What are you working on? How far along are you? How’s it going? What are the big mysteries? How did you spend your time today? Was it spent in pursuit of the answer to the aforementioned mysteries? If not, why not? What about yesterday?
If you could have an undisturbed lunch with any person currently living, who could be most helpful? If that person was to join your advisory board, would it change your answer? Who can we introduce you to?
What are you going to do next? Is it time to spend money? How big is your team? Would you bet 5 years of your life on it? How big does your team need to be? Could you do without them? How much money have you raised and from where? If a bank, an angel, and a VC were blindfolded in a room with signed blank checks in front of them, what would you take from each?
Have you let your co-founders down? Your investors? Your family or significant other? Are you still gun-shy from the first time you lost someone’s money or fired a friend? Is the vision now the same as the vision you set out in pursuit of? Is the path you are now on taking you toward or away from that vision?
When’s the last time you watched a user user your product? Was their joy in their eyes? Did they interrupt your monologue to ask when they can buy it? Do you see the problem in that question? How much money do you think you’ve lost thanks to monologues?
Do you believe the phrase, “scratch your own itch”? Are you cynical or sold on the value of an MVP? When you hear someone scoff about spending “other people’s money” do you feel worse for the investor or the entrepreneur?
Can you write code? Do you write code in this business? Which values drive your team? What about your business model? Does the team have fun together? When’s the last time you heard honest laughter in the office? What were you doing?
What percentage of your company’s total cash & time would you estimate has been spent checking hacker news and reddit? Will that number go up or down as time goes on? Do you believe one ought to follow the market or one’s passion? Do you become slightly enraged whenever someone uses the word “pivot,” even if it’s in the context of a meaningful question such as “will you pivot or persevere?” Do you know what the word “pivot” actually means, as opposed to what startup pop culture thinks it means?
Open plan or private offices? Does the answer change depending on whether you are running or working at the company? When the company is still struggling, should lunch be free? What is the most important meeting you ever personally dropped the ball on?
Are you being paid too much or too little?
Do you think of your product in terms of features or people? What is your preferred todo list? Does your office have a kanban board? Is it up to date? If I were to honestly report my weaknesses, failures, and shortcomings as a founder, would that make you more or less likely to work with me in the future? Do ping pong tables belong in offices?
San Francisco or Palo Alto? London or Berlin? Barcelona or Boston? Did you know Atlanta has a booming biotech startup scene? Did you know there are quite a few startups still figuring out creative uses for grain? Is it possible that we don’t get out enough?
When’s the last time you took notes on a business book? Why is that? What is the last novel which taught you about business? Are you one of those folks who gets jittery after too much coffee? Do you quite enjoy a cheeky pint at lunch? Isn’t it sad that before too long, you’ll never again be able to make photocopies on a hulking machine the size of a small fridge? Do you miss fax machines, or is it good riddance? Does your business own a stapler?
What are your KPIs? How long did it take you to decide on them? If you were somewhere pleasant (Mallorca, for example), would you know from the KPIs alone whether it was time to cut your vacation short and get on a plane back to the office?
When’s the last time you split tested copy? Do you build it or buy it? Are realtime analytics just a fad? Are you enjoying yourself? And if not, have you asked yourself whether or not you are okay with that, and for how long? How are you spending this week?