You told yourself it’d be different this year.  You had big plans. You swore you’d keep up with your books each and every month. You even scheduled the world “FINANCES” into your Google calendar every other week.

But now it’s early March, and the truth is staring you in the face. You got a little behind again.  And by “a little,” you mean, “a lot.”  (Like, starting last May.)

That’s okay. I’m not one of those people who will tell you to work against your style and get better at being organized, or worse, learn how to do your numbers!  I’m not here to add to your pain. I’m here to relieve it.

ideal bookkeeper

Yes, here is your typical “passionate” start up business owner!

After all, you and I both know that you didn’t start your business because of your financial prowess. (As evidenced by the receipts that are still jammed in your purse, the mileage log you forgot to keep, and a few straggling invoices you never sent to clients.)

You started your business because of your ideas, and your passion.

Problem is, as things get more successful, things also get more complex.  Which means invoices, receipts, P&L’s, Quickbooks, tracking and metrics.

Enter the bookkeeper.

I know. I know. You’re “shoulding” yourself YET AGAIN. You’re saying that things will be different this coming year.

Stop it. They won’t.

A bookkeeper will not only relieve you of this energy-sucking duty, but a bookkeeper will remove this pattern of convincing yourself that you can save a few bucks by doing your own numbers. (And the illusion that it doesn’t take all that much of your time.)

Ideal bookkeeper

The common pattern among business owners: constant stress created by continually trying to do the things they simply stink at doing!


TRUTH:  You can spend your time learning a lot of organizing, track-your-numbers information. (Which takes time away from, you know, MAKING the money you’re trying to manage!)  Or you can get hands-on help.

HINT:  You can’t scale your business unless you off-load the stuff that doesn’t create income.

So let’s make this easy.  Here’s your  5-step action plan for hiring the best bookkeeper for your business.  (Start this process on April 16th this year, and see how different next year can be…)

  1. Require Experience with Solo Business Owners

This is non-negotiable.

You’re a different breed. You run your own business. That means there are two critical factors you are seeking:

  1. – Experience with solo businesses
  2. – The ability to explain financial concepts in everyday language.




  1. Identify Technical Skills

The very reason you’re hiring this bookkeeper is because you want to avoid having to learn a new skillset and all the new software therein.  So, ask which programs s/he uses, and see if s/he can teach you how to use them as well.




  1. Require Trustworthiness

The most common question I get from clients when they’re considering a bookkeeper is about trust.  “How do I know this person isn’t a thief, or manipulative, or won’t share all my secrets with others?”

Well, start by taking a strategic approach in your vetting process:

✔ Get at least 3 references (and call them!).

✔ Get a list of the kinds of businesses they’ve served.

✔ Get detailed information about their process of working with clients.*

*In other words, make sure they take their business seriously enough to have trustworthy systems. For example, if you ask how s/he receives payment, and s/he says something like, “Just pay me whenever,” that’s a red flag. You need a professional who uses systems, not someone who’s making it up as they go! (That’s what you do, remember?)

  1. Measure Personality

Don’t hire a jerk.

Don’t hire an egomaniac who talks down to you.

And don’t hire someone who is too much like you. (No offense. But you suck at this stuff, right?)

Personality may be the most important aspect of your bookkeeper..




  1.  Get Clear On their Services

A great bookkeeper doesn’t just keep your books. They can give you guidance and be kind of a financial coach as well.

Ask your bookkeeper:

  • Will s/he provide you with articles, books, or materials to help you learn?
  • What kind of coaching s/he does to help you understand your own finances?
  • Is she willing to check in on a more frequent basis at first so that you can get regular feedback or ask questions?

Okay my friend – you’re ready.  This will get you started. Take the time you need, and make this happen. You’ll thank me next year!

But let’s get the excitement rolling now…

What’s the most pain-in-the-ass thing about your finances you’re most excited to offload once you get a bookkeeper?

  • Jodi

    I’ve found a CPA who helped me work out a system that now takes me 2-3 hours every Friday. I’ve offloaded to her the categorizing of expenses for the LLC rental properties and to balance out the accounts each quarter. Yay! That was so yucky and took me hours to do just one month. One of these days I’d like to delegate the things I do those few hours on Friday, but I can’t let go yet!

  • Christi

    As a CPA who works with lots of solo-preneurs I have finally figured out a system they can use…. and love….. print – color – scan. Done. Christine is right….the entrepreneur is not like any other creature and they need a super simple system to support their success!