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When to Hire Help in Your Business & How

I am so excited to share this month’s blog post on When to Hire Help in Your Business & How.

I started my business in February of 2021 and I’ve been working at it tirelessly ever since! Which is normal at the beginning of entrepreneurship. However, we all know that there is no longevity in that.

Let me share with you the process I went through in hiring my first assistant to help me run my business! Sounds easy, ends up being kind of easy, but mostly complicated because it's the first time hiring EVER!


I would say the best time to know when you’re ready to hire help for your business is when you are overwhelmed and feeling like you’re drowning – 3 months before that!

If you’re spending a lot of your precious time doing tasks that someone else can do for you - it’s time to hire.

If your business is starting to fail - i.e. things are being done to your standard or you are not hitting deadlines, maybe you’re losing clients - it’s time to hire.

If you’re thinking to yourself “Wow. I’m just getting started with this business and I have much bigger plans for this. This will be impossible.” - it’s time to hire.

Once you’ve come to your senses and you remember that you are a strong and capable person who has been running a successful business thus far, it’s time to start the prep work for hiring someone to help you.

Another important factor to consider early on in the process is your budget. Can you afford to hire someone in your business? If this financially doesn’t make sense for your business then you likely need to pivot elsewhere.

I completely understand the need for this because my business coach recently told me I am on the Entrepreneur Roller Coaster - a book by Darren Hardy you can find HERE - that I am now reading per her recommendation and homework haha. Basically, as an entrepreneur, I’m spending all of my time coming up with and starting these amazing projects as a way to avoid actually doing the work to see them through and create a source of income for my business.

This is what I mean by pivoting. If you’re spinning your wheels like I was and not focusing on creating a consistent source of income then you don’t have a business. You have a very, very expensive hobby.

In order to have a successful business, you need a recurring income. You are not ready to hire someone, you need to pivot. Focus on your business and getting a regular source of income first and once you have that AND a source of income to afford hiring help - then come back to this blog.


The prep work for hiring someone is a bit tedious, but it will give you clarity and confidence with this entire process.

I started with (and I recommend you start here too) taking a tip from Gogo Bethke. Gogo taught me to make a list, two lists actually. The left side of the list will be the green light tasks, the right side of the list will be the red light tasks. Green light tasks are the items that you do that can and should be outsourced to whomever you hire. Red light tasks are the items that you cannot outsource.

Now that we understand the tasks list, you’re going to take a week or two and write down literally everything that you do all day everyday. Every single task will fall either to the green light or red light list.

Once you’ve done that, you have just created your list of items that you need to hire help for.

Take a look over your tasks. Can they be done virtually? Or do you need a local assistant for maybe running errands or picking up dry cleaning, etc.?

Now that we know what tasks we need help with, take some time to jot down some ideals for you and your business.

What hours would you like them to work? Can they have a flexible schedule so long as the tasks are completed on time? Or would you prefer they work Monday thru Friday from 9-5pm and that’s that?

Also, think about wages. Are you offering a salary or hourly wage? I recommend doing some research on this to have an idea of what the typical pay rate is for an assistant.

I had no idea what a virtual assistant makes and there are so many factors.

Something I’ve found that is very popular right now is to hire people that live in another country. They’re rates are more affordable compared to those in the US. This was an option that I considered and I did interview a few candidates located in the Philippines, but ultimately the time difference was going to be an issue.

You don’t have to have all of the answers and everything set in stone today, but it is good to get an idea of what you have in mind for this position, where you can be flexible and where you can’t.


If you’re anything like me, this is the fun part!

Now that we’ve done the prep work and we know exactly what we need help with, it's time to get out a piece of paper and imagine the kind of person we would love to hire.

Describe your ideal assistant:

What is this person like?

Do they communicate well?

Are they honest?

Are they creative?

What experience do they have that can relate to the position you need them for?

When I did this, something I came up with that really stuck out to me (and I feel like I totally manifested it in my assistant) is that I really wanted more of a team player than an assistant.

While I needed someone to help me with tasks, yes, my personality really thrives in a team setting. I think this comes from me growing up playing on sports teams as well as having shitty jobs in the past working with horrible, horrible management and co-workers.

For those reasons I knew that trait was going to be important to me along with a few others.

When you write these things down, you will also find yourself unpacking things and why they are important to you.

Pro-tip: Take what you’ve learned from the prep work and the wish list and turn it into your interview outline guide. The things we discussed above are important to communicate and set expectations during the interview to know if it is a good fit for both of you or not.


Now let’s dive into putting it out there, starting the process of finding candidates and interviewing them.

My first step was posting in some of my favorite, high vibe Facebook groups about finding a virtual assistant.

I actually did this before I was ready to hire anyone and I don’t recommend that!

Wait until you are ready to schedule interviews. I had a handful of people reach out to me. They were available and wanted to start asap and I was not ready for that.

I did collect their contact info and told them I would touch base after the holidays and I ended up hiring one of those girls that waited for me - I was so thankful!

I know a lot of business owners that have utilized Upwork in finding potential assistants and they have had great success with that.

For some reason, I wanted to reach out to my sphere first before going to a website. As I mentioned above, I know a great deal of highly successful entrepreneurs that have found great workers on Upwork, so you decide which approach is best for you.

Once you have your candidates, schedule their interviews.

For the actual interviews, I find it’s best to ask them to tell a little bit about themselves as well as their professional experience.

From there I would usually tell them about myself and my business. Most importantly what I am needing help with, what I am looking for in an assistant and what my expectations are for that position.

Refer back to the prep work we did earlier to gain clarity on this. You want to be prepared to get the most out of the interview as well as respect their time and yours. You’re crazy busy after all, remember?!

Pro-Tip: Be sure to jot down plenty of notes. Let the candidate know you’re taking notes, you’ll want to be thorough here because you will not remember everything.


Now that you’ve interviewed all of your options, take some time in reflecting on and deciding.

I structured my interviews within a few days during one week, and I communicated to each of them that I would be taking the weekend to think it all over before deciding who I wanted to hire.

This worked out really well because I had my notes - and even after I completed the interviews I sat down and took even more notes that I had running around my head. I tried hard to think if our personalities would be a good fit, if I could see them working on my business together in the long run, etc.

This is so important because for probably 3 out of the 5 interviews that I did, immediately after the call I thought, “they're the one! This person would work out really well and be a great fit for the business”.

My husband chimed in and said, “well, sleep on it, take a day or two and make sure that you feel the same way that you do now, later on”. We all know by now that Drew is right 99.9% of the time, so I listened. I’m glad that I did because I realized that the initial excitement had worn off and I started to see the answer clearly. I let my intuition guide me and I felt that I made the best decision.

Looking back now, I realized that they were all nice, they had the experience I was looking for, and we each had a great conversation, but that doesn’t necessarily make for the best fit.

I’m a people person, but I needed to put on my CEO hat for this decision.


Now that you’ve taken the time to process and decide it’s time to reach back out to your number one choice candidate.

Let them know that you think they’d be the best fit and begin the discussion on what you agree to pay them and all that.

I also would strongly encourage you to have an agreement signed by all parties. This is your business and no matter how well you think everything will go you should ALWAYS put your business first and protect it.

Be sure that there are items in your contract that are necessary for your business. For example, if you have creative projects that include original designs, or clients’ private information - you are responsible for that. Have that in your agreement what information is private and cannot be shared whether they continue to work for you or not.

Another thing to think about is termination. I would recommend doing a trial period or simply have it in the contract that either party can terminate the agreement with written communication and two weeks notice, or something to that effect. It’s a story for another day, but you don’t ever want to get stuck into a long term agreement with someone that turns out to be a horrible fit!

I would encourage you to work with your attorney on this. If you don’t have an attorney, check out Andrea Sager Law and Associates, her website is HERE.

Once everything is agreed upon and the contractual agreement is signed, it’s time to let the other candidates know.

Be sure to thank them for their time, maybe throw in a complement or two and wish them the best. Never, ever burn a bridge and please don’t leave someone hanging on.

It takes a few minutes to send out a few emails simply communicating with people so that they don’t have to wonder and they can move on and find a job that works for them.

Also, you don’t want to burn that bridge. What if your new hire doesn’t work out after a few months? Wouldn’t it be nice to reach out to your next choices as opposed to starting the process over from the beginning? Yes.

I hope this blog was helpful for you! I put a lot of time, effort and research into hiring my first assistant and so far I am extremely pleased with the results - I swear I manifested her and she is exactly what I needed in my business. I wish the same for you and yours!

I would love to write a follow up piece to this in the future. As entrepreneurs, we know that it is a constant process of learning and growing.

A final thought I wish to leave you with is this: this is new territory. As entrepreneurs building our own, usually unique, businesses, there is not a one-size-fits-all handbook for this. Remember to breathe, the fact that you can always adapt and adjust, as you see fit. The right candidate to assist you in your business - they will understand and adapt easily as well.

Okay - ACTUAL FINAL THOUGHT - don't forget to celebrate the fact that your business IS growing and you needed to hire someone to help you. That is something to celebrate!


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