Nora Philbin: Where we left off in this discussion of the battle between the generations was you saying that leaders don’t like being challenged by millennials to be good managers.
John Philbin: Yes. And it’s not that today’s leaders don’t want to be good managers, it’s just that it’s often a lot harder to be a good manager and leader, and it can be frustrating when you feel challenged by folks who work for you, who often don’t know the whole story. So, it can feel to leaders like they are being criticized by co-workers in the cheap seats, where things might look easier than they really are, and there is something to this.
Companies are much more complex now and the flow of information often isn’t great, sometimes even to people in senior level jobs. Also, with the delayering of companies, people I work with are often trying to manage a lot more: more people and more decisions. Technology has helped make people much more efficient, but it has also led to large increases in the amount of information that leaders have to and manage and sift through and make heads or tails of. And on top of all of that, we’ve taken away a lot of the ways we train people as managers. So, what you have, is that a lot of leaders aren’t set up for success, yet they still feel a tremendous pressure to succeed.
And into this challenging job walks a group of employees, millennials, who have their own expectations of how things should work. And maybe some millennials act like their working relationship is reciprocal. They’ve been told to speak up and let people know if they have a good idea and then they go ahead and do that. They’re told, “If you can make this place better, go ahead and do it.”
N: Shouldn’t we be trying to always make things better? Are you saying, maybe leaders really don’t want millennials to speak up?
J: I am saying that some leaders can get tired of feeling criticized by their co-workers with a lot less experience, especially when these younger co-workers don’t have access to the whole picture. And to be sure, there are some leaders out there who would like to say, “Keep your mouth shut, watch me and learn for a while,” but they are the minority.
N: Why do you think millennials are so willing to speak up today?
J: For years people have been talking about the redefinition of the social contract in work. In my father’s generation, you were supposed to have a job for life, and so there was loyalty in both directions. That died a long time ago. But the two or three generations since then, including mine, have basically been afraid and given the company most of the power in the relationship. Workers were afraid to challenge or ask for more. So, leaders today are people who tended to take what the company gave them, if you will, and now we have a generation that’s really been hearing their whole life that the company is not going to be loyal to you, and you shouldn’t expect it. Millennials now have an expectation that, ‘The reality of my career is going to be good, or I’m going to look for a place where it’s going to be better.’

N: I think that’s really true. My generation saw that giving loyalty (or power) to the company didn’t provide any kind of security anymore. Our generation wants to take back some of the power so we can be in charge of our own careers because we know that companies are looking out for themselves and not for us. People my age want to have financial stability, AND we want to have a great career, and we want to learn, and we want to be able to grow, and have balance and have a well-rounded life.

J: Yeah, I think that is right. The way millennials want to work can just look different to someone my age, and I agree that your generation, millennials, are looking for more out of their career than just a good paycheck. Working from home or Starbucks or from their parent’s lake home is just different than most of my cohort would have done when we were coming up. Same with going to an educational seminar or an online class or a webinar. I hear from my clients that younger workers sign up for a lot more of these and expect that they can take the time to go and focus on their training. Even just taking the time go out to coffee with your friends in the middle of your work day because you’re going to be working at 6, 7, 8 p.m. The weird thing is, successful people my age have been doing the same thing for 20 years now. Laptops have been around for a long time for the professional world.
And the last part is this idea is that for those with high-demand skills, they have learned that you don’t have to get all your money from one place. This is an idea that is starting to catch on, and I think there’s some confidence building in the marketplace among those who have the belief, ‘I’m going to thrive in this marketplace.’
For generations, people were afraid to send out their resume because if it got back to your company that your resume was out there, that was dangerous for you, and now basically everybody’s resume is on LinkedIn, and you can troll the career sites all the time. It’s not as hard to make a switch.
N: That leads me to a question: culturally there’s a shift that’s happening in the workplace, and it’s happening on the shoulders of the millennials. But why does that resistance exist? Is it just change? Are people just scared of it? Is it because the controlling majority will soon no longer the controlling majority, and they’re scared of that?
J: So, I think it’s emotional, and some of these changes we’ve been talking about mean something very different to older leaders than they do to the millennials. Going out for coffee, or asking to work from a family get together, and being open about the fact that you might not be around in a few years because you’ll want to go and learn at a different company all means that you’re not dedicated in the way I was dedicated. And it’s very natural for people to believe that, ‘Hey this is how I achieved all this success,’ and it’s sort of like you’re saying, I don’t have to do all of that in order to be successful, which can sound like that dedication wasn’t all that valuable, or you can kind of do it and still go camping on the solar eclipse day.
If I feel the need to defend my success, then I really feel like I’m in competition with you.

What leaders should feel is, ‘Hey, I achieved a level of success that I am proud of, and I did my way, when the economy expected certain things and now that the nature of work is changing, there may be different paths to success.’ This would allow leaders to give up feeling like the next generation needs to go through what they went through in order to be successful.

So, to go back to an earlier part of the conversation, for some leaders it does feels like entitlement that you want what I had and something different. You should just order what I ordered off the menu and accept it.
N: Yeah, I totally get that. But I know so many young people who are always plugged in. Today, even if you’re not at the office, so many young people I know are always thinking about work and always tuned into their email and always making sure they’re on top of what they need to be. So, like you said, the way we millennials go ‘all in’ looks really different from the way that you had to because you always had to be in the office, and that does stink for you, but it is — I’m not going to say easier — but it’s really different the way we’re able to put ourselves all in for our careers. Rarely as a millennial do I get defensive, and that’s one of the things where I know so many people who work so hard, constantly, but they’re just not always in the office.
J: Yeah, and we older folks actually get it, at least intellectually, but it hasn’t sunk in emotionally, and I think that makes it hard for leaders my age to always be smart and constructive about what they think and believe and even the policies they put in place for younger workers.
In a lot of ways, I think this idea that we might be learning a thing or two about what might have been (more) possible than we thought when we were younger, and when we were trying to get ahead professionally. It’s like we have to stop and look back at our life and ask ourselves, ‘Oh gosh, what if I would have gone swimming for an hour every day my whole career,’ or ‘What if I had taken that two month trip to the south pacific that I always wanted to take. Would it really have been a bad career move or was I just too worried about my career to take the chance?’
So, one of the things I think is happening is that millennials are unintentionally showing us things that we were kind of silly about, and we don’t like that.
N: That wouldn’t feel good.
J: And I think part of this is, people my age don’t like to be shown up, really nobody does. We thought we were pretty damn smart. We thought our parents were foolish in some ways and we don’t want to be those foolish people. We’re still cool. We still go to concerts. We wear jeans on Friday.
N: So, this may just be the natural evolution. Younger generations will always push forward farther than the generation that came before them. And the older generations will resist because they don’t want to feel outdated.
J: Yeah, and I just think this disconnect between leaders and millennials is getting in the way of success at a lot of companies, or at least the company’s ability to get the most from their younger employees. And there is something that older leaders can do and something else that millennials can do that can make this a whole lot better.
Leaders need to recognize that millennials want their company to be successful. Badly. And they are going to bring new ideas and different ideas for how to get that done and being a good manager has to be about harnessing that motivation and turning it into something good for the company. There is an old saying that you can teach employees everything they need to be able to do their job but motivation. So be excited you are starting with people who are motivated to make things better.
And if I could give a little advice to millennials to help them get their message across it is to give their managers and leaders the benefit of the doubt more often. Start with the assumption that your manager wants to do a good job but is not in a perfect situation. Help your manager see how things could be better but in a way that doesn’t leave the message they aren’t doing a good job overall (even if you think they aren’t doing a good job.) Sometimes a relationship is strengthened by a lie of omission.

Nora Philbin

Nora is a co-founder of Happy Spectacular, which she still can't really believe, and she's on a lifelong quest for the world's best cheeseburger (applicants accepted).