How to Retain Your Perfect Personal Assistant

working at a coffee shop

Once you hire a personal assistant, you’re probably ready to sit back, relax, and let them work their magic. We don’t blame you! Your personal assistant should be ready to reduce your mental load and clear your plate so that you can find more time for yourself and your family. 

However, like any relationship working or otherwise, it’s important to do your part to maintain a good working environment so that your new personal assistant will feel appreciated and want to stay and grow with you in your employment.

Here are just some ways you can keep that successful relationship going and retain your perfect personal assistant.

[Related: The Best Interview Questions for Personal Assistants]

Respect and Trust Your Assistant

We know it can be hard to let someone “take over the reins” and start doing things for you. Especially if you’re used to doing it all yourself.

A little trust goes a long way. Let go a little and have faith in your assistant to do quality work and keep your best interests at heart. 

Schedule Regular Check-ins

Regular check-ins are crucial in retaining your personal assistant. This allows both you and your assistant time to ask and answer questions that can help your assistant better do their job. 

Check-ins should be scheduled consistently so that they are expected and normal. We recommend weekly 30 minute check-ins for the first month to make sure your assistant is feeling supported. 

After a month, 10-15 minutes a week depending on current projects might work just fine. Conduct more formal check-ins at the 30, 60, and 90 day mark, and after that every 6 months should suffice.

One way to structure these one-on-ones is to ask your assistant to come with a win, a challenge, and at least one question to start off. 

[Related: Do Successful People Outsource? The Answer Is Yes.]

Give and Receive Feedback

Both parties should be continuously sharing their honest feedback — not just during scheduled check-ins. To build a culture of feedback as a gift rather than a punishment, give both positive and constructive feedback and be open to listening and taking action on any feedback from your personal assistant as well.

Set Up a Permanent Schedule and Establish Business Hours

Having your PA come on the same day and time each week will create consistency in your routine, which is the best way to add balance to your busy life. 

Additionally, boundaries are important for a work-life balance. Respect that your assistant has a life outside of work, and establish strict business hours for communication. Let them know that they’re not required to ever respond to any messages outside of those hours unless it’s a true emergency.

Be Transparent and Over Communicate

No relationship will work out in the long-run without communication, so clear communication and transparency from day one is important. Have conversations about your preferences and expectations in order to set up a long and happy partnership with your PA.

Moreover, let them know when they’re doing great, as well as what they can improve on. For example, if you’d prefer they store clean, folded linens in the laundry room cabinets instead of in the bathroom, or if you like each meal prep container labeled in a specific way, don’t hesitate to let them know! If you aren’t sure whether they’re comfortable doing a particular task — such as taking your dog to the dog park — just ask. 

Your PA is on your team and wants to do everything possible to make your life easier (even the small stuff).

[Related: Our Advice for Getting Started With Your Personal Assistant]

Set Goals to Maintain Focus

To respect the time of both yourself and your personal assistant, it’s crucial to set goals and work off of lists of things you’d like to see done.

Start a “bucket list” of things you’d like to get off of your plate. You and your PA can prioritize these tasks so that there is always something they can work on each week, and they’ll feel guided and supported.

Going on a vacation? Ask your assistant to come up with some remote projects, organizing tasks, or home improvement projects that they can work on while you’re gone. This way you can enjoy your time away without stress, and they’ll have some direction while you’re out of town.

Use Tech Tools to Your Advantage

Use tech tools to communicate and be productive. One such tool that has been a life-changer for Pepper’s Personal Assistants is Slack, which offers both a desktop and a mobile version. Slack allows clients and PAs to keep track of all communication in one accessible interface. It also features an easy-to-use search function to find past conversations.

Other project management, organization, and communication-oriented apps that we recommend include AnyList, To Do, Trello, and Voxer.

[Related: Personal Assistant Apps — Do They Really Help?]

Show Appreciation

The biggest and perhaps simplest tip on our list for retaining your personal assistant is showing basic appreciation. Genuine recognition of hard work goes a long way — you never know how much a “thank you” can mean to someone.

Start Your Journey and Reclaim Your Time with Pepper’s Personal Assistants

Are you interested in hiring a personal assistant? Pepper’s Personal Assistants can provide you with the help you need, when you need it most. We make it easy to find the perfect personal assistant for your lifestyle and goals. 

Learn more about us, or contact us today for a free 30-minute consultation to answer any of your questions.

Related Blogs

Pepper’s Personal Assistant Reviews

See what it’s really like to work with a Pepper’s personal assistant!

A True Game-Changer

“Having Mary as my personal assistant has been a game-changer. I don’t have to think about laundry or the cat litter—she handles all those daily tasks I’d rather not do. She’s proactive, assertive in all the right ways, and totally in control of every detail. I’d rate her a 5 out of 5, no question!”

Brian T.

Proactive, Reliable, Caring Support

“Sarah has been such a reliable support—always proactive, spotting things that need to be done before I even ask, and taking care of them. She has such a positive attitude and is constantly looking for ways to add value and make things easier. And I love how much happier and more spoiled my dogs are thanks to her care. I barely have to think about her day-to-day, and I mean that in the best way possible!”

K.W.

Exceptional Home Management

“Bernice is simply amazing—I just can’t say enough good things about her. She excels at physical tasks and knows my habits so well that she can anticipate my needs without me even saying anything. As a house manager, she’s exceptional; she takes care of all those little things that I wouldn’t even think of. Over time, we’ve developed a wonderful rhythm, and it’s such a relief to have someone who just knows what needs to be done and does it effortlessly.”

J.H.

Exceeding Expectations Every Day

“My PA has truly exceeded my expectations. I really enjoy coming home now because everything in my home is something I know and love. She’s helped me with tasks I didn’t even know where to begin, and her ability to do the background work and present options has been invaluable. She has made it possible for me to manage things without feeling overwhelmed, and it’s been a game changer for me!”

W.W.

Bringing Joy and Efficiency

“My PA Tess is proactive and handles everything beautifully, from small tasks that bring joy to big projects like planning trips. She balances recurring tasks with high-priority work, and everything gets done perfectly. I didn’t realize how much joy small things like making the bed could bring until Tess started doing them. She has truly made a difference in our home, bringing both efficiency and a level of organization and joy we didn’t realize we needed.”

K.H.

Support That Makes a Difference

“Having Missa as a PA has taken me from daily treading water to swimming to the shore. I’ve gone from never quite keeping up with things to actually having extra energy to do more. She has been a tremendous help, reducing my stress and allowing me to rest and recover. The support I receive is perfect; Missa is a 5 out of 5 in meeting all my needs. I’ve already recommended Pepper’s to a few friends because having extra help makes all the difference.”

Kathy M.

Back-to-School Unmatched Support

“Having Jay as my personal assistant has been fantastic. She helps me tackle projects that were just looming over my head and has built a great rapport with my teenage son. She’s helped my son pick out his back-to-school wardrobe and coached him through decisions — I couldn’t ask for better support. I sometimes think about when I could handle everything on my own, but now I can’t imagine doing it without Jay’s help.”

R.B.

PA to the Rescue

“I am very satisfied with my personal assistant. The biggest relief is knowing that when things get hectic with work my PA is there to help us from lighting on fire, especially when one of us is traveling.”

Ana V.

Dream PA Experience

“I am very satisfied; My PA has everything dialed in and the schedule works really well and is flexible when needed. Honestly: My PA and I click very well, I love it, it’s a dream!”

Jodi K.

Stress-Free Travel

“One of the massive benefits of having a PA is during travel disruptions. When flights are delayed, the kids are upset, and you’re stuck in customs, coming home to a stocked fridge and a prepared meal eliminates the need for a late-night milk run. You don’t realize the stress these tasks add until you have someone to handle them for you.”

A.S.

11/10!

“My PA is incredible—an 11 out of 10—really thoughtful, thorough, intuitive. She is professional but friendly; she has just been great. A couple of times because of things going on with her calendar, Kandis has been flexible—coming 15 minutes later to drop the dog off at puppy play. She has been really great.”

Libby

Thoughtful and Detail-Oriented

“My PA is a thoughtful and discerning assistant. She pays attention to details in our home and makes great suggestions for how to improve and optimize our lives. We trust her judgment, and she communicates proactively and frequently. She is always on-site on time and patient with my unpredictable schedule. We communicate frequently, but she’s also very efficient in how we communicate. Great work!”

Client

Super Happy!

“[I] really do think Kandis is setting the bar! Having a new person come into your house can go either way. [I’m] very grateful for the time and energy and people that Pepper’s has. It’s a big step; no suggestions around onboarding. [I’m] really happy that we were able to board Kandis quickly; super happy for the West Seattle support.”

Libby

Organizing Superhero

“My PA is really good at organizing; it’s one of her superpowers. Some of the simple reorganizing things that she has done have made a big impact. She organized all the cat stuff in the garage and took the initiative on her own. She’s bright and cheery—no moaning, whining. Very great.”

Emma

One of the Best Decisions I’ve Made

“I just wanted to take a few minutes to tell you how much I have appreciated working with all of the Pepper’s staff. My assistant is so generous and thoughtful — she brings value to every interaction. I can’t remember a time when I’ve hired anyone with such a professional and high standard of customer service. Working with you all has been one of the best decisions I’ve made in a very long time!”

Libby

10/10 for Sure!

“Missa is a 10/10 for sure! She has been wonderful, and we check in regularly. I’m comfortable communicating with her about questions or requests, and she’s always been very responsive and also seems comfortable checking in if she has any questions for me. [The] biggest help remains pet care and household chores support, plus the help with one-off projects that come up. Missa has all kinds of skills she brings, (e.g., she’s currently putting together a ‘cat highway’ for the living room rafters).”

Homeowner

My Quality of Life Has Improved

“I used to spend every weekend and every evening doing chores and running errands. Now, I’m able to spend the time that I need to on my business, and then I get to enjoy my home and my life and the precious unstructured time that I have. The truth is, my quality of life has improved by having a Pepper’s household assistant here.”

Libby

Takes Initiative

“I want to mention what a fantastic personal assistant Billie is to me. We were on vacation last week, and she managed my household and vendors flawlessly. I even had her redecorate my office, and I gave her very little direction other than just to make it nice and functional, and, my goodness, did she ever! She takes initiative in my house in so many other ways but does not overstep or overspend. To strike that balance is really something unique and special. I feel really lucky to have her.”

Anura

I’m Blown Away

“[I’m] blown away by how much better the house looks already :)”

Graham

Kind, Caring, and Proactive

“My PA is a very caring person. I was incredibly ill last year, and my PA connected the dots that the washing machine had a lot of mold and thought the black specs on my clothes were from that. On her own time, my PA sent me an article about the impact of mold/washing machines. It was so kind of her.”

Emma

Goes Above and Beyond

“My PA has gone above and beyond. She’s organized my laundry room while keeping on top of laundry, which made it much easier to stay on top of stuff. She’s always ready to jump in and tackle items. It made this holiday season way less stressful.”

Andrea