Maintaining a high-performance lifestyle, whether you’re an entrepreneur, executive, creative, or private individual with a full plate, comes at the cost of time, focus, and peace of mind. Tasks accumulate. Priorities clash. The calendar starts to run your life instead of the other way around.
That’s often the moment people start asking: “Should I hire a Personal Assistant?” Hiring a Personal Assistant (PA) prematurely, or for the wrong reasons can lead to more chaos, not less, and can turn you into a micromanager if you’re not quite at the stage where you’re ready to employ others personally yet. And waiting too long can be equally troubling.
Before you make the leap, ask yourself these six pointed questions. The answers will help clarify what kind of support you actually need and whether a Personal Assistant is the right next hire.
1. Are you spending your time on high-value work, or just staying busy?
There’s a saying in medicine: Why pay a doctor for something a nurse could do? The same logic applies in business and life. If your days are spent booking travel, organizing calendars, or chasing follow-ups, you may be operating far below your earning potential.
A good Personal Assistant won’t just clear your schedule, they’ll increase your leverage. They handle what’s urgent but not strategic, freeing you up to focus on the parts of your work and life that truly require your judgment, expertise, or relationships. Harvard Business Review calls this prioritizing your “highest and best use.”
Start with an honest audit. Look at your calendar and your to-do lists from the past two weeks. Highlight every task that could have been handled by a trusted assistant with minimal oversight:
- Scheduling meetings or calls
- Managing travel logistics
- Sorting, flagging, or replying to emails
- Researching restaurants, vendors, or gifts
- Running errands or placing orders
- Following up with service providers or staff
- Tracking receipts or submitting reimbursements
Then ask yourself: what did those hours cost you? Not just in money, but in mental bandwidth. What could you have done with that time instead – strategic planning, time with family, creative thinking, client development?
2. Are things slipping through the cracks?
If you’re constantly putting out fires but never getting ahead, it’s not necessarily a time management problem. It may be a capacity problem.
The reality is that as your responsibilities grow, so do the administrative layers that come with them. Travel logistics. Scheduling coordination. Vendor follow-ups. Event RSVPs. Inbox triage. Each one may only take a few minutes, but they add up, and the mental load of juggling them can create hidden drag.
You don’t have to be forgetful to fall behind. You just need more on your plate than one person can realistically handle. A Personal Assistant acts as a second brain, a second set of eyes, and a built-in failsafe system. Tools like Asana and Calendly can help, but a trusted human gatekeeper brings strategy, nuance, and foresight that automation tools often lack.
3. Do I need help with my personal life, professional life, or both?
If your calendar feels like a game of Tetris that’s constantly rearranging itself, a PA can restore structure. They don’t just plug in meetings. They make sure your time aligns with your priorities.
That might mean blocking time for deep work, guarding against context-switching, or holding space for last-minute priorities. It might also mean saying no on your behalf. As one productivity expert put it, “You can do anything, but not everything.” A skilled assistant becomes the filter between you and the noise.
Michael Hyatt and other leadership coaches emphasize the value of designing your ideal week, and then protecting it. Most leaders know what their schedule should look like. Few have someone making it happen behind the scenes.
4. Do I want someone to do what I say, or anticipate what I need?
There’s a difference between an order-taker and a strategic assistant.
A junior admin will wait for instructions and execute tasks as requested. A resourceful PA, on the other hand, learns your rhythms, preferences, and priorities. Then they get ahead of them. They set reminders before you ask. They notice when your car’s registration is due or your passport is about to expire. They anticipate delays, prevent bottlenecks, and suggest tools or workflows to make things run more smoothly.
If what you really need is a second brain and not just a second pair of hands, then yes, you’re ready for a PA. But that also means hiring the right caliber of person. Not all assistants are trained or temperamentally suited to play that strategic, anticipatory role.
5. Am I willing to delegate and let go of control?
Here’s a hard truth: the assistant you hire is only as effective as the access and authority you give them. Even the most organized, discreet, and capable PA will struggle if you insist on managing every calendar invitation, replying to every email personally, or redoing every task they complete. Ask yourself:
- Am I comfortable giving someone access to my inbox, calendar, or credit card?
- Can I let someone else take the lead on planning or executing tasks?
- Am I open to a professional relationship that blends deep trust with clear boundaries?
Hiring a PA means investing in a partnership. That partnership works best when the principal is ready to delegate meaningfully and not just offload specific chores.
6. What is the cost of doing nothing?
Sometimes, the most persuasive argument for hiring a Personal Assistant isn’t what you’ll gain. It’s what you’re already losing. Start calculating the opportunity cost of your time. What’s your hourly rate, or the value of your most productive hours? And hour many hours each week are you spending on non-essential task?
The math often speaks for itself. A skilled PA can cost anywhere from $40 to $100 per hour, but your time may be worth a multiple of that, so if they can meaningfully free up even 10-20 hours of your week, and reduce errors or delays, their value quickly compounds.
And the cost isn’t just financial. Burnout, decision fatigue, strained relationships, and missed opportunities can all stem from trying to manage an unsustainable load alone.
So… Do You Need a Personal Assistant?
If you answered yes to 3 or more of the questions above, you’re likely past the threshold where a PA would be useful. At this point, they might be essential.
The good news? The role doesn’t have to be full-time, live-in, or overwhelming to manage. Many of our clients start with 20 to 30 hours per week, hiring someone local and experienced who can grow with their needs.
At Old State Staffing, we specialize in recruiting Personal Assistants who bring not just skill and discretion, but structure, insight, and calm. Whether you need a dedicated gatekeeper, a detail-oriented organizer, or a trusted hybrid PA for both business and life, we help you define the right role and then find the right person to fill it. Because at a certain point, doing everything yourself stops being impressive, and starts being expensive. Contact us today to get started finding you the perfect Personal Assistant!
