How not to screw up as a first-time millennial manager

Eric Goldschein
Two Types Of Managers
8 min readMay 23, 2018


I’m a millennial. I was also a manager of a group of writers for a digital media outlet for several years. While my time in that position was mostly successful, I narrowly avoided more than a few disasters. In my first week, I nearly fired an employee who called me a dick while I was shopping at Costco on a Saturday morning.

It was not an auspicious beginning, and I spent a lot of my first year or so stumbling from one questionable decision to the next.

While every generation of new managers steps into the role with little idea of what “a manager” really does or needs to be successful, there are some unique challenges to being a “millennial manager”.

Millennial managers are not only managing other millennials, but people in generations both older and younger. I had direct reports who were in their 50s as well as their 20s. That incredible variety of expectations takes some navigating.

We spoke to seven management experts on how to not screw up as a millennial manager. These are 7 lessons I would have appreciated back then:

1. Invest in coaching

Myths about millennials abound. It’s thought that they require more workplace guidance, or that they have less workplace loyalty than generations past. In reality, millennials are just as excited about exploring career and development opportunities as any other group.

However, according to a recent report by the International Coach Federation, management styles of the future will call for fewer “bosses” and more “coaches,” who can “help them reach career development goals… moving from command and control to a new style based on inclusion, involvement, and participation.”

Unfortunately, according to the ICF, while 60 percent of polled millennials want training from their employer in leadership skills, only 36 percent of organizations offer coach-specific training to new leaders.

It may be in your best interest to look outside your organization for this kind of development help. According to Jenna Filipkowski, Ph.D., ICF member and Head of Research for the Human Capital Institute,

“Coaching is a tool to invest in managers’ development so they are effective at leading their teams. Coaching is a personalized approach to development that meets the individual manager where they are in time.”

2. Master the one-on-one with your direct reports

Photo by Charles Deluvio on Unsplash

How do you build trust and understanding with someone? Simple: Talk to them. For many millennials, that’s a lost art.

A recent poll found that 68 percent of millennials actively avoid talking face-to-face if they can (!), citing work colleagues in particular as a group they avoid. That’s a problem.

“One-on-one meetings with your team are critical to building trust and feeling connected to each person on your team”, says Tess Ausman, owner of CLT Leads, a virtual leadership development company. “They are not a waste of time. Not something that can be cancelled or blown off because other things come up. Not a time for you to give each person a task list of what you want them to accomplish”.

What managers need to understand about these meetings is that they’re not for you, but for your people. That, Ausman says, is the secret of stepping into a management position: The world no longer revolves around you.

“More seasoned managers know that they can get what they want from this meeting by putting you first and focusing on you and your needs”, says Ausman.

3. Don’t avoid conflict or hide behind technology

Photo by on Unsplash

Millennials avoid face-to-face conversations, instead often opting for text or social media communication. They spend more time interacting with their smartphones than with anything or anyone else. At the office, doing so is a coping mechanism for avoiding awkward or uncomfortable situations.

That’s a problem, because sometimes it’s important to engage in conflict at the office.

“Conflict is not the enemy, it’s a powerful source of energy”, says Nate Regier, psychologist, CEO of global advisory firm Next Element:

“Engage conflict with a supportive and curious mind. Don’t see it as a win-lose, but rather an opportunity for growth. Focus on validating people’s feelings, collaborating to find win-win solutions, and clarifying key priorities and principles.”

Why should millennials take particular note of this? “Younger generations are more prone to either avoid conflict or turn that energy into drama through passive-aggressive comments, gossip, and triangulating. Conflict skill is a necessity and rare commodity to work through differences and leverage diversity”, says Regier.

4. Try for stewardship delegation, not “gopher” delegation

Remember when you were a student or someone else’s direct report, and you hated when your teacher or boss was breathing down your neck? Like, hey, can I live?

So don’t do the same once you step into a management position. As Zach Hendrix, co-founder and CTO of GreenPal notes, there’s a difference between “stewardship” and “go-for” (or gopher) delegation.

“The primary characteristic of a boss versus leader is a leader delegates through stewardship delegation,” says Hendrix. “Meaning she defines the roles and goals of their team members and gets out of their way to let them create their methods to achieve those goals.”

Meanwhile, a boss delegates and micromanages, saying “go for this and go for that.”

In Hendrix’s experience, millennials like to think that their work is creative, and like to connect their work to the central purpose and goals of the company.

“You can get more discretionary effort managing millennials by defining what their role is and what their goal is for the company, and giving them suggestions on the means to achieve those goals — but ultimately allowing them to choose how they want to accomplish the objective,” he says.

This distinct difference in management styles leads to a large gap in effectiveness and accomplishing results, Hendrix says. It took him awhile to learn this.

“I screwed up for years,” he says.

5. Be a downward-facing leader

One of the biggest sources of tension for me as a manager was balancing the needs of the people I reported to and the people I was tasked to lead. Their wishes rarely aligned.

You’ll often have to pick sides in disputes, disagreements, or differences of opinion between employees and bosses. And though this isn’t a hard-and-fast rule, you should generally be a “downward-facing leader,” according to Kyle Wierks, the millennial thought leader behind Great North Dynamics.

“A great leader puts their team before themselves, even if it means looking bad,” he says.

“That means you don’t throw your team under the bus, ever, and that you fight for your team when they need a champion. In the long run, having a reputation as a team player who fights for your people will serve you far better than throwing your team under the bus for short-term gain.”

This bit of advice seems almost counter-cultural to millennials, who forever hear that they want (or perhaps actually do want) autonomy and flexibility in their role. Some of that goes away when you become a manager.

“As soon as you enter a leadership role, that message of ‘hard work leads to success’ is irrelevant. It’s not that hard work isn’t important. It’s that as a leader, your success is tied to the success of the people around you. No matter how hard you work, if your team isn’t successful, you won’t be either,” says Wierks.

6. Understand the relationship has changed

Photo by Annie Spratt on Unsplash

Humans aren’t good with change. And when you step into a management position, your relationship with your co-workers will do just that.

First, it’s good to know how to get people to embrace change. But then you have to specifically address your relationship with the people who report to you.

According to Keith R. Sbiral, certified professional coach with Apochromatik, the inevitable relationship change is the number one issue he faces, particularly if the new management role is a promotion for a younger worker.

“Working to manage this relationship, through adopting methods of communication used across the organization as well as setting clear boundaries with direct reports can be very helpful. It may seem uncomfortable at first, but the transition from ‘one of the team’ to the team leader is one that can be very delicate.”

Basically, you should recognize that your relationship to people in the office has changed, and work to maintain the same levels of trust, respect, and loyalty that you built up as a peer over the months and years.

For millennials, this shift may be more difficult than for Boomers or Gen Xers, who built a stereotype of being more clock-punchers who head home after work. Millennials have blurred the lines a bit between the office and personal life. Some companies, such as millennial-founded Mic, take pride in blurring those lines.

“I think that as a generation, millennials have more of a tendency to desire friendship-relationships in the workplace, which makes it more challenging when you move into the management role, because you have personal relationships more likely than not with folks you work with now,” says Sbiral.

7. To gain respect, don’t try too hard to gain respect

It’s one thing to be an advocate for your team — it’s another to bend over backwards for them.

“While you don’t want to be the hated boss, you also don’t want to be seen as the phony one either. Your role as a leader isn’t to make friends or be liked, but it’s to impact and make meaningful connections,” says Dionna Appling of Business Advocates PRO.

Ah yes, the ol’ “I’m not here to make friends” tactic. So how do you balance making connections without pushing too hard to be liked?

“The millennial generation is known to be innovative, purpose and mission-driven, vision connected, and they respect authenticity,” says Appling.

“A leader who tries hard to appear perfect or all-knowing will very quickly be perceived as a fraud to millennials, as it seems like there’s an ulterior motive. Likewise, a leader who is a people-pleaser will also been seen as a fraud by millennials and unfit to lead.”

To gain respect, millennial leaders should try “being honest, allowing opportunities for millennials to offer creative and innovative insight, bringing meaning to their work, leading the team towards a vision, and working collaboratively with them instead of barking orders,” she says.


There are lots of ways to fail as a new manager. You can be too nice, you can be too mean. You can think you know too much, you can not know enough. You can avoid the tough conversations, or have nothing but tough conversations.

It’s all a balancing act, and it takes time to figure out how to do that without dropping the plates.



Eric Goldschein
Two Types Of Managers

I’m a freelance writer originally from Brooklyn. I write about travel mostly but also business and “culture.” I hope you like what you read.