How to successfully lead people older than you

Dean Woods
4 min readSep 11, 2019
Leading older employees is difficult
Photo by Simon Wijers on Unsplash

A while back, I wrote a piece about how to create your very own personal leadership development plan. It was a really fun piece to write and talked about some of the most pressing leadership development pieces.

For example, you need to always think about the dinosaur’s tail! When a dinosaur turns around, it’s tail is so large it accidentally knocks down and destroys things in it’s path.

Think about it: as a boss, you have a dinosaur’s tail. Your people will always over-analyze what you do. Any small decision you make will have a much larger impact than you anticipated.

If you’re a boss, let’s say you ask a team member to meet on Friday afternoon. You could be busy and that’s the first time you’re available to meet.

However, if you don’t actually say that, all your employee is going to hear is: “My boss wants to meet Friday afternoon….I’m about to be fired.”

That’s why thinking about how to develop a plan to improve as a leader is so important. It’s why I wrote that piece.

But I’ve heard one question over and over since then: How does this change if I’m managing someone who is older than me?

The reason that question was asked is the implications of the age difference. Candidly, if you are younger than them but are…

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Dean Woods

Startup executive, recovering consultant, Wharton Grad. I write about real startups (my venture backed day job) and micro-startups (my bootstrapped nights)