Troubleshooting Tool #6 – Cross-Training Employees

Updated: Sep 28

In this Financial Protection Toolkit series, we have been focused on internal controls business owners can implement to increase transparency, reduce fraud risk and improve operational performance. Each control on its own is important, but the real power in these controls comes from the combination of most if not all in tandem.


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The sixth control in our series is “Cross-Training Your Employees”. Even though this control is time-consuming and has some direct and indirect costs associated with it, it is highly effective for breaking down “information” silos internally, creating transparency and reducing fraud risks.

Cross-Train Your Employees

As a small business owner, you certainly have already engaged in training to some extent. You probably handled most everything related to the business when you first started out. Over time, you’ve hired one or more employees and offloaded these responsibilities through training. Cross-Training is not much different; however, it does require more than one employee. So, for those of you reading who don’t have more than one employee, you might keep this post bookmarked for future reference.

Cross-Training is defined as: “The action or practice of training or being trained in more than one role or skill”. What action or practice are we talking about? For businesses you can interchange actions or practices to jobs or roles. In the context of this series, you should focus on those areas most susceptible to fraudulent behavior – all covered earlier in this series.

Because Cross-Training is an investment of time and money, it is important to start with why it matters.

  • Cross-Training improves continuity by creating redundancies. If an employee leaves unexpectedly, another employee can manage elements of that person's job, keeping the flow of business processes uninterrupted.

  • Cross-Training reduces the risk of fraud. When more than one person is involved in the completion of the same work periodically, neither party is likely to engage in fraud.

  • Cross-Training improves employee morale by building new skills, reducing boredom, fostering teamwork, and deepening the connection to your business. All incredibly valuable attributes!

  • Cross-Training extends overall staffing capacity, allowing you to defer hiring before you are ready.

  • Cross-Training improves processes overall and a significant element necessary in scaling your business.

Now that we have covered the importance and benefits of Cross-Training, how do you get started?

  • Explain your intentions to your team before you start. Don’t skip past this. Nothing makes employees more skittish than having the boss drop someone else in on their job with no explanation. Yikes!

  • Start with just one process. Choose the process that is most vulnerable to interruption or abuse. Necessity is often a good motivator!

  • Identify the individual to train. This can be a difficult decision, but often it is an obvious choice. If not, sit down with a few internal candidates and see how they respond to the opportunity.

  • Map out the process (digitally). Most employees keep some record of their specific job processes and some do not. Ideally, you want to encourage all job procedures and processes to be documented, preferably in digital format. Below are two best practices you might consider:

On-screen recording: Software like Loom are great options for Cross-

Training others on specific processes and saves a lot of time. Most people

are visual learners, so seeing a process done on-screen is very powerful and

effective.

Workflow system When it comes to business finances, in particular, it is

valuable to have a software solution for storing all of the recurring

procedures, processes and checklists involved. There are a proliferation of

options in the market (Todoist, Clickup, Monday, Asana, etc.) at almost any

price point, so find one that fits your organization and budget.

  • Give time for Cross-Training. Be sure to set aside time for Cross-Training to happen. In our practice, we typically Cross-Train in-person over three separate sessions. (1) I Drive, You Watch. (2) You Steer, I Navigate. (3) You Drive, I Watch. After that we have video recordings of each job step that the new person can queue up if they need a little extra help on their own. It’s been highly effective for us!

  • Schedule periodic coverage. Once an individual has completed their initial training, it is critical to complete the work periodically to stay effective. How often depends on the frequency of the process, the complexity of the process and the individuals involved. Bookkeepers as a rule are notorious for protecting their turf, so enforcing a set schedule for the trainee is often necessary to reap value from the process.

  • Check in on the process. As a business owner it is so tempting to set something in motion, then walk away from it, hoping everyone knows what to do. The reality is you must check in and make sure each step of this process meets your expectations. Ask questions until you’re satisfied that you could follow the process if you were inclined to do it. Lastly, it bears repeating. Ensure periodic coverage is happening. Without it, Cross-Training does not work.


Starting any process is painful at first, but Cross-Training your employees has profoundly positive impacts on your business that cannot be overstated. It will help your business function at a high level, necessary for the growth you want to achieve.

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