How to Hire a Personal Assistant Who Saves You 10 Hours a Week It starts with taking a hard look at yourself.
By David Finkel Edited by Frances Dodds
Opinions expressed by Entrepreneur contributors are their own.
While it's no secret that hiring a personal assistant can help founders and executives save time, few know how to truly do it well. On one hand, early-stage companies try to conserve financial resources — and oftentimes executives' valuable time is spent on tasks that they don't need to do themselves, leading to talent shortages in small teams. On the other, executives at larger organizations have the resources to hire assistants but don't know how to set up a partnership that optimizes their time and makes their assistants' talents go the extra mile.
Over the last 24 years, I've hired a dozen different assistants, many of whom have been pivotal to my company's growth and success, and who have helped me save well over 10 hours every week. Several others, however, taught me important lessons that I keep in mind whenever I look to hire a new assistant to support my team's executives.
Through the lens of someone who's had both great and not-so-great experiences hiring personal assistants, I want to share with you my process and criteria to help you hire a personal assistant who is a great fit for you — someone who, from day one, can be a big asset to your team and help you reclaim what would otherwise be valuable time lost.
Start with introspection to define the ideal fit
The biggest mistake I made when I first started thinking about hiring an assistant (and a big mistake I've seen my clients make) is undervaluing the introspection step of hiring a great assistant. Too often, the sentiment is that a high-performing assistant can be an asset to any busy executive, but this is simply untrue. To work well together, your assistant and yourself don't just both have to be competent — your assistant needs to fit your work style and informational preferences.
Do you prefer to keep to yourself at work or are you driven by interaction with your colleagues? Do you find multiple updates in the same email to be more efficient or would you instead want one update per email? (Surprisingly, I've seen about 60 percent of our clients prefer batch updates while 40 percent prefer individual updates — so everyone's different.) No worries either way, but if you don't ask yourself these and other personal questions, you simply won't be as informed in your search for the right fit.
Related: The 3-Step Process to Hiring Your First Assistant
It's mandatory to hire someone who can handle "fuzzy" tasks
While every assistant brings a unique set of personality traits and skillsets to the table, the one that I don't compromise on is a strong capacity for handling ambiguity. Hiring a personal assistant shouldn't be thought of as automation — your assistant should be able to synchronize with your operational behavior and be an extension of what you're doing in your busy day.
Chances are, you don't have the time to sit down with your assistant and review every email that goes out, every meeting document that's prepared, or every call that's being set up. And that's not even accounting for new challenges that come up that need to be solved. Hiring someone who needs every detail laid out on your end is a logistical nightmare, not to mention an easy spiral towards micromanagement.
Systematize a delegation structure that works for you
Once you've found a personal assistant who's both a good workstyle fit and can manage organizational ambiguity, it is crucial to get on the same page about how you prefer to delegate tasks to meet certain key performance indicators. For instance, you might prefer meeting at the beginning and end of each day to touch base, or you might prefer email communication throughout the day.
Or maybe you might not want to "meet" at all unless it's for something urgent and instead prefer to delegate projects and communicate progress through screen recordings and audio messages. In situations where you need to approach an important line item, you might even prefer a text message as opposed to email to make sure you see it right away.
Whatever the preference may be, your delegation structure may often benefit from the utilization of project management software. I've found that regardless of the delegation structures I've chosen throughout the years, having a project list and making it easy to keep track of progress is critical for accountability.
Related: Do You Need an Assistant, or Do You Just Have to Work Harder?
Part of your assistant's job is to create and refine the system of being a world-class assistant for you
This last strategy is one that has time and time again paid dividends in the long term. It's based on a simple principle: if you're doing something right, make sure you're documenting what it is exactly so you can replicate those results. Not only does this give your assistant meaningful work to do early in the relationship as they learn to be a great assistant for you, but before they know enough to really take things off your plate. It also means that a future assistant starts with a huge head start toward becoming a productive partner in helping you get stuff done.
When making those kinds of decisions, it is nearly impossible to build the kind of rapport you've had with your former assistant with a new one. But if you constantly work with your assistant to document the tasks, functions, and preferences of the role, then whoever steps into that role next will have an advantage. This systems work should be done by your assistant, with you spot checking to give feedback as he or she creates new systems. These systems include but are not limited to your travel preferences, how to manage your calendar, and how to handle a portion of your low value email.
