If you haven't been asked already, at some point in your time as a CEO and business owner, someone you know and love will ask you if you have some work they can do.

Let's call her Sally.

Sally might be your neighbor's daughter, your best friend who is inspired by you and wants to learn from you, your baby sister… You name it!

It doesn't matter who it is – friend or stranger. You need to put your CEO hat on and answer this question as a leader of your business:

Should I hire Sally? 

Some people have a hard and fast rule against working with friends and family. I am not that person. I have had success with this and think you can get this right if you separate the people from the problem and proactively lay out expectations.

I am not going to recommend do not hire Sally just because she is a friend… There is a method to the madness. Let's dig in.

#1 Does Sally have the skills you need her to have to support you in your business?

Ideally you will answer this question based on role description. A role description describes what you need someone to do, the skills they need to have, and may even outline measures of success. If you don't have a role description set up, consider the activities you want to get help with or activities that are not revenue generating or client facing. These are easy things to start with when it comes to outsourcing.

If Sally does have the skills, move on to question 3.

If Sally does not have the skills, move to question 2.

#2 Are you willing and do you have the time to train Sally?

Your time is limited. Be fair and brutal when you answer this question. It isn't fair to Sally ifyou say you have the time, when in reality you don't even have time to go to the bathroom.

If you are stretched so thin that you don't have the time to train Sally, you probably need to hire someone who is already trained up so they can jump in and immediately support you.

Don't throw Sally into the deep end of the pool without floaties unless she can swim!

If you do have the time to train Sally, move onto question 3.

If you do not have the time to train Sally and she does not have the skills don't throw Sally into the deep end of the pool without floaties until she can swim!

I recommend not brining Sally on board. Here’s a starter script you can build upon to let her know your decision. Naturally, you will change it up based on what is true and accurate form your situation.

Hey Sally,

It would be a blast to work with you. Based on our conversations, it will take some time to get you trained up. I am so busy right now I won't have time to train you up and I don't want to throw you into the deep end of the pool without some support. I really need someone who can jump right in.

If that changes in the future or as I grow the team and get someone onboard that can help train you, I will reach out. Let’s stay connected on this!

If it matches your voice, take it as it is. If not, update it so it matches your voice and take it away!

#3 All things considered, will Sally be successful in the role?

Beyond skills and training, consider if Sally is a fit for this role more broadly. I am talking hours, equipment and tools needed to do the job, values, professional skills, etc.

If so, you have a winner! Move Sally through your hiring process.

It is easier to say yes and hire family and friends than it is to sever the relationship. If you go this route, set clear expectations up front. You can point back to those expectations when things go sideways and take time to reset the expectations or determine if you will continue the working relationship or not.

In it to Win it!

Sure, you might bring people onto your team as a favor to your grandma when you are bigger, but now – when you have an eye on your profit margin and time is a scarcity – is not that time.

Tell us in the comments, any other advice for hiring people you know and love?

Bring it on!