Hiring Your First Assistant

Operations

Jul 8

Find The Help You Need in 5 Easy Steps

As a long-time solopreneur I always shrugged off the idea of hiring help. I was used to doing it all myself, and it seemed like I never quite had the margins to pay someone yet (let alone take time to train them). Once 2021 got going, my perspective quickly changed. I was buried in deadlines and knew it wasn’t sustainable, especially if I wanted to scale. I tried hiring freelancers through Upwork in hopes that an expert could jump in and quickly take things off of my plate, but didn’t get great results. When I finally had a second to catch my breath I took the steps below to hire our two fabulous design assistants, who are now amazing at completing many of the production tasks that come with every project we deliver. To say it has been a game changer would be an understatement ✨.

But before we dive in, let me preface this by saying there are lots of different models for getting help in your business. Many business owners start with getting some household help—childcare, a cleaning service, grocery delivery, someone to handle laundry or errands—to free up more of their time. Some can get by with temporary help from sites like Fiverr and Upwork to get them through a busy season. And some prefer to hire on an experienced pro (bookkeeper, legal help, or someone skilled in their field) who costs more but can jump in with little to no training and immediately get to work. Those are all great options, and depending on your situation they may work well for you. I was personally ready to expand my team a bit and have some reliable, trained help to take things off of my plate and allow our business to grow. The following tips are focused on a part-time assistant role, either someone who has some experience in your field and can handle specialized projects, or someone who is skilled in general business tasks like a virtual assistant. Let’s get started!

Step 1: Track

One of the best things I did in the weeks leading up to hiring was create a Google Doc and keep a running list of all of the repeatable tasks I was doing for each project and noting which things I felt comfortable delegating. Turns out there were a lot! It’s easy to get in the mindset that no one else can do things quite like you do, but truthfully if you have some solid systems and templates in place you can easily train someone to complete many pieces of a project at just as high of a standard. I also began adding notes around some of the tasks, which made it easier for training later (and will be super helpful once I get around to documenting all of my SOPs—or standard operating procedures).

Step 2: Plan

Once you’re ready to start thinking more seriously about hiring help, you can review your Google Doc and find the common threads. It should help you answer questions like…

Do I need a more general virtual assistant (VA) who can help with administrative tasks? Or would I like to take a specific set of tasks off my plate (like social media or blog post writing)? Maybe you need a more junior version of yourself who is interested in learning more about your industry and has some skills unique to your niche.
How many hours of work would you like your new hire to complete? Can you define a set number of hours per week or month that you have adequate work for someone to do? This is where it’s helpful to start thinking about budget and estimated costs for bringing on your new hire.
Will your new assistant be a 1099 contractor or a part-time employee? If you have a bookkeeper or accountant for your business, this can be a great thing to discuss with them, as there are pros and cons for each.
Are you considering a trial period for both you and the new hire (i.e., circling back after 30 days to determine the arrangement is working well for both of you)? What are the terms of your work together?
Where will the new assistant work? From home? At your office or work place?
What other things will your assistant need to be successful? In some cases a business email address, uniform, or something else may be necessary.

After thinking through these questions and reviewing your Google Doc list of tasks, it’s time to write a job description. Be sure to include the job’s title, pay rate, employment type, responsibilities, required skills, software or other tools, location (if applicable), etc. Include a short bit about your company’s culture or other information that will be helpful for applicants to know.

Step 3: Post

I would recommend posting the opening and job description on your own business web site and social media accounts first, as well as asking people you trust for referrals (or in any professional groups you’re a part of). See what kind of response you get. If you’re still looking for more applicants, sites like LinkedIn and Indeed.com will generally guarantee you a huge number of applicants to consider. If you are opening the post to a wider audience, I recommend including specific instructions on how to apply (such as emailing you or answering a question/referencing something specific) to weed out the folks who simply hit the “Apply” button dozens of times a day on job posting sites. You want applicants who have read the full job description, taken the time to learn about your business, and are genuinely interested in working for you.

Also be sure to include a cutoff date for accepting applications, then set aside one day to go through them all to determine who is most qualified, followed your instructions, and seems like the best fit. Reach out to your top 2-4 choices to schedule an interview by phone or Zoom.

Step 4: Interview

Prior to interviewing your candidates, type up a list of questions to ask them. It’s important to ask each person the same set of questions, and you can print multiple copies of the interview questions to take notes on during your call. Some questions will be straightforward (about skills or software knowledge) and some should be more open-ended to allow the candidate to share more. Of course you’ll want to review each candidate’s portfolio or work history ahead of time too. I found 30 minutes per interview to be plenty of time to get to know each person, go through my list of questions, allow them to ask me questions, and go over next steps.

Step 5: Hire

Finally, you’ll need to choose a candidate and make an offer! Craft an offer email or letter that reiterates the work arrangement and terms (or you can put those in a separate contract), and ask for written acceptance if they would like to move forward. Also send a W-9, NDA, or any other tax or legal documents that the new hire should complete prior to their start date. As a courtesy, it’s always nice to notify other applicants that the position has been filled (LinkedIn and Indeed have a blanket way of doing this in the settings).

Throughout the process you should be thinking about how you would like to on-board your new assistant, such as asking them to review certain materials, install apps or other tools needed to do the job, or planning times to shadow you or watch training tutorials. Once they know the basics and have been trained on how you would like things done, it’s time time to start handing things off 🎉.

Congrats! We hope your hiring process goes smoothly and that you find someone who is a great fit for your business. Have more questions or want to tell us how it went? Continue the conversation at hello@duewestdesign.com!

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