September 3, 2021

How to successfully work with a Personal Assistant, from a former PA


Who better to learn how to best work with a Personal Assistant than from someone who has done it for years? We asked Dru Erin, whose former clients include families, CEOs, a musician, photographer, creative director, and wellness coach to help us navigate the world of Personal Assistants. Knowing that hiring this type of help can certainly make life easier for busy Executives, we dove into all the questions you want answers to before hiring a Personal Assistant.

Can you give us a quick overview of your experience working as a Personal Assistant? Dru: Amazing! I loved working as a PA. As challenging as it could be, I learned so much. I knew how to manage, run and start several businesses at once, manage multiple households at once, and still tap into my creative outlets. It was fast-paced, expansive, and challenging all in the best ways. I would definitely be open to working as a PA again if the right position came up.

What were your responsibilities as a Personal Assistant? Dru: Handling day to day scheduling, making sure household appointments were kept up, getting all employees paid in time, handling correspondence with the accounting team and all household team members, travel planning, customer service, marketing and sales...pretty much everything and anything having to do with home life and work life went through me. I wore a million hats in the role as a PA!

What were some of the things you found yourself doing that weren’t in the original job description? Dru: My PA positions all did an excellent job outlining everything from work responsibilities to household responsibilities. I rarely found myself doing things I “didn’t sign up for”. I also made sure that when I was applying for positions I read all the details so that I knew what I was getting into.

What are your top tips for an Executive looking to hire a Personal Assistant? Dru:

  • Attention to detail is key because no one wants things falling through the cracks or mistakes made, as this could lead to dropped projects or clients and low-quality work.

  • Know your applicant’s intentions. Are they applying because they believe in your work, to collect a paycheck, or to learn from you to start their own company like yours? Once you know their intention behind applying then you know how to approach the hiring and training process.

  • Understand their prior experience so that you know how hands-on you and your team will have to be during the training process.

  • See how they carry themselves. Remember, they are now an extension of you and your brand.

What should an Executive look for when hiring a Personal Assistant? Dru: Honestly, I got lucky! Of course, like with any position, there were challenging moments. The main things I learned in order to maintain a solid working relationship were communication, transparency, and acceptance. My ego definitely got in my way a few times so coming back to these three helped bring me back to earth!

  • Communication & Transparency: If I did not know how to do something, if I did not understand, or if I was uncomfortable with anything I spoke up and my bosses were always there to listen and find a way to work through in a healthy direction.

  • Acceptance: As we are all different people with different backgrounds and ways of thinking, we all have completely different realities. Coming to this realization helped in the challenging moments. Accepting that my way of working, thinking, or acting is not the only way or the “right way” helped me to take a step back before reacting, which then led to creating paths where my bosses and I could meet each other in the middle.

What skills are most important for a Personal Assistant to really help their boss? Dru:

  • Time management: I am naturally pretty good with time management but when you are juggling your life and your boss’s life you have to write everything down, time it all out, and be on your A-game! If there were meetings across town I would put the address in my navigation two hours before and watch traffic patterns to be sure we always arrived with at least 5-10 minutes to spare.

  • Household dynamic & listening to your intuition - If you are working in a household environment this can be challenging at times. I have worked as a PA in a few private households so knowing when to take my laptop outside or closing certain doors is a key intuitive skill to catch onto ASAP! Not only is this important for the household’s privacy, but it’s also important for the quality of your work.

  • Flexibility - You have to be on board with last-minute schedule changes, rework the schedule, and problem-solve on the spot.

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