How to Manage an Anxious Assistant
We’ve spent years working with executive assistants, and we’ve seen one thing come up again and again: executive assistant anxiety is common in this role. But few executives are prepared for how to navigate and manage an anxious assistant, especially when that anxiety starts to affect them.
You may have an assistant who cares deeply, anticipates well, and wants to get everything right—but who also second-guesses decisions, spirals after feedback, or overcommunicates in a way that takes up more of your time than it saves. Managing an anxious assistant can feel overwhelming when you’re trying to balance compassion with productivity.
You want to be kind. You want to support them. But you’re also leading a business, juggling a thousand priorities, and your job isn’t to be someone’s emotional manager.
So here’s the truth we wish more leaders heard: You can support your assistant without taking on their anxiety. You can be empathetic without over-functioning. You can care without carrying. And if you want a sustainable relationship with your assistant, you’ll need to learn the art of working with an anxious assistant effectively.
Recognizing the Signs: Where Executive Assistant Anxiety Shows Up
An anxious assistant doesn’t always look anxious. It doesn’t always sound like “I’m worried.” Sometimes the signs are subtle, showing up in behavioral patterns that might seem like perfectionism or dedication at first glance.
Common signs include:
- Constantly double-checking decisions, even on routine tasks
- Over-apologizing or needing frequent reassurance from you
- Freezing or avoiding tasks when they’re unsure of the outcome
- Replaying conversations or fearing they’ve “messed up” something minor
- Being overly responsive or overexplaining in emails and communications
- Taking on extra work to prove their value or competence
How Assistant Anxiety Impacts Your Leadership
When you’re working with an anxious assistant, the effects ripple into your daily operations in ways you might not immediately recognize:
- More interruptions throughout your day as they seek confirmation
- Meetings that feel emotionally heavy or require more energy to navigate
- A tendency to feel like you need to tiptoe around feedback
- An instinct to take work back instead of pushing it forward
- Increased mental load as you anticipate their reactions to decisions
Recognizing these patterns is the first step in developing strategies to manage an anxious assistant without compromising your own effectiveness.
So what do you do? You lead with boundaries.
The Foundation of Working with an Anxious Assistant: Boundaries as Structure
Your assistant’s anxiety is not yours to solve. But your leadership can either calm the chaos or amplify it. Successfully handling an anxious assistant requires understanding that boundaries aren’t punishment—they’re the framework that allows both of you to thrive.
This is where boundaries come in. Not as walls, but as structure. Not as distance, but as clarity. When you’re consistent with boundaries, you create predictability that actually helps reduce executive assistant anxiety over time.
When they spiral after feedback, don’t walk it back. Stay calm, consistent, and constructive. Say: “This isn’t a failure, it’s something to learn from. We’re giving you this because we trust you can adjust.”
When they over-check or over-communicate, acknowledge their care, then redirect it: “You don’t need to check with us on these, this is yours to own.”
When they vent emotionally, you can listen, but don’t absorb: “Thanks for sharing that, let’s focus on what needs to happen next.”
When you feel the emotional weight, notice it. Take a breath. Ask: “Is this mine to carry?” Often, the answer is no.
Boundaries let you model the regulation they may not yet have.
Boundaries create space for clarity, not chaos.
Boundaries make room for growth.
Practical Strategies for Supporting Your Assistant (Without Over-Helping)
If you want to support your assistant without slipping into the role of emotional caretaker, here are practices that actually help when managing an anxious assistant:
Be steady with your feedback. Don’t withhold it out of fear you’ll upset them. Share it clearly, calmly, and regularly. This builds resilience over time and helps them understand that feedback is normal, not catastrophic.
Clarify what they own. Anxiety thrives in ambiguity. When assistants know their lane clearly, they’re less likely to spin in uncertainty. Create detailed job descriptions, decision-making frameworks, and clear escalation paths.
Model boundaries for yourself. Take breaks. Say no. End meetings on time. When you model healthy pacing, they’ll feel less pressure to overextend. Your behavior sets the tone for the entire working relationship.
Encourage, but don’t rescue. When they hit a wall, don’t solve it for them—coach them through it. Confidence comes from working through uncertainty, not being protected from it. Ask guiding questions rather than providing immediate solutions.
Redirect emotional energy toward action. It’s easy to get stuck in “what-if” thinking. Instead, ask: “What’s the next step you can take?” Or, “What do you need from us to move forward?” This helps break the anxiety cycle.
Creating Systems That Support Success
Beyond individual interactions, managing an anxious assistant effectively requires creating systems and processes that reduce uncertainty:
Establish regular check-ins. Schedule brief, consistent meetings to review priorities and address concerns before they escalate. This prevents the constant interruptions that can drain your energy.
Document procedures and preferences. The more your assistant knows about your preferences and standard procedures, the less they’ll need to guess or worry about making mistakes.
Create decision-making guidelines. Help them understand what decisions they can make independently, what requires consultation, and what needs your direct approval. Clear authority levels reduce anxiety-inducing ambiguity.
Implement feedback loops. Regular, structured feedback helps normalize the process and reduces the emotional intensity around performance discussions.
The Long-Term Benefits of Managing an Anxious Assistant Well
This isn’t about fixing someone. It’s about building a working relationship that works for you both. Because when an assistant feels calm, clear, and empowered, they’re able to support you at a whole different level. And when you feel protected from emotional overflow, you can lead from a place of focus and strength.
The investment you make in learning how to manage an anxious assistant pays dividends in several ways:
Increased productivity as interruptions decrease and independent decision-making increases. Improved job satisfaction for both of you as stress levels normalize and communication becomes more efficient. Better business outcomes as your assistant becomes more confident in anticipating needs and taking initiative.
Enhanced team dynamics as your assistant’s anxiety decreases and their positive contributions become more visible to others. Reduced turnover costs as your assistant feels supported and valued rather than constantly stressed about performance.
When to Seek Additional Support
Sometimes, despite your best efforts at managing an anxious assistant, additional resources may be needed. Consider recommending professional development opportunities, executive coaching, or employee assistance programs when anxiety significantly impacts work performance.
Remember that your role is to create a supportive work environment, not to serve as a mental health professional. Knowing the difference between supportive leadership and therapeutic intervention is crucial for maintaining appropriate boundaries.
Managing an anxious assistant requires intentional leadership that balances care with clear boundaries. You don’t have to carry their worry—you just have to lead with empathy and clarity.
If you’re working with an anxious assistant right now, remember: sustainable support means creating structure that helps both of you thrive. The investment in clear communication and consistent boundaries pays dividends in reduced stress and improved productivity for your entire team.
