This question combines two of the things I contemplate most often: work and peak experiences. Work isn’t just what you do to pay your bills; it’s what you do with the best years of your life. It’s where you are spending your life’s best energy, best years of health, and most creative days. Your work should really matter (at least to you). And as far as peak experiences go, I’m very interested in the moments that people feel most “in the zone.” It’s my theory that maximizing the number of peak experiences in any given community is a pretty great way to improve quality of life for everyone. Mashing these two things together yields this question: When was the last time you left work feeling on top of the world? I like this question as one you can ask your employees or team. But it’s also a great question to ask your friends. Asking it can lead people to more peak experiences at their current jobs or it can lead them to different work entirely. Continue reading When was the last time you left work feeling on top of the world? →

This is indeed a phenomenal question to ask in a work setting, but it’s also a great question to ask in ANY setting when you and someone else are trying to decide what to do. Here’s further explanation from “Decisive” where this question comes from:

“Roger Martin says the ‘What would have to be true?’ question has become the most important ingredient of his strategy work… Martin said, ‘If you think an idea is the wrong way to approach a problem and someone asks you if you think it’s the right way, you’ll reply ‘no’ and defend that answer against all comers. But if someone asks you to figure out what would have to be true for that approach to work, your frame of thinking changes… This subtle shift gives people a way to back away from their beliefs and allow exploration by which they give themselves the opportunity to learn something new.”

If your business partner is strongly opposed to a potential merger, ask her: “What would have to be true for the merger to be the right decision?”

If your son wants to quit the soccer team, ask him: “What would have to be true for staying on the team to be the right decision?”

This question puts everyone on the same team. It’s a thought exercise. It’s productive and creates forward motion. “I’m not saying that this IS the answer, but what conditions would you need to see in order for it to be the right answer hypothetically?” Works like magic. Continue reading What would have to be true for this option to be the right answer? →

Your doctor has told you that if you work a minute more than one hour each day, your heart will explode. This is how Tim Ferriss sets up the question. So what would you do? This is a thought exercise…but also not. I tried this for two days over the summer. How did I spend my one hour of work? 15 minutes high level email. 5 minutes nit-picky email. 30 minutes working on new resources for my language learning business. 10 minutes updating my Workflowy to-do lists and planning out what should happen the next day. (The last 10 minutes was the real revelation for me. I’ve only got 60 minutes before my heart explodes and 10 of them go to planning and to-do’s? What the hell? Turns out having a well-defined to-do list for the next day is CRUCIAL for me.) What does your 1 hour look like? What does that tell you about your (and your colleagues’) “normal” 8+ hour workday? Continue reading If you could only work for one hour each day, what would you do? →

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? →

This question needs a bit more setup. It’s just the tip of a very useful iceberg. For the whole scoop, you’ll just have to read “The Art of Possibility.” But the gist is this: When trying to reach someone (a colleague, a family member, a neighbor) who seems disengaged or disaffected, “the secret is not to speak to a person’s cynicism, but to speak to her passion.” Author Benjamin Zander is an orchestra conductor. And in this part of the book he’s taking about transforming interactions by “Giving people A’s,” meaning that everything changes if you assume the best about people’s motivations – you default to giving A’s instead of F’s. Benjamin explains this through a story about one of his underperforming musicians, Tanya:

“When I initially approached Tanya – not to reprimand a recalcitrant member of the team for not pulling her weight, but rather with the attitude, the certain knowledge, that she loved the music, that she wanted the concert to be a success, that she wanted to “get into the string” with her bow – I gave her an A. My question to her, “Is there anything amiss?” was a question to someone I imagined to be completely committed to the project we were engaged in together, someone who, for whatever reason, was having a hard time.”

Ask this question (or any question, really) after you’ve given an A, and see how the interaction unfolds differently. Continue reading Is there something amiss? →

Making your success very, very clear and real in your mind makes you that much more likely to achieve it. You have a better sense of what intermediary steps will be necessary, you will anticipate road blocks sooner, and you will possess a stronger sense of purpose. That’s why this is a great one to ask family members, teammates at work, friends… Continue reading If you succeed, what does that look like for you? Exactly what does it look like? And how does it feel? What do you hear? Taste? Have? →

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? →

It’s a bit of a nebulous question but let your team or employees run with it and you’re likely to hear two vital things: 1) Their most creative ideas and 2) The ways that your company culture is affecting risk-taking (even GOOD forms of risk-taking). Continue reading What is the least safe thing you’d want to do in your role? →