No joke, this question will change your life if you learn how to ask it regularly and act on it. Any time you feel the urge to procrastinate, ask this question. The answer will be: “Well I can start a word doc and give it a title,” or “I can look up gyms on Google maps,” or “I can go find a piece of paper and make a list of 2 things.” The goal is to find the SMALLEST thing and to do just that thing. No more. Do it again the next day. Things will change. Continue reading What is literally THE SMALLEST possible thing I can do that will move this project/task/goal forward?
Who will our customers become after they interact with us?
Business thinker, marketing guru, and super blogger Seth Godin asks this question in his book, The Icarus Deception. Seth is constantly reminding us that connection matters, that if we market something it does no good to think only of the sale; we need to think about the impact we have on the flesh and blood people that make up our “market.” Selling a product changes everyone involved. What kind of change do you want? Continue reading Who will our customers become after they interact with us?
How has this position evolved since it was created?
The answer here will tell you a lot about how this company or organization grows and responds to changing circumstances. Has the job remained unchanged for the last 10 years? Or is it evolving in a direction you like? Does the interviewer seem ready to answer this question? Continue reading How has this position evolved since it was created?
What would you change about your current job? (or what would you have changed about your last job)
You’re checking for a few things here. Was/is this person irked by things that will be present in the new job? Does the candidate have a good grasp of what he really needs in a workplace to be happy? Is he a culture fit? And how does he talk about previous teammates? Maliciously or with a spirit of generosity? Continue reading What would you change about your current job? (or what would you have changed about your last job)
Which of your possessions have you owned the longest? (It could have been purchased or given to you.)
It’s always buy-buy-buy! Ads are constantly trying to make us feel bad about the things we haven’t upgraded in *gasp* 2 years. But how about the possessions that stand the test of time or have been handed down the family tree? We should celebrate these more often. We should brag about them more often. Continue reading Which of your possessions have you owned the longest? (It could have been purchased or given to you.)
What does the absolute worst case scenario look like? What does it look like EXACTLY? How would I recover?
This is sometimes called “Going to Zero” and it can be a powerful unsticking agent if you find yourself afraid to make a move. Ask this question and then paint an EXCEEDINGLY detailed picture of the “doomsday” scenario. “I try to start this business but I fail. I lose the money I’ve invested in it, my family mocks me, my kids have no college savings…” Write it all down. And then go back and ask yourself, really and truly if this happened, would I survive it? How would I recover? You’ll find that in most cases you are more resilient than you imagine. Spend an hour on this exercise and it can unleash the next year or more of productive, brave work. Continue reading What does the absolute worst case scenario look like? What does it look like EXACTLY? How would I recover?
When you think of your mom, what do you think of first? What is/was important to her?
Beautiful question. Like it or not, your parents strongly dictate who you are. Either we become them slowly or we consciously push against qualities in them we dislike. This question will tell you about your grandparent, your parent, and yourself all at the same time. Continue reading When you think of your mom, what do you think of first? What is/was important to her?
What’s the biggest difference for you between this year and last year?
This question is solid because it implies that you understand how weird and tumultuous the teenage years can be. You’re not telling your kid to be different in any way. You’re just asking how the landscape is different (and how she’s different). Continue reading What’s the biggest difference for you between this year and last year?
What games did you play at recess today?
Simple enough. Not loaded. Just “What did you play?” This should definitely get your little one talking. You’ll also find out who your kid plays with. Continue reading What games did you play at recess today?
What do you need most from me right now?
The difficulty level on asking this question is close to maximum. The answer you get from your significant other will usually be along the lines of: “I need you to really listen to what I’m saying,” or “I need you not to doubt me right now,” or “I need you to admit that you’re wrong sometimes.” Not easy stuff to hear. But if you can ask this question and act selflessly on the response, it’s a relationship saver. 100%. Continue reading What do you need most from me right now?
What’s one thing I could do differently?
Be coachable. Ask this question. It will give your boss an opportunity to tell you point blank about how to improve (particularly helpful if your boss is not good at giving you direction or constructive criticism). Take the response seriously and it will probably improve your everyday work life as well as what you hear during your next performance review. Continue reading What’s one thing I could do differently?
What book have you gifted the most to other people?
Not only does this question tell you what your friend reads, it tells you what she thinks is worth sharing with the people she’s close to. This question could also add a title to your “to-read” list. Bonus! Continue reading What book have you gifted the most to other people?
What’s something you’re really into right now?
If the person you ask wants to make this question about work, he can respond accordingly. If he wants to make it about passion projects, creative hobbies, family, books, or whatever, then he can do that too. Let’s get out of the “work” box! Continue reading What’s something you’re really into right now?
What was the nicest thing you remember me doing for you when we were growing up?
Even if you weren’t always the best brother/sister ever, your sibling will remember some act of kindness you showed in those formative early years. You might be surprised what they remember. And just in general, we don’t have enough opportunities to thank each other about what matters. This question is perfect for helping us show gratitude. Continue reading What was the nicest thing you remember me doing for you when we were growing up?
What was your room like, growing up? Can you describe it? And did you share it with other family members?
Sometimes knowing the details is what really makes you feel connected with someone. Also, if your grandparent is not “touchy-feely” enough to open up about life regrets or emotional memories, this kind of question is perfect for getting the conversation going. Continue reading What was your room like, growing up? Can you describe it? And did you share it with other family members?
What are you reading at the moment? (Book, magazine, blog, essay, article online…)
TV and movies are great, but the way we come across really substantial and life-changing ideas is primarily still via writing. This can come in all mediums – a book by Tara Brach, the WaitButWhy blog, an article on Medium. So this is a great question to ask someone you’re trying to get to know more deeply. Also, when you start asking this question you’ll want to be able to answer it yourself, which means you’ll start reading more too. Continue reading What are you reading at the moment? (Book, magazine, blog, essay, article online…)
What do you want people to be able to answer after looking at your data?
Sounds simple, but keep this in mind and it will dramatically improve the quality of your presentations, pitches, and team meetings. Don’t just show people the numbers. Make sure your data answers a specific question. Think to yourself: “After my talk, I want Jim to be able to articulate which of our competitors is most effectively capturing qualified search traffic and what they are doing better than us.” Remember that and it will influence how you title your charts, what order you bring up your talking points, etc… Continue reading What do you want people to be able to answer after looking at your data?
We know this thing can be built. But SHOULD it be built?
Eric Ries says it best: “We have the capacity to build almost anything we can imagine. The big question of our time is not Can it be built? but Should it be built? This places us in an unusual historical moment: our future prosperity depends on the quality of our collective imaginations.”
The tech might be there. You might have the team in mind already. There may even be demand in the market. But SHOULD this thing be built? This thing instead of another thing? This social media gadget over, say, an innovation in education that could serve public school students? Continue reading We know this thing can be built. But SHOULD it be built?
What constraints can I put on this?
As creators, often when we’re stuck it’s because there are actually TOO many possibilities out there. There are TOO many directions we can go with a project or piece of work. The blank page is too blank. This is the perfect time to ask yourself what kinds of constraints you could put into place. Maybe you say: For this sketch, I’m not allowed to lift my pen from the paper until it’s done. For this short story, all the action happens in a single room. For this new online business, let’s imagine that it has to succeed without relying at all on Google search results. Constraints can be freeing. Continue reading What constraints can I put on this?
It is 5 years from today. Our company/product has folded. Step by step, how EXACTLY did it happen?
This “post-mortem” exercise is magic. When you and your team start explaining IN DETAIL how your company/product failed, it reveals the holes in your business model, your market, your funding strategy. The conversations cut right to the chase. Take up to 2 hours with this question. And then when you’re done, it’s still today, not 5 years from now. Plenty of time to get out in front of your known weaknesses. Continue reading It is 5 years from today. Our company/product has folded. Step by step, how EXACTLY did it happen?