4 tips for hiring your first personal assistant

Contributed by Daria Tsvenger, a recent guest on the EO Wonder podcast. Daria is a life coach for high achievers and a neuroscience nerd who founded The Dream Sprint, a personal growth challenge aimed to motivate and inspire people to fulfill their goals. She is also a mentor at 500 Startups, where she helps entrepreneurs manage stress, increase confidence and supercharge productivity.

“The inability to delegate is one of the biggest problems I see with managers at all levels,” said Eli Broad, an American businessman ranked by Forbes as the 233rd-wealthiest person in the world.

He’s right, of course. As entrepreneurs, we know that delegation is essential. In theory, it sounds awesome and makes sense. But in practice, it’s hard to find the right person you can trust and manage well.

Smaller business owners may think hiring a personal assistant is a luxury, and it would be wiser to save money and do everything yourself. In larger companies, executives have the resources to hire, but nobody teaches them how to manage a personal assistant’s time and delegate daily work beyond calendar management.

Hear more from Daria Tsvenger as she speaks with Kalika Yap on the EO Wonder podcast.

I hired my first personal assistant in 2019—and it’s been a game-changer. I’ve been a one-woman show since 2018 when I started my first business. I hired freelancers for specific tasks, including website design, copywriting and SEO. But, managing those freelancers was always on me, on top of the actual client work and content creation. In 2019, I realized that I wanted somebody to be my right hand and essentially replace me on specific tasks.

I’ve heard horror stories about personal assistant relationships gone wrong. For me, the experience was a breeze, especially because I adhere to a thorough process before making a hiring decision. 

Here are four things that helped my personal assistant hiring process go smoothly:

1. Establish trust

Your personal assistant will likely have the passwords to your Gmail and Upwork accounts, your credit card information, and know the detailed ins and outs of your business. All of this information is sensitive, but an assistant can’t be of much help without it. With this top of mind, I knew I needed to find an assistant via a trusted source. I asked my friends if they knew anyone looking for flexible, remote work. Because if there’s a personal connection via a common friend, the trust element is automatically there. That’s how I got to the top of my funnel. 

Another tip for establishing trust is to create a sound non-disclosure agreement (NDA) and ask candidates if they’re comfortable signing it. Of course, contracts are only as good as the people who sign them. For my candidates, it was not a problem—they understood and respected the confidential nature of the position.

2. Interview wisely

First of all, I chose to conduct video interviews, which helps establish trust.

Second, as a psychologist, I realized that a personal assistant position isn’t necessarily a long-term career, so it was critical for me to receive an honest answer as to why they wanted to take this gig and be successful in it. The reply I hoped for was that they needed extra cash and wanted a good referral for future opportunities. I recognized that being my assistant would be a career stepping stone, and I knew that in a best-case scenario, we’d work together for up to two years. 

Another question I asked is, “What tasks are a “no-no” for you?” I provided a few examples, such as reaching out to new people, doing manual data entry, and negotiating prices. My goal was to find a person who had zero “no-no’s.”

3. Create a conflict resolution manual

I have an authoritative management style—my answers can be short, my feedback is direct, I can get angry, and (sometimes) act not as my best self. Maybe it’s because I’m the big sister of three younger brothers, so I’m accustomed to being obeyed. I communicated this in advance to my personal assistant, and we set up a “conflict resolution” method to deploy every time there was a miscommunication. I did this to ensure that if I snapped at them, my assistant wouldn’t take it personally or hold a grudge, and we could follow our conflict resolution protocol to make life easier for us both.

It was one of the most helpful tools I implemented. Because, as we know, 99 percent of professional relationships go wrong due to miscommunications and having no idea how to resolve the conflict.

4. Set up your delegation structure

When I hired my assistant, I wasn’t sure what tasks I could delegate because it seemed that every task required my personal attention. As entrepreneurs, we often think we’re irreplaceable—it’s the major mindset block every busy entrepreneur has. And it’s multiplied by the addiction of being busy. But it’s an illusion.

The most helpful question I asked myself was, “What do I wish I could do that I’m not doing now?” I soon realized that “It’d be cool if I could pitch more companies about my Mental Wellness and Communications Keynotes,” and also that “I’d like to engage with my target audience on Instagram.” The main thing is that these tasks should be ongoing and recurring enough to fill your assistant’s time until you’re ready to delegate additional tasks with even more responsibility.

For more insights and inspiration from today’s leading entrepreneurs, check out EO on Inc. and more articles from the EO blog. 

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