Chapter 10 - Managing the Gatekeeper

October 23, 2025

Managing the Gatekeeper - Recap

In this chapter, the author stresses the importance of close associates and assistants of the people we want to connect with, the ‘gatekeepers’. Oftentimes, executive assistants are more than just assistants. They are trusted associates that have tremendous sway. They manage the calendars of those important people. They schedule in meetings and screen appointments. Honestly, I’m no where near the point where I’d go through any assistant. Nobody I know has a personal assistant. But I can see the point and it is really simple, be kind and friendly to everyone. If people don’t like you then life becomes really difficult. If people like you then they will help you, they will put you in spots where you can shine.

Most of that kinda isn’t part of the chapter. The author gave an example from his experience on how he has treated his boss’s assistant with respect and gratitude. How when he was well received by the assitant, his connection to his boss became smooth. Once his relationship with her turned sour he wasn’t able to easily get appointments and his messages don’t get through anymore. Another example was from when he had his own personal assistant, a sales person whom it’s not his job to entertain persistently got on his assistant’s good side and finally got an appointment to meet with him because his assistant vouched for the guy.

While the chapter focuses on the ‘gatekeepers’ of the world, I think the takeaway is to simply be a good person. Being kind, respectful, generous and well-liked opens up doors.