How Do I Know When to Hire Someone?

Last week, I talked a little bit of how I schedule my time on a per week basis with a team of other people and the whole idea of “less, but better” from Essentialism.

When To Hire Someone: Scheduling Time Plays a Role

Though this isn’t a regurgitation of that post (because that’d be dumb 😇), it is a meant to show one way in which I go about doing that when there are some projects, project management, presentations, and other responsibilities all happening at the same time as I’m writing this post.

So what are we do to when our plate is full of things to do, and we’re not sure how to manage the time and responsibility? Perhaps that’s how we know when to hire someone.

Or maybe not.

When to Know When to Hire Someone

That last question was a little bit baiting in that I don’t mean to say I’m “not sure how to manage time and responsibility” but that doesn’t mean it doesn’t create a sense of pressure.

And pressure isn’t always a bad thing. It can be a signal that you need to action to do something to release. Sometimes it’s letting something go, sometimes it’s muscling through it, and sometimes it’s having someone help you shoulder that burden.

But pressure, in and of itself, is not a signal of hiring someone.

  • it could be saying yes to too much,
  • it could be poor time management,
  • it could be a lack of personal responsibility.
  • it could be something else.

But assuming that it’s none of the above and you’ve done all you can to run your business properly, then maybe it’s time to look at bringing someone on board.

My Experience

First, and to be clear, the second best thing I’ve ever done for Pressware is to hire the right people at the right time (the first thing being offloading my books to a CPA).

Pressware: WordPress Goods & Services

And to clarify both of these statements:

  1. Hiring is a loose term to refer to bringing contractors into Pressware to help me with projects. This doesn’t mean that I don’t see them as part of my team nor that I see them as expendable. I’m incredibly grateful for Eric and Toby, and I want them around for the long haul. (There are reasons we have the contract arrangements versus the employer arrangement. That’s content for another post.)
  2. “The right time” is making sure that it’s not done prematurely and it’s not done too late.

I have to give credit where credit is due – there are a handful of people I spoke with when deciding whether or not to do this and they all gave great advice.

What Are the Signals to Look For?

If you’re wondering if your business is ready to bring someone else on, here are some half-baked notes on how to consider it:

  1. If you have more work than you can handle but the work that you can’t handle, are projects that align with your mission and vision,
  2. And if you’ve hit an income ceiling with the amount you’re able to do, and you want to change that,
  3. Then you’re likely in a position to bring someone else on board.

The above are just points – quite literally – and an entire post could be written about that, but it’s all to show that there are ideal times that appear to be true regardless of the type of business you’re running (with a few exceptions, I’m sure).

It’s Not Definitive (But Don’t Ignore It)

I’d like to say that this is the definitive guide to what to look for when hiring someone. But we know that isn’t true because each business is different.

That doesn’t mean things can’t be generally true, though. For instance, the advice that I received around this came from those in the software industry, the commercial glass industry, and even from a non-profit.

So if you’re looking for when to hire someone, maybe this will help.

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