Great leaders ask great questions. Great questions result in great solutions. Let’s dive into some of those questions.
The answers are all out there, we just need to ask the right questions.
— Oscar Wilde
IDEA PHASE
1. Where is my dollar going to work the hardest?
When choosing between investments, ask yourself [that question.]
Naval Ravikant, co-founder of AngelList
2. Is this product a net positive in our world?
When building products ask yourself:
1) Will this product uplift people?
2) Will this product make people more money?
3) Is this product a net positive in our world?
If you answered yes twice, then you are on the right track
Greg Isenberg, advisor of Reddit
3. Am I going to be excited about this in 3 or 5 or 7 years?
I’ve seen friends get excited about an idea, raise money and then the excitement evaporates. And now you’re stuck building a company you’re only moderately interested in. Ask yourself, “Am I going to be excited about this in 3 or 5 or 7 years?”
Irving Fian, founder of Bowery Farming
4. If this works, how big can it be?
Lesson 3: You can diligence yourself out of every deal
It takes a lot for a startup to succeed.
If you just focus on “What can go wrong”, you will say no 100% of the time.
Instead ask yourself, “If this works, how big can it be?”
Flip the framing in your mind.
Romeen Sheeth, president of Metasys Technologies
5. Am I willing to keep my head down, focus on the path, and spend my life walking up the side of a very big hill?
Before you dream about the view from the summit, ask yourself if you’re willing to keep your head down, focus on the path, and spend your life walking up the side of a very big hill.
It takes years of walking to earn a minute at the top.
James Clear, author of Atomic Habits
STARTUP PHASE
6. For the time I will spend working today, how do I have the most impact?
Work is infinite, time is finite.
That’s why I focus on managing my time, not managing my work.
Every day I ask myself: For the time I will spend working today, how do I have the most impact? What’s the one thing that is top of mind?
Dharmesh Shah, co-founder of Hubspot
7. What happens when an error is discovered?
There’s a quick way to determine if your company has embraced the negative definition of failure. Ask yourself what happens when an error is discovered. Do people shut down and turn inward, instead of coming together to untangle the causes of problems that might be avoided going forward? Is the question being asked: Whose fault was this? If so, your culture is one that vilifies failure. Failure is difficult enough without it being compounded by the search for a scapegoat.
Ed Catmull, former co-founder of Pixar
8. What do you need to make your product and service and your go to market strategy happen?
As a founder, it’s important to determine the sequence of baseline questions your startup needs to answer, in order to be successful. The key decision center around the four layers of capital, talent, market, and product. You need to be simultaneously solving for all four of these layers and putting all of these strategic layers together.
Consider questions like what do you need to make your product and service and your go-to market strategy happen? What are the proof points needed to get financing? What’s the team that is needed to make all of this work? What are the things that we’re going to derisk and improve in order to both maintain the confidence of our current investors and gain the confidence of future investors? You need to be simultaneously solving all four of these layers. You’re actually putting all of these strategic layers together in terms of how you’re, how you’re looking at it.
Reid Hoffman, ex-founder of LinkedIn
IN CRISIS
9. If we got kicked out and the board brought in a new CEO, what do you think he would do?
I remember a time in the middle of 1985, after this aimless wandering had been going on for almost a year. I was in my office with Intel’s chairman and CEO, Gordon Moore, and we were discussing our quandary. Our mood was downbeat. I looked out the window at the Ferris Wheel of the Great America amusement park revolving in the distance, then I turned back to Gordon and asked, “If we got kicked out and the board brought in a new CEO, what do you think he would do?” Gordon answered without hesitation, “He would get us out of memories.” I stared at him, numb, then said, “Why don’t you and I walk out the door, come back in and do it ourselves?”
Andy Grove, former CEO of Intel
10. If our company isn’t good enough to win, then do we need to exist at all?
There comes a time in every company’s life where it must fight for its life. If you find yourself running when you should be fighting, you need to ask yourself, “If our company isn’t good enough to win, then do we need to exist at all?”
Ben Horowitz, co-founder of a16z
11. If I wasn’t ALREADY doing this. Would I do this?
If your startup feels like you’re pushing a boulder up a hill.
And you try this. try that. It just stays uphill.
You don’t want to quit.. But time is ticking..
Ask yourself this question
if I wasn’t ALREADY doing this. Would I do this?
If this whole project dissapeared tomorrow. And I had total freedom.
Is this the project I would pick to work on?
Are these the first people I would call to work on it with me?
If yes – keep calm and carry on
If no – end it
Shaan Puri, former CEO of Bebo