Make Time Great Again

A couple months ago, CEO Andrew Lee met up with a successful entrepreneur friend for dinner. The friend had just wrapped up a successful PR tour and was trying to make sure that he was doing everything he could to guard his most precious resource, his time.

He pulled out his phone at the dinner table and showed Andrew a “calendar audit.” This calendar audit showed all of his calendar events matched against his company’s strategic goals. The friend had exported all the data from his calendar, created a spreadsheet to assign categories to all his events, and calculated the total time he spent on each category. His friend remarked how useful it was, but that he was told this secret by another entrepreneur. His friend remarked, “Turns out the top CEOs, politicians, and leaders all do this in some form – heck, even Steve Ballmer does this.” However, he also observed how difficult it was because there was no readily available tool.

Weekly Percent Table

Andrew soon found others with this same problem. Sam Shank, CEO of Hotel Tonight, spent four weeks conducting his own labor intensive calendar audit. Keith Rabois, partner at Khosla Ventures, conducts periodic “calendar audits” for CEOs of companies he has invested in to make sure that their schedule allocation matches their goals. No one had a dedicated tool to help them solve this problem.

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Since then, the Esper team has been working tirelessly to bring this concept to life, following its mission of solving the problem of time mismanagement. With that in mind, we are excited to announce Esper – a quick and easy way to track how you are spending your time. Just as you track your expenses and maintain a budget, you can now do the same with your time. Let’s “make time great again.”  😉

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.

Four Misconceptions about EAs

How can you stop wasting energy on everyday decisions, improve your work-life balance, and still stay on top of your professional life? Get an executive assistant! When asked what an assistant does most people can only name a few things and can’t see the real benefit. Given all the time we spend talking with and thinking about assistants, we thought we should share some of the biggest misconceptions we hear about this profession.


1)  You only need an assistant if you are scheduling a lot of meetings

Busy Calendar ImageAssistants perform lots of useful tasks – their job is to help you stay organized, find ways to save you time, and perform tasks you wish you had time to do but never would have done. Spending time on contact management, fact checking and proofreading, expense reports, or car/home repairs means you have less time to focus on the high-level, high-impact decisions that shape your business. An assistant might help send cards for friends’ birthdays, set up exercise sessions, or keep track of your communications to make sure you’re checking in with key teammates and contacts.


Those of us who travel and take meetings might use an assistant more, but there are hundreds of possible uses for a great assistant!

2)  An assistant can only help you with your professional life

This is one of the most common misconceptions, and it seems to come out of previous generations’ boundaries between work and home. In reality, most busy professionals have blurry lines between their personal and professional lives.  And regardless, we’re all strapped for time.  


A great assistant is on top of everything in your life that you’re comfortable sharing. This does not mean you should forget important birthdays or anniversaries, but it does mean that there is another person there who can help make sure you’re on top of and dedicating enough time to your family and personal life. Whether they are saving you from having to coordinate with the person who picks up your dry-cleaning, ordering the right baseball bat for your child, researching a fun event for your house guest, or booking your back-up babysitter, a great assistant is on top of whatever it is that you need to make your life function more smoothly.


3)  An assistant isn’t supposed to deal with your stress or problems

That’s not very helpful!  A great assistant understands when you have a tough day. They want to know what’s stressing you stress v productivityout and what they can do to make things better. If you’re in a bad mood, it’ll likely have negative effect on your organization. Your assistant wants to make sure you are performing at your best so you can lead your organization to success. If you’re worried you’re going to be late, they can send you a reminder. If you aren’t sure what’s going on with your team, they can check in on key projects and report back. Some of the best assistants will even make sure you have a snack bar, so that you won’t get cranky in your afternoon meeting (which benefits both you and the rest of the team). Whatever you have on your plate, there are ways a top assistant can help.


4)    Only a top executive can afford a great assistant

Gone are the days when the CEO in the corner office was the only one with an assistant. Since most people in the knowledge economy are primarily paid for their thoughts, energy, and time, it’s become even more important to make sure everyone has a great assistant. Silicon Valley will give perks ranging from shuttles to and from work, free food, and massages, all in the name of making people more effective. Esper believes that everyone needs a high quality assistant. An assistant will give you more productivity gains anything else. In a freelance, sharing economy finding a well priced EA is easier than ever.

We at Esper are focused on creating the most productive and highest quality assistant workforce for your company. We have top-tier technology and training that can empower everyone at your company to reach their true potential. So why not get an assistant?!

Communicate Like an Executive Assistant

Forget about communicating “like a boss.” Here are some successful communication tips from the best Executive Assistants:

  1. Create a Successful Handoff

A good Executive should call out the Executive Assistant by saying something like “Blake will help us schedule a time/place (thanks Blake!)” Clearly calling out who is in charge of next steps prevents items from falling through the cracks.

  1. Establish Autonomy

An Executive Assistant immediately takes control of the conversation and establishes their autonomy. “Certainly! I’d be happy to help…”

  1. Maintain Inside Knowledge

An assistant always displays specialized knowledge related to not only their bosses preferences, but also knowledge for the other parties involved. “Dinner at The House restaurant would be great. If you’re a fan of distinctly Asian American flavor, I think you’ll be in for a treat.”

  1. Positive Personality

We all know Assistants are never negative. More important though, Assistants are also not overly formal or formulaic. Templates are fine, as long as they have personality. “Congrats on the promotion Amy. Did you hear that sound? Leslie Knope said – ‘it’s the sound of the glass ceiling cracking!’ 

  1. Keep it short

Whether it’s e-mails back and forth or extraneous conversation, a great assistant will decrease interactions to maximize time. Providing relevant information and making clear what you need from the other party minimizes the need for extraneous emails.

  1. Give Passive Updates

To give an Executive peace of mind, a great Executive Assistant should give passive updates to the executive. Whether it’s the completion of a project or key milestones along the way, knowing when and how to update the relevant individuals is critical to effective communication.

Executive Assistants are masters of communication! Use these six skills to up your game or use Esper to help your communication- personalized templates, task updates, and much more to help you achieve these skills!