Getting to know anyone takes time. When your CEO or VP has never had an assistant, it can be especially hard for them to open up and communicate with you. More so than in other relationships, giving someone the lead on major parts of your life takes time. On the one hand administrative assistants need to get personal information and preferences to book travel and schedule meetings quickly, but on the other hand, administrative assistants want to make their teams feel comfortable around their leaders and not apply too much pressure.We surveyed some of our Cabinet members and asked how they established trust and a level of understanding when their leaders were apprehensive and uncertain about the value of an assistant. Here were the most frequent paths forward suggested by our members:

1. Have regular meetings: During the first month, set regular meetings. Tell them all you can do for them, but tell them it will take frequent communication and trust. Even if there is nothing to discuss, having a recurring meeting on the calendar, such as daily for 15 minutes, will enable you and your leader to get comfortable with each other quickly. Sometimes small talk during meetings is the magic ingredient.
2. Ask lots of questions: In these meetings, ask lots of questions to your leaders, such as: Do you take notes during meetings? How do you want your files from XYZ stored? What are the names of your children? The more you ask, the more you learn.
3. Create a file for each leader:  Create a file in OneNote or Google Doc that has all of this information stored. Label the sections: Personal Information, Preferences, and Priorities. This is a living, breathing document so everything should be easily changeable. Anytime you learn something new and interesting, add it in there. It's also an amazing resource if you decide to leave the company. Don't you wish someone had a document like this prepared for you already?
4. Get access to emails: Ask for access to email as soon as possible. This will allow you not only to stay on top of their future plans and priorities, but also understand a history of people, projects and tasks. Read everything that comes in. Email digestion will become your super power!
5. Attend meetings / Listen on phone calls: This will help you understand your leader's style of command. Seeing how he or she reacts to other people will give you a sense of what they really mean when they are talking to you.

So, it's been a few months and you've done everything on this list. Now, how do you know when your leader has been successfully "onboarded" and you can back off a little? This is a great question. The signs of a successful onboarding are fewer mistakes and faster transactions. For example, imagine your leader asked you to book a trip to St. Louis, including a restaurant reservation for two people one night. Now, normally, you would find three choices and present those to your leader. However, when you are finished getting up to speed with your new exec, restaurant preferences should be known to you. So, when you can go to Cabinet or TripAdvisor looking for recommendations, you already know what they will or will not like, without having to ask your leader to make the final decision. Reducing the number of decisions your leader has to make is a definition of success.