Executives: The Right Questions To Ask Yourself

The sales are off track. CAC is too high. The product is delayed. Positions are unfilled. Operations are a mess.

This is what most startup CEOs call Monday morning. A myriad of problems across the company greets me every morning along with my coffee. When I was first learning how to be a CEO, this shock to the system on Monday really got me down but now not so much because I learned about the right questions to ask myself when facing these difficulties.

Startup CEOs Roll Up Their Sleeves

As a startup CEO vs a large company executive, I don’t have a large team. I don’t have tons of resources at my disposal. I have me and a few great colleagues to solve problems in the most capital-efficient way possible. This situation leads startup CEOs to ask the wrong questions.

What are the wrong questions?

Most founders have a technical background of some sorts (like myself) and when faced with a technical issue my mind immediately gets curious about What experiments can I run to solve this and How can I run these tests. As an engineer, individual contributor, or a hands-on manager this is a fine approach however it is not the job of the CEO. If I’m asking myself these questions, I am clearly not acting like a CEO.

What are the right questions?

Now when I face a technical requirement, I always try to take a deep breath and get curious about Why this problem occurred and Who do I need to fix it. My job as CEO isn’t actually to fix problems but to understand the problem at its core then apply the proper resources to attack that problem.

Quick Summary

Individual contributors should ask What and How

Executives should ask Why and Who