When I was a lieutenant in the Air Force I had the privilege of serving as an Executive Officer to Major (now Colonel) Heather Blackwell while she commanded the 87th Communications Squadron at McGuire Air Force Base, New Jersey.

One of my many takeaways from the experience stems from a conversation we had about her taking leave and who would take over her various responsibilities while she was away. She said “One of the measures of how effective I am as a leader is not how poorly the unit performs while I am away, but how well it performs.”

It’s counterintuitive at first because you might think that if someone who plays an important role within an organization suddenly leaves, that the organization would suffer as a result. But her point was that if things fall apart, that means she hasn’t done an effective job teaching us about what she does and how to do it. That’s not only important if she goes on vacation, but also because by teaching us she’s helping us become more effective leaders and preparing us for commands of our own one day.

I’ve been thinking about this a lot lately because I realized that in my role at Automattic, there are several things that I work on where I’m basically the only one who knows how those things work. For example, I built a system for tracking visitors who click on our ads so that we can measure our return on ad spend, but haven’t done a good job making sure other developers on the team understand how it works. Similarly, I work a lot on building email marketing lists for WordPress.com users who meet certain criteria, but never took time to document how to do it until recently.

Teaching others has so many advantages:

• It ensures you’re not a bottleneck for the work that you do
• If you go on vacation, change roles, or leave the organization, it ensures your team will continue operating smoothly because someone else will be able to carry out the tasks that you previously performed
• It helps you learn from others because they’ll likely have feedback that will help you improve the way you do things
• It helps you clarify your own thinking and processes
• It will help others develop their skills and grow professionally

Also, if you’re an entrepreneur, teaching everything you know also has huge advantages which Nathan Barry has written about at length (there’s even a t-shirt!).

If you find yourself in a position where you’re the only one who knows how certain things work, find ways to involve your coworkers or hold a learn-up or just write documentation – whatever you do, don’t let yourself continue being the only one who knows how to do those things. Good things will follow.