How to hire your *first* employee, helper or assistant.

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Hey friends! Stephanie here. 

As many of you know, I own Cleveland Flea and Creative Clubhouse. And I'm not the only one who does work around here. Thankfully. I have all sorts of help– full-time employees, part-time employees, contract workers, collaborators, interns and volunteers. I honestly can't believe I made it here because just a few short years ago I was a hot mess of a busy entrepreneur who had no time to hire but also no time NOT to hire. It felt like a catch 22. I needed help, but I had zero time to find that help. 

First. That is untrue. Bummer, right. It's time to put on our boss hat and do what we need to do. I talk about this in my Handcrafted Method content series (hopefully to be a book someday!!) but when you get to a point when you're CRAZY BUSY, it means you need to buy yourself more time. It doesn't mean that you need to wait for life to calm down. Because it won't. You need to recognize what's going on and if you want to scale up or have some sanity, you need to get to work hiring. 

So, let's talk for a moment about how you go about this process. 

Your first employee / helper will most likely be a clone of you (sort of).

  • They will just be taking 50% of your work off of you, in most cases, not being hired for a specialty position. If you are NOT a hot mess, then maybe your first hire will be for a more specific position, but in my experience most of my clients just need someone to help with the workload in general and they have little time to give direction.
  •  They will need to be ok with the fact that you are an actual hot mess. Be up front with them.
  • They will need to have a range of skills, as you do. 
  • They will need to be as into your business as you are. Don't hire anyone who doesn't get what you do. It won't work.
  • They will need to be BETTER at a few things than you. Combine forces. You're going to typically be the technical genius in your biz (chef / baker / coach / jewelry designer / etc) but you will probably lack other skills that they can have a slight proclivity in. Look at your business, where are you suffering? Social media? Website management? Marketing? Organizing? Make sure your hire is good at the things that your business needs in order to get better.

How do you figure out how to pay this person?

  • To get good help, you've got to be willing to pay a competitive rate. I'd pay above minimum wage, because you get what you pay for. 
  • How much work do you need taken off your plate? How busy are you? From this you can figure out how many hours a week you'd need them there.
  • How much work do you *wish* you could get to but you just don't have time? List all the things that you wish you had in your business (new website? better turnaround time on emails? lots more marketing and social media?) and then that becomes your list for what this person needs to be capable of doing. 
  • Think through how much this will be bi-weekly and monthly.
  • Make sure you know what your business will now need to bring in to pay this person. 
  • It's possible you can even structure a percentage or incentive-based payment. If you think their sales skills are strong, and they can secure you more work maybe you give them a percentage of sales. Just a thought. 
  • You're going to need to do some math. It's not that big a deal.
  • When you've listed all the things you ideally want them to do, make sure you list the things YOU want to do daily. Remember that you should hire people based on how you want to live your biz life. Create a situation that's better for you, not worse (speaking from experience here)

How do you spread the word?

  • First, draw up a job description in word or google docs. 
    • Hours per week or month. 
    • Schedule.
    • Name of position.
    • Any qualifications this person must have (copywriting experience? any programs they need to know? what about certifications?)
    • List of tasks.
    • The culture of your place / what they can expect from you or the experience. Be up front. If you're an early entrepreneur, that's a different boss than one who is supported by a ton of corporate structure. And that's ok.
    • Compensation. Besides money, are there other ways you can compensate people? Maybe you're a chef and you routinely have extra food from your business. Or maybe you offer a work-from-home schedule, or even Monday's off. All these bring value to people's lives in a way different than money. 
    • 6 month to 1 year snapshot. What might their next year look like? What will they have learned and experienced? Where will they have grown? 
  • Post it on your social media and ask your biz friends or family to share. Many times your biggest fans turn into your best employees (speaking from experience here!)

Interview Process

  • Make sure you have an interview process in place. Even if it's just a phone interview, make sure that before you post this you know what the next step of your potential hires might be. You can use scheduling app Calendly to set your schedule up in a way that makes it easy for both of you to connect via phone. Or maybe decide on one day you'll spend at a café conducting 30minute interviews. 
  • Maybe you want to have a working interview. We do this with all our entry level or non C-suite employees. We start them super part time and have them come in for at least 1 working interview to assess if we're a good fit. And if they're not cool with how the place feels (startups can be slightly chaotic) then they know immediately. 


  • Listen. The government wants your money. And they also want to make sure you're treating people right. 
  • SOOOOOO if you have someone work 30 or more hours a week and you're directing them, you're supposed to officially make them an employee or at least make sure they're filing taxes appropriately. Basically, you'll want to discuss this with your potential hire. Taking taxes out for them is helpful so they don't have a giant tax bill at the end of the year. However, they can be responsible enough to manage their finances appropriately if you discuss it with them and they agree.
  • Getting set up on payroll can be fairly simple, but if you're nervous, an accountant can actually help pretty simply. 
  • We use GUSTO for our payroll, and our accountant set it up but it seems super simple to set up yourself. 
  • If you don't want to get into any of this business, you can only have part-time help. You can only have independent contractors. Just do it all legally. Independent contractors don't have to be your employees or be where you need them to be. If you want to direct someone, plan their schedule and have them perform certain things then they are your employee. 

When is it necessary to hire someone?

  • When you consistently can't keep up with things.
  • When you are 'running around super crazy'.
  • When you don't have a personal life.
  • When you're losing money through inefficiency or not being able to get back to clients.
  • When you want your life to be better.

Will you ever become a good boss?

  • Most likely. 

Will you have enough money to pay an employee?

  • Sure! You're probably losing money without these people. It's sort of their job to make you money.

Will you like managing people?

  • Who knows! But the good news is that you get to be any type of boss you want. Just make sure you're up front and understand that not everyone wants to work for every type of boss. I don't like managing people, but I have people that help me with that now (my own employees!!)

Go out there and get some help, friends! 

If you want to talk it through with me, I'm happy to help you shape your Hiring Campaign and find the best darn help for you!