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Why Cross-Training is Essential for Privately Held Businesses

Why Cross-Training is Essential for Privately Held Businesses

March 27, 2026

We work exclusively with privately held business owners, and one recent experience underscored a common challenge. I was working with a small tax and consulting firm, where operations were heavily tied to the founder. While the business ran well under his guidance, it wasn’t easily transferable or valuable to anyone else.

During our assessment, the founder shared a troubling incident: a new hire, though an experienced tax consultant, accidentally wiped out historical client data while using software the founder had managed alone for years. The employee had been assumed capable without training, exposing a critical risk to the business.

This illustrates two important lessons for any business owner:

  1. Cross-train key processes: If only one or two people know how to do something, you risk operational errors and loss of value.
  2. Provide oversight and training: Even experienced hires can make costly mistakes without guidance.

By investing time in cross-training and hands-on onboarding, you not only prevent mistakes but also make your business more resilient and valuable, especially if you ever plan to sell or transfer ownership.

Inside every business is a better one; we see it every day with our clients