You are using an outdated browser. Please upgrade your browser to improve your experience.

How To Get Started With Your New Executive Assistant

Written by: Sandra Lewis

It’s a wonderful day when you finally get an executive assistant. It feels like a burden is about to be lifted, with so much less to worry about.

Then you realize you have to turn over the keys.

Keys to your email. Various online accounts. Banking. Personal scheduling. Vital personal and professional areas that require real trust to let someone else in.

Did you choose your executive assistant wisely, or are you about to give significant control of your professional life over to someone who could make things worse?

We’ll tell you how to know if you made the best hire, and the best way to get started with your new executive assistant.

Listen To Your Gut About Your Executive Assistant

Listen to your gut, especially when it comes to ferreting out trust.

You’re choosing someone who will be working closely with you, an executive assistant with a well-matched personality. All the perfect and impressive credentials in the world don’t hint at personality fit, which is crucial to building trust.

There are several areas of trust to watch for:

  1. Performance. Can your new executive assistant do the work needed? This is about executive assistant experience, references, and education.
  2. Judgment. Do you think your new executive assistant will do good work without your constant input? This is about decision-making ability and application.
  3. Representation. Will your new executive assistant represent you and your company well to clients? You don’t want someone who would bring negative light on your brand, or do anything that goes against company mission statements.
  4. Principle. Is your new executive assistant discrete? Private and internal concerns should stay as such. Without this kind of trust, communication will never be direct and true.
  5. Motivation. Is your executive assistant motivated by the same things you are? A clash in motivations will affect how you work together, and how results are achieved.
  6. Relational. Will your new executive assistant foster positive experiences in your organization? The wrong personality could create a poisonous situation for other team members who need to work with you. Conflicts could balloon instead of dissipate.

Hopefully your hiring process did some of this work, and you listened carefully as candidates responded to interview questions, whether it was a remote interview or in-person, before committing to the hire. It’s easy to give perfect answers to typical questions, so ask questions and pose scenarios that wade into these realms of trust.

An executive assistant that you can’t trust or rely on is a big mistake. Not only does the work not get done, but you won’t have much peace of mind. Say goodbye to being able to enjoy a vacation or truly be away from staying connected to work.

That’s unfortunate, because that’s a significant reason you got an executive assistant in the first place.

Get Started With A Launch Meeting

When you’re sure everything is a go, it’s time for a launch meeting.

A launch meeting (or several, if it takes that many) is where you overtly let your executive assistant know what they’ll be doing—it’s also a good time to continue to vet. If they don’t ask the right questions, it’s a sign that things might not work. Look for questions that reveal real working knowledge and experience, that show they’re anticipating potential difficulties and want to know your expectation in resolving them.

A launch meeting starts with you explaining what you want the executive assistant to do.

Then both of you come up with a plan for ramping up to full speed.

At this point, they should have plenty of questions on how to do things, style preferences, processes, systems used, and other expectations. They’re trying to get a full picture of what you want. If they don’t have many questions of this nature, that’s a warning sign.

First Tasks To Start With Your Executive Assistant

Start small with your new executive assistant. Let them dip their toe into the pool before diving in. Give yourself continued room to decide if the fit is right.

Maybe you’ll begin with having them handle your email, learning your voice in responding, and getting used to how your email is archived. Then add in scheduling so they get a bird’s eye view of regular activity. Both of these will quickly acquaint your new executive assistant to the people they’ll be working with while giving you a chance to see if the trust is there.

Think of that as the warm-up level.

Then, move onto the activities that require higher trust. Think bank accounts, travel planning, sensitive personal issues, and so forth. These aren’t things you hand to someone right out of the gate.

Do not move from the first level to the second if there are any concerns nagging at you internally. That’s your gut telling you to put on the brakes until you figure out the issue.

Get Started With A Ridiculously Talented Remote Executive Assistant

Hiring an executive assistant the traditional way is a significant chore. Even after the hiring process is complete, there are questions, training, and gradual levels to work through to make sure you’ve hired the right person.

There’s an easier way to get started with an executive assistant right now, and that’s by choosing a remote executive assistant.

Boldly has done all the work for you. The best qualified executive assistants. A process to help find the assistant that’s right for your personality and work style. All compliance and related headache taken care of. No shortage of pleased customers ready to vouch for trustworthy assistants.

Be more productive, starting right now, by finding the perfect executive assistant you can trust through Boldly.

Topic: Remote Executive Assistant

Updated on October 12th, 2023

About the author: Sandra Lewis is the Founder and CEO of Boldly. She's passionate about helping Businesses, Organizations and Executives increase productivity and move their work forward with the right skills and resources. Setting an example of the efficiencies gained working remotely, she’s been leading her entire team on a virtual basis for the past decade.