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The CEO’s Secret Weapon: A Strong Executive Assistant

Often referred to as the gatekeeper, the position of executive assistant can be a very powerful and lucrative career, but it certainly isn’t for everyone.

"The CEO's Secret Weapon" by Jan Jones.

“The CEO’s Secret Weapon” by Jan Jones.

To get a better grasp on what it really takes to be an effective executive assistant and what executives should look for I spoke with Jan Jones, author of the newly released book The CEO’s Secret Weapon.

A former executive assistant to some of America’s high profile bosses herself, Jones tapped her network to interview the assistants of such high profile executives as Donald Trump, Richard Branson, and Barbara Cochran to get their views on what it takes to make it.

As Jones explains these are the individuals who keep their executives on track and focused on the right issues in a turbulent business environment. Think of them “as your face to the world” says Jones. No executive can have sustained success without a strong executive assistant at their side. She points out that some of the most noteworthy executives have had long-time assistants. Jones shares some of the key elements executives should look for, particularly when hiring an assistant for the first time.


First and foremost you must hire for values and to do that you must be clear on your own values. In order to bring on an effective assistant you have to understand how you work and the kind of person it takes to effectively work with you.

Jones advises that you take the time to understand the principles and standards that inform the thoughts and actions of each candidate to see how well they align with your own. “They must be a reflection of your values and who you are as an executive” because they will be representing you both internally and externally. Find out what values have driven their decisions in times when there was an absence of knowledge or the ability to get guidance from their executive.

Trust and Loyalty

Think of your executive assistant as a business partner. Keep in mind you are going to spend a great deal of your time with this person, which means you are going to have to trust this them. When speaking to candidates Jones advises “listen to how they talk about current and former bosses.” Are they loyal or do they readily share the kind of information that would make you uncomfortable if you were their boss?

Trust is also about sharing. Jones points out that you have to be willing to turn over responsibilities and provide open access to such personal information as emails, notes, confidential files… Although this may feel uncomfortable at first, Jones makes it clear this is a critical aspect of the relationship and advises you “to get over it” if you are serious about being a successful executive.

Often your executive assistant will have access to information that even your spouse doesn’t see. Granting open access is critical to a successful relationship. Without it, your executive assistant will be minimally effective at best.

Anticipation and Filtering

Executives don’t like surprises. A good executive assistant must be able to anticipate what their executive needs to know and by when. What many refer to as the gatekeeper function is more often a triage function in that executives are constantly being barraged with a great deal of information, challenges, and noise. It’s up to the executive assistant to determine what their executive needs to know and what they don’t. Often times requests that come in may need action, just not from the executive.

Thus, it’s up to the executive assistant to determine how to best respond and redirect these requests so they are resolved without having to disrupt the executive. It’s also important to anticipate which requests will likely bubble up again or who may look for other routes to get to your boss, so you can prepare the executive just in case.


At times your executive assistant will be speaking on your behalf. As an executive you need to be comfortable with your assistant speaking for you. This is why they need to reflect your values, philosophy, and style while complimenting any weaknesses you may have as a communicator.

This will certainly vary by executive, which is why you must have quality conversations about what, how, when, and where to communicate. Jones also notes that you must show them respect and let others know they clearly speak for you, so they are not easily dismissed.

Article from Dr. Woody Woodward, originally published on Fox Business last November 2015.

4 Ways to Ensure Successful Assistant-and-Executive Communication

Today’s featured article comes from Julia Schmidt and Carla Stefanut of the European Management Assistants official website, published in February 2016.

“An assistant cannot passively wait to be told something.” (From "The CEO’s Secret Weapon” by Jan Jones)

“An assistant cannot passively wait to be told something.” (From “The CEO’s Secret Weapon” by Jan Jones)

Julia Schmidt and Carla Stefanut were inspired to write this post after reading the book “The CEO’s Secret Weapon: How Great Leaders and Their Assistants Maximize Productivity and Effectiveness” by Jan Jones. Julia and Carla agree that the CEO and the Assistant are both responsible for making their partnership a success.

Adapted from “The CEO’s Secret Weapon” here are 4 recommendations to ensure successful Executive-and-Assistant communication:

1. Start laying the foundation for good communication during your interview.

Ask the executive you will be working for what skills they want to see in the new assistant. Ask why these specific skills are important to him/her. Discuss the company’s values and ask how the executive applies these values to the workday. Clarify expectations – not only the executive’s, but yours as well.

JULIA: When I was interviewed for my current job, I was curious to find out how the CEO would explain to me the company’s values. I was positively impressed by the way the company lives the leadership values. I could feel authenticity from a great CEO and founder.

CARLA: When I was interviewed, my boss asked about my favorite hobbies and sports and I asked about his. Soft skills are important to set the foundation for an open relationship.

2. Understand the value of feedback and ask for it often.

“An assistant, in order to help her manager helps her, needs to learn to appreciate feedback. If my boss gives me feedback that I don’t like, I can’t take it personally. I’ve realized that he’s helping me to improve.” (Assistant Ann Weaver, quoted in “The CEO’s Secret Weapon” by Jan Jones)

“An assistant, in order to help her manager helps her, needs to learn to appreciate feedback. If my boss gives me feedback that I don’t like, I can’t take it personally. I’ve realized that he’s helping me to improve.” (Assistant Ann Weaver, quoted in “The CEO’s Secret Weapon” by Jan Jones)

Feedback from your executive is an excellent benchmark for you to know if you are performing up to expectation.

Get in the habit of asking for feedback and find out if your boss is open to feedback from you, not necessarily about his or her performance, but about things you notice happening in the business. If you are asking for feedback, be prepared to take the criticism along with the praise. That is how you will learn and grow in your position.

An assistant must be proactive in asking the boss about a phone call or meeting, in order to find out if there is any follow up the assistant must handle. Some of Jones’ standard follow up questions are:

“Is there any follow up for me from this meeting?”
“Is there anything I should be aware of from this phone call?”
Or, “Do you need me to…”

3. Become a mind reader

Get in the habit of finding out the actions you can take independently to become your executive’s best business partner.

To learn the skill of anticipating, the assistant must ask questions, listen, be curious, take notes, read up about the industry and develop an understanding about the business. Don’t be afraid to ask your executive to explain things to you, or to recommend how you can develop your understanding of the business and your executive’s job. This will allow you to start taking independent action.

“If you need to ask the boss something, ask yourself the question first. A lot of times you’ll know the answer already and save your boss time.” (Donald Trump, a businessman who was interviewed for the book The CEO’s Secret Weapon” by Jan Jones)

4. Face-to-Face conversations are an essential routine to make certain you are in sync with each other


“When the boss communicates frequently, the assistant develops a knack for knowing what the boss wants, and over time appears to be a mind reader.”

“A lot of issues between assistant and executive can be resolved through dialogue. Assistants should not use technology as an excuse for not having that dialogue.” (Adam Fidler a top trainer of EAs, who is interviewed in “The CEO’s Secret Weapon” by Jan Jones)

The above quote refers to a trend among younger assistants and even younger executives of sending each other text messages when they are sitting next to each other in the office.

One-on-one meetings give you the opportunity to check in with each other relevant information, make sure projects are on track and that each person has whatever they need, nothing is being overlooked, or any miscommunications are happening.

These times together give the assistant the opportunity to learn first-hand what the executive is thinking, what are the latest projects, business goals, etc. They are good opportunities for learning about each other and building the personal side of the relationship so that you can build trust and rapport with each other.

Change and urgency are ever present in all C-level offices. As assistants we know that what is a priority today, might not be a top topic on the agenda tomorrow.

Put your one-on-one meetings on your boss’ calendar and come prepared to get down to business. Have your questions ready, and be willing to answer questions about any projects you are working on.

Remember top executives have to make good use of their time. Use this opportunity to learn about current projects, new products and customers. If you are informed and show interest, your executive will realize that you want to know more about the business and will start sharing the big picture and goals with you.

Being proactive is crucial to earning the trust of your executive and helping the relationship to evolve into a valuable partnership. You need to take responsibility for growing the relationship.

We wish you a successful journey.

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