How to Hire a Reliable & Trustworthy Personal Assistant
Between endless meetings, urgent emails, personal errands, and family responsibilities, even the most organized people can start to feel like they’re drowning in details. If your days feel like a constant scramble and your to-do list keeps growing faster than you can check things off, it might be time to get the help you deserve.
Hiring a reliable, trustworthy personal assistant isn’t about extravagance—it’s a smart, strategic step toward building a life where you can breathe easier, think more clearly, and focus on what truly moves you forward.
But how do you find the right assistant—someone who’s organized, professional, and genuinely dependable?
Here’s everything you need to know to hire a PA who will help you stay ahead, not just keep up.
5 Tips for Hiring a Personal Assistant for Your Business
1. Get Clear on What You Need
Before you start searching, take time to map out the tasks you’d like to delegate, such as:
Calendar and scheduling
Travel booking and itineraries
Email and inbox management
Research and online shopping
Errands or vendor coordination
Decide whether you need someone part-time or full-time. The clearer you are on your needs, the easier it will be to find the perfect fit.
2. Calculate the Time You Need
Before hiring, take an honest look at your workload to determine how many hours of support you truly need each week. Here’s how you can break it down:
Track your tasks for a few days or a full week—write down everything you do, how long it takes, and what could be delegated.
Identify repetitive work, such as:
Scheduling meetings or appointments
Managing your inbox
Conducting research
Updating spreadsheets or databases
Posting or monitoring social media
Look for patterns to estimate how many hours per week these tasks add up to.
Start small by beginning with 5–10 hours per week so you can adjust based on actual needs.
Be flexible, scaling hours up or down as you get more comfortable delegating or as your workload changes.
Remember: overcommitting can waste your budget, but underestimating can lead to burnout for you and frustration for your assistant.
3. Ask the Right Questions
Think about what’s important to you: do you prefer hands-on collaboration or a more independent, hands-off approach? Clarifying this helps you craft targeted interview questions, such as:
“How would you handle conflicting deadlines?”
“Describe a time you needed to keep information confidential.”
“What’s your system for staying organized?”
Pay close attention to their communication style, punctuality, and professionalism—these small cues often reveal how they’ll handle your day-to-day needs
4. Consider Availability & Flexibility
Be upfront about whether you need someone with strict 9–5 availability or if you might occasionally need after-hours support. Some PAs prefer fixed schedules, while others are comfortable with flexible or on-call arrangements.
5. Build Trust Through Clear Expectations
Once you’ve found your assistant, set expectations around:
Working hours and response times
Communication tools (email, phone, Slack, etc.)
Priorities and deadlines
Confidentiality (consider having them sign an NDA)
Clear, proactive communication helps you build a relationship based on mutual trust and respect.
The Boutique COO Difference
When we talk about hiring a personal assistant, we don’t mean a faceless AI or someone who treats this as “just a side gig.” At The Boutique COO, our assistants are real people—trained to think like owners and act as partners in your life and business.
Here’s what one of our wonderful clients shared about working with us:
“As a "serial entrepreneur", I've always dreamt of having an assistant. . . someone who gets me, my business and could help support me in multifaceted ways. The Boutique COO is all of the above and MORE. They’re quick, brilliant and introspective!”
- Jen Jones Wedding Photography (Read Full Case Study here)Ready to Find the Right Assistant?
You don’t have to do it all alone. You deserve reliable, professional support that helps you focus on what truly matters—while staying organized and ahead of the curve.
Book a free discovery call with The Boutique COO team today, and we’ll help you figure out the kind of personal assistant support that makes sense for your lifestyle and goals.
