I remember I was driving to the beach when I hired my very first part-time employee.
(We used to live in Delaware, and it’s a 2-hour drive to see the ocean. But we did it every weekend because we love surfing! It makes me so grateful for my beautiful penthouse in California, where I live now! We are right on the beach!)
I turned to my husband, who was driving, and told him, “Hey, just hired a part-time assistant. I wanna be really good about making sure I consistently pay her because that’s such an important value to me.”
Little did I know that at that moment, my role as “team leader” was born.
So from one team leader to another, I want to say, “Congrats!” You’re thinking of leaping solopreneur to a small business owner with a team!
This is very exciting.
But you probably also have a lot of questions and maybe some fear, too. How do you make sure you don’t mess this up? How can you make sure this is profitable for both you and your new team members?
(By the way, Lesson One is that I usually never call my team members “employees.” They are my team members; we are part of a team. This helps establish your company culture.)
In this article, I share 12 nuggets of wisdom I have learned over the years. These are lessons I’ve earned working with a team of about four full-time team members and around ten part-time contractors as of the time of publishing. (This number has varied over the years.)
Tip #1: Get clear on what you are doing daily and what really should be outsourced.
Many business owners make the mistake of outsourcing just because they feel overwhelmed.
That is a classic beginner mistake.
Instead, what you need to do is sit down and figure out where exactly your time is going.
What are you spending your day on? Rate your tasks Red, Orange, Yellow & Green (with Green being “I directly make money with this.”).
This will help you understand what tasks you should be outsourcing to a team member first.
How can you properly outsource if you don’t know what your bottlenecks are?
Tip #2: Start small, ease your way into it.
I hired my first team member by giving them a small, specific job to see how they handled that.
It ended up being a total success, so I gave her an additional task. And then another and another until she was working for me pretty much full-time.
Many entrepreneurs find it much easier to start small with one little job; this keeps them from being overwhelmed.
It also has the additional benefit of allowing you and your team members time and space to make sure you work well together.
I do not recommend your first hire being a full-time person; in my own experience, it can feel like you’ve bitten off more than you can chew.
Tip #3: Understand it will always be scary at first, that’s normal.
Bringing on a team member changes the dynamic of your business.
If you do it right, this is a good thing. You will feel supported, guided, and assisted.
If you do it wrong, it can feel like you made a huge mistake. You might feel like you’ve paid all this money for nothing or that this new hire is taking up more time than it’s freeing up.
All of this is so normal. If hiring a person is new territory for you, it’s very typical to have fears around it.
So be sure to take a deep breath and know you’re not the only one. You will get through it; you will figure it out, you will be an extraordinary team leader.
Tip #4: You may have to make personal sacrifices to afford it at first.
When I brought on my first team member, I wasn’t making a ton of money yet in my business, and it wasn’t a consistent income that I could count on.
So, how did I afford to pay my team member every single month, consistently?
My husband and I sacrificed. We didn’t eat out, ever, not once. We cut back on all the splurge things we did. We even canceled little things like our Netflix account.
We looked at our budget and deeply cut back our personal expenses so that we could make hiring this team member happen.
It was a giant leap for us, but it was one of the best things I did for our business because it essentially allowed me to get twice as much done in the same amount of time.
Tip #5: Give your team member clear metrics to succeed.
This was something I had to learn the hard, painful way.
Your new team member wants to succeed. However, many entrepreneurs are unclear in their instructions, vague in their work scope, unclear in what they want the result or product to look like.
They end up disappointed, and their team member ends up discouraged.
It takes time on your part to properly teach your team member how to succeed in their assigned role correctly but, believe me; it’s worth it.
Tip #6: Consider a virtual assistant as your first hire.
This may not apply to everyone, but a virtual assistant is a fantastic first hire for many entrepreneurs.
It allows you to free up some time to focus on your business’s critical drivers, things that will help you make more money.
You can get them started on a couple of initial tasks (see tip #2), and that will help you test the waters and allow you to ease into it.
My uncle-in-law once shared some sage words of wisdom with me, “The first person you hire should be a jack-of-all-trades; someone who can help you with many different things.”
There’s a lot of strategy behind that, and most virtual assistants can help you with a variety of things.
Tip #7: Strike a balance between being kind and firm.
Depending on your personality, you will either lean towards being too kind or too harsh. It’s a balancing act, in my experience.
If you’re generally more kind and avoid confrontation, you must hear that you cannot put up with bullsh*t.
If they aren’t doing their job correctly, call them on it every time. Demand respect. On the flip side, if you tend to be a very firm person, consider that kindness does go a long way.
Micromanaging will crush your team member’s spirit.
As a team leader, it’s not an easy crown you wear, and likely, you’ll mess up.
It’s okay; mistakes can be fixed.
Tip #8: Consider not hiring friends or family, at least at first.
I have only recently hired my sister full-time after being in business for eight years, and I am glad I made that choice.
Everyone is different, but here’s what I’ve noticed; in order for a family or friend hire to be successful, you all have to have very professional boundaries.
Your family member or friend needs to respect your authority, to a fault. I feel very fortunate that my sister (and my brother-in-law, who also works for me full-time) are consummate professionals.
On the flip side, I have also learned how to be a good team leader, how to honor and respect the people on my team, how to create a fun company culture, how to handle confrontation, how to give everyone a voice, and countless other strategies to ensure a great work environment.
If you don’t have experience managing people, you’ll struggle to set boundaries and enforce when needed.
You will struggle to create compartmentalization between work and family. I have seen many terrifyingly dysfunctional family businesses.
My advice would be to do what I did; hire a professional first, learn how to manage a team, and then consider bringing a family member on, if that’s something you want to.
Of course, every family is different, so use your best judgment here.
Tip #9: Mentally commit to never missing a paycheck ever.
Your teammates need to know there will never be any funny business about their money, ever.
I have never missed a paycheck once in my entire history of running a business.
Not going to lie; it’s stressful at times. (Imagine being responsible not just for your own bills but five other families? That sh*t is serious, my friends.)
But if you are going to hire a team member, it’s essential you take this very, very seriously.
You cannot, in good faith, be late on a payment.
Your team member trusted you. They count on you to help them pay their bills. They have decided to take a risk on you, rather than working a stable, corporate job.
This is something I have taken beyond seriously since Day 1.
My team is loyal and here for the long haul, partially because they know my word is my bond.
Tip #10: Hire slowly, fire quickly.
That was a big mistake I made. I hired too quickly, and then I was slow to fire.
Now, we do the opposite. We really take a slow approach to hire, and we make sure we set very clear, measurable marks for success.
If a team member does not hit those metrics, it makes it much easier to have an initial “What is happening here?” conversation and then an “I am sorry, we are going to have to let you go.” conversation.
Take your time, ask for references, vet your potential hires very carefully. This will ensure you have to have far fewer unpleasant discussions later on.
Of course, if you do need to let someone go, do it immediately. It’s much more kind to do it as soon as you know a team member isn’t working out.
Dragging it out is the safe, comfortable thing to do, but you’re being incredibly unfair to your team member if you do this.
They deserve to know so they can start looking for other work opportunities.
Hire slowly, fire quickly.
Tip #11: Be sure to spend your newly freed-up time wisely, whatever that means for you.
For some, it means more time with family.
Maybe to you, it means more time to take care of yourself?
For others, it means more time spent growing the business.
If you are going to pour that time back into the business, be sure to spend that time on income-generating activities, tasks that will actually generate more revenue to justify the hire.
Tip #12: Commit to learning how to be a strong leader.
You have a team now. That is a responsibility that should not be taken lightly.
Commit to learning how to serve your team (that’s right, you serve them.)
A book I highly recommend is Extreme Ownership by Jocko Willink.
I recommend you embrace your new identity as a team leader.
Leadership, when executed properly, can be incredibly fulfilling.
Working with my team is one of the big joys of my career. We work hard; we play hard.
We are very respectful of each other; we all pull our weight.
Every Monday morning at 8 am, my team and I have a meeting. We connect, share how our week was, and share what we are working on for the week.
As we are there on our Zoom call, I look at everyone’s happy faces as they chat amongst themselves, and I feel incredible pride rising up in my heart.
I’m very proud of the team I’ve built. And I’m excited for you to build one, too!
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