How to Manage Spoiled Millennials - SimpleData

“I’m not happy with my work right now,” I told my manager.

“What do you want to be doing?” he asked me.

“Creative work that I enjoy. And I want to be making more of an impact,” I said.

If you’ve ever managed a millennial you’ve probably had a conversation like this. My generation is spoiled, entitled, and determined to be happy every minute of the day. We think we should follow our passion, do what we love, and {insert another cliche piece of life advice from a Medium blog post here}. In other words, we’re a manager’s worst nightmare. But if you know the recipe to our fulfillment we’re easy to manage, hard working, and willing to do the grunt work. 

When I had that conversation with my manager about happiness, I was doing grungy work. My job was to build the sales development program at my company which meant cold emailing strangers and setting up appointments for the account executive team 8 hours a day. It was soul-less, and I told my manager I thought so. 

He understood, but it was one of the most important marketing and sales programs we could build as a B2B company. This put him in a tough spot: on the one hand, he didn’t want me to leave the company; but on the other hand he needed me to do the work. He handled the situation brilliantly.


“You want to be a founder, right?” he asked.

I nodded.

“Well listen, Michael, I understand that it’s shitty work at times, but let me tell you about my job for a second. My equivalent of ‘creative work’ is product strategy, but do you think I work on that all day? No, that’s 5% of my job. The rest of it is creating sales quotas, looking at financial projections, and solving conflicts between teams. Being a founder is about solving the grungy details. If it was easy or fun, someone would have done it already and there wouldn’t be an opportunity in the first place.”

Ingredient One: Put the conversation in the context of their aspirations.

“Let me tell you what’s most important to the marketing team’s success right now. It’s two things: brand awareness and leads. We need people to hear about us and we need to send the sales team leads.”

Ingredient Two: Remind them of the goals of the company

“So here’s what I want you to do. Over the weekend think about what you’d want to do if you could work on anything at the company. As long as it helps achieve one of those goals you can work on it for the next 30 days for 50% of your time.”

Ingredient Three: Give them “guided autonomy”

I left the office that night more inspired than I had ever been at the company. And the reason was simple: my manager reminded me how my job fit into my career aspirations; he reinforced the goals of the company; and he gave me the autonomy to choose what to work on. 


Over the weekend I thought about how I could make the biggest impact on the company. It turned out sales development was the answer. And so I went in to the office on Monday with an entirely new attitude. I was no longer doing soul-less work that someone had told me to do. I was pursuing my aspirations of being a successful founder. I was making an impact on the company. And I had the freedom to work on what I wanted. Same work, very different attitude.

In the time following that conversation sales development became the most cost effective marketing channel at the company. For every $1 spent, I generated $7 in revenue. And all I needed was a little millennial pep-talk.

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