The Importance of Regular One-on-Ones with Your Executive Assistant
Behind every great leader is an effective support system, and few roles influence your success more than your Executive Assistant. Yet many leaders overlook one simple habit that strengthens this working relationship: regular one-on-one (1:1) meetings.
Many leaders hold regular one-on-ones with their direct reports, but not with the person who supports them most closely: their Executive Assistant. It’s easy to assume that quick messages or daily check-ins are enough. But without regular meetings with your Executive Assistant, small misalignments can easily snowball into inefficiencies, misunderstandings, or missed opportunities.
Your Executive Assistant isn’t just administrative support, they’re a strategic partner who helps you operate at your highest level. Setting aside time for consistent 1:1s builds the trust and alignment that turn this partnership into one of your strongest leadership assets.
When you make these meetings non-negotiable, you’re choosing to lead with clarity and build a partnership that keeps you both aligned.
Why One-on-Ones with Your Executive Assistant Matter
Regular one-on-ones with your Executive Assistant aren’t just check-ins, they’re a leadership habit that drives clarity, trust, and stronger performance.
Keeps Priorities Aligned
Your priorities can shift weekly, and without structured touchpoints, your Executive Assistant is left guessing what’s most important. A consistent 1:1 ensures you’re both working toward the same goals. It gives your Executive Assistant a clear view of what matters most this week, not just what’s urgent at the moment.
Builds Trust
An Executive Assistant can only anticipate your needs when they feel comfortable asking questions, sharing ideas, and clarifying expectations. A recurring 1:1 creates that space. It signals that you value their perspective and gives them the confidence to bring forward insights that can make your workday smoother and more strategic.
Encourages Proactive Support
When communication is limited to quick messages or reactive updates, your Executive Assistant can’t plan ahead effectively. Regular meetings open the door for proactive problem-solving before issues surface. It’s where they can share what’s working, flag potential challenges, and suggest improvements that make your operations run more efficiently.
Consistent 1:1s strengthen the foundation of your partnership. They’re not about adding another meeting to your calendar. They’re about creating alignment that saves time, reduces friction, and helps both of you perform at your best.
Pro Tip: Treat your 1:1 as a dedicated space to realign priorities, not as an afterthought to squeeze between meetings. Protecting this time pays off in fewer surprises and smoother weeks.
How Often Should You Meet with Your Executive Assistant?
Leaders often ask, “How often should I meet with my Executive Assistant?” The answer is simple: often enough to stay aligned, but not so often that it disrupts momentum.
For most executives, a weekly 1:1 is the sweet spot. It creates a dependable touchpoint to review priorities, upcoming deadlines, and new developments. Once your partnership is well established, bi-weekly meetings can work, too, but if you notice things slipping or communication starting to lag, return to weekly sessions. What matters most isn’t the frequency, it’s the consistency and commitment to keeping that time protected.
A predictable rhythm builds stability. Holding your 1:1 at the same time, on the same day, and with a familiar agenda creates flow for both of you. It also signals that this time is protected and important, not something to squeeze in when things slow down.
Even 30 focused minutes can make a difference. The consistency allows your Executive Assistant to plan ahead, anticipate your needs, and keep projects and schedules on track without constant back-and-forth.
A regular meeting might seem like it’s adding to your to-do list, but it actually saves time in the long run by preventing missteps and keeping priorities clear.
Pro Tip: If you find yourself sending long recap emails or constant quick messages, it’s a sign your 1:1 cadence might need adjusting. A quick weekly touchpoint often prevents the back-and-forth later.
What to Cover in a One-on-One with Your Executive Assistant
A productive one-on-one shouldn’t feel like another status meeting. It’s your space to align, plan ahead, and stay connected on what matters most. Here are a few topics worth covering each time you meet:
Top Priorities: Start by confirming what matters most this week. Clarify where your time should go, what can wait, and what your Executive Assistant should help protect or prioritize.
Calendar Look-Ahead: Review the next 1-2 weeks. Spot potential conflicts, block focus time, and ensure you’re prepared for key meetings or travel.
Follow-Ups: Check in on open action items, pending approvals, or updates from previous discussions. This keeps progress visible and avoids dropped details.
Feedback and Alignment: Take a few minutes to exchange feedback on both sides. What’s working well? What’s causing friction? Open communication helps your partnership evolve smoothly.
Strategic Conversation: Use part of the meeting to think ahead. Ask your Executive Assistant for insights on workflow improvements, tools, or processes that could make things run more efficiently.
Pro Tip: Treat your 1:1 as a two-way feedback loop. The best partnerships thrive on shared insight, not just task updates.
How to Make Your One-on-Ones More Effective
Effective meetings with your Executive Assistant don’t need to be long or formal. What matters is that they’re consistent, intentional, and built around clear communication.
Protect the time. Avoid rescheduling or canceling unless absolutely necessary. When your Executive Assistant sees that this time is non-negotiable, it reinforces the value you place on the partnership.
Come prepared. Bring key decisions, open questions, or blockers that need input. Preparation makes the conversation focused and productive, especially when time is limited.
Start and end with clarity. Begin by asking, “What’s most important this week?” and close with clear next steps or follow-ups. This simple rhythm keeps both of you aligned on outcomes, not just updates.
Make space for ideas. Encourage your Executive Assistant to bring forward observations or improvements, not just status reports. They often see patterns or pain points that can make your systems stronger.
Use a shared document or dashboard. Keeping an ongoing agenda and notes in one place prevents things from slipping through the cracks and helps both of you prepare quickly each week.
Consistency and intention are what make these meetings effective. Over time, your 1:1s will shift from tactical updates to strategic conversations that strengthen your working rhythm and help you both operate at your best.
Pro Tip: End every meeting by confirming who’s doing what next. Clarity is the best way to turn good communication into consistent follow-through.
A Small Habit with Big Impact
Regular one-on-ones with your Executive Assistant might seem like a small commitment, but over time, they transform how you work together. These conversations create space for alignment, trust, and thoughtful decision-making and can strengthen your relationship.
When your Executive Assistant has clarity, they can operate with confidence and foresight. And when you’re aligned, the benefits ripple through your entire workflow: fewer missteps, smoother operations, and more time for meaningful work.
Making these meetings a consistent part of your routine creates clarity, builds trust, and keeps you focused on what matters most. Investing that time strengthens communication and helps both of you bring your best to the work ahead.
