How to Build a Relationship with your Executive Assistant

April 9, 2024

This write-up will teach you how to build a great relationship on the foundation of trust between you and your executive assistant, so they can help you collapse time even further and make you into more of a Superhuman.

How to Build a Relationship with your Executive Assistant

All relationship-building takes time and trust.

This isn’t any different for your relationship with your EA, which is arguably one of the most important people for you to build your relationship with.

Why is that? It’s simple.

Your EA has the ability to make your life significantly better. In a world where you can’t buy more time, having a highly competent and effective EA is the closest thing you can get to buying it.

EAs perform well based on two things: how much you two trust each other, and how well they know your life. The better relationship you have, the better they perform. And the better they perform, the better your life will be.

And if they can make your life significantly better, why not invest that time to strengthen it?

Like I said, relationships are based on time and trust.

The bad news is, you can’t speed up the duration of time. If you’ve known them for one week, you can’t know them for longer than one week. You’ve known them for one week.

But here’s the good news: while you can’t speed up the amount of time you have known and worked with each other, there are a few things you can do to build trust in a short amount of time.

Below are a few things that have worked well for me in the past, as well as for the CEOs I coach with their assistants, leadership teams, and beyond. These principles apply broadly across many of your relationships, so feel free to use them beyond the scope of working with your EA.

1. Give them complete, unfettered access to the information they need.

For your EA to do their job well, they will need access to information, and lots of it. You can’t expect your EA to work magic if you don’t give them the information they need.

I once met an assistant, Anna, who told me she was tasked with helping her boss with their emails… except, the boss didn’t want to give Anna access to their email account “until they trusted her more.”

The boss would forward emails to Anna, who would reply as best as she could with the limited information she had. But by working in this way, Anna would be frequently missing crucial pieces of information that would have enabled her to do her job well. This included other emails not forwarded to her, context on who the emailee was that she could have found on her own by reading previous emails between her boss and the emailee, and more.

In addition, the boss set Anna up for failure by never clearly defining what “trusting her more” actually looked like. It was an arbitrary, ever-moving goal.

Needless to say, this relationship was doomed to failure from the beginning.

Here’s the deal: if you want your assistant to do well, they have to have access to the tools and information that will let them do well.

For example, for all of the assistants I have worked with, I have always given full, delegated inbox access for all of my emails, both work and personal.

Because of this access, with some training, my assistants were able to…

  • Study how I wrote emails to personal friends, work colleagues, and business partners
  • Draft excellent emails for me to send out that sounded like my voice
  • Gain additional knowledge on who was important in my life and who I interacted with on a regular basis, as well as what mattered for each of these people
  • Label things in my inbox that required my attention or signatures
  • Forward receipts for bookkeeping on my behalf
  • Search for extra context to make overall better decisions on tasks

…all with a simple act of delegating inbox access! Seems like such a no-brainer, asymmetrical upside.

Giving complete, unfettered access doesn’t mean you have to do it ignorantly. Certainly, you want to protect yourself. That’s why you can use smart tactics.

For example, rather than handing over your entire password vault, see where you can create their own accounts for them instead. In the rare occasion where there were passwords I did have to hand over, in the early days, I would set up 2FA to my cell phone to show up every few weeks, to ensure I had control over when my assistant was logging in. (By the way, no assistant ever logged into my stuff for unexplained reasons.)

Instead of giving my direct login information for my email addresses, I created an email address for my assistant to use that I have control and login access to. Then, I granted that email address delegated access. That way, they don’t send messages from my account as me. (By the way, no assistant has ever impersonated me or sent emails from my account pretending to be me without my permission.)

Instead of giving my direct login information for my bank accounts, I created a dedicated user to that email address and disabled wire transfer abilities on their permissions. (By the way, I and no one else I’ve known who has worked with EAs in this manner has ever been stolen from.)

When it made sense, I gave them access to their own credit card number with a limit, so if there were fraudulent or unapproved purchases, I could do a chargeback and freeze the card. (By the way, it’s never happened.)

- - - -

You can see, there are many ways to be smart about it. It takes a little extra time to set it all up, sure, but remember what I said in the beginning: your EA can be one of the most promising relationships with the highest ROIs if you invest just a little time building trust.

So take that time and give your EA the access he or she needs to do their job well.

I know this one can be scary, because there is always that one story of a person being given too much access, and then that person using the access in ways that aren’t okay.

That is, however, the anomaly. And if you’re going through a vetted agency like Atlas Assistants to get paired with your assistant, there are precautions in place to weed out any bad actors. This is really one of the reasons I like going through agencies - because I know there’s someone I can talk to should the absolute worst ever happen.

2. Communicate feedback frequently, kindly, and often.

Your EA can’t improve if you don’t tell them how to improve.

Therefore, prioritize time to share what’s on your mind with your EA on how they can perform even better for you, hence further building your trust in each other.

Your EA will likely book off time for a 1-1 for you both to discuss pertinent information for both of you to do your jobs well, you as a CEO and them as an EA. If they haven’t done this already, you should do this, frankly because it’s in your interest to invest in your relationship with your EA (see above.) By carving out 1-1 time, you are showing your EA you believe in him or her and want to build that relationship with them.

During the 1-1 meeting, do cover feedback as well, where they give you feedback on how you can be a better CEO/person, and you give them feedback on how they can be a better EA/person.

There’s plenty of content on how to do feedback well, so I won’t write any more than this here.

The DEAR Method

To provide feedback kindly, I like using the DEAR method. I first learned about the DEAR method from my therapist during my Gottman Marriage Counseling sessions on how to communicate with your partner and with your children. It’s from dialectical behavior therapy (DBT) and used in clinical settings. I believe it works in this context as well.

First, describe the situation. You may say, “I noticed that…” or, “When X happened…” Stick to the facts that have happened, without inserting your own emotional coloring.

Next, express what that situation means in terms of resulting consequences. This is the part where you go into how you feel by saying, “This made me feel…” or, “As a result, Y happened…” Nonviolent communication at this portion works extremely well, because you get to share how this impacted your life. You can’t skip this step, or else your EA won’t understand why this action is non-ideal/sucks/is bad.

After that, make your assertion: what do you want to happen instead? You can say, “In the future, I’d like…” and then you state the desired behavior instead.

Finally, you’ll reinforce what you’ve just said by giving them reasons to grant your request. You could say something like, “I can see this making your life easier too, by…” or by stressing how this impacts your relationship for the better: “I can’t express how much more at peace I would feel if you would do X, and I think it would really help our relationship get stronger too.”

Here it is in action. 👇

(Describe) Hi [EA], I noticed that you were going through my inbox and archiving a bunch of the emails without letting me know what you were intending to do. Because of this, there were some emails that I ended up missing that actually needed my immediate attention.

(Express) This made me feel very sad and concerned, because I got a few frustrated and angry text messages from our customers, who thought I was ignoring them and their messages to me. I also feel scared, because customer trust is something that is so hard to build but so easy to lose - I’ve worked really hard to get our customers to trust us, and now I’m worried they will think I am a careless CEO.

(Assert) In the future, I’d like for you to do two things: first, I’d like you to spend more time coworking with me and asking me questions as I share my screen with you on how I handle my inbox. That way, you’ll know what’s important to me and what’s actually OK to archive, and you’ll gain a better understanding behind the “why” on how I work. The second thing is, I’d like for you to provide a written digest each day during your Start Of Day (SOD) reports of everything you did in my inbox - it could be as simple as a list of emails you’ve archived, emails you have outstanding questions on, and emails you’ve drafted replies for me that need my attention.”

(Reinforce) Again, I’m hoping these steps can help us work better together in the future, because I know you were trying to save me time and help me focus on what matters, and I really appreciate that. I also want to make sure that you feel fully prepared to handle my inbox confidently, and I think these two things will really help us avoid these kinds of mistakes in the future. What do you think?

If you follow these steps while you give feedback, you will have a high degree of trust and transparency in your communication with your EA, and it minimizes the chances that your EA will get defensive or overly apologetic. They will simply make the appropriate changes, and everyone will be satisfied.

3. Share an action tracker.

There should be a single source of truth for all of your action items. This way, your EA can see what you’re working on and hold you accountable, and you can see what your EA is working on and help them reallocate their time well by providing feedback.

The anatomy of a good action tracker is made up of:

  • What the task is
  • Who is responsible for completing the task
  • When it is due by
  • What the level of urgency is (how it should be prioritized against all other tasks)

(For further reading/watching, I recommend checking out my video playlist on Using Asana as an Agreements Tracker here. You can also download your free Notion action tracker with all those components here.)

If you have a preferred action tracker, communicate this explicitly with your EA and make it clear that’s where you expect the single source of truth to exist.

For me, I didn’t care where the actions were stored, so long as it was in a single place and I knew how to use the technology well enough. I’ve used everything from Notion, to ClickUp, iPhone Reminders, Asana, and more.

In this case, my EA picked what worked best for her, and communicated her decision with me.

Each day when you have a standup with your EA to go over both of your respective agendas, this becomes a helpful foundation so that nothing is ever lost through the cracks. It also allows you to actively communicate prioritization and urgency with your EA, until they get the hang of it and can prioritize everything themselves.

This single source of truth will help with trust-building, as you’ll have clear visibility on who is doing what and by when.

4. Make it easy to reach you.

Your EA will have lots of questions, especially in the early days. Don’t see this as a nuisance. See it as a gift. Your EA is asking questions and unafraid of pulling valuable knowledge out of your brain and into a database about you.

Therefore, make it easy for them to ask you those questions.

For my EA, I like giving her explicit permission to call, email, or text me any time with her questions. She calls me if she needs something that is time-sensitive. She emails me if her question is related to a task in my inbox. And she texts me if it’s something that isn’t urgent but important.

With previous EAs, I created an asynchronous Slack channel with each of them so they could throw all their questions in there and I could answer them when I had time. I did this because it wouldn’t give my Slack a DM notification badge, allowing me to batch-answer everything without disrupting my deep work time.

But there’s an even easier, low-tech way to do this. All you have to do is tell your EA that you expect him or her to ask you questions whenever they come up and you have time to answer.

Say this explicitly. Your EA won’t ask you questions otherwise - they will be too afraid they are bothering you, or they are afraid you will think their question is dumb.

Instead, train your EA to ask you questions during your Start of Day standup sync, during 1-1s, literally any time the two of you are meeting.

With this method, you won’t need an async Slack channel. They’ll just ask when you’re not in deep work. Their questions will get answered, they will understand you more, and that’s when they will be able to begin making decisions on your behalf as if they were you. And that’s when the real magic begins.


If you do these four things (giving them complete, unfettered access; communicating feedback frequently and kindly; sharing an action tracker; and making reaching you easy), you will hyper-accelerate the trust you both have in each other.

Your EA will be the most effective at their job, and feel confident in their ability to help you in the way you need to.

To go a step further, feel free to send this write-up to your EA - it teaches them how to build their trust with you.

Please let me know if there are other ways you’ve found helpful to build your relationship with your EA. I am always interested in learning what works for you.

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Regina Gerbeaux

Who’s Regina Gerbeaux?

Regina Gerbeaux (@_rpgbx) is the executive coach to some of the fastest scaling startups in the world. She is also a founder currently interested in the food delivery and logistics space.

Regina was the first person trained by Matt Mochary (executive coach to the CEOs of Coinbase, Brex, and many more) in the Mochary Method Curriculum.

Her tactical templates and operational write-ups have been referenced and used by fast-scaling companies, including BioRender, CoreDB, dYdX, and many more.

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