who of your friends is the best?

 

My friend JB could be a professional friend. Truly. He’s in the major leagues of friendship. He calls every couple of weeks just to catch up. Odds are he’s the one to initiate the email thread to get people together for a reunion. He remember birthdays. He recommends books. If he sees an article or video online that aligns with your interests, he’ll forward it to you or tag you in a post. He comes to visit you where you are — uses vacation days for it and everything. He just prioritizes you as a friend, even with everything else going on in life and the world. And he’s joyful to see you. It’s deeply inspiring. I try to emulate him. It’s my theory that the JB’s of the world are the “friendship glue” that hold larger networks of friends together. Without them, the individuals in any given friend crew would not be as close with all the others. Agree or disagree? Is this a gender thing? Do you know someone who serves this role? Continue reading When it comes to the actual skillset of being a friend, who of your friends is the best?

If you could go to a fancy “tasting” of any kind of food or drink, what kind of tasting would it be?

 

Alright. So personally, I’m not that into wine or beer so those kinds of tastings don’t really appeal to me. I’ve never liked cheese and I’m pretty lactose intolerant so cheese tastings are not my thing either. Coffee is nice but I’m not discerning enough of a coffee drinker to get much out of sampling lots of variations of that… But if ANYONE ANYWHERE put together a “tasting” of gummy candies, I would be all over that mess!! All over it. It would be like, “And these Haribo fizz bears are available only in Germany. You’ll notice how different the consistency is from the Lychee jelly rounds we just tried from Japan.” Oh man, I wish that were a thing!!! What would your “tasting” be? Continue reading If you could go to a fancy “tasting” of any kind of food or drink, what kind of tasting would it be?

What one article of clothing or accessory of mine would you donate away if you could?

 

Chaco sandals. No contest. I would donate away my wife’s Chacos. While they are in good shape, durable, extremely useful, and very practical, something about me growing up in Southern California and loving SoCal beaches makes my face scrunch up when I see Chacos. I can’t help it! I swear. (This says as much about me as it does about Chacos which, by all measures, seem to be very well made.) Meanwhile, I have a SNEAKING suspicion that my wife would want to throw away this No Fear t-shirt I still have from (no joke) 7th grade. It is so full of holes, huge and not as huge, that it barely clings to my torso anymore. Haha! But it’s the softest thing you’ve ever felt in your entire life. And I have this totally crazy “goal” of wearing it around the house and then one day, I go to get up off the coach and the shirt just rips and falls off of my frame and I nod my head approvingly and say “Huh!” and go find a real shirt. Anyway, ask your S.O. this question. It’s a funny one. Continue reading What one article of clothing or accessory of mine would you donate away if you could?

What would you do if you couldn’t do this?

 

If you’ve sought out an informational interview to learn more about a particular field or profession, this question is always a great one to ask. You’ll learn what a person truly loves about her work (the relationships, or the challenge, or the creative aspects…) and where else those things can be found outside of a single field. (As a total aside, a friend of mine is a medical dosimetrist. I had no idea that was even a profession until recently! It’s pretty cool. Google it.) Continue reading What would you do if you couldn’t do this?

What’s your favorite flavor of shit sandwich?

 

I can’t explain this question better than Mark Manson who wrote it in his great blog post titled “7 Strange Questions That Help You Find Your Life Purpose.” So I won’t even try. Here’s Mark:

“What unpleasant experiences are you able to handle? Are you able to stay up all night coding? Are you able to put off starting a family for 10 years? Are you able to have people laugh you off the stage over and over again until you get it right? What shit sandwich do you want to eat? Because we all get served one eventually. Might as well pick one with an olive.”

The whole blog post is worth reading. I’d encourage you to check it out. So how about it? What flavor for you, then? Continue reading What’s your favorite flavor of shit sandwich?

Of all your close friends, who made the worst first impression on you?

 

This is an awesome question because all the answers involve funny stories. And every single one of those stories is like a feel-good movie with one of the main characters making a 180-degree change for the better. You know the ending will be happy because, well, you know the 2 people ended up being close friends at the end of the day. Continue reading Of all your close friends, who made the worst first impression on you?

When’s a time that I said “thank you” to you that really sticks out in your mind?

 

And why was that a memorable moment? Thank you’s are to people what water is to a plant. No joke. It pays off to get good at saying thank you — noticing when to get one ready, actually remembering to do it, understanding when your significant other is running low on them. We all just want to be appreciated genuinely. This question helps you sharpen your “thank you skills.” Into skillz. With a z. You want that mad thank-you game. Trust. Continue reading When’s a time that I said “thank you” to you that really sticks out in your mind?

When it comes to this issue, can you tell me what is at stake for you?

 

If you find yourself in a disagreement and the words passing between you and the other person sound like they could be on a daytime “news” show, then you’re not actually talking to each other; you’re just waving picket signs in each others faces. The conversation becomes much more real when you are talking about one of four things: 1) personal hopes, 2) personal fears, 3) specific people you know and care about, or 4) what it means TO YOU to be ___________ (American, Christian, pro-choice, a gun owner, etc…). This question will nudge you closer to all 4 of these avenues. Continue reading When it comes to this issue, can you tell me what is at stake for you?

In the past 5 years, what has become more important to you? And what has become less?

 

I value balance in life. And I seek it out when I’m praying, or exercising, or breathing deeply. But I also try to remember something I read about imbalance (I think in David Whyte’s excellent book called The Three Marriages). We often forget that we need imbalance as well. Walking, after all, is a controlled form of imbalance. Swinging one leg out in front of the other is not as stable as standing with your feet firmly planted. But without that motion, we go nowhere. It’s with this in mind that I’m drawn to the question. How have priorities shifted in the last 5 years? Does the shift feel right to you? Do you imagine it will shift back? Continue reading In the past 5 years, what has become more important to you? And what has become less?

Who is the youngest person that’s taught you something you’ve never forgotten?

 

In college I studied abroad for a semester in France. I was waiting for a bus in Toulouse, where I lived, and there was a very little boy – maybe 3 years old – who was also waiting at the stop with his mom. This little boy was completely in his own world, jumping up and spinning in the air and almost doing a full 360. He’d look at one foot while he spun. Then he’d look at the other. Then he’d spin again while looking at one hand held out in front of himself. It was joyful. He wasn’t laughing or even smiling; it was a serious thing he was doing apparently. But it was joyful. At his age, he was still learning and marveling at the sacred machinery of his own limbs. And I just thought to myself, “Dang, little boy. You’re right. It’s a beautiful thing to have our bodies.” Where have you found wisdom in a young soul? Continue reading Who is the youngest person that’s taught you something you’ve never forgotten?

What makes you feel rich?

 

There are multi-millionaires who feel like they can barely scrape by in life. They’re stressed and anxious about money. If you asked them if they’re rich, they would say absolutely not. This fact is important to remember.

I am definitely not a millionaire but I’ve gotta tell you this: My wife and I were driving home from Trader Joe’s the other weekend and we’d spent exactly $51.92. In the car with us we had red lentils, ricotta cheese, light champagne salad dressing, whole garlic, pizza dough (2 of them), pork potstickers, handmade tortillas, fresh Serrano salsa, pie crusts, lemons, extra large red bell peppers, a bottle of red wine… the list goes on. And man, I just felt – like aking. I did. I felt rich. And since then, I’ve noticed that bringing awesome ingredients home to cook up at our house does it for me every time. You’re not rich unless you feel rich. What does it for you? Continue reading What makes you feel rich?

Why? Why? Why? Why? Why?

 

In the Lean Startup, Eric Ries shares about a tactic that startups can use to solve internal problems and build an adaptive company. It’s called the Five Whys. Here’s Eric:

“The system takes its name from the investigative method of asking the question “Why?” five times to understand what has happened (the root cause). If you’ve ever had to answer a precocious child who wants to know “Why is the sky blue?” and keeps asking “Why?” after each answer, you’re familiar with it. This technique was developed as a systemic problem-solving tool by Taiichi Ohno, the father of the Toyota Production System. I have adapted it for use in the Lean Startup model with a few changes designed specifically for startups. At the root of every seemingly technical problem is a human problem. Five Whys provides an opportunity to discover what that human problem might be.”

Eric Ries goes on to examine Five Whys as it’s used to diagnose an app update glitch all the way down to its root cause: a deficiency in training new engineers due to an issue with one manager in particular. You can learn all about Five Whys in Chapter 11 of The Lean Startup. Continue reading Why? Why? Why? Why? Why?

What, if anything, is too serious to be joked about?

 

I’m a fairly strong proponent of not taking yourself too seriously. I think we all need to be able to laugh at ourselves and the imperfections in our institutions. (I think this kind of laughing is closely related to humility.) But some things should be sacred, right? Off limits? I have to be honest, I struggled to answer this question for myself. After a good long think, I could say I’ve never poked fun at either of my grandmothers. And I doubt that I’d tolerate someone else (my own parents, aunts, and uncles excepted) having a laugh at my grandmothers’ expense. They are the matriarchs of both sides of my family. Institutions. (I never really knew either of my grandfathers. Both had passed by the time I was 5 years old.) My mom’s mom turned 90 this past year. My dad’s mom is well into her 80’s. They are sacred women to me. Certainly. Ask your friends this question. In the age of South Park and SNL it’s interesting to know what is sacred in your social circles. Continue reading What, if anything, is too serious to be joked about?

What gave you the information you needed to move confidently from A to B?

 

This phrasing might not be right for your particular situation. But let me explain the essence of this question with an example: A good friend of mine made a career switch from software engineering to high school teaching. He now cannot imagine doing anything else. I asked where he got the information that convinced him he should make the switch. He said that coaching high school football with his alma mater proved to him that he would enjoy the high school environment and find fulfillment in working with young people. After a season of volunteer coaching, he was able to leave his software job with confidence and start his new career in public education.

If you’re meeting with someone for an informational interview, chances are she works in a career field that you are interested in exploring, or she’s earned a degree that you’re eyeing, or she’s moved from one kind of job to another and you want to learn how she managed it. For all of these things, it’s important to know HOW someone started with an idea, said “Yes this is a good idea for me,” and moved on to action. Was it an intermediate experience (like volunteer coaching before full-time classroom teaching)? Was it observing? Was it talking with a certain person? Was it attending a Meetup event? It’s important to ask because these are the experiences you want to create for yourself. Continue reading What gave you the information you needed to move confidently from A to B?

What is the most interesting sound I can “find” on a short walk?

 

These days we tend to be so visual and so cerebral. How we experience the world is dominated by what we see and what we’re thinking about at any given time. If you find yourself with a bad case of writer’s block or painter’s block or problem-solver’s block, switching to your other senses for a while can be a powerful way to open yourself back up to creativity. Go for a 30 minute walk with the mission of “finding” the most interesting sound you can. Is it powerlines crackling at the end of a cul-de-sac? Is it cars passing through a short tunnel? Is it a crazy warbly bird call? Try it. I promise you that walking around this way makes the whole world feel different. And when the whole world is different, the thing that had you stuck will probably look different too. (You can do the exact same thing trying to “find” the most interesting smell or texture. Most interesting taste? Ehh, not for the faint of heart or weak of stomach, but who knows!) Continue reading What is the most interesting sound I can “find” on a short walk?

What is the most complicated thing you could explain to me and get me to understand?

 

This one is particularly good if you’re hiring for a communications role, a client success role, or a programming/developer role. It’s a challenging question so you get to see how the candidate thinks under a bit of pressure. You also get to see how adept she is at thinking through complexity and communicating effectively. Finally, the way the question is structured also allows you to learn something about the candidates judgement. You’re not asking her to tell you about the most complicated thing she’s ever come across in her life, you’re asking her to choose the most complicated thing that she could get you to understand. Does she choose something impressive but ambitious when it comes to teaching you about it? Or does she go with something simpler that she’s sure she can get you to wrap your head around? Continue reading What is the most complicated thing you could explain to me and get me to understand?

What have you always wanted to ask someone who believes what I believe?

 

As far as bridge-building goes, this question is a 10/10. But when you ask it, you better bring your A-game. You’ve got to be patient, non-judgmental, and not defensive. You have to give first by granting full benefit of the doubt that the person you’re talking to is acting in good faith. But if you can manage it, and if you can hold open the space for meaningful exchange, this question does so much to humanize one person to another. Continue reading What have you always wanted to ask someone who believes what I believe?

You say you care about the poor… Then tell me, what are their names?

 

And then he dropped the mic. This question is directly from Father Gustavo Gutierrez. He’s one of the founders of liberation theology – a social justice movement and philosophy that started in the Catholic church. I love this question because it reminds me that for any issue it’s essential to bring everything back to ACTUAL relationships with REAL people. Without barbecues and phone calls, birthday greetings and actually knowing people’s names, how can I say that I care about the poor? What I also love about this question, “What are their names?” is that it applies so broadly. How can I say that I care about the political process and healthy democracy if I can’t remember the last time I had a meal and a laugh with someone not in my party of choice? Or how can I say that I care about peace in the world if I’ve never had a conversation longer than a few sentences with someone of a different faith? Tell me, what are their names? This is crucial. Continue reading You say you care about the poor… Then tell me, what are their names?

What mistake in your life are you most grateful for?

 

I love the 180 that happens within this very short question. Asking it shows you something about your friend’s perspective, resilience, and sense of gratitude. I’ve put this question in the “Ask your friend” category but you could ask it of literally anyone and get an interesting response.

As an aside, this question reminds me of 2 things. That 17th century haiku that goes:

Barn’s burnt down —
now
I can see the moon.

And also one of my favorite TED talks of all time about humanity’s “psychological immune system” and what actually makes people happy. Continue reading What mistake in your life are you most grateful for?