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How to Know You're Ready to Grow Your Team

Being a CEO is hard work, no matter how strategic and systematic we are. There are countless responsibilities and every decision ultimately rests on our shoulders. 

One of the biggest decisions we make as CEOs is when and how to grow a team. How do you know if you’re ready? Who should you hire? And, for what position?

Graphic with a photo of a business woman looking at files with the title, 'How to Know You're Ready to Grow Your Team.'

I’ve been running Grid + Glam, a full-service professional organizing company with an online Membership and an online coaching program, for almost three years. During that time I’ve hired five women for my in-person organizing team, and three women to help run our online programs including the  G+G Membership, and Organizers Academy. I also have a lawyer, an accountant, and a bookkeeper on retainer, and strategically leverage a copywriter and photographer.

But how did I know when to hire them? And how did I know who to hire? There were a few key experiences that showed me when and whom to hire. Read on to see if you’re ready to hire someone for your team.

When to hire someone on your team

1. You’re getting burnt out

Running an organizing business is so much harder than most people realize. It’s important that we don’t burn out. There may come a point where you decide that it’s worth making a little less profit to be able to do this for the long-haul. Hiring an assistant or multiple assistants can make the day-to-day so much easier. Oftentimes, this strategic hiring does grow revenue and profit over time. But even if it doesn’t, it might still be worth it for your sanity.

Now, what should an assistant do for you? A major benefit of being in charge is that YOU get to choose what you want to do, and what you don’t want to do. If you’re feeling burnt out...why? What part of the job doesn’t light you up? Hire someone to take over whatever it is that you dislike doing the most.

It’s critically important to hire the right person for the job. But how do you do that? This blog post gives great guidance on the hiring process. 



2. You’re turning down work

If you have more work than you can do on your own and you’re either losing clients because of it (because they don’t want to wait for your next available appointment) or you’re actually turning down clients altogether, that’s a good sign it’s time to expand your team.

If this is your situation, hire someone to join your in-person organizing team. You’ll want to choose someone who is incredibly organized like you AND who can be trained in your unique process.

To be clear, bringing on this new person won’t necessarily pay for itself initially. There is always a ramp up as she learns the ropes, which takes time and costs money that you won’t make back initially. But if you’re turning down work, hiring someone to go on jobs you can’t, or hiring someone to join you to get the work done more quickly, can absolutely pay you back in the long-run.

So, do the calculations on whether or not over the long term you’ll actually be able to increase your profit (not just your revenue) by expanding your team in this way. One important point is that you should be charging your clients at least double what you are paying each assistant. 

3. You’re spending time doing things someone else could easily take over.

As entrepreneurs and small business owners there is SO MUCH work that we don’t get paid to do. And it can be really hard to justify to ourselves paying someone to do work that’s not revenue-generating. 

But that’s not the best way to look at it. Our biggest asset as CEOs is our time. And when we have to spend time on tasks that we could outsource, it’s taking our time and attention away from other areas that could generate revenue. Ultimately, you need to calculate what your time is worth to you and if these smaller projects could easily be delegated to someone else.

Woman sitting at a white desk working.

If this sounds like where you're at right now, you may want to consider hiring a Virtual Assistant (VA). Including a tech-savvy VA on your team can take the burden of the behind-the-scenes work off of you, so you can focus your time and energy on other projects that demand your attention. Oftentimes the projects they work on do not directly impact revenue. But they always do indirectly. This blog post gives great tips about hiring a VA.

4. You lack expertise 

It’s hard to do, but we all must admit that we lack expertise in some (or many!) areas. And as your business expands, you may want to bring experts in to be sure you’re covering your bases. 

This is the exact reason why I’ve outsourced work to a lawyer and an accountant. As you know, both fields are complex, and there are major implications if a misstep is taken. 

These hires also do not directly help my bottom line. Obviously. But, ensuring that I’m following the law and filing my taxes correctly brings me peace of mind AND may save me money down the line by reducing Grid + Glam’s liability. 

One Final Note on Hiring…

You’re getting burnt out, you’re turning down work, you’re spending too much time on work someone else could do, or you lack expertise are all good reasons to hire someone. The FINAL reason to hire is...to have someone on your side. 

Going it alone is thrilling. But, having someone on your team who is better than you are at something (or many things!!) is reassuring. The old adage “two minds are better than one” is true. If you can gather people around you who care just as much about your business as you do, who bring their own wisdom and expertise to the table every day, your business (and your LIFE) will be better off for it. 

We do indeed go further together. 

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