How to Onboard an Executive Assistant [Complete Guide]

You’ve found the perfect executive assistant. The interviews went well, references checked out, and you’re excited about finally getting some help.

But here’s where most executives stumble: the onboarding process.

Poor onboarding is like buying a Ferrari and never learning how to drive it. You end up frustrated, your new EA feels lost, and that investment you made doesn’t pay off.

We’ve seen this happen countless times over our 16+ years supporting C-suite executives. And we’re here to solve this problem today!

TL;DR – Executive Assistant Onboarding Checklist

Here’s your executive assistant onboarding process in a nutshell:

• Share all of your preferences, contacts, and procedures (we call it “executive’s Bible”)
• Grant access to email, calendar, and essential systems
• Introduce them to your team, clients, and key stakeholders
• Begin delegation with simple, low-risk tasks
• Hold weekly check-ins for the first month, then monthly reviews

The goal is simple: cut the learning curve down by front-loading as much information as possible about your preferences, your world (both business and personal), and your objectives.

Pro Tip: You can download our free guide “The 29-Hour Work Day” to discover the proven framework for maximizing executive assistant relationships from day one!

Who Needs an Executive Assistant?

Not every business leader needs an executive assistant, but if any of these sound familiar, you’re probably ready to work with an executive assistant:

• You’re spending time on $50-per-hour tasks when your time is worth $200+ per hour
• Important emails sit in your inbox for days because you’re too busy to respond
• You’re constantly double or triple-booked
• Administrative work prevents you from focusing on strategy and growth
• You find yourself thinking, “I wish I had a clone”

Executives should consider hiring an EA as one of their first key hires. The reason is simple: time arbitrage.

An EA gives you back your most precious resource—time—so you can focus on what only you can do.

Certain types of professionals see the greatest impact from executive assistant support:

• C-Suite Executives: Need comprehensive support for strategic decisions, investor relations, and complex calendar management. Executive assistants to CEOs handle high-stakes communications and serve as trusted advisors.
• Managing Directors: Require specialized support for client relationships, deal management, and extensive travel coordination. An executive assistant to a managing director becomes essential for maintaining productivity at this level.
• Small Business Owners: Often trapped in daily operations when they should focus on growth and strategy. The right executive assistant support helps small businesses scale without hiring full-time staff.
• Board Directors: Juggle multiple board commitments requiring meticulous coordination across organizations. Board members need specialized support for meeting schedules and document management.
• High-Net-Worth Individuals: Need seamless business and personal support, including investment coordination and complex travel logistics across multiple properties.

How to Onboard an Executive Assistant

Here’s how to turn your new hire into an effective partner. The key is integrating your executive assistant into your world from the very beginning.

1. Create Your Executive’s Bible

Think of this as your instruction manual. This document should include basically any and all information you can provide in the initial onboarding push.

We call it the “executive’s Bible” because it becomes their go-to reference for making decisions on your behalf.

Your executive’s Bible should cover:

Personal Information:

• Contact info for family members, including birthdays and anniversaries
• Preferred doctors, dentists, and other service providers
• Home address(es) and any vacation properties
• Emergency contacts and important relationships

Business Preferences:

• Your daily rhythm and peak productivity hours
• Meeting preferences (back-to-back vs. buffer time)
• Travel preferences (airline seats, hotel chains, dietary restrictions)
• Communication style and priorities (Email vs. text vs. phone for different urgency levels)

Key Contacts:

• Board members and stakeholders
• Most important clients and prospects
• Direct reports and their responsibilities
• Vendors and service providers you work with regularly
• Family members, close relatives, and friends you regularly hang out with

Standard Operating Procedures:

• Birthday and special occasion handling (gifts, cards, celebrations)
• Email signature and communication templates
• How you like calendar invites formatted
• Family calendar and priority management
• Personal appointment scheduling rules
• Expense reporting procedures
• Travel booking requirements
• Home services coordination

2. Grant Appropriate Access

This step requires trust, but it’s essential for your EA to be effective.

They need access to:

• Email: Full access to read, respond, and manage your inbox
• Calendar: Complete control to schedule, reschedule, and manage appointments
• Contact Management: Your full contact database with relationship context
• Financial Information: Credit card details for bookings and business expenses
• Travel Systems: Access to your preferred booking platforms and loyalty accounts

You’re essentially giving them access to represent you. This level of trust enables them to use their superpowers effectively.

3. Schedule Intensive Onboarding Sessions

Plan for dedicated onboarding meetings during your EA’s first few weeks.

These aren’t casual check-ins—they’re intensive training sessions where you download everything they need to know.

Week	Focus Area	Key Activities
Week 1	Fundamentals	– Review the executive’s Bible together – Walk through your typical day and week – Explain your communication preferences and style – Set expectations for responsiveness and availability
Week 2	Systems and Processes	– Train them on all the platforms and tools you use – Show them how you like things formatted and organized – Practice common scenarios like scheduling conflicts – Begin small delegations to test understanding
Week 3	Relationship Building	– Introduce them to your team and key stakeholders – Explain the dynamics and personalities they’ll work with – Practice your “velvet no” for managing requests – Start involving them in routine communications

4. Use Technology to Speed Up Training

Don’t reinvent the wheel every time you need to show your EA something.

Use these tools to create reusable training materials:

• Screen Recordings: Use Loom or Zoom to record yourself doing tasks
• Video Explanations: Create short videos explaining your thought process
• Template Creation: Build templates for common requests and responses (Canva presentation templates, email signatures, meeting agendas)
• Process Documentation: Write down step-by-step procedures for recurring tasks

These resources become invaluable references that your EA can return to instead of asking the same questions repeatedly.

Mistakes to Avoid When Onboarding an Executive Assistant

Even well-intentioned executives can sabotage their EA’s success during onboarding.

Here are the most common pitfalls to avoid:

• The “I Can Do It Faster Myself” Trap: Yes, you probably can book that flight faster than explaining your preferences. But think about the compounding nature of time. If you spend 20 minutes training your EA to book travel exactly how you like it, you’ll never have to book travel again. Over a year, that 20-minute investment saves you dozens of hours.
• The “Testing Period” Trap: Many executives treat the first few months as an extended interview, withholding meaningful work while their assistant proves themselves with simple tasks. If you’ve hired an experienced EA, leverage their expertise from day one rather than wasting it.
• Avoiding the Trust Leap: Many executives want their EA to earn trust over time through small tasks. We recommend trusting first and pulling back if necessary, rather than slowly building trust. This approach unlocks your EA’s potential much faster.
• Information Hoarding: Executives often underestimate how much context their assistant needs to be effective. Share strategic information, upcoming challenges, and long-term objectives so your assistant can anticipate needs rather than just react to requests.
• Micromanagement Disguised as Training: There’s a difference between providing clear guidelines and hovering over every decision. Create standard operating procedures for recurring activities, then step back and let your assistant execute without constant approval.
• Rushing the Process: Some executives try to throw everything at their EA immediately, thinking they’ll figure it out. This overwhelms your new team member and leads to mistakes that erode trust early in the relationship. Remember, even the best executive assistants make mistakes when they’re overwhelmed or lack proper guidance.
• Neglecting Personal Tasks: Many executives create artificial boundaries around personal work, but this limits time arbitrage potential. Rescheduling a dental appointment takes the same skills as coordinating a client meeting. Why handle one yourself while delegating the other?
• Not Putting in the Time: If you don’t invest time upfront, your EA won’t feel confident making decisions on your behalf or creating that shorthand communication where they know what you mean when you say X, Y, and Z.

Best Practices for Supporting a New Executive Assistant

Here are proven strategies to partner with your EA better:

1. Provide Context, Not Just Tasks

Don’t just tell your EA what to do.

Explain why you’re doing it and how it fits into bigger objectives. Even if they don’t need the context to complete the task, having it helps them immensely down the road.

For example, don’t just say “Schedule a call with Sarah.”

Instead, say “Schedule a call with Sarah because we’re considering her for the VP role, and I want to gauge her interest before the board meeting next week.”

2. Include Them in Communications

Copy your EA on emails even when they don’t have specific action items. This helps them understand relationships, priorities, and upcoming needs.

The more context they have, the better they can anticipate your needs.

3. Add Their Contact Info to Your Email Signature

Your EA’s effectiveness depends heavily on how others perceive and interact with them.

This simple step signals to everyone that your EA is an important team member and the right person to contact for many requests. It also helps establish them as your single point of contact.

If you don’t properly introduce them to your team, they’ll struggle to get cooperation and respect.

4. Establish Clear Communication Protocols

Set up a communication hierarchy so your EA knows when to interrupt you and when things can wait:

• Phone Call: Urgent, handle immediately
• Text Message or Slack: Important, respond within an hour
• Email: Standard priority, can wait until next business day
• Email + Text: High-priority email that needs immediate attention

5. Schedule Regular Check-ins

During the first month, meet weekly to discuss what’s working, what isn’t, and what adjustments need to be made.

Don’t micromanage, but course-correct early before small issues become big problems.
After the first month, shift to monthly check-ins, then quarterly reviews as the relationship matures.

How ProAssisting Can Help You

At ProAssisting, we’ve refined the executive assistant onboarding process through our work with executives over the years.

We provide fractional executive assistant support, which means you get an experienced EA for 50-80% less than hiring in-house.

Our ProAssistants come pre-trained in the fundamentals of executive support and understand the five performance multipliers:

• Business partner,
• Chief of staff,
• Project manager,
• Assistant/scheduler, and
• Personal assistant.

This dramatically reduces your onboarding time while ensuring you get world-class support.

What sets our ProAssistants apart:

• Proven Experience: Minimum 5 years supporting executives at globally recognized brands (J.Crew, Fidelity, Target, Oracle, JP Morgan Chase & Co.)
• Elite Caliber: Capable of commanding six-figure salaries in major metropolitan areas
• Dedicated Support: Maximum of three clients per ProAssistant for focused attention
• Quick Response: Typically respond within an hour during business hours

If you’re ready to work with a proven US-based EA, get started with ProAssisting.

Frequently Asked Questions (FAQs)

Here are the most common questions executives ask about onboarding and working with executive assistants.

What Are the Key Qualities of a Great Executive Assistant?

The best executive assistants combine hard skills with exceptional soft skills.

Hard skills include technology proficiency, organization, and attention to detail. But it’s the soft skills, emotional intelligence, communication abilities, and work ethic that separate good EAs from great ones.

Look for someone who has demonstrated longevity in previous EA roles, shows genuine interest in supporting executives, and has the poise to represent you professionally in any situation.

How Much Does It Cost to Hire an Executive Assistant?

The costs of hiring an executive assistant vary based on location, experience, and employment structure:

• Full-time executive assistants in major metropolitan areas typically command $85,000-$150,000+ annually, plus benefits and equipment costs.
• Remote executive assistants offer more flexibility, with experienced professionals charging $35-150 per hour for contract work.

ProAssisting’s monthly retainer model starts at $3,300 for one-third of a ProAssistant’s capacity, providing elite-level support without full-time commitment.

How Do I Choose Between a Virtual and In-House EA?

The decision depends on your specific needs:

Choose in-house vs. remote support if you:

• Need someone physically present for meetings and events
• Handle confidential materials that require in-person security
• Prefer face-to-face collaboration
• Have the budget for a full-time salary plus benefits

Choose remote/virtual if you:

• Want access to a broader talent pool
• Need flexibility in hours and availability
• Want to reduce overhead costs
• Are comfortable with digital communication and collaboration

What Tasks Should I Delegate to an EA?

Delegate anything that doesn’t require your specific expertise or decision-making authority.

Primary tasks to delegate to your executive assistant include:

• Calendar management,
• Inbox management
• Travel coordination,
• Research projects,
• Vendor management,
• Meeting preparation,
• Routine correspondence.

Expand delegation as trust builds. Many executives eventually rely on their assistants for preliminary screening of opportunities, drafting communications on their behalf, and coordinating with other executive team members.

Conclusion

The difference between a successful EA partnership and a frustrating one comes down to how you handle those first few weeks. Executives who invest in proper onboarding see immediate returns and build relationships that last for years.

ProAssisting eliminates the guesswork from this process. We’re extremely selective about who becomes a ProAssistant, admitting less than 5% of applicants. Our three-to-one executive-to-assistant ratio ensures dedicated attention.

Plus, 75% of your monthly retainer goes directly to your ProAssistant, ensuring they’re fairly compensated and committed to your success long-term.

Schedule a free consultation with Co-founder Ethan Bull to determine if we’re the right fit for your business.