How to Know if You are Ready to Hire a Team

Are You Ready to Hire a Team?We self-employed business owners can be a bunch of control freaks.  Think about it, you likely left a more institutional job (think corporate, academia, etc.) for the freedom and flexibility of being your own boss. You wanted to be in charge and in some cases were adamant about never having to take orders from anyone else again.


I work with my fair share of (recovering) control freaks and perfectionists, and I would put myself squarely in that category.  When I am clear about what I want and why, I am particular. (My family would call me FUSSY…let that word drag out on your tongue a bit and you’ll have their tone…)

Being particular is not the problem. Being unwilling to let go can be.

There comes a point in every business where you reach a tipping point at which you must address the question “Do I bring on a team?”

What Constitutes a Team?

Many people mistakenly believe that bringing on a team needs to a look a certain way. It doesn’t. For the sake of this conversation let us define team as:

            One or more person(s) who performs tasks in your business that either you cannot perform yourself or do not want to.

So a team could be as elaborate as having full or part-time employees that work exclusively for you or as informal as a local high school or college student who helps you out from time to time. It can be anything in between or mix of all of the above.

It can cost you thousands of dollars a month or $50 every now and then.  However you want it to work, it can.  Creativity is your friend.

Are You Ready for a Team?

I was resistant to having a team at first but now I know the value it brings.  What frustrates me about conversations on this topic is that there appear to be two schools of thought:

  • The do-it-all-yourself forever camp
  • The bring on an elaborate team as soon as possible even before you’re ready school of thought.

The first camp will work them into an early grave and never really enjoy their business unless they consciously define their business to be a certain size that is manageable to the life they want to lead. It can work, but it is limiting not just in earning potential but also more importantly in the freedom you have to go travel, play, and explore (which to me is the whole point of this journey called life!).

Back when I was drinking the Mega Coach Kool Aid, I jumped on hiring an assistant.  First I went through my fair share of disasters such as:

  • Using virtual assistants on the cheap from overseas that couldn’t communicate, had questionable skills, and frequently went MIA. (Were they in a witness protection program?)
  • Hiring help from Odesk from technical people in the Middle East who managed to blast my entire newsletter list with garbage without permission and then threatened me when I didn’t give them a five-star rating. (That was fun!)
  • Over-hiring for my needs paying hundreds of dollars a month for assistance that was not helping my business grow, was so far out of my budget that it was tanking cash flow, and damaging customer service. (NOT how you do things folks!)

For a time I had an assistant who was a perfect fit in terms of skills and budget. It was a dream and sold me on having the right kind of help at the right time. Then, as many virtual assistants often do, she tripled her rates within a few months and changed her business model.  She also moved to the other side of the world in a time zone with working hours that didn’t even remotely match my customers or my own. Now, there is nothing wrong with any of these choices of course. After all I believe you need to build what you want. However, for the stage of my business it became a detriment to my overall desire and operations instead of boost.

Avoid Common Pitfalls When Hiring a Team

I have also spent a great deal of time doing it all myself.  Chief of Everything. In some ways it wasn’t all-bad. Cash flow improved, I tightened up my operations, and pruned all the non-essential tasks.

I still used a virtual assistant on an project basis and I have always used team members (as subcontractors) to perform work that is not one of my core skills (example: graphic design), but I could control the timing, scope, and cost of the work versus having a fixed cost.

Yet, as in every business, my business has grown again and it is time to bring back more of a team. This time I am more mindful and creative with my solutions.

To answer this question for your business ask:

  • Do you need to free up time and energy for more important tasks?
  • Is your business bursting at the seams with no time, energy, or room to grow?
  • Are things dropping through the cracks because you’re too busy trying to keep up?
  • Are you spread way too thin that the joy of it all has vanished (or is on its way there)?

If you’ve answered yes to even one of these questions then you are ripe for hiring a team.

Now, ask yourself this question:

How much budget do you have to invest in this help?

Be honest and look at the numbers. Don’t guess.  My business got infinitely more robust once I created solid budgets and money habits.

Start where you are. Even if you hired an intern for 1 hour a week at $15/hour your mindset and business will change.

There’s the argument that it makes perfect financial sense to hire someone for $30/hour to do low-value tasks if you make $100/hour.  I would agree. Here’s the caveat for this reasoning to hold water. You need to have:

  • billable work to do
  • sales conversations to conduct
  • a proven system for actions you can take that lead directly to sales conversations that lead to work
  • extra budget to fund creative incubation time for your business (product creation, reinvention time, etc.)

If you don’t have one of these to fill in this “found time”, the math doesn’t work. You simply create another fixed expense that your business likely does not need.

What to Do Next

If you want to learn more about when and how to build an effective team, join me on Thursday, November 17th at 1pm EASTERN for a free webinar Create Leverage: How to Hire a Team. Click here to sign up!



Scroll to Top