As entrepreneurs and company leaders scale operations, the question isn’t if they need an executive assistant — it’s how to ensure that partnership works effectively from day one.
At Smart and Talented — an agency specialising in the recruitment of executive and personal assistants — we’ve seen the same patterns again and again. Leaders invest in hiring, but the collaboration falls short of expectations.
Why? Because hiring is only half the equation. Working effectively with an executive assistant requires clarity, process, and trust.
Based on years of experience and insights from this video guide with real cases, here are the 10 most common mistakes entrepreneurs make when managing an executive assistant — and how to avoid them.
1. Vague Job Descriptions
Hiring without a clear definition of roles leads to confusion, overlaps, and dropped balls. Before recruitment, define:
- What exactly will you delegate?
- Which tasks are recurring vs. one-off?
- What results do you expect?
2. No Onboarding Process
Even experienced assistants need time to adapt. Skipping onboarding is like expecting someone to run a marathon without warming up. Provide:
- Business context
- Communication preferences
- Key contacts and systems access
3. Over-controlling Leadership
If you're still checking every step, you're not delegating — you're supervising. Let go of micromanagement, and focus on outcomes.
4. Hiring Based on Chemistry, Not Capability
Liking someone is not the same as trusting them with your business. Use structured interviews and ask for evidence of ownership, project management, and initiative.
5. Assuming They "Just Know"
Your assistant isn't a mind-reader. Clear instructions and context early on lead to fewer errors and faster autonomy.
6. Lack of Feedback
Silence breeds confusion. Regular check-ins help course correct, maintain alignment, and build trust.
7. Expecting Immediate Perfection
Even top-tier executive assistants need a learning curve. Treat your partnership as a long-term investment — not a quick fix.
8. No Tools or Systems
Still juggling everything on WhatsApp or email? Time to upgrade. Use tools like:
- Notion, Trello, or Asana for task management
- Shared calendars
- Google Workspace for documents
9. Ignoring Soft Skills
Your assistant is often your gatekeeper, communicator, and proxy. Look beyond admin skills — evaluate for emotional intelligence, discretion, and anticipation.
10. Hiring Without Strategy
Hiring an executive assistant isn’t just about “offloading tasks.” It’s about strategic leverage — freeing up the CEO’s time to focus on growth, leadership, and vision.
Executive support is not a luxury. It's infrastructure.
The demand for high-performing assistants has skyrocketed. Today’s assistants are expected to think ahead, manage workflows, coordinate teams, and act as force multipliers.
If you're still asking yourself:
- Do I need an assistant?
- Where do I find a personal or executive assistant I can trust?
- How do I avoid wasting time on the wrong hire?
— then you’re ready to explore executive assistant hiring strategies that actually work.
More insights here 👉 Watch the full video on the 10 mistakes
Need help finding a right-fit executive assistant?
Many European founders now turn to assistant recruitment agencies, such as Smart and Talented, who specialise in vetting for not just skills — but mindset, ownership, and cultural match.