I've been a solopreneur for a number of years now, and when my son was old enough, I got him involved in helping with my business. But he is off to college soon and I will need to hire a replacement that will do his work and hopefully much more as the business continues to grow.

I have a person in mind to hire, but I need to put together an offer, and the new employee will start part-time and grow to full-time. I feel confident in the persons abilities and that they'll be a good fit.

So what things do I need to be concerned with -- administrative-wise, tax-wise, legal-wise -- when hiring my first employee?

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    Hey Mark, welcome to Freelancing SE. Is it possible to toss out a more specific question? We'd like to think we're here for more than just book recommendations and would like to help with a more specific question you might have. For instance, perhaps you might want to ask what your biggest concern you have in hiring employees? Hope this helps. – jmort253 Aug 11 '14 at 3:31
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    Thanks @jmort253 for your suggestion. As a techy myself, I'm not an accountant, tax expert, HR manager, or lawyer. So I really am looking for something that covers the range of topics when a freelancer has to make their first hire. If I ask What is your biggest concern hiring employees, I don't want to get answers like, "making sure they are self-motivated" or "are they trustworthy". I have an specific person in mind and I feel confident in the person I want to hire. I just don't have a clue on the administrative side what I need to do in hiring an employee. – MarkS Aug 13 '14 at 0:12
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    Okay. Just so you know, if none of the answers you do get answer your question with what you're looking for, I encourage you to edit with more details/clarification if anything more comes to mind. – jmort253 Aug 13 '14 at 4:23

Mark, Your state department of labor/employment ought to be able to help you with the regulations and policies. I remember that Texas Employment Commission had sample employee handbooks for employers on its web site, so I did a Google search on that as a search string.


You can peruse the samples and see what the responsibilities you'll need to cover.


There are books on exactly what you're asking:


I'd run down to Barnes and Noble to see what they have to offer. It will vary from state to state (I assume you're in the U.S.)

On the "money" side of the issue, I'd recommend you find yourself a payroll processor. I use ADP Run, and for $40/month they'll do direct deposit, calculate and transmit fed and state taxes, and generate W-2s at the end of the year for up to 10 employees. There are lots of other companies but you'll have to dig around for what suits your needs and budget. I did this 'cause I don't want to be a payroll expert -- I just need it to work.

  • Not sure if I'm ready for something like ADP Run. I have a friend that works for a company that outsources their entire HR department to a company that handles payroll, benefits administration, vacation and sick day administration, time sheets, 401k, taxes, and more. Again, that's more than I think I need at this stage of the game. – MarkS Aug 13 '14 at 0:17
  • There's always quickbooks :P I couldn't stomach an all-in-one. – Xavier J Aug 13 '14 at 0:19
  • I always thought of quickbooks as strictly accounting software (a business version of quicken). – MarkS Aug 13 '14 at 0:21
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    No, it's always had a payroll module. The online version has it also. – Xavier J Aug 13 '14 at 0:22

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