Lead Upwards

CHAPTER SEVENTEENWhen Things Go Pear‐shaped: Navigating Challenges, Setbacks, Failure, and Departures

It's not always rosy in startup‐land. A lot can go sideways when you're building a fast‐growing disruptive business in a competitive market. Here's how to navigate some common setbacks and conflicts, and advice for how to handle yourself and your organization when things go south.

Even when things are going well, startup life is hard. Market conditions change, a key customer churns, a competitor shifts their strategy, your app goes down, and so on. As a leader, you're expected to help your team navigate these changes as well as steer the ship in the right course, correcting as you go. Every day it seems there's a new challenge. While many of these will be unique to you, the types of challenges you'll face are predictable and have data‐driven ways of overcoming (how to deal with missing a number, a team member quitting, a customer churning, etc.).

Knowing there are landmines won't help you avoid them entirely, but you can understand how to deal with and contextualize your experiences so you feel less alone. This chapter was one of the hardest to write, not because of lack of material (my network and I have faced many, many setbacks), but because of how endemic failure and struggle is to the startup ecosystem. It's like the water we're swimming in, so woven into how we build and grow new companies to the degree that it's almost, ironically, less visible. This, I believe, ...