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How Trusting Your Executive Assistant Changes Everything

Written by: Katie Hill

Maybe you’ve just hired a new executive assistant, or maybe you’ve had one assigned to you. Either way, the secret ingredient of a productive senior executive and EA relationship is trust — here’s how to build it.

Fabian Delahaut, after launching his startup, was used to an overfull inbox he had to sort through every evening.

One night at 8 p.m., while winding down with his wife, he picked up his phone out of habit to catch up. Instead of an endless string of unanswered emails, he found a tidy inbox with every urgent communication already handled.

This was when he realized he could trust his executive assistant, Pauline, just a short time into working together. And from then on, he was free to work in his sweet spot, delegating freely, increasing profitability, and focusing on the big-picture.

As Stephen Covey put it so well, an organization moves at the speed of trust. The more merited the trust, the faster we can win.

Trust will move the needle for you, multiplying what you and your EA are able to accomplish.

Building Trust Takes Both Sides

While you can’t build trust overnight, a high-level executive assistant already knows what it takes to kickstart that critical element. From day one, they’re looking for those tiny cues that will give you the confidence they’ve got it covered.

As AnnMarie Brockhouse, a Boldly Executive Assistant, describes below, an experienced EA will find out those VIP details.

Trust is a lot of work. On the surface level, it may sound too trivial to bother with. On paper, skills and experience ring loudest.

From the beginning of the hiring process, make sure you’re prioritizing hiring an executive assistant you can trust.

Trusting Your Executive Assistant Comes First

Without trust, a productive working relationship won’t last, even with the best hire.

Imagine the headache of having to double-check every schedule or travel or meeting arrangement your executive assistant made. 

Or, even if your EA was completely reliable and a great worker, you still had to be a task manager and spell out what you needed done.

In either scenario, your assistant isn’t saving you much in terms of time or energy. You’ve shifted the load you’re carrying, but you haven’t removed it.

That’s what happens without trust.

However, with trust, your life can look something like it did for our previously-mentioned executive, Fabian.

He left the office for his first vacation in years, sailing the ocean for 12 days, completely out of contact. When he arrived at his destination, he checked in only to learn Pauline, his remote executive assistant, had handled everything perfectly.

“I don’t have to manage her,” he explained. When she started working with him before the trip, she’d asked him what his priorities were, quickly learned what he expected, and was completely self-motivated from that point on.

Having trust enough to let go; how long has it been since you’ve been out of the loop for 12 days and arrived back to find everything humming along just fine? If you’re like many execs, the answer is probably never.

How To Build Trust With Your Executive Assistant

A great executive assistant should understand both what you need and expect, as well as anticipate these things before you’re even aware of them. Here’s how to build that kind of trust with a new hire from the onset.

6 Steps To Building Trust With Your Executive Assistant

  1. Meet. Don’t skip out on regularly scheduled meetings at the beginning. Although another meeting may seem like the last thing you want, this will get you both on the same page about working styles, priorities, and communication expectations. (Which will get the rest of your schedule triaged, faster!)
  2. Start small. Let your EA get a sense of your preferences and priorities while you get a sense of their work quality. Figure out if this is the right person for you. Give them smaller tasks that don’t require huge trust so they can learn how you work and how to represent you. You don’t hand over your bank accounts and important travel plans on the first day.
  3. Give feedback. While clear and consistent feedback (both good and bad!) is important at every step, it is critical in the beginning as you build a foundation of trust and decide if your EA is the right fit.
  4. Evaluate. Within 3-4 weeks, you should start to feel in sync with your EA. If you’re still hitting roadblocks, evaluate if they’re the right person. If not, find someone else — it’s worth the effort.
  5. Level up. If you’ve found someone that’s proving trustworthy in those smaller things, go ahead and give your EA increasingly sensitive access. Personal tasks. VIP clients. Finances.
  6. Enjoy long-term. Great working relationships, built on trust, last longer and are exponentially more productive.

The best thing about the steps above is that you can use them to build trust with any executive assistant, whether they’re right outside your office door or working remotely across timezones.

Remember, when you trust your EA, you don’t have to micromanage; they don’t have to be on call to handle the latest crisis because, if they’re doing their job well, there won’t always be one.

Hiring through a staffing firm can make the process of finding a high-level EA easier and less awkward. A reputable company will be experts in knowing how to recruit and hire qualified, experienced, and trustworthy assistants. The best staffing agencies will take the time to understand your working style and preferences, then personally match you with an EA that you can meet ahead of time. You’ll be able to hit the ground running faster than with traditional hiring.

In fact, a remote executive assistant, via premium subscription staffing, gives you the flexibility to scale up and build trust in this methodical approach, whereas a standard full-time hire restricts you when it comes to step four.

Build Trust, Then Scale It

Remember, trust is circular.

Until you get a handle on being exhausted with all the work you’re required to do—including those pesky admin tasks like scheduling meetings and getting expense reports in on time—your own team can’t trust that you’ll provide what they need on time. 

Plug a trusted executive assistant into that equation, and see how quickly your entire team can move the needle towards growth.

Looking for an executive assistant you can trust without the headache of hiring?
Learn more.

Topic: Remote Executive Assistant

Updated on December 19th, 2022

About the author: Katie Hill is a Content Writer at Boldly, which offers Premium Subscription Staffing for demanding executives and founders. When she isn't writing about remote work or productivity, she can be found adventuring in Colorado's backcountry.