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How to Hire your First Assistant and Reclaim your Time, with Amanda Hamilton – Episode 94




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Last updated Nov 3, 2023


How to Hire your First Assistant and Reclaim your Time, with Amanda Hamilton – Episode 94

Last updated Nov 3, 2023 | 0 comments



This Wednesday, we’re joined by Amanda Hamilton of Hamilton Raye to discuss how best to hire an assistant. Why should you onboard an outsourced admin? To finally buy back your time, of course!

About Amanda Hamilton

Amanda Hamilton is the founder of Hamilton Raye, Your Outsourced Admin®, which brings professional remote administrative support to startup organizations and businesses!

Prior to starting Hamilton Raye, she spent ten years working in the corporate retail industry. She had a very successful career in production and sourcing, where she learned best practices for staying organized, managing priorities, and honing process efficiencies to reduce workloads.

While loving the scope of her work, and her team, Amanda craved personal and professional growth, with a focus on remote work. Intrigued by ‘digital nomads’, Amanda decided to follow suit. Connecting with Founders, CEOs, and small business owners, she saw a white space opportunity to enable these individuals to shed a few of their multiple hats, thus freeing more time in their day!

Points of Interest…

  • When to hire a personal assistant 1:46
  • Common misconceptions when hiring an assistant 5:51
  • Can’t afford to hire an assistant? Think again! 9:58
  • Importance of process when hiring an assistant 17:49
  • Potential pitfalls when first hiring an assistant 18:57


When to Hire a Personal Assistant

Amanda works in a space that has been nothing short of transformative for me, so I’m extra excited to have her share her insights on the show this week.

In short, Hamilton Raye essentially provides fractional executive assistant solutions for businesses. Their vision is to allow every size of business to have access to a professional executive assistant.

In my line of work, I often hear people musing about hiring an assistant, with one such cohort wondering if earning $2 million in revenue was the sweet spot for hiring. In my experience, you need to be onboarding an assistant prior to that point. By way of context; I hired my first assistant when we were barely doing $10K a month. I just started with 10, 15, 20 hours a week, but – man – did ever make a big difference.

As for when Amanda reckons you should consider hiring? Well, pretty much from the offset…

“If it’s something that you can do right in the beginning, I think it’s the best. Otherwise, just when you’re busy enough that you’re starting to feel a little bit stretched – but not too stretched! When you’re too stretched, you can’t then commit the necessary time to train somebody, or build that rapport with them so that they can learn your voice.”

In short, the more you can shift from your plate onto someone else’s workload can only be a good thing. Plus, if you have an assistant, you look more established, right? As you build your business, if you have an assistant, people may view you differently.

Common Misconceptions when Hiring an Assistant

Given a lot of people are unaware of the optimum time to hire an assistant, you won’t be surprised to learn that there are a lot of preconceptions surrounding the subject. Sadly, such misconceptions only serve to hold people back from potentially accessing all of the upsides of having an assistant onboard! In Amanda’s experience, some preconceptions include…

“The cost. It can be a little scary to people – especially if you’re just starting out or if you’ve never worked with somebody before. I don’t think people immediately see the value until you start working with an assistant. Then, you’re a month in and you’re like, ‘How did I survive without them before?!'”

As for some of the other prevalent preconceptions? People can be put off by the notion of delegating to someone, or leading a team, especially if they’ve never been in such a position before. You need to learn to trust that someone – if trained properly/given the right processes – can do some aspects of your job. They might even be better than you at it, and that’s exactly what you’re looking for.

The trust needs to go far beyond that. For example, I had a tricky time getting my head around giving someone access to my email and my calendar. How is this person ever gonna respond to my colleagues, friends, my family, and use the right voice and the right tone?! But the thing that allowed me to keep pushing forward was the wealth of proof that it could be done, simply because everybody around me had assistants doing this very thing – and doing it well.

Can’t Afford to Hire an Assistant? Think again!

If you think you’re not earning/working enough hours to warrant having an assistant, that’s not the case. Put it this way; if you’re an agency owner that can deploy your time for X amount of dollars per hour – let’s say $150, $200 per hour as a consultant – the math is super simple.

If you can buy an administrative assistance hour for $20, then you just bought back a rake load of time. For one hour that you work on client work, you can buy 10 hours of your time back. Once you can get your head around what an opportunity that is for you and your business, your next hurdle is fully comprehending how much of my time is going to all the things that an assistant can undertake for you.

So, in addition to managing your email, what are some of the time-consuming things an administrative assistant can take off your plate? Well, you need to ask yourself three questions – honestly…

  1. Is there anything I don’t enjoy doing?
  2. What am I bad at?
  3. What takes up a load of my time and stops me from focussing on the growth of my business?

One of the first items that Amanda and her team usually relieve clients of is their calendar. While that seems such a personal and intricate thing to take on, it’s often one of the easiest to manage.

“If you have a really busy calendar, Calendar Management can release anywhere from like three to five hours a week, give or take… We have a lot of really cool tools that we’ve built along the way that we can actually do it, we can learn it in a matter of a week and we can take it out quickly.”

Amanda also provides a lot of solutions for wider leadership teams. ***She expands on this from 12:52 minutes***

Importance of Process When Hiring an Assistant

Listen, there is no way we weren’t going to acknowledge the importance of process. ALWAYS acknowledge the importance of process. Anytime you can create an operational process or a workflow for something, that should then be handed off.

“Document everything; ‘After this type of call this document should be sent to them. Then, this email should be followed up with them three days later’, and so on. Anything that can be standardized and operationalized like that – just hand it off!”

Perhaps it takes a month until somebody really builds trust in the process, but once it’s nailed, handing off a duty is a no-brainer. If the stuff is super-nuanced, maybe give a tool I use a whirl – a voice communication app for remote teams app called Voxer. Literally life-changing.

Potential Pitfalls when First Hiring an Assistant

There are a lot of people trying to encourage entrepreneurs to buy back their time, but doing it is hard and scary – for a lot of the aforementioned reasons. What are some of the mistakes that Amanda sees people make when they try to do this for the first time on their own?

“People not committing the appropriate amount of time and resources, in the beginning, to get the assistant or admin set up on the right foot… You have to go into like a partnership if you want to see a positive end result. If you’re not willing to do that, you’re likely not going to get as much bang for your buck.”

This has certainly been the case in my experience. It’s not a very large volume of time; 15-30 minute check-ins every day for the first little while, filling in the gaps, like writing emails together that they wouldn’t know how best to respond to. 80% of it is you can do in process, the other 20% it’s that kind of stuff.

In addition to not investing adequate time in the partnership in its infancy, some of the other routine issues Amanda has seen clients encounter include compensation expectations. For example, if you’re looking for somebody that’s a “doer”, that’s good and all, but you must make sure you’re compensating them appropriately. After all, you get what you pay for – and a good admin can truly drive a business and profitability. You just need to find them… and make sure they’re vetted adequately.

This is where an agency like Hamilton Raye can really help because they undertake both sides of the vetting process for you. ***Amanda expands on this from 22:26 minutes. Meanwhile, I recount my own experience hiring my assistant via Upwork from the 23:19 mark***

Key Takeaway…

Time is your most valuable asset and it’s something that you’re never going to get back… All of your seemingly “quick” jobs, which take a minute or two, stack up throughout your day.

There you are, at your desk at 6pm, when you have to start all these stacked tasks to do, like following up on sales calls, adding notes to a CRM schedule, sending the sales deck to this person, and responding to this email… Next thing you know, it’s 9pm and you’re still at your desk. It doesn’t have to be this way.

The importance of humanizing your brand and reclaiming your time can not be overstated. The most necessary piece of being a business owner is to maintain maximum efficiency and productivity, by keeping your schedule moving and remaining highly organized.

See more from Amanda…

Did you learn anything new from this episode? Let us know in the comments below! We have helpful blogs designed to bolster your agency profitability, such as How To Calculate Your Billable Employee Cost-Per-Hour.

Our next installment of #APP, on September 7th, will see Marcel chat with Rachel Jacobs. Our previous blog – Episode 93 with Bryan Adams – can be viewed here…

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