Challenge Accepted: Bring Order to My Messy Books [Part One]

tangled roots Challenge Accepted

We are going to zero in on six different challenges that affect almost all business owners at some point in time. This will be an ongoing series called Challenge Accepted. Over the next couple of months, we will discuss each challenge and give you some ideas and solutions for each challenge you encounter. Here is a preview of the challenges we will discuss:

  1. Bring order to my messy books – this is today’s topic
  2. How to set up my business properly
  3. Compliance issues – What are they and how can I avoid them?
  4. How to find and set priorities to focus on
  5. Am I profitable? How much can I pay myself?
  6. Where to find advice on my business

We hope that this Challenge Accepted series will be helpful to you! 


It can be especially hard to keep your books orderly with a paper-based system. It feels like the paper just keeps growing and growing. Where will you store all this excess paper anyway?

Even if you are already paperless, you may still struggle with a lack of organization and struggle with finding necessary paperwork. Often, records are stored on various platforms and systems, making it hard to find what you need when you need it. There may be more disorder if your systems do not communicate or share information with each other.


  • Examine your current workflow
  • Get rid of paper
  • Choose apps that talk to each other

Examine your current workflow

By looking at your workflow you can see what needs to be adjusted. You will want to ask yourself these questions:

  • How does data get through the pipeline?
  • Where are there disconnects?
  • Does the disconnect come from people or technology?
  • Can any of these steps be simplified? 

Get rid of paper!

You will need to switch to an electronic-based storage system. Two that we like are Hubdoc and Google Drive. Hubdoc is great because it can automatically fetch bills and statements and stores them. And there is no end to what you can do with Google Drive. You can store, you can share, you can collaborate. 

Choose apps that talk to each other

Many apps communicate with each other and share information and/or sync up.

Let’s look at some workflow solutions that can be improved with the following applications:

  • Hubdoc – an app that can automatically fetch bank and credit cards statements and other bills and documents
  • – a cloud-based bill payment system
  • Xero – a cloud-based accounting system
  • Gusto – a cloud-based payroll application

Example 1 – Set-up Hubdoc to automatically fetch your statements and bills, and configure Hubdoc to automatically push those statements and bills to Xero.

Example 2 – Set-up Hubdoc to automatically fetch your bills. Next, we can configure Hubdoc to automatically push those bills to for approval and payment. Once you have approved and scheduled your bills for payment, can sync the bills and payments to Xero.

Example 3 – Set-up Gusto to process your payroll and integrate it with Xero.  Each time complete a payroll run in Gusto, it will send payroll data into Xero automatically.  Gusto will also automatically withdrawal payments from your bank to cover payroll costs. Once these withdrawals come into your bank feed in Xero, you can post the payments to the Gusto bill that was automatically generated.  No messy reconciling of paper payroll checks!

The diagram blow shows the examples we discussed above. We recommend this workflow for many of our small business clients.

What are the benefits?

By following the steps above, you can build a workflow that provides several benefits:

  • Clients no longer need to chase down paper documents, and we don’t have to keep bugging our clients for these documents either!
  • With all systems talking to each other,  you set yourself up to keep your records clean.
  • You can save time and you will have fewer headaches!

Keep an eye out for the next article in our Challenge Accepted series: How to Set up Your Business Properly.

Updated 10/27/2020