We waited too long to hire more senior managers, which led to a chaotic environment in the early stages of the company.

It's crucial to consider who, why, when, and what when choosing leaders in a company, as pushing individuals into leadership roles prematurely can hinder their success.

In a startup, early hires often grow into leadership roles. However, it's crucial to recognize that not everyone is naturally good at management, and developing these skills takes time and effort.

In the early days of Airbnb, we were hesitant to hire senior leadership too soon, but I now believe it's crucial to bring in experienced management when you know you're going to scale.

We believe in promoting from within, but as we grow, we sometimes need to hire external managers, which presents new challenges.

In our first year, we faced significant challenges, including a tough go-to-market transition and hiring the wrong team for our stage of growth.

The best way to develop leaders is to allow them to take responsibility and make decisions, even if it means they might fail at times.

As organizations grow, leaders can no longer communicate directly with everyone, which can lead to turnover if early employees feel disconnected from the company's direction.

Organizations often lose sight of their original goals over time due to generational turnover, leading to misalignment between current leaders and the founding mission.