You've made the hire. Or you're about to. Either way, a question lingers: How do I actually work with an executive assistant?
The good news is that working with an executive assistant is simpler than most leaders expect.
If you've built your business to the point where hiring an EA is even on the table, you're more prepared than you think. You already know how to communicate, lead, and collaborate. Working with an executive assistant is essentially a working relationship - trust, communication, and systems. Nothing more exotic than that.
But here's what separates good EA relationships from great ones: intentionality. The CEOs who get the most from their assistants aren't necessarily better delegators. They've built better systems.
This guide covers everything you need - whether you're a first-time EA user figuring out where to start, or an experienced leader looking to optimise an existing partnership.
Working effectively with an executive assistant means building a partnership based on trust, clear communication, and structured systems. It's not about offloading tasks - it's about creating leverage. The best EA relationships transform how leaders operate, saving 40-60+ hours monthly while improving decision quality and reducing mental load.
Many first-time users overthink this. They imagine complex delegation formulas or worry about being a "perfect manager."
The truth: if you've brought your business this far, you already have what it takes. You've sold a vision, kept clients happy, built a team. You understand humans. That's the foundation.
Working with an EA is a working relationship. The skills transfer.
Talk to any founder who has an assistant, and you'll rarely hear "I should've waited longer."
What you will hear: "Why didn't I do this sooner?"
According to DonnaPro, the most common regret among clients isn't about delegation challenges or communication issues - it's simply waiting too long to start. Life with an executive assistant is easier. Not perfect, not frictionless, but easier.
Without an EA, you're the bottleneck for everything. With one - even part-time - you still lead, but you're no longer doing it all alone.
One of the top concerns from first-time users:
Valid concerns. Control matters - especially when you've built your business from the ground up.
But here's the mindset shift: you're not losing control. You're designing a system of control that doesn't require your constant presence.
You still have visibility. You still approve. You still lead. But now someone maintains the machine instead of you being chained to it.
Learning how to work with an executive assistant starts with recognising you already have the core skills.
The difference between a mediocre and exceptional EA relationship isn't the assistant - it's the dynamic. Let's make this concrete with an example.
Scenario: Your company is launching a Corporate Social Responsibility initiative. It involves identifying a non-profit partner, organising a kick-off event, developing communications strategy, and setting up employee volunteer opportunities.
The difference comes down to three things: trust, access, and alignment.
A bad dynamic creates inefficiency and frustration. A good one provides support but still requires significant oversight. Only in a great dynamic - where the assistant operates as an empowered extension of you - does true leverage emerge.
Knowing how to work with an executive assistant effectively requires more than good intentions. You need systems.
Here's what works:
Consistency creates rhythm. Schedule a weekly check-in to review priorities, progress, and challenges.
Format that works:
Even leaders who hate meetings find this one worth protecting. It prevents the constant back-and-forth that fragments both your days.
One centralised place tracking every task and project. Not your head. Not scattered across email threads. One source of truth.
Simple structure:
Whether it's a shared spreadsheet, Notion database, or project management tool - the format matters less than the discipline of keeping it updated.
One of the biggest mistakes: assuming your assistant can read your mind.
For every delegated task, communicate:
This takes an extra minute upfront. It saves hours of back-and-forth and rework.
Define what your assistant can handle independently versus what requires your input.
Example boundaries:
Clear boundaries build confidence on both sides. Your assistant knows when to act. You know what to expect.
Simple visual system for your shared task list:
This lets both of you scan quickly and focus on what matters.
For important meetings, record them (with permission). Your assistant can review recordings to:
This ensures nothing gets missed and removes you as the bottleneck for information transfer.
From day one, have your assistant document:
This playbook becomes invaluable - for your assistant's effectiveness, and for continuity if you ever transition to someone new.
DonnaPro is a virtual assistant agency that works exclusively with CEOs and founders, offering a turn-key solution to finding, interviewing, vetting, onboarding, and managing executive assistants. As the world's first agency specialising in part-time, dedicated C-level executive assistants, DonnaPro helps leaders save up to 60 hours per month - freeing them to focus on what matters most.
Book Your Free Strategy SessionUnderstanding how great assistants think helps you build a better partnership.
According to DonnaPro, the most successful client relationships share one trait: the CEO treats the assistant as a partner, not a task-taker. That shift in mindset changes everything.
This mindset kills delegation. Yes, you can do many tasks faster in the short term. But you're sacrificing long-term leverage.
Solution: Treat delegation as investment. Training your assistant on "complex" tasks saves countless hours over time. The first time takes longer. The second time is faster. By the fifth time, it's off your plate forever.
Confusion about what your assistant can or should do creates friction.
Trust doesn't happen overnight.
You're working hard, but on different things.
Miscommunication derails even strong partnerships.
Solution: Establish clear channels for different communication types:
One source of truth for tracking work prevents "I thought you were handling that" moments.
Feedback feels uncomfortable but enables growth.
If you're learning how to work with an executive assistant for the first time, here's a practical roadmap:
By end of month one, you should feel the weight lifting. Not everything is perfect, but the system is taking shape.
When working with an executive assistant for the first time, start with clearly defined recurring tasks before moving to complex projects.
As Harvard Business Review explains, the biggest barrier to effective delegation isn't capability - it's the leader's willingness to let go.
Working with an executive assistant effectively isn't about being a perfect delegator - it's about building systems that compound over time.
It requires:
The leaders who get the most from their EAs aren't delegation experts. They're system builders. They invest the upfront time to create structures that compound over time.
According to DonnaPro, clients who implement these systems consistently report saving 60+ hours monthly - not through working harder, but through building better leverage.
The only real mistake? Waiting too long to start.
Most leaders feel meaningful impact within 2-4 weeks. The first week involves setup and shadowing. Weeks 2-3 bring initial time savings as recurring tasks transfer. By week 4, you should have a working rhythm. Full optimisation - where your EA operates with significant autonomy - typically takes 2-3 months.
Start small. Hand off one recurring task that's clearly defined - weekly scheduling review, expense categorisation, travel booking. Master that handoff, then expand. You'll build delegation skills alongside building the relationship.
More than feels comfortable initially. Calendar access is essential. Email access (at minimum, the ability to view) dramatically increases effectiveness. The more context your EA has, the better they can support you. Start with read access if full access feels too vulnerable, then expand.
Treating delegation as a one-time event rather than an ongoing system. Effective delegation requires upfront investment in communication, context, and feedback. Leaders who throw tasks over the wall without systems end up frustrated with results.
Weekly check-ins create predictable space for alignment, preventing the constant interruptions of ad-hoc communication. They let you course-correct quickly, ensure priorities stay aligned, and build the relationship through regular contact. Most successful EA partnerships protect this time rigorously.
Yes, with appropriate trust-building. Start with less sensitive work. As your EA demonstrates reliability and discretion, expand to more confidential areas. Professional EAs - especially those from agencies like DonnaPro - are trained in handling sensitive information and bound by confidentiality agreements.
This is normal and solvable. The key is explicit communication about preferences. Document your working style in the playbook - when you want to be interrupted, how you prefer information presented, your pet peeves. Good assistants adapt. Regular feedback helps calibrate.
Three signs of a healthy EA relationship: (1) You're spending less time on low-leverage tasks, (2) Things happen without you having to follow up, and (3) Your EA brings solutions, not just problems. If you're still doing most of the work or constantly checking on tasks, something needs adjustment.
Start with high-frequency, clearly-defined tasks: calendar management, email triage, travel booking, expense reports, meeting scheduling. These create immediate time savings and let you build the delegation muscle. More complex project work comes once the foundation is solid.
Agency EAs come pre-trained, often with existing playbooks and systems. The onboarding burden shifts from you to the agency. You also get backup support - if your EA is sick or on holiday, the agency provides coverage. Trade-off: slightly less customisation compared to someone you hire and train directly.
DonnaPro provides dedicated executive assistants specifically trained to support first-time users. Our system includes pre-built playbooks, quality management, and strategic account support - so you're never figuring it out alone.
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