How to Get Through the Gatekeeper and Connect With Anyone

by Positive Hustle

What is a gatekeeper in business?

Think of the bouncer at the door of an upscale restaurant, the muscle sorting out who to let in and who to keep out. Likewise, successful business professionals, politicians, authors and VIPs have someone that is in charge of protecting their time and space, letting in only a few based on certain criteria. You may not be aware of the power they wield, but it would be wise for entrepreneurs seeking contact to take heed of what it takes to get through the gatekeepers. 

Do your research first

Stop, look and listen. Your business could transform when you connect to the right people, so take the time to research your target connection before sending that email. What are their goals, struggles, and to whom have they already granted time? 

Prior to reaching out, spend time on their social media reading current and past content. Review everything on their website and listen to their interviews. 

5 insider tips from a high-profile assistant

1. What not to do

Do not approach with entitlement! While Stanley Goldberg, Robert Greene’s assistant (6x NYT bestselling author with his most recent being The Daily Laws), tries to give people the benefit of the doubt, some requests come in aggressively and cross the line. For example, complaining about the speed of an email response. No one wants to put a person like that through! Persistence is appreciated, but there is a difference between persistence and being demanding, and it’s usually those without big platforms that can be belligerent. If you approach with respect, an assistant will usually respond graciously as they know they are acting by proxy; it’s their boss’s reputation on the line. 

2. Recognize the privilege

An assistant is very careful with their boss’s time. As insiders, they witness the day-to-day diligence of how their boss takes their craft and business seriously. Scheduling, coordinating podcast interviews and appearances, managing social media platforms, and working on getting their boss’s name and business out to as many people as possible is usually part of their job. 

Goldberg is strongly aligned with Greene’s mission of teaching power, mastery, and psychological topics on human nature to the masses and believes that all people can benefit from at least one of Greene’s books. Working with the hope of somehow touching someone’s emotions so that they are prompted to buy one of the books is a very gratifying and privileged part of the job.

If you are a huge fan, say so! Detail what you got out of a VIP’s work, and be respectful in your communication, as that goes a long way in obtaining a possible connection. When asking for time, ask for a short time frame. It could be extended if you get a meeting and it goes well.

Who are you? Make sure that you include valuable accomplishments of your own in your email by way of links, a bio, and anything you have had success with, such as a podcast. Gatekeepers often go through it all, as they are looking to include whoever they can on their boss’s schedule. Additionally, many successful people like to pay it forward and help out a smaller podcaster and entrepreneur. While they can’t grant everyone an interview or personal interaction, they hope that people are respectful of that. 

4. Add a personal touch

Be vulnerable! Show that you genuinely care about the person and their work. Your courage in taking a shot at connection is admired by the assistant that knows what it takes to reach out to someone who is more famous and accomplished, trying to get a piece of their time that will mostly benefit you to grow your audience or impact your business.

Additionally, your personal request may not initially seem like the usual interview or connection granted, however if it seems like an unusual and interesting conversation may develop, you could be put on the schedule.

5. Be patient

Many gatekeepers have a lot of respect for the person they are working for as they are up close and personal with them. They are calculated with their boss’s time, making their own work-related interactions concise. When an assistant replies to an email asking you to contact them again in a few months, most do not – so keep trying.

Be confident and go for it. Goldberg says he himself got the job by a stroke of luck. While he had a love of publishing and marketing he was working as a soccer coach in NYC for kids trying to figure out his own direction when he answered a Tweet put out by Daily Stoic, and landed the job coveted by many.

In conclusion

Some additional tips: Use social engagement as well as your own network to get a referral and make a connection that way. Maybe someone you know could connect you. As far as who will benefit from the connection, think about how it will benefit them as well. 

Can you solve a problem for them? Value the gatekeeper, their perspective, and their job. They could end up putting you and your company in a strategic place on the map you could have never otherwise reached.

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