Personal Assistant

The 3-Step Process to Hiring Your First Assistant

What sort of assistant do you need? Read this guide before you make a hire.
The 3-Step Process to Hiring Your First Assistant
Image credit: Ariel Skelley | Getty Images
VIP Contributor
CEO and Founder of Keller Media, Inc.
9 min read
Opinions expressed by Entrepreneur contributors are their own.

In the never-ending quest for increased profitability, greater efficiency or just feeling less overwhelmed on a daily basis, finding the ideal assistant is a critical growth step for every entrepreneur or small business owner. We all dream of finding that perfect person who can read our minds, get the work done as fast, do it as well as we could, take the little annoyances off our plates, and maybe even become a fun and trusted colleague. 

So why isn’t finding a great assistant as easy as it seems? Because of fear: fear that the assistant will make mistakes, take advantage of us, or won’t get stuff done on time. Some fear that we cannot afford this person, don’t have enough work for them to do, or that we won’t use our time profitably if an assistant takes the busy work off our shoulders. What’s your reason?

“The average entrepreneur wastes at least two hours per day on emails, phone calls, scheduling, re-scheduling and research,” according to Jennifer Maffei of VEA Services, an assistant placement and training firm that teaches business owners and their assistants to become more organized, efficient and productive. “Multiply those two hours by five days and you’re losing 10 hours a week.” Over the course of a year, that’s around 520 hours -- or three months of work time. That’s a lot of time to waste when you could be making money with it.

Assuming you’d like to save three months this year on all the stuff that isn’t making you money, here are the best ways to get yourself the right assistant with the least amount of hassle, drama and waste.

1. Figure out what you want to delegate.

In most small businesses, everyone wears many hats. That’s why hiring an assistant is a very big step! First, you need to untangle what you do now that could be delegated. Start by listing everything you do -- and everything that you should be doing -- for a week straight. (It pays off later, really!)

  1. Set a literal notebook on your desk with a pen and a timer. Set and reset the timer for 20 minutes all day, all week. 
  2. Using shortened versions of tasks, like “posting social media” or “talking to vendors” or “sales call”, note what you are doing in each 20 minute segment. 
  3. At the end of one week, add all the things you wanted to do that week but didn’t get done. 
  4. Take a highlighter and highlight anything that could have been delegated if you had an assistant you trust. Things like scheduling, social media posting, haggling with suppliers, buying office supplies, putting toner in the printer, rescheduling the client meeting, checking airfares, etc. can be delegate 

Look at this list of highlighted items. Think about what you earned per hour in your last hourly job, or what your pay/would like to pay yourself per hour now. Maffei says, “Ask yourself, ‘Would I pay someone else my salary per hour to do these tasks?’ If you wouldn’t, delegate it!” If you squandered an hour sorting the mail and answering basic emails, is it worth $50 per hour? Is it worth $200? Obviously, no.

After a week, you have a very clear list of things that you really ought to be having someone else do. Transfer this list to a clean Word document (since you don’t yet have an assistant to do that for you!) 

Print and review the list. How many of them require someone’s physical presence in your place of business? Dropping off shipments at the post office is something that must be done, but buying supplies can be handled online from anywhere. So can answering the phone. Just use a routing system like Grasshopper.com. But greeting patients as they come into the clinic requires a physical presence.

Do more than 20 percent of your tasks require someone’s physical presence? Are you certain there’s no other way? If so, then you will need a person in your space. A part-time or full-time assistant will likely need access to a computer, a phone and a printer, at a desk. Anyone in your physical space -- home or office -- is also going to need a clean bathroom, a parking space and probably access to a fridge. They’ll need to take breaks, lunches and take time off. The tax and insurance requirements change with an in-person assistant, so check with your local government. You may need the assistant to be there even when you’re not, and you may need to be in your place of business while they are present, even on days you don’t want to be.

A virtual assistant can be anywhere in the world, and are increasingly common because they are flexible and economical. Cloud computing and other technology means people can and do work from anywhere. Some virtual assistants sell their time in packets, such as 15 hours a week or 40 hours a month. If you hire someone in another time zone, work can be delegated at the end of the day and it will be ready when you come in the next morning.

2. Figure out what kind of assistant you need.

An executive assistant is someone who is supporting one or a few executives. This person is the boss’ right hand.  “An executive assistant will use her knowledge and experience to make decisions on behalf of the leader,” according to Gayle Transon, an executive assistant with American Express in Phoenix. Executive assistants perform tasks specific to the boss’ duties, and are even capable of attending meetings in your stead and taking useful notes. An executive assistant manages the executive and his/her schedule.

An administrative assistant is someone who generally supports the whole company. They are more of a generalist and may do many diverse tasks. This person might post to your business social media pages, order office supplies, field incoming calls and keep the files organized. 

Think through the long term effects of your decision, and the “brand” of assistant you want to hire. The training process will be minimized dramatically if you start out with the right person, with the right expectations. 

3. Figure out the hiring process.

Write and post your ad for an assistant in more than one location. Perhaps a job listing site for your industry as well as a few online venues, or hire an assistant search firm like Maffei’s. It’s worth paying money to find the right person. “Try to avoid the trap of paying your assistant the least amount possible,” Maffei warned. “When it comes to assistants, you really get what you pay for. You know you have hired the right person when you are able to communicate effectively, delegate without worry and feel like you truly have a partner.”

In his seminal book Your Virtual Business, author-entrepreneur Alan Blume advises would-be employers to include all the information in the ad to attract the highest qualified candidates. When you write your ad, include the list of tasks from Step One at the bottom. Below that, use Blume’s clever strategy: tell the applicants precisely how to apply – with a twist. For example:

How to Apply:

  1. Reply by email and attach your current resume.
  2. Change the subject line to “Your Excellent New Assistant.”
  3. Include a short cover note explaining why you want to (work in a doctor’s office/work part time/work virtually/work only on Tuesday mornings) -- anything from your ad that might elicit an interesting note that shows the applicant’s personality a bit.

The genius bit: The second instruction matters the most! This step reveals whether they did/didn’t read the whole ad and do/don’t pay attention to details. Since an assistant must be quite detail-oriented, you want someone who pays attention and who has read the whole thing. If these directions are not followed, delete the email application unread.

Transon said, “To hire the right assistant, match the (person’s) requirements and qualifications, compare expectations, get a gut feel and then it’s trial and error.” 

Maffei, who has hired and trained many assistants, offers three valuable interview questions.

  1. Why are you leaving your current position? Their answer will tell you a lot about the candidate’s personality right away. 
  2. What do you feel are the most important qualities in an assistant? This will reveal how they view themselves and the responsibilities of their job;
  3. How do you continually educate yourself? Maffei explained that "it is vital that an assistant continue to train – either with the company or on their own -- to continually hone their skills and stay up-to-date in this rapidly changing business environment.” It also reveals whether or not the person views being an assistant as a stop on their career path or a profession in itself.

The decision to hire an assistant is a big one. Realizing your company’s growth is being stymied without help means you’re doing something right in your business -- congratulations! The three steps above will help you find and hire the right assistant.  

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