How to Hire an Executive Assistant: 5 Hiring Mistakes We See

In 15 years of placing executive assistants, we’ve seen the same executive assistant hiring mistakes— from solo entrepreneurs building their first team to executives with established businesses running complex organizations. We’ve placed EAs for creative agency founders, construction company owners, wealth management partners, tech startup CEOs, law firm principals, and countless other business leaders across most industries.

And here’s what surprises people: they all make the exact same five mistakes when trying to hire an executive assistant on their own.

Every leader thinks their EA needs are unique to their industry, but these hiring mistakes are universal. “You don’t understand,” they tell us, “my business is different. I need someone who gets the construction world.” Or “I need an EA who understands the creative process.” Or “This person has to know financial services.”

The truth? While industry knowledge can be helpful, it’s rarely the reason an EA placement succeeds or fails. After years of successful placements and maintaining an exceptionally high retention rate, we can tell you that the businesses that struggle to find and keep great EAs make these same fundamental mistakes, regardless of what industry they’re in.

Mistake #1: Hiring for Skills Instead of Fit

This is the big one. We see it everywhere.

We’ve seen a fast-growing marketing agency put a high priority on HubSpot experience, social media knowledge, and graphic design skills. Meanwhile, a manufacturing company owner insisted their new hire have some kind of understanding of supply chain, with experience in the specific industry software.

Both were focused on the wrong things.

Here’s what actually happened: The marketing agency hired someone with perfect technical skills who couldn’t handle the fast-paced, ever-changing priorities of a growing creative business. They lasted three months. The manufacturing owner found someone with industry experience who couldn’t adapt to his direct communication style and need for quick turnarounds. They were gone in six weeks.

Skills can be taught. Personality fit, work style compatibility, and the ability to adapt to a specific leadership approach? Those are much harder to change.

The most successful EA placements we’ve made paired people based on working style, communication preferences, and growth potential, not just resume bullets. The EA we placed with a detail-oriented CPA had never worked in accounting, but they naturally thought systematically and loved process improvement. Five years later, their practically running the back office. The EA working with a visionary tech founder had zero startup experience, but thrived in ambiguous, fast-changing environments and could translate their big ideas into actionable next steps.

Mistake #2: No Clear Role Definition

“I just need someone to handle everything I don’t want to do.”

We hear this from business leaders often, and it’s a recipe for disaster. Whether it’s a real estate developer, a consultant, or a restaurant group owner, vague role definitions create frustrated employees and disappointed leaders.

A wealth management partner can hire an EA with this exact approach. Then, three months in, they’re frustrated that the EA isn’t reading their mind, while the EA is overwhelmed trying to figure out priorities with no clear direction. The worst mindset to have is thinking ‘I thought an executive assistant would just know what to do.

Here’s the reality: even the most experienced EA can’t succeed without some expectations. The best EAs we’ve placed work with leaders who can articulate not just the tasks they want delegated, but the outcomes they’re looking for.

Successful role definitions focus on:

• Your biggest time drains and energy leaks
• The work only you can do vs. what can be delegated
• How decisions get made and communicated
• What success looks like in 30, 60, and 90 days

We worked with a busy law firm partner who initially said, “I need help with everything.” After we dug deeper, we identified that their real need was someone who could manage client communication, coordinate with other attorneys, and handle the administrative side of case management so they could focus on legal strategy. With that clarity, we found them an EA who transformed how their practice operated.

Mistake #3: Rushing the Process

“I need someone to start next Monday.”

We get it. You’re overwhelmed, behind on everything, and desperately need help. But whether you’re running a boutique consulting firm or managing a multi-location retail operation, rushing the EA hiring process almost always backfires.

A construction company owner recently called us in a panic. Their previous assistant had just quit, they had three big projects starting, and they needed someone immediately. “I don’t have time for a long search process,” they said. “I just need someone competent who can start right away.”

That urgency led them to hire the first qualified candidate they interviewed. The new hire had great administrative experience but couldn’t handle the constant interruptions, last-minute changes, and high-pressure environment that comes with managing multiple construction projects. Two months later, they gave notice, leaving the owner in an even worse position.

We see this pattern everywhere. A marketing consultant hires quickly and gets someone who can’t keep up with the creative, fast-paced nature of the work. A medical practice owner rushes the process and ends up with an EA who struggles with the detailed compliance requirements and patient interaction demands.

The businesses with the most successful long-term EA relationships? They invest time upfront in the search and selection process. They understand that finding the right person takes time, but replacing the wrong person takes even more time.”

Mistake #4: Not Involving the EA in Goal-Setting

This mistake shows up differently across industries, but the result is always the same: an EA who feels like a task-taker rather than a strategic partner.

We placed an EA with a busy financial advisor who was great at delegating tasks but never explained the bigger picture. “Just handle my calendar,” they’d say, or “Take care of these client files.” Six months in, the EA was competent but not proactive, helpful but not strategic.

Compare that to another financial advisor we worked with who took a different approach. From day one, they explained their business goals, client acquisition strategy, and how they wanted to grow the practice. They helped their EA understand not just what to do, but why it mattered. That EA now anticipates needs, suggests improvements, and has become instrumental in client retention.

The same pattern plays out everywhere. The restaurant group owner who only gives daily tasks versus the one who explains expansion plans and operational goals. The consulting firm partner who treats their EA like a secretary versus the one who includes them in strategic discussions about client management and business development.

Great EAs want to contribute to something bigger than just completing tasks. When you help them understand your vision and goals, they become invested in your success rather than just completing their job description.

Mistake #5: Assuming Any Assistant Can Be an Executive Assistant

This might be the most expensive executive assistant hiring mistake we see.

“They were a great office manager at my last company, so they’ll be perfect as my EA.” “They’ve been doing administrative work for years.” “They’re super organized and efficient.”

Being a good administrative assistant, office manager, or secretary doesn’t automatically translate to being an effective executive assistant. The skill sets overlap, but the roles are fundamentally different.

A successful entrepreneur hired their former office manager to be their EA when they started their own company. The new hire was incredibly organized, detail-oriented, and reliable. But they struggled with the ambiguity, quick decision-making, and proactive thinking that executive-level support requires. They were used to clear procedures and defined processes, not the fluid, ever-changing demands of supporting a business leader.

Executive assistants need to:

• Think strategically, not just tactically
• Handle ambiguity and changing priorities with ease
• Anticipate needs rather than just respond to requests
• Communicate confidently with high-level contacts
• Make decisions independently within defined parameters
• Adapt quickly to new situations and challenges

We’ve seen talented administrative professionals struggle in EA roles, not because they weren’t capable, but because the roles require different strengths and mindsets.”

How We Address Each of These Executive Assistant Hiring Mistakes

Over 15 years, we’ve developed our process specifically to avoid these common pitfalls:

For Skills vs. Fit: We use a proprietary personality assessment developed with a psychologist to evaluate personality traits and characteristics. We also conduct assessments to gauge their ability to read social cues and navigate complex interpersonal dynamics – all key indicators of how they’ll perform in high-pressure executive support roles.

For Role Definition: While many leaders are unsure where to start with role definition (especially for new positions), we guide them through the process. Our approach focuses on finding EAs who can work through ambiguity by asking the right questions, understanding desired outcomes, and anticipating needs rather than waiting for detailed instructions.

For Rushing: Our curated approach takes time upfront to ensure long-term success. We’d rather spend extra weeks finding the right fit than months replacing the wrong hire.

For Goal Alignment: We help leaders understand how to onboard and integrate their EA as a strategic partner, not just administrative support.

For Role Clarity: We specifically recruit for executive assistant skills and mindset, not just administrative experience.

The result? Our high retention rate and replacement guarantee prove that when you avoid these five mistakes, you get an EA partnership that transforms your business and creates capacity for what you do best.

Your Next Steps

No matter what industry you’re in or what size business you’re running, these five executive assistant hiring mistakes will derail your hiring process. Whether you’re a solo entrepreneur ready for your first assistant or an established leader looking to upgrade your support, success comes down to focusing on fit over skills, clarity over speed, and partnership over task completion.

If you’re ready to avoid these mistakes and find an executive assistant who will stay and grow with your business, we’d love to help. Our curated approach addresses each of these issues upfront, so you get a long-term partnership instead of another hiring headache.

Ready to find an EA who will transform your business instead of just completing tasks? Schedule a consultation to learn about our placement process and guarantee.