Most executive assistant advice online reads like a collection of productivity hacks that sound great in theory but fall apart in practice.
After years of supporting billion-dollar company leaders and training hundreds of assistants at ProAssisting Academy, we’ve learned that real success comes from understanding what makes an exceptional assistant, not chasing the latest productivity hack.
If you’re considering executive assistant support or want to maximize your current partnership, let’s cut through the noise and focus on what actually drives results.
TL;DR – Executive Assistant Tips and Tricks
Here are the executive assistant best practices that high-performing executives should look for:
- Ensure your assistant gets principal buy-in before implementing any new system
- Prioritize assistants who demonstrate speed in communication and persistent follow-up
- Look for someone who thinks three steps ahead using “and then what?” reasoning
- Value emotional intelligence and soft skills over technical tricks
- Build trust through consistent execution of small tasks first
- Choose industry-agnostic assistants rather than sector specialists
- Develop shorthand communication with your assistant over time
The best executive assistant support centers around one core principle: giving you back time while representing you at the highest professional level.
Need an executive assistant who already understands these principles? ProAssisting connects you with experienced EAs who know what truly matters in executive support.
Schedule a consultation to see how our fractional model delivers premium assistance for 50–80% less than hiring in-house, without the overhead of a full-time hire.
What Most Executive Assistant Tips Get Wrong
The biggest problem with most executive assistant advice is that it assumes assistants can implement systems in isolation.
Here’s what actually happens when you hire someone who follows generic tips without understanding your specific needs.
- Your new assistant reads about a brilliant CEO schedule management system online.
- They spend hours setting it up, excited to show you how organized everything will be.
- When they present it to you, you’re confused.
- You don’t understand the new system, you don’t want to learn it.
- And suddenly their “improvement” has created more work for both of you!
This scenario plays out constantly because most tips for executive assistants ignore a fundamental truth: if your assistant doesn’t get your buy-in to work in a specific manner, their efforts won’t create value. Period.
You have your own rhythms, preferences, and decision-making patterns.
You might prefer back-to-back meetings, or you might need fifteen-minute buffers between appointments. You might want immediate email alerts, or you might prefer your assistant to filter everything first.
The approach that works brilliantly for one executive might be completely wrong for you.
The most effective executive assistant advice starts with understanding your specific needs, then adapting systems to serve those requirements. Not the other way around.
The Hidden Value Executives Expect But Rarely Voice
When hiring an executive assistant, you probably focus on obvious qualifications like experience and technical skills. But there are hidden expectations that separate adequate assistants from exceptional ones.
Understanding these unspoken requirements is crucial for making the right hiring decision.
- Speed Is Everything: Top executives value assistants who respond quickly and move fast. Not just adequately—genuinely fast. When you send a request at 2 PM, you want to see progress by 2:30 PM, not tomorrow morning. This doesn’t mean accepting sloppy work; it means finding someone who operates with efficient urgency.
- Polite Persistence Delivers Results: When your assistant needs information from external parties, vendors, or internal team members, you want someone who gets answers. You don’t want to hear “I’m still waiting for them to get back to me” three days later. You want someone who makes multiple attempts and finds creative ways to get the information you need.
- Poise and Confidentiality Are Non-Negotiable: You need an assistant with enough emotional intelligence to know when they’re overstepping or asking questions they should research themselves. You want someone who can represent you professionally in any situation, from interacting with your most important clients to managing sensitive family matters. Someone who recognizes when you need space after a difficult board call.
- They Should Enhance Your Reputation, Not Compete for Attention: Exceptional assistants understand their role is to make you look good, not to showcase their own abilities. You want someone who ensures everything runs smoothly so you can focus on high-level decisions and strategy.
These hidden expectations form the foundation of truly valuable executive support. An assistant who masters these areas becomes a genuine force multiplier for your productivity.
8 Executive Assistant Tips That Actually Matter
If you’re looking to hire an executive assistant or improve your current partnership, these strategies will help you get real results.
1. Look for “And Then What?” Thinking
The best executive assistants think through entire processes, not just individual tasks. When you ask them to arrange a business trip, they don’t just book your flight.
They put themselves in your shoes and think through all the steps: “And then what?”
- If we book this flight and send you here, and then what?
- You’ll need ground transportation to get to the meeting. And then what?
- Where exactly is the meeting location? Is the hotel around the corner, and can you check in early if needed? And then what?
- Once the meeting wraps up, will you need to walk three or four blocks with your luggage to get back to the hotel, or can you go directly to the airport?
This type of systematic thinking means fewer last-minute surprises and smoother execution of everything you delegate.
Look for assistants who naturally put themselves in your position and anticipate what happens next at every step of the process.
2. Choose Someone Who Builds Trust Through Execution
You can’t expect an assistant to become your strategic partner immediately. The best assistants understand that trust builds through consistently executing smaller tasks without mistakes.
- They handle scheduling perfectly for weeks.
- They manage travel arrangements flawlessly.
- They prove reliability through consistent performance.
Once they’ve demonstrated competence with foundational work, they naturally earn opportunities for larger projects and more decision-making authority.
Assistants who try to skip ahead to strategic work before proving themselves with execution often damage the relationship.
3. Develop Shorthand Communication
One of the most valuable aspects of a mature executive-assistant partnership isn’t a tool or system—it’s developing shorthand communication. This happens over time as your assistant learns your preferences, priorities, and thinking patterns.
Eventually, you reach a point where you can say three words, and your assistant understands exactly what you need. A six-minute conversation can address twelve items on your to-do list because they know what you mean without lengthy explanations.
This efficiency develops through consistent interaction and an assistant who pays attention to how you approach different situations. The best assistants document your preferences and build mental databases of your decision-making patterns.
4. Prioritize Emotional Intelligence Over Technical Skills
The most important factor in choosing an executive assistant is emphasizing emotional intelligence and soft skills over technical abilities.
We recommend a 51:49 ratio—51% soft skills, 49% hard skills.
Technical skills can be taught quickly. Emotional intelligence and the ability to read situations, adapt communication styles, and represent you professionally—these capabilities are much harder to develop and far more valuable.
- Can they have comfortable conversations with other executives?
- Can they handle frustrated clients with grace?
- Can they read the room and know when to speak up versus when to stay quiet?
These abilities matter more than knowing every feature of the latest project management software.
5. Choose Industry-Agnostic Talent
One of the biggest mistakes executives make is thinking they need an assistant who specializes in their industry.
Great executive assistants are industry and principal-agnostic. Their core skills—organization, communication, project management, relationship building—transfer across any sector.
Sure, working in finance means understanding market rhythms. Healthcare means knowing about patient privacy. But these are surface-level adaptations. The fundamental skills of exceptional assistance remain the same whether you’re running a tech company or a hedge fund.
This mindset also makes your assistant more valuable long-term. They can adapt as your business evolves or work effectively with different leaders in your organization.
6. Expect Proactive Documentation
Don’t expect to hand your assistant a manual for how you work. The best assistants create one as they learn your preferences. They document how you like your calendar formatted, your travel preferences, your communication style, and your decision-making patterns.
This documentation serves two purposes: it helps them stay consistent in their support, and it becomes valuable if they ever need to train someone else or if you need to explain your working style to other team members.
7. Insist on Context-Rich Calendar Management
Your calendar entries should never just say “John/Sarah call 3 pm.”
Instead, your EA should specify “John to call Sarah at 3 pm regarding Q2 budget review” and include the phone number plus relevant background.
They should attach related email threads directly to calendar invites. This saves you from scrambling for information minutes before important calls.
8. Focus on Time Multiplication, Not Task Completion
The ultimate goal is to multiply your available time. Every action your assistant takes should be evaluated through this lens:
- Does this save you time?
- Does this prevent you from having to think about this issue again?
Sometimes this means they’ll take longer on a task upfront to create a system that saves time later. Sometimes it means having conversations with team members so you don’t need to.
The best assistants always think about the bigger picture of time management, not only checking items off lists.
Building Executive Support on Capability, Not Shortcuts
The foundation of exceptional executive support rests on having an EA who delivers consistently, not one who knows the latest productivity app.
As an executive, you need assistants who write everything down, never let details slip through cracks, and move with urgency on your behalf.
This means finding someone with what we call “type A reliability”—the ability to take your directives and act quickly without losing accuracy.
- When you mention something once, they remember it.
- When you ask for something, they’ve already started working on it.
They don’t need to be psychic for that; paying attention and taking initiative is the key here.
The path to working effectively with an executive assistant is through partnering with someone who has fundamental capabilities that compound over time.
- Each successful interaction teaches them more about your preferences.
- Each completed project adds to their institutional knowledge about your business.
- Each crisis they navigate smoothly increases your trust in them.
For executives seeking this level of support without the commitment of a full-time hire, the fractional executive assistants of ProAssisting offer an ideal solution. These experienced professionals can perform upwards of 95% of the functions of an on-site EA while working remotely to provide flexible, high-level support.
The most successful executive-EA relationships develop into true partnerships where both parties understand their roles and excel within them. This takes time, patience, and mutual respect.
No amount of executive assistant organization tips can replace the value of this foundational relationship.
Ready to work with an EA who focuses on real capability rather than surface-level tricks? Discover how ProAssisting can match you with an experienced assistant who understands what you need.
Frequently Asked Questions (FAQs)
Let’s address common questions executives have about implementing effective assistant partnerships.
Can Following Too Many Executive Assistant Tips Backfire?
Absolutely. We see this frequently when executives hire assistants who try to implement too many systems at once. Effective assistants need continued exposure to your working style before they can serve you efficiently.
They should try approaches gradually, get feedback, and adapt based on your preferences.
Why Is Proactivity Essential for Executive Assistants?
Proactivity—looking around corners and thinking three steps ahead—is what every executive wants their assistant to be, hands down.
But onboarding an assistant is a dimmer switch, not a light switch. You need to take time to get them on the same page so they have context around the tasks, projects, and responsibilities you give them.
Once they understand your patterns, that partnership turns into shorthand communication—both verbal and written. Eventually, you’ll be able to say, “I want this done like we did it in February with XYZ Corporation. Let me know what you come up with.”
Should Executive Assistants Specialize in an Industry?
No, great executive assistants are industry agnostic. While sector experience can be helpful for understanding business rhythms and terminology, the core skills of executive assistance transfer across all industries.
You’re better off finding someone with proven executive-level experience who can quickly adapt to your industry than settling for someone with sector knowledge but limited high-level support skills.
What Are the Most Overrated Executive Assistant Tips?
Many popular tips focus on tools and systems rather than core competencies. Color-coding systems, elaborate filing structures, and complex project management software often create more work than they save.
The most overrated advice usually involves forcing standardization where flexibility would serve you better.
Another overrated category includes tips that promise to make your EA “indispensable” through some secret technique. The reality is that no one is truly indispensable. Focus instead on finding an EA who is consistently excellent at the fundamentals that matter to your success.
Conclusion
The difference between adequate and exceptional executive assistant support comes from the quality of the partnership you build.
When you find someone who truly understands your business rhythms and can represent you at the highest level, you gain more than an assistant; you gain a strategic advantage.
ProAssisting bridges the gap between expensive full-time hires and unreliable virtual assistants. Our ProAssistants bring 5-20+ years of elite executive experience that commands six-figure salaries in major cities, delivered through a fractional model.
Starting at $3,300 monthly, you get US-based professionals who’ve supported leaders at globally recognized brands like J.Crew, Oracle, and JPMorganChase. We pass 75% of your monthly retainer directly to your ProAssistant, ensuring we attract and retain top talent for long-term partnerships.
Schedule your consultation today and discover how a ProAssistant can transform your productivity.
