What have you failed at recently?

 

Helping your kids have a healthy perspective on failure is a TREMENDOUS service to their lives at work, with others, and within themselves. In a video interview with Business Insider, Sara Blakely – the CEO of Spanx, shares how her dad at the dinner table would ask her every week how she’d failed at something. The terrible auditions and other “failures” were celebrated and high-fived. If Sara had failed at nothing that week, her dad was actually disappointed. As a result, for Sara the real failure became not trying new things. The other “failures” were recast as wins on the way to valuable lessons. Start redefining failure early for your kids and the resilience that grows will pay off for a lifetime. Continue reading What have you failed at recently?

If we got kicked out and the board brought in a new CEO, what do you think he would he do?

 

In their phenomenal book, “Decisive: How To Make Better Choices In Life And Work,” Chip and Dan Heath argue that emotional attachments very often get in the way of making the right decisions. We’re too close to the issue at hand and too emotionally invested to counsel ourselves correctly. To artificially create some necessary distance, the leadership at Intel once asked themselves what a new CEO would do if he were brought on board. They asked this at a time when Intel’s legacy business (memory) was waning but still lucrative and its upstart business (in computer processors) was starting to boom. Intel leadership instantly recognized that a fresh CEO with no emotional attachments to Intel’s legacy market would see computer processors as the no-brainer new market to double down on. “What would my replacement CEO do?” is the business equivalent of “What would you tell a friend to do if he was in your situation?” It gifts us with the distance we need to see the best way forward. Continue reading If we got kicked out and the board brought in a new CEO, what do you think he would he do?

If an alien scientist were observing you in daily life, what would it conclude was your day’s most important ritual?

 

Let’s be honest. I would love to say that morning yoga or a calm tea break during the day or something instagram-able like that was my vital daily ritual. But I rarely do any of that. An outside alien observer would totally guess that the 20-minute window that begins with me taking a shower and ends with me going to bed is the most crucial daily ritual I have. It goes like this: shower, brush teeth, squeegee the shower walls, get into bed, set phone alarm, pray, fall asleep. I literally can’t remember the last time I was at home and didn’t do this. The aliens might theorize that any other order would cause me bodily harm. All my yoga aspirations aside, THIS, really, is my most protected ritual. So the question becomes, how can I make this time more intentional, more appreciated, more rejuvenating? Continue reading If an alien scientist were observing you in daily life, what would it conclude was your day’s most important ritual?

Is this “sponsored content?”

 

If you’re anything like me, you tend to avoid clicking on the “sponsored content.” In a Google search, the sponsored results are the ones that appear at the top of the page. They look almost like normal search results but they’re really advertisements related to what you searched for. Ads. From companies. In a news or media site, sponsored content are articles/videos that look normal but are also paid for by the companies selling the product featured in the article/video.

Cnet_sponsored_content
[One of these things is not like the others!]

Sponsored content is mostly annoying and not useful. But at least it’s labeled “sponsored” which makes weeding it out for the ad that it is much easier.

If only all marketing messages in life (digital and otherwise) had to be labeled “sponsored”! That would be so fantastic. But it’s sadly not the case. Instead, we have to navigate all arenas of modern life and ask, “How is this sponsored content?” But the more you do it, the more informed a consumer you will become. This is especially useful when applied to things that are pitched as “common knowledge” in your circles.

For example, when an article about weddings insinuates that EVERYONE starts planning their weddings 18 months out, is that really because it CANNOT be done in 12 or 6 or 3 months or was that sponsored content? Is that article trying to help YOU out or trying to help out the wedding industry which knows that people who start planning 18 months from the big day are drastically more likely to outspend their 6-month counterparts?

Or how about this: when your Facebook feed is lined with PSAT prep course sales, is that because organizations want your high school freshman to succeed or is it because the SAT is owned by College Board whose annual revenue tops out just south of a billion dollars?

Ask, ask, ask. “Is this sponsored content?” Continue reading Is this “sponsored content?”

Am I needlessly making this a “whether or not” question?

 

Here’s another one from Chip and Dan Heath’s genius book, “Decisive: How to make better choices in life and work.” The book lays out the 4 biggest stumbling blocks when it comes to making good decisions. The very first one is “Narrow framing (unduly limiting the options we consider).” According to the brothers Heath, any time you catch yourself pondering a “Should I ________ or not?” question or a “I’m deciding whether or not to _________,” statement, a loud warning alarm should go off in your head and you should realize 3 things: 1) You’re not even considering two options – you’re just giving an up or down vote to ONE option; 2) Other alternatives are out there (“Should I quit my job or not?” hides alternatives that become visible when you widen your scope (“Should I quit my job outright to become a sculptor or should I try to negotiate for part-time hours first and free up more time for sculpting?”); 3) The research overwhelmingly shows that considering more than one option leads to better decisions. The trick is realizing you’re stuck in a narrow frame. Continue reading Am I needlessly making this a “whether or not” question?

If you could hold on to one memory from your life forever, what would that be?

 

My wife and I got married not quite 2 years ago. As is customary, we took a moment during the reception to thank and acknowledge our families and all our amazing guests. Weddings, as occasions, are special because people HAVE TO TRY THEIR DAMNEDEST to show up. There’s no other life event with that power. Graduation? Nope. Birth of a child? Nope. Retirement? Nope. Only weddings. So there was this moment as Emily and I spoke that I looked over the room at all these faces, BELOVED faces, that had never been in the same place before that night and would never all be in the same place ever again (my grandmother who’d made the trip from Manila sitting a few tables to the right of my college roommate and a few tables to the left of Emily’s childhood best friends and swimming teammates). I just thought, “Wow. I hope this is what heaven is like.” If I lose all my memories but one, standing with Emily in that room of those people would be the keeper. Continue reading If you could hold on to one memory from your life forever, what would that be?

How did you choose what to draw/make?

 

It’s all about the process. Helping a child to understand her own creative process and feel comfortable making creative decisions is one of the MOST important skills you can teach her. This will pay off not only in grade school, but in the new age of work that we are rapidly entering. Seth Godin nailed it in a blog post from a few years back.

“What to do next. This is the most important decision in your career (or even your day). It didn’t used to be. What next used to be a question answered by your boss or your clients. With so many opportunities and so many constraints, successfully picking what to do next is your moment of highest leverage. It deserves more time and attention than most people give it. If you’re not willing to face the abyss of choice, you will almost certainly not spend enough time dancing with opportunity.” -Seth Continue reading How did you choose what to draw/make?

If you were just entering your profession now, what would you do differently?

 

Hindsight is 20/20. But perhaps one of the most beautiful things about that fact is that it doesn’t even have to be your own hindsight. Asking this question in an informational interview will give you the words of wisdom from someone’s hard-earned experience as well as the predictions they might have for where the field or industry is headed. It’s also a better question than some of the alternatives because you’ll leave with actionable insights. By contrast, if you ask someone: “Would you do it all again today? Would you make the same decision to go into this profession?”, they’re probably just going to say “Yup!” Because who wants to admit to an acquaintance that they regret one of the bigger life decisions they’ve made? Continue reading If you were just entering your profession now, what would you do differently?

Do you remember any songs that you used to sing to my dad/mom? Can you sing them now?

 

I’m automatically a fan of any question that gets a grandparent singing! And this question in particular has some magic in it. Any answer will give you some texture and insight into two people you can’t ever really know: 1) your own parent as a toddler and 2) your grandparent as a new mom/dad. Continue reading Do you remember any songs that you used to sing to my dad/mom? Can you sing them now?

How did you choose my name?

 

My whole first name is “Rafael Carlo.” Embarrassingly, I didn’t actually know this until I was 5 years old. I’d always just gone by “Carlo” and I still do today. It turns out my parents picked “Rafael” because it was a family name in the Philippines where both of them grew up. Part of my dad’s name is “Rafael” and my great uncle’s name was the same. But when my mom found out that Americans might pronounce the name instead of the more Spanish sounding , she made sure to hedge with a second name that could only be pronounced one way. And I became “Carlo.” I like this question because it can bring out a lot about culture, about family, and about what your parents hoped for you when you were just starting out in the world. Continue reading How did you choose my name?

Where was your maternal grandmother born?

 

No matter how long you’ve worked with a team, this question has a way of bringing to the surface something new about your colleagues. I’ve seen this work wonderfully across all kinds of settings, meetings, and organizations. It doesn’t take long to go around the table and answer but all of a sudden the energy in the room will change and you’ll hear things like, “No way – I lived in Akron for 2 years growing up!” or “I didn’t know you had family in Germany.” Plus, people love grandmas! You can hardly start a meeting on a more positive note! Continue reading Where was your maternal grandmother born?

If you knew for a FACT that miracles were real and that one had already happened in your own life, what would you guess it to be?

 

Maybe you already believe in miracles. Maybe you do not. But just play along here for a minute because the framing for this question is essential. Pretend you know it’s ALREADY happened in your life. For a brief moment, the impossible became possible for your benefit. When would you guess that was? What moment? What outcome? This is a beautiful question to ask your friends and family members. You inevitably learn about the moments in people’s lives that are filled simultaneously with mystery, gratitude, and awe. Continue reading If you knew for a FACT that miracles were real and that one had already happened in your own life, what would you guess it to be?

What’s the most recent new thing you’ve learned (skill, process, piece of information…)?

 

I love lifelong learners and try to surround myself with them. The subject doesn’t matter in the least; it’s the consistent habit of learning new things that counts. Did you just learn how to sew a button? Did you just pick up some techniques for better public speaking? Did you just read about the history of National Parks? It’s all good! ALL of it! I have a printout of the beautiful Merlin quote from T.H. White’s “The Once And Future King”.

“The best thing for being sad […] is to learn something. That’s the only thing that never fails. You may grow old and trembling in your anatomies, you may lie awake at night listening to the disorder of your veins, you may miss your only love, you may see the world about you devastated by evil lunatics, or know your honour trampled in the sewers of baser minds. There is only one thing for it then — to learn. Learn why the world wags and what wags it. That is the only thing which the mind can never exhaust, never alienate, never be tortured by, never fear or distrust, and never dream of regretting.”

This is a great question to ask of literally anyone. Your friends, yourself, a potential new hire, your grandparent… This one is no-fail! Continue reading What’s the most recent new thing you’ve learned (skill, process, piece of information…)?

What was the most challenging part of creating what you’ve made here?

 

Or as you were creating, what didn’t work out exactly like you thought it would? These questions make it clear to kids that you are already ASSUMING that in the creative process there will be road blocks and dead ends. Normalizing this and getting kids to talk about it will mean that in the long term they will be more creative and more creatively resilient. The alternative is ending up like the guy in this Onion article titled, “Lifelong Dream No Match For First Brush With Adversity.” Haha! Continue reading What was the most challenging part of creating what you’ve made here?

What would you say has been the biggest change to your job or field since you started?

 

This question will give you a sense of how a field has changed over the years and where it’s headed in the future. And just as with the question about surprises in a profession, it’s particularly useful if you get two responses to this question as well: one response related to a positive change and one related to a negative change. Practicing medicine today is not what it was 25 years ago. Writing a blog today is not what it was 10 years ago. Mining bitcoin today is not what it was two days ago on July 9, 2016. These fields are moving targets. The ones you are exploring probably are too. Continue reading What would you say has been the biggest change to your job or field since you started?

Who has been the kindest to you in your life?

 

If a thing travels far and efficiently through the air then it’s called “aerodynamic.” If it travels far and efficiently through water then it’s called “hydrodynamic.” Is there a word for something that travels far and efficiently through time? Would that be “temperodynamic”? Because if that’s the word for it then kindness is that. An act of kindness now just carries forward through the days and years ahead. People don’t forget it. It stays with them, moving right alongside them and influencing moments big and small. It’s like Maya Angelou said: “I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” So who has been the kindest to you in your life? And how has that kindness influenced your life? Continue reading Who has been the kindest to you in your life?

When in life have you felt most alone?

 

This question might at first seem like you’re trying to diagnose a problem with your significant other. But I don’t think that feeling alone means something is wrong. You can feel alone when surrounded by people and you can feel alone when you’re in a healthy, loving relationship. For me, in fact, very often creativity grows out of first feeling alone. I find that it’s a fertile place even if it’s not always the most comfortable. Ask your partner this question out of a spirit of curiosity (not “fixing”) and you may learn something new. Continue reading When in life have you felt most alone?

What about being an adult are you most looking forward to? Least looking forward to?

 

Conversing with grade-school kids as if they’re adults (whenever possible) just seems like a good idea to me. I don’t mean talking with a 10-year-old about escrow. I mean engaging with that 10-year-old in a way that makes it clear that you’re interested in his perspective on the world and care about how he experiences things. This question is a great way to get into a meaningful and potentially enlightening conversation (for both parties). Continue reading What about being an adult are you most looking forward to? Least looking forward to?

What do you say that sounds just like mom or dad?

 

This is a great question to ask your sibling(s). You’ll get to laugh about which of your parents’ characteristics you’ve absorbed (intentionally or unintentionally). Are you constantly telling people to turn off the lights when they leave a room, just like dad? Are you regularly advising people to “do what you love and the rest will follow,” just like mom? And if you’re not sure what you say that sounds like your parent, your bro/sis will probably be able to help you learn something about yourself. Continue reading What do you say that sounds just like mom or dad?

If you had to introduce the soul of your hometown to someone in just three places, where would you take them?

 

I’m a firm believer in the idea that getting to know a person’s hometown helps you understand them on a deeper level. After all, to a large extent, we are the product of our environments. If I had to introduce you to the soul of El Segundo, CA, my hometown, I would take you to: 1) the public high school in the heart of town. It’s got a very old-school 1950’s “Americana” look and for that reason (and proximity to Hollywood) has appeared in lots of movies and TV shows over the decades. That makes the school an interesting mix of old and new. Next, I’d take you to 2) the five blocks of Main St. that constitute our “downtown”, – mostly mom and pop shops, restaurants, and the empty building where they recently closed our branch post office. And finally, I’d take you to 3) the beach. There’s no understanding El Segundo (or me) without understanding the beach. Continue reading If you had to introduce the soul of your hometown to someone in just three places, where would you take them?