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What I Learned While Trying to Hire My First Employees

I am a huge believer in hiring out ALL tasks that can be performed by someone who is far more skilled and experienced than I am. And let me assure you when I say: that list is long and impressive.

I know that many of you are at the stage of your business (whether you want to admit it or not!) that you *need* to be hiring out help. It’s a scary thought to be spending money on a business that might not be rolling in tons of cash, but you will never be able to grow your business if you insist on doing everything yourself.

Let me repeat that one more time: You will never be able to grow and scale your amazing, life-changing, so needed business if you insist on doing everything yourself.

Because it’s just you, there are only so many hours in the day, your mental capacity will at some point hit it’s limit, and frankly you aren’t an expert in everything!

So leave it to the experts, and give yourself more time to work on future growth, that thing you’ve been putting off, to train another client, or just take a minute to breathe.

That sounds nice, doesn’t it?

This year I have been incredibly fortunate in my business and have been able to stop doing everything myself. I started hiring out tasks and projects, but it became clear to me that I needed constant support to move the needle forward. A few months ago I put out a rough call to action looking for 1) tips in hiring an assistant, and 2) any hot leads/referrals from my existing small business owner friends for a local assistant or strong virtual assistant (VA).

I ended up receiving tons of applicants, lots of feedback and oh man - what a learning experience that was. Long story short - I did not end up hiring a full-time assistant. I hired out multiple, long-term projects. But through this process I learned so much about people and hiring, so I have to share with you all my takeaways, advice, and cautionary tales.

Because the new year is coming, you have *BIG* growth plans, and you know there’s no better time to start building that empire than today. Let this be you putting your toes into the water of the hiring pool. Or heck, dive right in!

1 - Be super specific in what you’re hiring for. Trust me I get it - it’s a really cool feeling to say “I’m hiring my own assistant.” You finally freaking made it. But there’s hiring an assistant because you have lots of stuff to do, and my goodness will they help with all this *stuff*; and there’s hiring task-specific people to help grow your business by applying their expertise to your products and services.

My biggest mistake was not taking the time to create a truly comprehensive list of what tasks I needed done, on what timeline, and what I valued the tasks at. I should’ve created a typical day/week for my assistant, which would have allowed me to see what they’re doing and how they’d be spending their time. Because I didn’t get super specific, I had an idea in my head of all the things I wanted done, but it didn’t occur to me that what I needed done wasn’t going to get accomplished by one person.

I thought I’d be able to find a flexible, highly tech-savvy, social media proficient, and affordable assistant who only wanted 10ish hours of work a week with zero interest in regularly attending VIP wellness events, or “raiding my closet” *face palm*

In the future I would write out everything: what tasks I needed done immediately versus long term, local or in-person versus virtual, simpler admin tasks versus more complex or technological. Basically every day I’d look at my calendar and see what tasks could be assigned out. And then I’d do my market research on what each of these tasks should cost (Upwork, Fiverr and TaskRabbit are great resources for this) - to see if I could justify hiring one person a flat fee for all of the tasks.

Which leads me to my second point:

2 - If you can’t hire one person, hire three and piece the job together. Running a business involves so many facets and tasks, and they’re not all on the same skill level. For example, one day I will need help copywriting, creating graphic designs, and listing clothing on Poshmark. The next day I need a skilled web developer, a proof-reader, and someone to manage a giveaway I’m running on social media.

When the tasks require different levels of education, skill, experience, and compensation structure - break them out accordingly a la step 1. This way you’ll make sure that you’re hiring the best person for the job and paying the appropriate amount for the task at hand.

My solution: I went back to my list, broke down the tasks, and then grouped the tasks into what one person could realistically do (ie - one person to work on my website, another to work graphic design, another to help with email marketing). And then I contracted out work to 3 distinct people/companies who specialize in each of these groups of tasks. I feel better knowing that tasks are assigned to experts, and I’m paying each person appropriately given the complexity of what they’re doing. That also means I’m keeping certain things on my plate that I realize aren’t quite worth handing off yet.

3 - Consider only serious candidates who have relevant experience. When I put out that I needed an assistant, I received a lot of messages from people who were looking for work in general. Friends that were willing to help. People that wanted to work in the fitness industry, though unclear why. A lot of “pick me!” that wasn’t necessarily for long-term, purpose-driven work. And that’s ok. But it’s not what I needed.

I needed candidates who were committed to their own careers and growth and would take pride in their efforts and products. I needed candidates who weren’t just desperate for money looking for any job but were desperate to be part of something bigger. I also just needed people who could do the work that needed to be done.

My solution: my friend Elizabeth gave me great advice about really being clear in what I was looking for in a person, and not being afraid to ask them lots of questions. I created a checklist of the characteristics, qualities and experience I needed from my candidates, and judged everyone against this. This also took any personal bias out of the equation - if you couldn’t check all the boxes, you weren’t right for me no matter how great of a friend/person you are.

4 - You can’t hire someone you’re not comfortable firing. This one to me is the most obvious, but let’s just say it anyways: You cannot hire someone unless you are comfortable firing them if they don’t meet your expectations.

You are giving someone money in exchange for performing a task that meets or exceeds your expectations. If they continuously fail at this without improvement, they’ve wasted your time and money. Part ways. Yes, even if they’re your friend/cousin/family friend. Yes, even if they’re friends with so-and-so who’s going to connect you with whoever. Yes, period.

If you have any doubts about firing someone if working together doesn’t work out, or how firing someone/parting ways will affect your relationship, you cannot hire them in the first place. If they ask why, tell them that you don’t want to jeopardize your relationship. If they can’t accept that answer, they don’t respect you and that should be enough of an answer for you too.

5 - You have to pay people their value. I know you know this. And you know that I know you know this. So I’m going to leave this right here - you must people for working for you. Unpaid internships didn’t fly with you when you were in school, and they don’t fly now.

It’s not a rite of passage. It’s not ‘invaluable experience.’ It’s not ok.

If you’re not willing to invest in the people who are helping build your business, you cannot expect clients to invest in YOU to help grow their business.

And if you are not in a position to be paying people appropriately, you aren’t in a position to hire. Even if you feel busy, start breaking down projects by level of priority and importance; those get your attention first and the rest can wait. PS: the most important projects and tasks are those that are making you money.

6 - Check Your Inbox!

xx, D

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