Dr. Paul Borosky, DBA, MBA
Business Plan Writer & Financial Projections
Why Should a Small Business Cross-Train Employees?
If Only One Person Can Do It, One Sick Day Stops the Business.
Everyone on your team is good at their own job, and nobody can do anyone else’s. Then someone takes a day off and part of the business stops. Business consultant Dr. Paul Borosky, DBA, MBA, walks you through how to cross-train a small team so every key task has a backup.
Last Updated: 11/08/2026 · Written by Dr. Paul Borosky, DBA, MBA
The Definition
What Is Cross-Training?
Short Answer
Cross-training is teaching an employee to do a second job in the business, so that no key task depends on only one person. It is usually done in small, regular blocks of time, with the person who already does the job teaching the person learning it.
Cross-training = one key job + one learner + one teacher + a protected hour a week
Doctor Owl, in Plain English
“Your routing clerk has not taken a day off in four years. That is not dedication. That is a business with no backup.”
How This Guide Works
Need the answer fast? Read the Short Answer above and the numbered steps. Want the full picture? Follow Otto, an octopus with a parcel shop from Dr. Paul’s Fabled Forest Business School Series, as his routing clerk cannot take a day off. His story shows up in a few short gold notes along the way. The math sits in one section, clearly marked.
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Meet Otto: Eight Staff, Eight Single Points of Failure
Some lessons stick better as a story. Dr. Paul’s Fabled Forest Business School Series teaches business through a forest full of small business owners. Doctor Owl, a dry-witted consultant who lives in the Lone Oak, helps them fix the same problems real owners face.
Today he is at the harbor hall with Otto the Octopus, watching other businesses celebrate their apprentices. Otto’s parcel shop has eight good staff and ships 1,400 parcels a month. Each person does exactly one job. His routing clerk has not taken a day off in four years, because nobody else can plan the routes.
Why It Matters
Why Should a Small Business Cross-Train Employees?
In a small team, each person is often the only one who knows their job. That works until someone is sick, on vacation, or leaves. Then the work stops, or the owner covers it.
Cross-training removes those single points of failure. It also gives people variety and a path to grow, which helps keep them. It reduces key-person risk across the team.
In the Fabled Forest
Every person at Eight-Arm Errands was very good at their job. Not one of them could do anyone else’s.
Where to Start
Which Jobs Should You Cross-Train First?
- Jobs only one person can do. The biggest risk.
- Jobs that stop the business if missed. Routing, payroll, opening, ordering.
- Jobs with busy-season spikes. Where an extra pair of hands helps most.
- Jobs someone wants to learn. Willing learners learn faster.
In the Fabled Forest
Otto asked each of his eight staff, over tea before the morning ferry, what they would like to learn next. Then he paired each one with whoever already did that job.
How to Do It
How Do You Cross-Train Without Slowing Down the Work?
Protect a small, regular block of time, such as one hour a week per person. Have the current expert teach while doing, then watch while the learner does it. Expect the first weeks to be slow and a little clumsy.
Track it on a simple chart: each key job, who does it now, and who can cover. Keep going until every key job has two names. That chart is the start of bench strength.
In the Fabled Forest
The first weeks were clumsy: the wrapper was nervous on the cart, and the cart driver wrapped too tight. By the sixth week, every job had two people who could do it. A week later, the routing clerk took three days off for a family wedding, and the routes ran without a hitch.
The Numbers
How Much Time Does Cross-Training Take?
Here is what it took to give every job at the parcel shop a backup.
| Result | |
|---|---|
| Staff | 8 |
| Training time | 1 hour a week per learner, plus a teacher |
| Hours a week | 16 (8 learners, 8 teachers) |
| Weeks to full coverage | 6 |
| Total hours | About 96 |
| Key jobs with a backup | All of them |
Step 1: The investment. 16 hours a week × 6 weeks = about 96 hours, all in the quiet afternoon between ferries.
Step 2: The payoff. No more single points of failure, and the first days off in years for a key employee.
Step 3: Your version. Count the key jobs only one person can do. Multiply by two hours a week (learner and teacher) for six weeks. That is your cost to remove the risk.
Illustrative numbers from the book.
Step by Step
How Do You Start Cross-Training?
Four steps, starting next week.
List key jobs and who can do each.
Mark every job with only one name.
Ask each person what they want to learn.
Match learners to those jobs.
Protect an hour a week.
Teacher and learner, same time every week.
Track until every job has two names.
Then keep the backups practiced.
In the Fabled Forest
Doctor Owl’s advice to Otto was to ask each person what they want to learn and give them an hour a week to learn it.
Otto’s Full Story
Who Ran the Routes on Wedding Day?
This page gives you the short version. The book gives you the whole season: an empty apprentice chair, eight cups of tea at the wrap bench, a wrapper afraid of the cart, and three days off after four years.
Every chapter of Human Resources for Small Businesses works the same way. One owner, one problem, one real idea you can use on Monday, plus a one-page worksheet to do it.
A Business Consultant’s View
What Do Business Consultants Cross-Train First?
Dr. Paul Borosky, DBA, MBA · Business Consultant
When Dr. Paul starts a cross-training plan, he cross-trains the job that would hurt most if its holder disappeared tomorrow, not the easiest one. For many small businesses that is ordering, scheduling, bookkeeping, or the owner’s own key tasks. He keeps the format simple: one teacher, one learner, one hour a week, and a chart on the wall. He also links it to pay ranges or titles where possible, so learning a second job is a step forward, not just extra work. Lenders and buyers notice when key tasks have backups, because it means the business does not depend on any single person.
FAQ
What Do Owners Ask About Cross-Training?
What is cross-training employees?
Which jobs should be cross-trained first?
How long does cross-training take?
Keep Going
Where Can You Learn More About Building a Resilient Team?
This term comes from Book 8, Human Resources for Small Businesses. New to a term on this page? Every one is in the human resources glossary.
Written by Dr. Paul Borosky, DBA, MBA, business consultant and author with 14+ years of experience and 1,000+ clients served. Hiring, paying, or managing a team and want a second set of eyes? See business consulting and prices.
This page is for general educational purposes only. It is not legal, financial, employment, or other professional advice. Figures are illustrations. The Fabled Forest and its characters are fictional. For decisions about your own business, consult a qualified professional.