What Does ‘Proactive’ Really Mean in an EA Role?
“I need someone proactive.” You have also thought of this whenever hiring, because this is the core quality in an EA
What Does ‘Proactive’ Really Mean?
If you’ve ever written or read an EA job posting, this phrase appears so often it’s practically mandatory. Right up there with “excellent communication skills” and “ability to work independently,” being “proactive” has become the universal requirement for executive assistants.
However, here’s the problem: everyone claims they want proactivity, but most people struggle actually to define what it looks like in practice. Is it anticipating your coffee order? Scheduling meetings before you ask? Taking initiative on projects? All of the above? None of the above?
After placing hundreds of EAs and watching the best ones work, we’ve realized that “proactive” has become such a buzzword that it’s lost all meaning. Worse, the vague expectation of proactivity often leads to mismatched expectations and frustrated working relationships.
Some founders think proactive means “reads my mind and does what I want before I know I want it.” Others think it means “takes charge of everything so I don’t have to think about it.” Both approaches usually end in disappointment.
The reality is more nuanced and more powerful than either extreme suggests. True proactivity in an EA role isn’t about mind-reading or taking over. It’s about pattern recognition, systems thinking, and strategic anticipation that multiplies your effectiveness without overstepping boundaries.
Let’s break down what proactivity actually means when it works.
The Myth of Mind-Reading Proactivity
First, let’s dispel the biggest misconception: proactive EAs aren’t psychic. They can’t read your mind, predict your every need, or anticipate requests they’ve never encountered before.
This “mind-reading” expectation sets both founders and EAs up for failure. Founders get frustrated when their EA don’t magically know what they need, and EAs get paralyzed trying to guess what actions might be welcomed versus what might overstep.
What Does ‘Proactive’ Really Mean for Executive Assistants?
One founder told us, “I thought proactive meant she’d just figure everything out without me having to explain anything. Turns out, the best proactivity comes after you’ve been very clear about patterns and preferences.”
True proactivity isn’t about mystical intuition, but about pattern recognition applied systematically. A proactive EA notices what you do repeatedly, identifies the underlying principles, and creates systems that anticipate future needs based on past patterns.
For example, if you always need specific reports before board meetings, a truly proactive EA doesn’t just remember to pull those reports. They create a board meeting preparation checklist, build templates that auto-populate with current data, and set up reminders two weeks in advance so there’s time to address any issues.
What Proactivity Looks Like
Real proactivity operates on three levels: tactical anticipation, strategic systems building, and contextual problem-solving.
Here’s how each one works:
Tactical Anticipation: The Foundation Level
This is the most visible form of proactivity. This means anticipating immediate needs based on established patterns.
Instead of: Waiting for you to ask for the quarterly sales report before the leadership meeting.
A proactive EA: Notices you always reference sales data in leadership meetings, builds a template that automatically pulls current numbers, and has it ready three days before each meeting so you have time to review and request changes.
Instead of: Scheduling the client call when you ask for it.
A proactive EA: Sees the client call request, remembers that client calls typically need the contract template and pricing deck, checks if both documents are current, updates them if needed, and schedules everything with all materials ready.
This level of proactivity is about removing friction from routine activities. It’s valuable, but it’s also the baseline, not the ceiling.
Strategic Systems Building: The Leverage Level
This is where proactivity becomes genuinely powerful. Instead of just anticipating individual needs, strategic EAs build systems that eliminate entire categories of future problems.
Instead of: Handling each travel arrangement as a separate project.
A proactive EA: Creates a comprehensive travel system with preferred vendors, template itineraries, automatic expense tracking, and contingency protocols for common problems like flight delays.
Instead of: Managing each client onboarding individually.
A proactive EA: Develops a standardized onboarding sequence with automated touchpoints, document templates, and progress tracking that ensures a consistent experience while reducing manual coordination.
This level turns reactive problem-solving into proactive problem prevention. Instead of constantly putting out fires, you’re building fireproof systems.
Contextual Problem-Solving: The Strategic Level
The highest level of proactivity involves understanding business context well enough to spot opportunities and potential issues before they become obvious.
Instead of: Just booking the conference room for your team meeting.
A proactive EA: Notices the meeting topic involves sensitive client feedback, books a private room instead of the glass-walled conference room, and prepares a backup technical setup in case the discussion runs long.
Instead of: Simply scheduling the vendor call you requested.
A proactive EA: Sees the vendor call, researches the vendor’s recent news, discovers they just announced a price increase, and prepares talking points about contract terms before the call happens.
This level requires a deep understanding of your business priorities and strategic context. It’s where EAs become genuine strategic partners rather than just exceptional task managers.
Is This You? (Signs Your EA Isn’t Actually Proactive)
Many EAs claim to be proactive, but their actions tell a different story. Here are some warning signs that what you’re getting isn’t true proactivity:
They ask the same questions repeatedly.
True proactivity involves learning from past interactions and building systems that eliminate repetitive questions.
Simple requests require detailed instructions every time.
A proactive EA builds on previous experience and adds value to basic requests without being asked.
They wait for you to notice problems.
Proactive EAs spot potential issues early and either solve them independently or flag them before they become urgent.
They complete tasks exactly as requested without considering improvements.
Genuine proactivity involves constantly asking, “How can this be better next time?”
They focus on activity rather than outcomes.
Proactive EAs think about what you’re trying to accomplish, not just what you asked them to do.
They need constant direction on priorities.
A truly proactive EA understands your priorities well enough to make good trade-off decisions when conflicts arise.
The Three Pillars of Genuine Proactivity
After working with hundreds of high-performing EAs, we’ve identified three core capabilities that enable true proactivity:
1. Pattern Recognition and Documentation
The best EAs are natural pattern-spotters. They notice what you do repeatedly, identify the underlying principles, and document systems that can be improved over time.
This is about understanding the logic behind your decisions so they can apply that logic to new situations.
What this looks like: Your EA notices you always ask for competitor analysis before product meetings. Instead of just remembering to do competitor research, they understand you’re trying to position new features strategically. So when you schedule a product meeting, they automatically include not just competitor analysis, but also customer feedback related to competitive positioning and recent market trends that might influence feature priorities.
2. Strategic Context Understanding
What does ‘Proactive really mean when it comes to a skill in an EA? ‘Proactive EAs don’t just execute tasks, but understand how those tasks connect to larger business objectives. This contextual understanding allows them to make better independent decisions and spot opportunities you might miss.
What this looks like: You mention in passing that you’re considering a partnership with a specific company. A strategically proactive EA doesn’t just file that information away. They start monitoring that company’s news, note when their executives speak at conferences you’re attending, and surface relevant information that might influence partnership timing or terms.
3. Systems Thinking and Continuous Improvement
The most valuable EAs think in systems rather than tasks. They’re constantly asking how to make processes better, faster, or more reliable. Every problem they solve becomes a system they build.
What this looks like: Instead of handling each client emergency as a separate crisis, they analyze patterns in client issues, identify common root causes, and build early warning systems that prevent problems before they become emergencies.
How to Develop Proactivity in Your EA Relationship
Proactivity is less about finding the right person and more about creating the right environment for proactive behavior to develop. Here’s how to cultivate it:
Start with Clear Pattern Documentation
Instead of expecting your EA to guess your preferences, be explicit about the patterns you want them to recognize and systematize.
Do this: “I always need these three reports before board meetings. Here’s why each one matters and what I’m looking for in the data.”
Not this: “Be proactive about board meeting prep.”
Share Context, Not Just Tasks
Help your EA understand the strategic reasons behind requests so they can apply that logic to future situations.
Do this: “I want this client call scheduled because we’re trying to gauge their interest in the new feature before we commit development resources.”
Not this: “Schedule a call with this client.”
Encourage Systematic Improvements
Create space for your EA to suggest process improvements and implement better systems.
Do this: “What patterns do you notice in how we handle these requests? How could we make this more efficient?”
Not this: “Just keep doing what you’re doing.”
Define Decision-Making Authority Clearly
Proactivity requires some independent decision-making. Be clear about what your EA can decide independently versus what needs consultation.
Do this: “You can reschedule meetings up to 24 hours in advance. If it’s less than 24 hours, check with me first unless it’s an emergency.”
Not this: “Use your judgment” (without defining the boundaries of that judgment).
Common Proactivity Pitfalls to Avoid
Even well-intentioned EAs can miss the mark on proactivity. Here are the most common mistakes and how to address them:
Over-Anticipation Without Context
Some EAs think proactivity means doing things before being asked, even when they don’t understand the full context. This can create more work than it saves.
Example: Automatically scheduling follow-up meetings after every client call, even when the call didn’t go well and you need time to reassess the strategy.
Solution: Focus on pattern recognition rather than automatic actions. Teach your EA to understand the context that drives decisions, not just the actions themselves.
Analysis Paralysis
Some EAs get so focused on being proactive that they overthink simple requests and delay execution while trying to anticipate every possible need.
Example: Taking three days to schedule a simple meeting because they’re researching optimal timing, room preferences, and agenda possibilities.
Solution: Set clear guidelines about when thorough preparation is valuable versus when quick execution is preferred.
Boundary Overstepping
In trying to be proactive, some EAs make decisions or take actions that exceed their authority or expertise.
Example: Responding to client complaints with solutions before understanding your company’s position on the issue.
Solution: Establish clear escalation criteria and decision-making boundaries. Define what falls within their proactive authority versus what needs consultation.
The Business Impact of True Proactivity
When proactivity works correctly, the business impact extends far beyond individual task completion:
Decision velocity increases.
When your EA understands your decision-making criteria, they can prepare better information and handle routine decisions independently, allowing you to focus on strategic choices.
Operational resilience improves.
Proactive systems building means fewer single points of failure and better contingency planning for common problems.
Team effectiveness multiplies.
A proactive EA often becomes a coordination hub that improves communication and efficiency across your entire team.
Strategic capacity expands.
With operational details handled systematically, you have more cognitive bandwidth for high-level thinking and planning.
Stress levels decrease significantly.
Knowing that someone is thinking ahead and preventing problems provides psychological relief that’s hard to quantify but impossible to ignore.
The Bottom Line
“Proactive” has become such a generic requirement in EA job descriptions that it’s lost its meaning. But when you understand what does ‘proactive’ really mean… pattern recognition, systems thinking, and strategic anticipation, it becomes one of the most valuable capabilities an EA can develop.
True proactivity isn’t about mind-reading or taking over your responsibilities. It’s about building systems that anticipate future needs, recognizing patterns that prevent problems, and understanding context well enough to make decisions that align with your priorities.
The EAs who master this don’t just save you time, but multiply your operational capacity and strategic effectiveness. They become genuine partners in building and scaling your business, not just skilled task managers.
But proactivity doesn’t happen automatically. It requires clear communication about patterns and priorities, well-defined decision-making authority, and an environment that encourages systematic improvement over reactive firefighting.
If you’re tired of EAs who claim to be proactive but still require detailed instructions for routine tasks, the problem probably isn’t their capability… It’s the lack of systems and context that allows genuine proactivity to develop.
The question isn’t whether your EA can be proactive. It’s whether you’re creating the conditions that allow proactivity to flourish.
Ready to Find Truly Proactive EA Support, and what does ‘Proactive’ really mean?
At Anywhere Talent, we specialize in matching founders with executive assistants who understand that true proactivity means building systems, recognizing patterns, and thinking strategically about operational challenges. Through our comprehensive vetting process, we identify EAs who go beyond task completion to create genuine operational leverage.
Let’s find you an Executive Assistant who turns proactivity from a buzzword into a competitive advantage.
