CM146: Is It A Waste Of Time To Understand The BOSS? - CounterMentors

CM146: “Is it a Waste of Time to Understand the BOSS?”

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Millennials often struggle to figure out the BOSS. In many cases they don’t even bother, and that’s the question in this episode: Is it a waste of time to even attempt to understand the old, out-of-touch, technology-challenged BOSS??

Scene: A group of Millennials get together at Happy Hour and before long they’re talking about the BOSS: “Dude. My boss is killin’ me. What a disaster.”

Yup. They don’t understand you. They think they know everything. They don’t have a clue about pop culture, and are trying to tell you how to do your job, and don’t give you any feedback. What’s the point of sticking around?

It’s a good question. But here’s an even better question: Have you even tried to understand your boss? Have you ever tried to connect and find out what’s important to him/her? Maybe, instead of griping about the BOSS, the really smart move (the one that demonstrates a little emotional intelligence) might be to try and understand them first? To work hard to make their job a little easier?

Join Kelly and Robby as they break down the over-generalizations and the bad communication that prevent Millennials and Boomers from connecting at work. And stay tuned until the end for a set of principles that can help Millennials maximize their success in the workplace.

Show Notes:

  • How the misunderstanding between Boomers and Millennials goes both ways (2:30)
  • Why Millennials should be invested in relationships with their Boomer bosses (6:15)
  • How a 1-on-1 Meeting can help Millennials engage their Boomer bosses (11:00)
  • Kelly’s best piece of advice for showing your leader how you add value (12:45)
  • How Millennials can apply the principles of high-performing salespeople to their relationships with their bosses (14:15)
  • Why you shouldn’t be surprised that Millennials gonna Millennial and Boomers gonna Boomer (16:45)
  • The role that emotional intelligence plays in the success of your career—why crushing it isn’t enough (22:00)
  • Some principles for engaging with your Boomer boss (24:00)


  1. How Millennials Should Deal with Baby Boomers at Work(LA Times)
  2. 5 Tips for Managing Baby Boomers” (
  3. How to Deal as a Millennial in the Baby Boomer’s Work Place” (