Lead Upwards

CHAPTER THREEUnderstanding and Evaluating Your Fit at Various Startups

A common cause of startup executive failure: taking a role that's a bad fit. Here's how to avoid that and find the right fit for you.

CHOOSING A STARTUP THAT'S RIGHT FOR YOU

Startups vary based on stage, size, maturity, location, founding team, company values, and market. If you're a startup leader at a scaling venture, many of these attributes will change over the course of your startup as it grows. When evaluating a new opportunity, decide what's most important to you and ask questions to confirm that the opportunity aligns with what you're looking for, knowing that you may need to re‐evaluate during key moments in your startup's life.

WHY QUESTIONS MATTER

As you ask questions exploring startup fit, the answers say a lot about the type of company you're being interviewing at, and whether or not it will appeal to you. Expect that there will be some underwhelming or even disappointing answers to some of the questions you ask. Remember, every startup has issues. That's why they are hiring you: to help make it better. The point of asking lots of questions is to know the priority issues of the business that you can solve, as well as whether the values and priorities of the business are aligned with your own. Don't be shy about asking financial questions. If you're taking a pay cut for a role, it's fair to want to understand what the equity is worth and what the company's long‐term priorities are. ...