Navigating Sticky Conversations: The Importance of Being Open & Honest with Your Executive Assistant

As a CEO or executive, your relationship with your Executive Assistant (EA) is a cornerstone of your daily operations. But how often do you take the time to have an open and honest conversation with them?

It’s no secret that having open and honest conversations with your EA can be tough. As a professional, you might know when something isn’t working, but since it’s directly related to your personal support voice it can sometimes feel uncomfortable. Maybe you’re worried about offending them or think, “I’ll just deal with this myself—it’s easier.” This internal dialogue, while common, creates a communication gap that can hinder your working relationship.

Why Do We Avoid Being Honest?

Let’s face it: honesty in professional relationships, especially with an EA, can feel vulnerable. You might find yourself thinking:

• “If I tell them I’m not happy with how they handled something, will they take it personally?”
• “They’re already busy—should I really add more to their plate by bringing this up?”
• “What if I’m the problem? Maybe I didn’t explain my expectations well enough.”

In these moments, it’s easier to stay quiet rather than risk discomfort. But silence doesn’t lead to improvement—it just leads to missed opportunities for growth, both for you and your EA.?

Let’s break down how to have these important conversations.?

The Right Time to Be Honest

The truth is, open and honest discussions are not confined to the start of your working relationship. The earlier you address concerns, the less likely they are to snowball into larger issues.?

Picture this scenario… You’ve noticed your EA has been missing deadlines for project updates and it’s starting to affect your schedule. Your first thought is, “Maybe I didn’t make the deadlines clear enough,” or “I don’t want to come across as demanding.” So, you push it aside.

The problem here is that avoidance only creates frustration.?

Instead, try scheduling a small block of time at the end of each week to review tasks with your EA. This regular check-in provides a space for honest feedback without it feeling confrontational. You might say:

"Hey, I’ve noticed that a few deadlines were missed this week. Can we discuss what happened so we can make sure we’re aligned going forward?"

By addressing it early and regularly, it becomes less about criticism and more about refining processes together. Making honesty part of your weekly rhythm helps avoid misunderstandings while keeping the dialogue open.

Tune in for Part 2 which will include more tips next week!?