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?
Here’s another question that’s not for your potential co-founder but about her. What kind of gut feeling do you get when you imagine your potential co-founder meeting 1-on-1 with an investor? An important journalist? Your longtime trusted mentor? You might feel awesome. Or you might have some reservations (this could be the case with a technical co-founder, for example). But either way it’s something you should think about as your founding team and first hires come together. Continue reading Who’s someone you want to impress? Would you let that person do a 1:1 with your co-founder?
A startup cofounder is someone you’re going to spend A TON of time with. Before you go into business together, your significant other should meet the potential cofounder. It’s best if your S.O. also vibes with this person. And your S.O., who knows you very well, might be able to spot signs of future friction that you may be blind to because of your enthusiasm about the startup idea. Continue reading What does your spouse think of this person? (Not a question for your Cofounder, but rather about your Cofounder)
This is a fun question. It gives you a sense of how other people see and evaluate opportunities. Buying a domain is usually pretty cheap – a couple bucks. But you still have to invest a bit of money to buy it. So asking someone this question gives you a glimpse into their “vetted,” more serious business ideas list. Even if it’s still kinda out there, like GlutenFreeBuddhists.com or something (that’s available btw – I checked!), you can learn a lot about the business mind behind the domain. Continue reading Can you tell me about some of the domains you already own but haven’t yet done anything with?
If the answer is “No” that doesn’t mean you should necessarily abandon your business for another one. But it’s just a good question to think about. Where does your energy come from? From the idea of meeting a demand in the market or from the idea of serving and knowing this particular set of people who like what you do? Continue reading If we are wildly successful in building and selling this product, would our customers be the kind of people we would like to hang out with?
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?
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?
If you’re AirBnB in the earliest days, you are assuming that people will be willing to allow strangers into their homes. If you’re Uber you are assuming that ride-sharing will be legal in the future.
If you’re Way Better Questions, you’re assuming that people will care enough to rate and review questions the way they review products online.
Get at your core assumptions. Once you uncover them you are half way to designing a lightweight way to TEST those assumptions. Continue reading What are the assumptions being made in the success case of our product?