I was recently talking with a business owner about one of their rising stars. She had been with the company for years. Everyone liked her. She was creative, organized, dependable, and consistently delivered great work. Whenever a special project came up, she was the person people wanted on the team. As the company grew, leadership identified her as someone with the potential to take on a bigger role, and they wanted to invest in her future.
So they did something many companies say they want to do, but never actually follow through on: they paid for her to attend a professional executive leadership program. The program focused on communication, leadership, accountability, delegation, and the skills required to lead people rather than simply do great work. The company viewed her training as an investment—and it was. But what happened next is what really caught my attention.
When she returned from the program, her boss realized something important: sending someone to leadership training isn’t the same as developing a leader. That’s when they started meeting regularly. These weren’t performance reviews, annual evaluations, or “how are things going?” conversations in the hallway; they were intentional coaching sessions. Every few weeks, they would sit down together and discuss what she had learned, where she was struggling, how she could apply newly learned leadership concepts, and what situations she was encountering inside the organization. And that’s when the real development began.
The leadership mistake many companies make
Many leaders believe coaching is something that can be delegated—that HR, training, a seminar, or an online course can handle it. While those things are helpful and provide information, information is not transformation. Leadership development happens when someone helps another person apply what they’ve learned to real-world situations. That requires coaching, and coaching is a leadership responsibility.
Why promotions are often where companies fail
One of the most common mistakes I see is promoting great employees and then assuming they’ll figure it out. Someone is excellent at project management, sales, or operations, so we promote them into leadership roles. Then we’re surprised when they struggle with these new roles.
The reality is that leadership requires an entirely different skill set. Suddenly, success is no longer about doing the work;
- it’s about developing others
- giving feedback
- holding people accountable
- navigating conflict
- communicating effectively
Most people are never formally taught these skills, and if they are, they need help applying them. That’s where coaching comes in.
Coaching should begin on day one
Too many leaders wait until there’s a problem before they start coaching. By then, they’re trying to fix something. The best leaders coach proactively: when a new employee joins the company, when someone gets promoted, or when responsibilities increase. Those are the moments when coaching has the greatest impact because people are learning new expectations, building confidence, and forming habits that will influence their future success.
Why this matters now more than ever
We’re living in a time when many leadership conversations revolve around AI, automation, productivity, and efficiency. Those conversations matter, but organizations still succeed because of people. People want growth, they want feedback, and they want to know someone is invested in their success. One of the fastest ways to lose a talented employee is to stop helping them grow.
I’ve seen companies spend thousands of dollars on leadership programs and development courses, only to wonder why nothing changed afterward. The answer is usually simple: no one coached the employee after the training ended. The learning stopped before the growth could begin.
Three things to remember
- First, coaching is not HR’s job. HR can support development, but the direct manager has the greatest influence on an employee’s growth.
- Second, leadership development doesn’t end when the training program is over; that’s actually when the real work begins.
- Third, coaching should be a regular rhythm, not an annual event. Small, consistent conversations create far more growth than one big conversation each year.
A final thought
The best leaders I’ve known weren’t necessarily the smartest people in the room; they were the ones who helped other people become better. Years from now, your employees may not remember every project they worked on or every goal they achieved. But they’ll remember the leader who invested in them, listened to them, challenged them, and coached them.
Because at the end of the day, your most important job as a leader isn’t just delivering results. It’s developing the people who will deliver the next generation of results.
Onward and Upward,
Karen Caplan
Executive Coaching and Consulting for business CEOs, Owners and Presidents
If you are looking to grow your business or amplify your personal leadership skills, I would love to have a conversation with you. You can email me at karen@karencaplan.com for a no obligation conversation.
