The ultimate guide to working with a Personal Assistant

Entrepreneur and career coach Essie Weiss knows the importance of having a Personal Assistant. She’s employed one for the last three years, and says that her Personal Assistant has changed her life. “My Personal Assistant allows me to have more time to focus on what I want to focus on (my family, my business, and taking care of myself)—and do so with less guilt.” She explains that a weight has been lifted knowing that she can give her Personal Assistant an idea of what she needs done and have full trust that things will be taken care of from there.

Former Personal Assistant, Dru Erin, has her own perspective on what the job entails. She’s assisted families, CEOs, and creatives throughout her career. “I loved working as a Personal Assistant. Leaving this title I knew how to manage, run, and start several businesses at once, manage multiple households, and still tap into my creative outlets.” Erin says her experiences were fast-paced, expansive, and challenging all in the best ways.

Once you realize all the responsibilities you can hand off to your Personal Assistant you’ll wonder what took you so long to hire one. On Weiss’ list is everything from getting a dress altered to finding her a copywriter to help with emails. She especially appreciates when her assistant can, “take a nebulous idea and work with others to make the vision come to life.”

Erin agrees, noting that her time as a Personal Assistant was spent wearing a million hats. “Handling day-to-day scheduling, making sure household appointments were kept up, taking care of correspondence and payroll for the household team members, travel planning, customer service, etc., she explains. Everything and anything having to do with home-life went through her.

Sample Personal Assistant task list

Household

• Managing lawn care, cleaning personnel, chef, babysitters, etc.
• Doing and folding laundry
• Pet sitting/dog walking/house sitting

Shopping

• Buying gifts
• Planning meals and grocery shopping/delivery
• Running errands

Administrative

• Managing personal email
• Managing family/household calendar
• Scheduling appointments (doctors, meals, personal care, etc.)

Planning

• Booking family travel
• Arranging events (dinner parties, family birthday parties, etc.)

Getting assistance in the workplace is natural for most people at senior levels. Executives understand that It doesn’t make sense to spend their valuable time on tasks that could easily be delegated to other people. Yet, when it comes to their personal lives, those leaders make that same tradeoff without realizing it. For example, is it worth it to sit on hold with the cable company for 45 minutes when you could be spending that time with your family or pursuing a hobby?

Getting on board with employing a Personal Assistant may require a mindset shift. Rather than taking the “I can do everything stance” consider adopting the same perspective you use at work. Weiss was able to overcome feeling guilty about having someone help manage everything going on in her personal life. Now, when she assigns a task to her Personal Assistant, “I know it's in good hands. And it's not a reflection of how good I am at juggling everything if there's something that hasn't been finished. It's been mentally freeing.”

Other things to consider when deciding if a Personal Assistant is right for you:

• Assess if you need in-person vs. remote help
• Determine how many hours per week you could use assistance
• Figure out if one person can pull double duty and serve as your assistant at work and home. For example, sometimes Double Assistants take on personal responsibilities for their Executives such as family travel arrangements or gift buying

Any kind of assistant is meant to make life easier for you. If managing everything outside of work feels hard, hiring a Personal Assistant can be a great answer.

While hiring the right Personal Assistant is crucial, the partnership doesn’t truly begin until you start getting to know one another. Ask for feedback during the onboarding process and be open to having things done differently. There may be a more efficient way of handling a task that you never considered.

The Executive’s Perspective

Weiss has three main tips that she says keeps her partnership with her Personal Assistant going strong.

• Communicate often (and well): It’s much better to clarify what you're looking for on the front end than to have to go back and fix it later.
• Pay well: Be willing to pay a decent wage! Doing so will attract stronger candidates and retain them longer.
• Assume positive intentions: While that goes for every relationship, it’s vital to maintaining trust with your Personal Assistant, especially!

The Personal Assistant’s Perspective

Erin’s top tips for working cohesively with her employer kept her satisfied in positions for years (and they’re not so different from Weiss’s)!

• Communicate and be transparent: Always be there to listen if your Personal Assistant has an issue. Making them feel comfortable coming to you with questions sets the tone for a healthy relationship.
• Choose to be accepting: Realize that your way of thinking and doing things isn’t the only way. Be open to compromise and understanding a different perspective before jumping to conclusions.
• Be clear: Know what you want and need, then express it. And if you can’t, have an open dialogue so that you and your team, together, can identify your wants and needs.

Once you hire a Personal Assistant and establish a strong working relationship, responsibilities will continue to evolve. They should be able to find additional areas where they can lend support, making life even easier for you.