Millennial Boss Talk: The Good, The Bad and the Ugly

When it comes to Becoming the Boss, I know far from everything, but I did write the book.

While I love to share my own #Boss Story, as you know I am not a millennial myself. So, this week I wanted to share a few great stories I’ve recently read from millennial bosses.

There’s something for all generations to learn from each of the experiences shared by these young leaders, and you might even see yourself in them – whether you’re already managing or still striving to get there.  

“How I Tried and Failed to Be a Cool Boss”

“Before becoming a boss, I made friends at my various workplaces easily; being friendly with my co-workers was integral to my workplace happiness. I had friends outside of work, of course, but work friends made the day tolerable. Of course, a large part of the nature of a workplace friendship is bonding over your shared misery, whether real or imagined. And that bonding tended to be sprinkled with complaints about our bosses. ‘Does she even do any work?’ I would type to a friend about my boss. ‘Like seriously I think she just sits in meetings all day.’ I laugh (ruefully!) now at my naïve misunderstanding, and the implication that meetings are somehow a way of blowing off more serious work. When I got on the other side, I quickly learned how misguided I’d been.” — Read more at NY Mag.

Rely on a Mentor to Smooth Your Path

“The most valuable asset you can have as a boss is a mentor. Choose someone whom you respect and is further down the professional path to show you the ropes. Turn to this advisor for regular advice, crisis management help and tips on how to maintain civility and peace in the workplace. Behind every CEO is the CEO who came before and taught her everything she knows. In the professional world, reputation is everything. You want to be lauded as a person who is easy to work with.” — Read more at Elite Daily.

Give Praise When and Where It’s Due

“I do not heap praise on my team for mediocre work. For some people, this seems a harsh thing to say. In my eyes, it is not harsh. It is merely pragmatic. A good boss values their employees. They will say please and thank you and recognize that they need their team to succeed. As a difficult boss, I do all of these things. I thank my barista at Starbucks for giving me the coffee I need to get through the day, why would I not thank my team? But while I understand social cues, I am not about to tell my team that they have done a fantastic job when they haven’t. Handing out praise left and right does not benefit anyone. My employees have to work to earn sincere and enthusiastic praise.”  — Read more at

The Buck Stops Here

“When you’re the big boss (whether you’re the CEO or just the department head), everything comes down to you. You’re the one who has the final say. You’re the one who signs off on things. When the financials stink, it’s your fault. Sure, you can blame your staff for their incompetence, but remember, you hired them (or didn’t fire them). You set the priorities. You chose where to put your best employees and where to put your worst ones. Sure, you get praised when things go great, but when they don’t? You’re answering to your boss, whether that be someone in the company or the board of directors.” — Read more at

What I Know Now: How You Interact Now Can Influence Your Future Progression

“I met my cofounder in my mid-twenties when I worked with her husband at The Huffington Post. I had no idea she’d be my cofounder ten years later. She asked me to join her at PowerToFly and I’m so grateful she took that leap to reach out. If I hadn’t treated her or her husband well (that might be up for dispute on their end) in my twenties then I wouldn’t be where I am today.” — Read more at

If you’re a millennial as the boss, what is one very surprising thing you found out, or something you wish you’d known? Please share in the comments below.

Lindsey Pollak is the leading voice on millennials in the workplace, trusted by global companies, universities, the world’s top media outlets — and, most importantly, by millennials themselves. A New York Times bestselling author, Lindsey began her career as a dorm RA in college and has been mentoring millennials — and explaining them to other generations — ever since. Her keynote speeches have audiences so engaged that, in the words of one attendee, “I didn’t check my phone once!”

Contact Lindsey to discuss a speaking engagement for your organization.

Share this post

hi, i'm lindsey!

Lindsey is a globally recognized career and workplace expert and the leading voice on generational diversity. She has spoken for more than 300 audiences including Google, Goldman Sachs, Estee Lauder, Stanford and Wharton. Lindsey is the author of four career and workplace advice books, and her insights have appeared in media outlets including The TODAY Show, CNBC, NPR, the Harvard Business Review and the Wall Street Journal.


Learn 25 Practical Ways to Manage Across Generations