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How to Successfully Groom Your Employees to Manage Your Business

Aug 14, 2020

In most cases, I get hired by a small business owner to coach them through some rudimentary business challenge like pricing, or time management, or work/life balance. Once they resolve these rudimentary challenges, their business grows. As their business grows, they run into an even greater problem. How to grow up managers within their own ranks.

The Trials & Tribulations

At first, the business owner is in denial. They somehow believe that they don’t need any other managers besides themself.  At some point, this denial runs its course and they know they need another responsible leader in their business, so they run through the typical options:

Option #1: Promote best worker to manager

The business owner recognizes one of their best, and most responsible workers and decide they’ll make him/her a manager. The problem with this is that their business is too busy and if they lose their best worker, who will be able to do the work?

Option #2: Best worker continues to work and mentor others

This usually involves a new swanky title like lead engineer, or head janitor or senior project manager. The business owner expects this person will still do their job, and in their spare time manage the rest of the workers in their group. The concept seems good on paper, but a leadership position IS a full-time job. The only way this can work is if the person is managing less than two people.

Option #3: Hire an outside manager

The business owner doesn’t think their workers are ready to manage and they’d love it if their best workers continued to stay productive workers. So, the business owner decides to hire an older person, pay them a lot of money and have them manage their current staff.  Again, this looks good on paper, but is a disaster.

Here’s what happens. The older person gets on board and the first thing they notice is that your team is doing everything wrong. They decide they’ll change the way the company works whether they know what they’re doing or not. The staff is angry because the owner wouldn’t promote one of them. And, forever the business will have a culture and expectation that the owner values strangers more than their own people.

The Result

I’ll often witness a few cycles of each option causing lots of frustration, wasted hours, failed hires, failed promotions, personal arguments… often returning to square one with no manager.

After all the wasted effort, the owner will continue to take on more and more responsibility with no help in sight.

A Better Way

There really is a better way, but it’s not an immediate fix. Before an owner needs a manager, it’s a good idea to groom leadership skills within their current staff. This prepares the staff for that ultimate promotion to manager. It also helps them understand how to be better employees.

If your staff is trained, you can promote someone from within your own staff, so you don’t deal with the outsider syndrome that happens with Option #3. If your new manager understands the “value of leadership”, they know that their team must produce more without them acting as a worker. This helps you eliminate the negative features of Options #1 or #2.

Leadership Matters Training

The leadership challenges that I just described come up so many times when coaching small business owners, that I decided to create leadership training system that teaches anyone how to learn to be a leader. This training program is called Leadership Matters.

If you’d like to learn more about Leadership Matters, you can read more about this program by following this link: Learn More About Leadership Matters.


  • Train leadership skills,
  • Promote from within, and
  • Grow profitably.

I truly wish you the best in leading your business and grooming the leaders you need, so that you’re free to live the life you deserve.


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