My incredible EA, Tabby, recently moved into a new role at Base. I’m so proud of her, but it also means something new for me: I’m preparing to start fresh with a new EA.
Transitions like this can feel exciting and emotional all at once. You might feel energized by the clean slate, a little anxious about losing momentum, or even unsure where to start. All of that is completely normal.
Over the years, I’ve supported dozens of executives as they’ve hired and onboarded new EAs, and I’ve seen this pattern again and again. The leaders who pause to reflect before diving in always build stronger, more trusting partnerships.
Step One: Reflect before you rebuild
Even a short pause for reflection can make your first 30 days with a new EA smoother and more productive. Here are some of the questions I’m asking myself right now:
- What are the small tasks I dread every day but that still need to happen?
- What are the items I always de-prioritize even though they matter to me?
- What categories of work, if handled by someone else, would make my life 10x less stressful?
- What are my known weaknesses (for me, it’s taking big ideas all the way across the finish line), and how can my EA’s strengths complement them?
- What are the projects I’m deeply attached to doing myself, and can I invite my new EA into any part of those processes?
- At 30 days, what will success look like, and how can I communicate that clearly from the start?
These questions help you move from hiring help to designing a real partnership.
Step Two: Listen to your EA’s perspective
After I shared some of these reflections on LinkedIn, I heard from many EAs about what they wish their executives thought about during transitions. Their insight was incredibly grounding. Here are some of the things they shared:
- “How can I make this person’s day easier from day one?”
- “How do you prefer to receive and share information, and does that change depending on the topic?”
- “What communication rhythm will help us stay aligned and avoid surprises?”
- “Who are the key players my EA should meet early on? What documents, reports, or past presentations can I share so they can learn quickly?”
- “Are there roles that might overlap with my EA, and how can I clarify those boundaries from the start?”
- “What should my EA know about my personal habits, family demands, or communication preferences?”
- “What does a progression in responsibility look like? What’s the ideal state a year from now?”
- “When and how do I expect my EA to push back, and what are the true non-negotiables?”
- “If the house was burning, how are we both getting out?”
- “What is the one thing only I can do, and what’s getting in the way of doing it consistently?”
These are such smart and human questions. They remind us that great partnerships are built on empathy and clarity, not assumptions.
Step Three: Onboard with intention
Once you’ve reflected and gathered perspective, the most powerful thing you can do is slow down. Intentional onboarding is where trust begins.Start with context. Spend the first week showing your EA how your world works before handing things off.
Create a working together guide. Outline how you like to communicate, what matters most to you, and how you prefer feedback.
Prioritize one early win. Give your EA a small project they can own in the first ten days. Early success builds confidence for both of you.
Schedule a 30-day reflection. Ask what’s working, what feels unclear, and how you can make collaboration smoother.
A final thought
Starting fresh with a new EA is one of the best opportunities a leader gets to rethink how they work. It’s a chance to be intentional, to lead with clarity, and to create the kind of partnership that makes both people better.
