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Episode 51: 3 in 30: 2025 Workplace Predictions with Lauren McGoodwin and Marnie Lemonik
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Hey Millennials, Here's The Ultimate Guide to Managing People

If you're a new manager—specifically a millennial manager, here is your guide to managing everyone, no matter what generation they belong to.

You've absolutely immersed yourself in your career, putting in the hard work to prove yourself, and it's finally paid off—you've been promoted to management level!
After a few well-deserved celebratory drinks and (virtual) get-togethers with family and friends, the euphoria begins to subside. And that's when a thought involuntarily pops into your head: "How can I tell if I'm a good manager?" This thought is quickly followed by a barrage of other similar questions (known in some circles as "fears"), thus causing you to pour a glass of wine for yourself and that looming, thirsty monster known as Impostor Syndrome.
Deep down, though, you know you're capable of putting in the work to tackle this position just like the last one. Besides picking up a Management for Dummies book, though, how do you learn to be a great manager? You may be new to this, but you're no amateur, and you're not about to resign yourself to guesswork. 
No worries, my dear boss lady—Career Contessa has you covered. We've put together a handy all-inclusive guide on managing people as a millennial leader (or as a first-time boss). Let's get started, yeah? 

First, A Helpful Table of Contents

Do Your Research on Good Leadership styles

If someone were to ask you right now to list your most influential managers or mentors, you could likely answer tick them off right away. When someone is a wonderful boss, teacher, or leader, they leave a lasting impression. Similarly, consider the worst leaders you have encountered. What are the overwhelming qualities did they have?
Consider how you can emulate the leadership skills that you admire, and avoid repeating the mistakes of those who were uninspiring and fell short in their given capacity.  
If possible, you should also consider reaching out to ask some of those great mentors for advice so you can emulate them in your new role. 

Interviewing & Hiring a Rockstar Team

In order to be a great manager, you need a great team, and hiring the best team out there starts with... you.
You must have an in-depth understanding of each position you're hiring for, and how it affects and benefits your company (especially the bottom line). Understanding the needs of your department and how those trickle down to each specific role is mandatory for any manager.
Have you ever had an interview where it was clear that the hiring manager had no idea what the position you were discussing really entailed? Painful.
Avoid this faux pas by creating a plan of action that details how each of your employees will contribute to the team. Identify which areas lack resources and/or personnel, and work backward to fix your company's pain points by mapping out projects and responsibilities.
When speaking with candidates, make sure to keep the human element present—your goal is to have an actual conversation and not just robotically rattle off generic interview questions. Consider the job you're hiring for and tailor your interview questions accordingly. Need help? Download our deck of interview question flashcards
Experience does matter, but remember that you aren't solely evaluating candidates based on what's within the four corners of their resume or on their LinkedIn. You're looking for a balance of competence, personality, and likeability. Ask yourself how you think they'll fit with the company culture overall.
As you interview them, keep these thoughts in mind:
  • Can you picture them working alongside you on that new project you're excited about? Do your work values align?
  • What are their professional goals, and are they in line with the position you're considering them for?
  • Is their excitement for the role palpable?
If you're at a larger company your HR department will likely assist with and/or complete the prescreens for you. But if not, a good rule of thumb for each open position is to review the resumes of 50-100 candidates, complete 10 phone screens, invite five final candidates for in-depth interviews, and finally, successfully offer one the job.  

Already Have A Team In Place?

If you inherited your team with your promotion, you may have skipped over the last section, but stop right there! It's still imperative that you familiarize yourself with their roles and responsibilities and consider current team pain points. Read this carefully:
No one will get you more up to speed on your new role than the people surrounding and supporting you.
Don't be afraid to lean on your team and show your respect for their knowledge. Start always by observing and asking questions. 

Establishing Trust and Boundaries

Honest, self-aware, consistent, respectful, and displays good judgment—are these ways you'd describe yourself? Great, because these are the qualities that will gain the trust of your team.
Make a genuine effort to get to know each of your employees better by scheduling one-on-one meetings each week. Take the opportunity to discuss open projects and address questions and concerns. When you're just starting, these early meetings are also a great opportunity to informally "interview" your team and get to know them on a more personal level. And, remember to give them the opportunity to get to know you, too—trust is a two-way street. 
People sum each other up quickly, and first impressions are a one-time deal. Be sure to be your authentic self, and don't push too hard. Genuine working relationships are built over time and take a little work, but they will develop naturally if allowed. 
If you're still feeling at a loss for how to connect, remember that no one is likely to turn down a free lunch—go ahead and send that invite! Bonding always seems easier over a good meal. 

Setting Boundaries

Here's a breakdown for setting boundaries with new employees, from start to finish.

Coach—don't micromanage

A study published by SuccessFactors concluded that millennials crave feedback from their managers. Yet, no one wants a manager that hangs over their shoulders or doesn't trust them to get their jobs done like the adults they are.
So, how do you strike a balance between the two?
Thoroughly train your employees, and use your one-on-ones to check in on their progress. Learn to delegate when appropriate, and always (always!) make instructions as specific as possible and your expectations clear. But then let go.
Encourage open discussions among your team and ask for their input and ideas on how to best approach a project or challenge. Not only does this encourage collaboration, but it can also potentially unleash real opportunity for innovation. Set your employees up for success, and then back off.
The greatest thing you can do for your employees is to nurture and develop their talent. Try to find out their goals and motivations. If you can find out what makes them tick on a personal level, you need to spend some time getting to know them better. If you know their professional goals, you can help to coach and guide them, better positioning them for success.
A great exercise is to ask each employee the following questions:
  • What is your favorite thing about working for XYZ Company?
  • What do you feel needs to be improved?
  • What is one interesting thing about yourself that others may not know?
  • What is your personal goal for this year?
  • What is your professional goal for this year?
With these questions, you'll not only gain insight into your employees' passions and motivations but also how they might benefit you and your company. You can then set about using them in the areas where their talents are strongest. Make it clear you're interested in helping them find projects they enjoy and tackle new, rewarding challenges. If an employee feels like you are personally invested in their success, they're that much more likely to feel happy in their role—and their productivity will skyrocket. 
 

Blurred Lines: Boss or Friend?

You're getting settled in your new role, and you feel a real camaraderie amongst your team—you're truly enjoying the relationships you're building with them. Then, one of your employees makes an inappropriate joke that crosses a definite line between manager and friend.
Feeling uncomfortable, you might worry about how to handle the situation appropriately. You've just really started to get to know your team, and speaking up can potentially damage the budding relationship.
Remember that your professional reputation holds more weight than being the "cool boss." If your boundaries become too blurred, you could open the door to bigger issues, like employees taking advantage of you, or your own manager thinking you don't have control of your team.
Be sure to address any issue immediately. The key is to be kind, but firm without sounding overly critical. If you can end on a high note or with praise, even better. (e.g. "Maya, I've really enjoyed getting to know you since I came on board—thanks again for your warm welcome. I wanted to chat, though, because the joke you shared earlier made me uncomfortable—which I'm positive wasn't your intention. I just wanted to bring it to your attention so we can avoid that in the future." And then, after the conversations winds down, "By the way, great job on the Smith project—you really rocked that!").
Career Contessa mentor Jill Jacinto weighs in: "Remember that Friends episode where Chandler gets promoted and morphs from boss to friend, only to discover he is no longer in the friend zone? If you are a boss, you can be friendly with your employees but you shouldn't be friends. Creating these boundaries will help you stay on track and make decisions for what is best for the company and not the 'friend/employee.' It'll also help you to not play favorites at the office."

Managing other Millennials

Millennials are often portrayed as a lazy generation. We're self-absorbed. We want everything handed to us with little-to-no effort.
We all know that any generalization is unfair and mostly inaccurate. And in reality, managing another millennial will have less to do with your age or generation classification and more to do with how your personalities mix. Hopefully, you should be able to avoid any issues if you carefully hired the best personalities for your team. But sometimes you just have to adjust, especially when it comes to team members you didn't hire yourself. 

Here's a real-life example

I inherited an employee on my team (we'll call her "Sara") who I was warned about from the start. In any given week, at best she'd "need" to come in late, at worst she'd call out two or three times. She was full of excuses, had little-to-no motivation to do her job beyond the bare minimum, and generally complained and spread toxicity to the other members of our team. 
I sat Sara down and discussed her role and performance with her, then asked what her overall goals were in her career and with the company. She struggled to define what her goals were, so I suggested we set some together. I then set aside an extra half-hour, extending our one-on-one to an hour, to give her more of my attention. I decided to be Sara's cheerleader and build her up to see how it affected her performance. 
As I built my relationship with Sara, she began to trust me and feel more comfortable in voicing her opinions. Eventually, she shared with me that she was experiencing a lot of issues personally (hence the frequent callouts), and just didn't feel passionate about the role or our company. With my attention and offers to help, she could no longer complain and find a scapegoat for her frustration—it wasn't us, it was Sara. She opted to move on, giving her two weeks' notice. 
In those first few days, I initially (and unfairly) labeled Sara as a stereotypical millennial. But it turned out there were more issues under the surface. The key to navigating this dilemma was focus and intent. Showing interest in my employee's success helped to pinpoint the source of tension. 

How to Manage an Older Colleague

Professionals recognize that title and talent are not correlated with a mere number. Age has no bearing on the quality of work one can produce. Still, certain people feel uncomfortable being managed by someone younger them, particularly if they feel they should be in a more senior role than they are or, worse, the role you currently hold. 
Jacinto advises, "It can be awkward being superior to someone older than you. But it's your job as a manager to squash that awkwardness on Day One. Treat this team member with respect and let them know you value their expertise and wisdom. Do not patronize, talk down to them, or act in a condescending manner—these types of actions will only hurt you."
If one of your team members has mixed feelings about working for someone younger, get to know and understand them better. Use your emotional intelligence to navigate the situation, but never be afraid to be the leader that you are. 

How to Deal with Conflicts and Confrontations

Though we are all professionals, we are also all only human, and sometimes we react to situations in a less-than-desirable way. A manager should always hold herself to a higher standard and conduct herself in a manner that warrants respect.
Jacinto reminds us, "As a leader, it is your job to always remain professional. If you have an employee coming in and raising their voice or acting in a threatening manner, don't lose your cool. Stay focused and remember to stay calm and handle the situation as even-tempered as possible. Once you tip over to the dark side, you'll lose that  'upper hand' and the respect you've gained as the manager."
If a coworker or particular circumstance has you feeling frustrated, don't react immediately. If need be, remove yourself from the situation (even if you just head out for a breath of fresh air or cup of coffee). Unless something requires an immediate response or decision, it's best to wait at least 24 hours to explore your feelings and determine the best course of action. Remember that your career-savvy self earned and deserved this promotion—now you have to act like it, even when it's most difficult. 

Terminating an Employee: How to Know When to Cut Ties

Everyone's least favorite moment? When you realize it isn't going to work out with a member of your team. You've coached them, given them incentives, and done everything in your power to make the relationship work, but alas, it wasn't meant to be. 
Jacinto says, "It never bodes well for a manager to have to fire someone from their team as it negatively reflects your managerial skills. As a manager, it's your job to train and guide your team. You need to create open lines of clear communication and outlines for reports and procedures. If someone on your team is behaving badly (missing deadlines, submitting sub-par work, being rude to clients) talk to them about it first. See if they acknowledge their mistakes and if it is possible to start fresh. After the first warning, if they still are lagging, it is time to cut them loose."
Firing someone is never easy, but know that it must be done when it impacts your team or your management. Be sure to follow these guidelines from Entrepreneur to be sure you're within the bounds of the law when doing so.

In Summary

Managing others is not always easy, but it will teach you a lot about others as well as yourself. Remember that attention and recognition go a long way in inspiring and motivating others, so always show your employees that you respect their input and hard work. They'll reward you for it. With a mixture of your savvy business sense, drive, and these guidelines, you'll carve a path toward continued growth and success in your career.

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