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Ethan Bull 16 min read

Integrating & Onboarding an Executive Assistant into Your World

There comes a time in every successful executive’s career where they transition from having to do everything for themselves to having an executive assistant

Whether you’re working with an in-house executive assistant, a remote executive assistant, a virtual assistant or an administrative assistant, these tips will ensure you get the most out of your working partnership with your assistant.

The “Before an executive assistant” Executive

The ‘having to do everything for themselves’ includes staying on top of email, calendar, contacts, to-do list, voicemail, etc. to make sure nothing falls through the cracks; balancing personal life against work commitments; managing travel arrangements including flight, hotels, ground transportation, conference registrations; the list goes on…

By being able to handle all of this information flow, keep all the balls in the air, AND STILL close deals and move business forward is a sign to the higher-ups that this executive is ready to be promoted onto the next rung of the corporate ladder, which provides them with an executive assistant.

This is a huge accomplishment and a signal to everyone else inside and out of the organization that they have ‘made it’.

Initially, almost all of these executives picture themselves leaning back in their chair with feet kicked up on the desk as their assistant manages the hustle and bustle of their new world. Not surprisingly, this vision—in the beginning—rarely comes to fruition without fits and starts and bumps along the way.

The "After an executive assistant” Executive

Are you eyeing those SVP, EVP or C-Suite stripes that would provide you with an executive assistant in your organization, but wish to avoid the initial pitfalls when you’re partnered with one?

Or, are you an executive with an assistant who believes you're not getting what you should out of working with an assistant?

In either case, this isn’t the first or last time that an executive will have to onboard a new executive assistant—or rebuild a relationship with their current executive assistant—so that the partnership works optimally and you are truly working as a team. 

Things to consider when onboarding an executive assistant:

We'll cover each of these time-tested considerations in more detail below.

  • Title is Executive Assistant, not Secretary
  • Introductions
  • To cc or not to cc
  • Take yourself out of the email back-and-forth with one sentence
  • The “I could do this faster” urge
  • Something done wrong or not how you like it? Communicate.
  • Mistakes happen
  • Give them the time they deserve
  • Mine your executive assistant’s past experience
  • Confidentiality
  • Follow your company’s rules
  • Don’t be afraid to ask for a favor
  • Don’t be afraid to let your executive assistant take one for the team

Commit to the title "Executive Assistant", not "Secretary"

This commitment is more than just semantics. Most executive assistants have college degrees—and the smarts to prove it. Combined with the technology at their fingertips, they are so much more than answering the phone, grabbing your coffee and ‘gatekeeping’ your office. The quicker you can view them as a business partner, the sooner they will be able to see around corners for you and become a valuable sounding board.

Make introductions

By sending an email to people within your organization, people outside your organization, as well as with friends and family, you’re signaling that you’re putting your trust in your executive assistant to be involved in all logistical questions and business needs as your ‘one point of contact’.

CC your executive assistant on every email you can

Any time you send an email that doesn’t have information your assistant shouldn’t see, you should copy them. You’re keeping them in the loop and making them feel like a valuable partner to you and your business while also showing the folks you’re emailing that your executive assistant has your respect.  

Take yourself out of the email back-and-forth with one sentence

The one sentence you should be adding at the end of your emails is: “[Assistant Name] is my executive assistant and cc’d here to help facilitate any logistics and information flow.”

Since you’ve cc’d your assistant based off of our previous tip, why not leverage their inclusion with this sentence? You’ll get less email back and forth filling your own inbox, guaranteed.

Fight the “I could do this faster myself” urge

Yes, you’ve been doing all of the things you should be having your executive assistant do for the first stage of your career and now it may feel slower to have to explain the what and how to your assistant. And this may be a little slower in the beginning, but once your assistant handles those first couple of trips, conferences, or major meetings, you’ll develop a shorthand that will pay valuable time dividends for years to come.

If your executive assistant does something that you want done differently, TELL THEM

By having an honest conversation when something needs to be done differently, you’re nipping any problems in the bud which, again, will pay dividends during that crucial first six months of partnering with an executive assistant.

Understand that mistakes will happen

We’re all human, but a great executive assistant keeps their own score and HATES to make mistakes. It’s guaranteed that your assistant will feel bad about making a mistake which will refocus their efforts so that such a mistake doesn’t happen in the future.

As long as the communication between you and your assistant is open and honest, after not too long, they will walk through fire for you.

Give your executive assistant the time that they deserve

A recent questionnaire of assistants asked how they best like to communicate with their principals and the clear majority preferred in-person/video/phone meetings.

Email, Slack and texting are very useful tools. However, the glue that holds those interactions together is the direct contact between principal and executive assistant. Direct interactions allow the assistant to:

  • Ask specific questions about plans, projects and schedules
  • Read their principal’s tone of voice which helps with prioritization
  • Build the relationship through a ‘in the foxhole together’ bond that will serve both of you as long as you work together

Maybe most importantly, a quick phone call is much more productive than five volleying emails. 

Mine your executive assistant’s past experience

Chances are that you’re not the first principal your executive assistant has supported.

The past occasions when a previous principal needed a creative way to congratulate a prospect or finesse a schedule to fit their needs will serve you, their new principal, well.

By leaning into your executive assistant’s previous experience, you’re showing them that you care about their ideas and ‘out of the box’ thinking when it comes to meeting your goals.


An executive assistant who is a pro understands the importance of confidentiality… it’s like attorney-client privilege or a doctor’s Hippocratic Oath.

Understand when onboarding an executive assistant that until they really know and understand their principal, they aren’t going to be sharing their principal's schedule, contacts or really any information with anyone else until the principal gives them the ‘OK’ to share. With this understanding, the executive can circumvent confusion by giving rules up front as to whom is privy to information. Executive assistants do not like to assume anything before sharing your sensitive information. 

Follow your company’s rules in regard to how executives partner with assistants

In an effort to streamline executive support within an organization, there are rules—whether in writing or not—about how executives are allowed to use their assistants.

If a company pairs each executive assistant with four executives and each of those executives expects the executive assistant to handle everything on the work side as well as all of their personal needs, the assistant will never sleep.

Knowing what is “OK” to ask your assistant to do and what should still be left to yourself is a great first step in forming a solid relationship with your executive assistant.

Many organizations don’t want to see their executives use their assistants for personal errands. However, if you have a one-on-one relationship with your executive assistant and you are their only principal, personal requests can be included in their service to you.

Don’t be afraid to ask for a favor

As a continuation of the above tip, you also shouldn’t be afraid to ask for a favor if you find yourself in a bind. Anything from booking a personal trip at the last minute to running to your home to grab something you’ve forgotten to buying a gift for an event that slipped your mind.

If you present such requests as a “favor”, you’re showing that you understand the rules but are in a bind and could use a hand. In this way, you’re forming a deeper relationship with your executive assistant and letting them really show that they are on your team and always looking for ways to streamline your time.

Don’t be afraid to let your executive assistant take one for the team

If there ever comes a time when something comes up that you just don’t want to do or need to get out of, if you’ve built a strong relationship with your executive assistant, you can let them take one for the team. They can be the bad guy or the one who made a scheduling mistake—even if they didn’t—so that you can save face and get out of their previous commitment.

Again, situations like these are what truly form a business partnership that stands the test of time.

Make onboarding an executive assistant easier and more efficient

This list is based on decades of experience as an executive assistant. Some of the suggestions might seem a little counterintuitive, but when the relationship between executive and executive assistant is built on a strong and trusting foundation, you will view your executive assistant as your business partner, chief of staff, project manager, scheduler, and personal assistant. Remember, the good ones can and will become the force multiplier you’ve dreamed of having.

When we partner with new clients at ProAssisting to support them remotely, we rely on our Client Onboarding Questionnaire to cut the learning curve down and provide their remote executive assistant with the information needed to hit the ground running.

In combination with the above list of tips for how to integrate fully with your executive assistant, this list will certainly get your gears turning for how you could be using your executive assistant to their fullest potential.

If you would like to view our Onboarding Questionnaire that we provide to our new clients, you can download it below.

Onboarding Executive Assistant | Download Free Questionnaire | Remote Executive Assistant

Ethan Bull

Co-Founder of ProAssisting

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