Having an Assistant is Awkward, But Necessary

Having an executive assistant can be a very awkward experience. Most executives have NO IDEA how to work with an assistant the first time. It’s similar to having a competent sibling who tags along and wants to help you, but you insist on “doing everything yourself.” It makes things harder for you, harder for people you’re interacting with, and makes the assistant feel awkward as well. Despite the enormous productivity gained from having an assistant, new executives become sheepish when they bring someone else in because they feel like it’s disrespectful to other parties.

Why do people feel this way? It varies city by city; Washington D.C. has a strong assistant culture (heck, the whole cabinet is filled with Secretaries). In Los Angeles, “I’ll get my people to talk to your people. Hold on, New York is calling” is a running joke.

Ari and Lloyd

In other cities though, like Silicon Valley, people are afraid to use an assistant. The do-it-yourself attitude of Silicon Valley just doesn’t seem to fit well with assistants.

Michael Cera 2.jpegAssistants are still perceived as a luxury item reserved for the most powerful executives in a company. If you aren’t the CEO then why do you have an assistant? This attitude can breed awkwardness so bad even Michael Cera would run away. Let’s look at how this arises in different situations.

1. Peer to Peer – let’s say you’re both equals.


If neither of you have an assistant then you both take a lot of time scheduling etc. It’s not awkward, but also not the most effective use of your time. However, if only one person has an assistant, they might feel incensed or think it’s a “power move,” making them hesitant to bring in their assistant. If both of you have assistants, great! Hello productivity, goodbye awkward power moves.

2. Junior and Senior – let’s say one person is higher up on the pecking order (SENIOR) and one person is much more interested in the meeting (JUNIOR).


If neither has an assistant, the junior person should try to arrange everything and work to accommodate the senior person’s schedule. While not awkward, the increased back and forth, and lack of timely replies causes problems all around. When you throw one assistant into the mix the time spent on scheduling will decrease for both parties, however if the junior person has the assistant, he/she doesn’t always feel comfortable using their assistant with someone more senior. Again, the most productive use of time is when both parties have an assistant, however this can still create some uncomfortable interpretations if the senior person believes the junior is TOO junior to have an assistant .

If bringing an assistant into the conversation has the potential to create strain on the relationship, why do it?

Numerous studies show that an assistant provides measurable productivity gains for everyone involved; especially in the area of scheduling. In one example a member of the Entrepreneurs’ Organization, Jeremy Choi, tracked his time and discovered that using an assistant freed up at least 15% of his time.Productivity Chart

Since we all ultimately want to save time, knowing when to delegate to an assistant is an important skill. If we also want to maintain important relationships, it’s critical to have a great assistant who can minimize any awkwardness. The more an assistant messes up correspondence, the more social capital the executive loses. The biggest problem with a new assistant AND a new executive is that they need to know the best practices. With the proper training and tools both executives and assistants can overcome the awkwardness gap and reach productivity nirvana.


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