10 Leadership Lessons You’ll Learn On the Job

Leaders, for all their wisdom, sometimes make the mistake of looking at the big picture only to miss the smaller, yet invaluable ways that they can be better at their job. But it’s important to remember that the new hires, the temps, the contractors—employees of all kinds—all play a vital role in that big picture.

Related: The 8 Most Common Leadership Interaction Styles

We asked the Young Entrepreneur Council, “What is the most valuable work lesson you’ve ever been taught by an employee?” so you can take a lesson (or 10) from their book:

1. It’s OK to laugh (or cry).

As a leader, I often act like a duck on the water: calm and cool on the surface and kicking or paddling beneath. An employee noticed I had been “off,” and I confessed that my grandmother was not well and I was overwhelmed by the amount of work. Not only did she take some work off my plate, she did a great job doing it. It reminded me that sometimes it’s good to let employees see the entire picture!

—Kim Kaupe, ZinePak

2. Trust your hiring gut.

As your company grows, you can’t be involved in every decision. Lots of times you’re going to want to pop into meetings to see what’s going on or give your input to the team. Asking questions is great but you’ve got to trust your employees to make the right decisions. If you trust yourself to make the right hiring decisions, you’ve got to let some things go and see what people are capable of.

—Andrew Saladino, Kitchen Cabinet Kings

3. Don’t assume.

If you assume an employee knows what you know, you’re likely to explain things in ways they find difficult to follow. The trick to effective communication is to put yourself in their shoes and make sure that they have the background knowledge to follow you.

—Vik Patel, Future Hosting

4. Show appreciation.

I learned the importance of making people in your organization feel needed. Money, bonuses and incentives don’t speak as loudly as sincere appreciation. When my employees feel they are needed, they begin to become that needed person.

—Raymond Kishk, Interstate Air Conditioning & Heating

Related: 10 Thoughtful Ways to Give Thanks to Your People

5. Be flexible.

Many people are surprised I don’t require previous finance experience for certain roles. But I’ve found if you get the right hire, any procedure or skill can easily be taught. A diverse staff brings a patchwork of perspectives excited to generate creative, inventive solutions. Fresh to the world of finance, they often have different ways of looking at problems.

—Elle Kaplan, LexION Capital

6. Be patient.

When training a new employee, it’s easy to want to quickly correct their mistakes. But, for most of us, the lesson really sticks when we make a mistake and correct it ourselves. Obviously to save time and money, we want new employees to be trained as quickly as possible, but you still need to give them the chance to fully process what they’re learning.

—Brandon Stapper, 858 Graphics

7. Be authentic.

This means it’s OK to show weakness or vulnerability. You don’t have to be perfect or right all the time, but you do need to be strong in your convictions.

—Sean Kelly, SnackNation

8. Know your weaknesses.

A very good friend (and former employee) once said to me, “Know your weaknesses and be stronger for it.” I never, ever, ever forgot this lesson. Failure to admit your weaknesses will ultimately be your downfall as a leader.

—Simon Berg, Ceros

9. Slow down.

I used to make lots of changes only to find out they weren’t being implemented. One of my employees told me they couldn’t keep up. I was moving too fast and losing them. I pictured the silhouette of a mountain—me on one side, my entire team on the other. It’s hard to follow when you can’t see where the leader is going. I learned to slow down so my team can focus and perform.

—Jon Tsourakis, Revital Agency, LLC

10. Don’t expect miracles.

Despite being a relative expert in the area, I had a task that I’d been unable to do myself. I eventually found someone who promised me the moon. I was so blinded by the desire to succeed that I expected the young woman to pull off a miracle. If it sounds too good to be true, it probably is.

—Alexandra Levit, Inspiration at Work

Related: 7 Personality Traits of a Great Leader


Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched BusinessCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.

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