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17 Lessons Most First Time Managers Make the Hard Way

By May 6, 2019 September 18th, 2023 20 Comments


I was a terrible first time manager.

It was early in my career as a communications pro, and I had showed some promise as a practitioner. (The job required me to do things like obsess over word choice and agonize over grammar, so I was a natural.)

With a few years of successful wordsmithing and journalist wrangling under my belt, it was time for me to make my big move to middle management.

In my mind, it was a meteoric rise. I had my very own direct reports (two!), an office (that I shared), and the kicker, actual business cards. All before the age of 26.

Next stop… corner office.

Not quite. I quickly found that management was a whole different ball game, and the skills that had made me a decent practitioner were much different from the ones I needed to be a good manager.

One major mistake – I thought I had to be the smartest person in the room. When people came to me with problems, I would just jump in and fix things. It was faster and easier than guiding my direct reports to the right answer, and when time was of the essence, it seemed like the right call.

In reality, I was doing my teammates a gigantic disservice. While I thought I was playing the hero, my team saw me as a martyr. And not only did I hinder their growth by always solving their problems for them, I eventually became a bottleneck.

Not awesome.

Luckily for me (and my team), I had great mentors who showed me what being a manager is really about. Eventually, I became a good manager, but not without some major growing pains.

Unfortunately, my experience as a first-time manager is more rule than exception. But there’s good news – you don’t have to suffer like I did (or like my team did).

We’ve asked around, and put together some sage advice from expert managers – people who manage managers, and know what it takes to overcome that initial learning curve.

So here are the top mistakes that most first time managers make the hard way.


1. Relying on the Same Skills that Got You Promoted

It’s easy to assume that the skills that made you a good salesperson will make you a good sales manager. But while knowledge of the role is important, management itself requires a completely different skillset.

This is probably the most common mistake first time managers face, and it’s easy to see why. At most companies, individual contributors are usually promoted to manager based on their stellar performance in the role, but aren’t given adequate management training.

Looking back, this was my biggest mistake. I focused too much on my knowledge of the role and not on what it actually takes to manage.

First time managers should be aware that management is a whole new ballgame that requires a distinct set of skills. Our Employee Engagement Guide breaks down exactly what it takes to be a good manager.


2. Trying to be the “Cool Boss”

By the time you take on your first management role, you’ve probably worked under a few different bosses with different leadership & management styles – some more pleasant than others. If you’ve ever worked for a boss that was a real pain, there’s a temptation to over correct.

When it’s your time to shine, you might think, I’m not going to be like some of the task masters I’ve worked for in the past.

No, you’re going to be relaxed. You’re going to be fun.

You’re going to be… The Cool Boss.


You might call it Michael Scott Syndrome – a desire to be loved that renders you an ineffective leader.

Why doesn’t this work? Because this approach misses the point.

Remember, your number one job is to have your team’s back and to set them up for success. You want to provide guidance and support for your team so that they can grow as professionals and hit their goals. In order to do that, you sometimes have to hold your team to a high standard, and being “the cool boss” usually undermines that.


3. Trying to be the “Mean Boss”

On the other side of the spectrum is the “Mean Boss.”


I’ve seen this time and again with managers who feel the pressure from above and below.

Think about it – middle managers are squeezed from both sides. There’s pressure from direct reports to be a strong leader, and there’s a newfound pressure from executive leadership to demonstrate results.

It’s the latter that keep many first time managers up at night. Eager to notch some wins, they push their team harder than they should. Instead of serving and supporting their team, they end up making their lives miserable.

The key here is to take the long view. It can be hard to see, but success comes with growth. If you focus on being there for your team and giving them the guidance and support they need, they will perform better – the wins will start rolling in.


4. Micro-managing

It’s become a bit of a cliche, but micro-managing is an all-too-common pitfall for many managers – especially first timers.

Micro-managing is corrosive for a number of reasons. First, it signals a lack of trust. When you step in and second-guess every decision that your team members make, you’re essentially telling them that you know better than they do.

Second, it’s not scalable. In order to be successful, you need to be able to delegate! Otherwise, you become a bottleneck and your team’s productivity grinds to a halt.

Make sure to give your direct reports some latitude, and let go of your desire to control every outcome. Remember too that mistakes aren’t the end of the world – they’re actually opportunities for your team to grow. Without having to handle every single situation, you’ll find your employees will feel more comfortable on their own and experience an increase in employee engagement around the office.


5. Playing the Hero

This goes back to my original story. I was convinced that I had to step up and solve every problem that came my team’s way, but this resulted in resentment and bottlenecks.

In a recent interview for The Awesome Office Show, Sun Basket CEO Adam Zbar described his own learning curve as the company transformed from a startup with only a few co-founders, to a 1,000+ person organization. As the team grew, Adam went from doing all the heavy lifting himself to being a leader on multiple fronts.

When his team faced problems, Adam’s first instinct was also to be the hero. He’d jump up to the whiteboard and lay out the perfect solution every time.

super skills development

But instead of being energized and appreciative, he noticed that his team wasn’t always sold on his ideas.

As an experiment, he tried something new. Instead of telling them the answer, he started asking his team pointed questions to lead them to their own solution.

This turned out to be the correct tack. More often than not, his team arrived at the same solution he had in mind, but they were much more enthusiastic about it. It felt like their idea, not something dictated from a boss.

Adam calls this “solving for the person, not the problem,” and it’s an ethos that applies to first time managers as much as it does CEOs. On top of being a better way to get buy-in, guiding your team instead of telling them helps support their development.


6. Not Establishing Crystal Clear Objectives

Which is a better goal:

Example 1: Improve inbound marketing.

Example 2: Increase qualified inbound leads by 30% and generate 15% more revenue.

(I hope you said the second one.)

First time managers often make the mistake of setting muddy objectives. Take the first example – improve by how much? Improve the output, or the result? Increase the volume of leads or the resulting revenue?

When it comes to objectives, success should be black and white. You either hit your goal or you didn’t.

On top of that, it’s important to always be clear in expectations, and to be fair and transparent with your team in setting and adhering to these expectations for everyone.


7. Saying “I” Instead of “We”

It might seem trivial, but it’s not. This one simple shift in language goes a long way toward instilling a sense of teamwork and togetherness.


Credit should always be shared. Good managers know that team success and individual success are one and the same.


8. Not Empowering Your Direct Reports

While setting clear goals is important, first time managers also make the mistake of dictating goals rather than collaborating on them.

The best thing to do is to empower your direct reports by having them draft their own goals and set their own meeting agendas. Doing so gives them a sense of ownership and helps them think critically about their role in the larger context of the business. If their priorities are misaligned, you can certainly still weigh in, but the point is to give your team members the autonomy to direct their own time and effort, and develop their own big-picture thinking.

For more tips on the best ways to run a one-on-one meeting, check out our handy guide.


9. Getting Too High and Too Low Emotionally

Business is a marathon, not a sprint.

The pressure of being a first time manager can cause a lot of first timers to live and die by their team’s wins and losses. But that can be draining – and ultimately untenable.

Business is also kind of like baseball. (Forgive the mixed sports metaphors.) The baseball season is a slog. Even the best teams lose a lot – around 40% of the time. The 1939 Yankees are considered one of the best teams in the history of the sport, and they still lost 45 games (or about 30% of their season). If you fall apart after every loss, you’ll never make it to the playoffs.

Same goes for business. “Losses” are inevitable, and getting down when your team misses the mark is exhausting for everyone.


Likewise, when things go well, becoming exuberant doesn’t necessarily help either – because a down performance can be waiting just around the corner.

As a manager, it’s all about the team. Your job is to help pick up your team when they are down and celebrate when they’re up. And, as SnackNation COO Ryan Schneider tells us, managers don’t have the luxury of getting down themselves.

“Leaders don’t get to be ‘down,’” he says. “No matter what is going on in your life you have to bring your best every single day and have the strength to pick yourself up when you are down.”

Never put your team on an emotional rollercoaster. Focus on the things you can control – like your team’s effort – and keep your emotions even-keeled so that you can keep stepping up to the plate.


10. Trying to Manage Too Many People

It depends on the team, but it’s a good rule of thumb to start managers out small. A first time manager should have 2-5 direct reports at first, and then gradually scale up as needed.

Once a new manager gains her footing, you can increase the size of her team, but it’s always smart to consider quality when increasing quantity. A team’s success in large part relies on a manager’s ability to provide support, and more reports can strain her ability to do so.

One example – sales teams. According to SnackNation CEO Sean Kelly, “As a rule, sales managers shouldn’t have more than 8-12 people under them no matter how much management experience they have.”


11. Neglecting Their Own Emotional State

Management and emotions go hand in hand. A lot of your day-to-day involves supporting team members in various emotional states, so the job requires a high level of emotional intelligence.

As we’ve mentioned, it’s important to stay even-keeled. Managers don’t have the luxury of getting down when times get tough.

One mistake that management rookies make is not being in tune with – or taking care of – their own emotions.

SnackNation CEO Sean Kelly explains. “Many first time managers don’t take the time for themselves that they need in the morning to get emotionally where they need to be. This means reading, meditation, working out. Remember, dealing with emotions is a huge part of the job.”

book club

The best way to level set your emotions by making it part of your morning routine. Here are Sean’s tips for setting yourself up for success each morning.


12. Taking Credit for Themselves

If you crave recognition, leadership might not be for you.

I might sound like a broken record, but leadership (and therefore management) is about sharing credit with your team. In fact, you will take more blame for failure and less credit for success. Know this going in.


13. Making Excuses for People

There’s no denying that as a manager, you’re invested in your team’s success.

Sometimes it’s tempting to make excuses for people who are underperforming, either because you hired them (and don’t want to admit you made a bad hire), or because you’re in denial about the extent of the problem.

If you have an underperforming team member, it doesn’t mean that he or she is a lost cause – far from it. It just means that there needs to be a more open communication about expectations when it comes to effort.

But relaxing your standards of conduct and performance doesn’t help anyone. If you’ve taken a hard look at the support you’ve given and the expectations and goals you’ve set, and a team member is still underperforming, it might be best to look at moving them off your team.

Remember that the hiring process isn’t perfect, and companies inevitably make bad hires here and there. It’s best to make a change for the better than to constantly prop up a team member who is dragging down the best efforts of the rest of your team.


14. Confusing “Fairness” with “Equality”

This one’s a little nuanced, but no less important.

“Fair” does not mean “equal” when it comes to management. Your engagement with each member of your team should be determined by their commitment, effort, and performance.

Your primary job is to support your team, but that relationship isn’t totally unconditional. Your team members have a responsibility to give their best effort and make team and company success a priority. Your engagement with your team should be proportional to their engagement.


15. Focusing on the Wrong Success Metrics

So what does success look like from a manager’s point of view? Is it hitting team goals? Is it hitting company-wide objectives?

While certainly important, the best metric of success is actually the growth of your team.

SnackNation COO Ryan Schneider explains again: “Your best metric of success is the next step for your team – whether that means promotions or just genuine growth and development.”


This is similar to the idea that companies should value “graduation” over “retention.” Your goal shouldn’t be to keep your employees at the same level their whole careers. Instead, you should create a growth-oriented environment where employees “graduate” into new roles. Hopefully they move into new roles at your company, but if not, that’s ok too.


16. Your Team Should Be Just as Strong Without You

Rookie managers sometimes think that they need to be indispensable. Not so. Truly great managers have built their teams up to a point where the team can still perform, even when they aren’t there.

Being a leader is sort of like being a parent. Do the kids throw a rager or wreck the family station wagon when you leave them home alone for the weekend? Or do they do their homework and stay out of trouble?

Ask yourself, at what point is your team able to succeed without you? The best leaders make themselves obsolete.


17. Not Learning from Your Team

Finally, we’ve talked a lot about growth and learning for your team. But what about your own growth?

Managers often make the mistake of ignoring their most important learning resource – their direct reports.

The fact is, the people you’re managing know more about the ins and outs of their job than you do. Afterall, they’re the ones on the front lines every day, actually executing all those high level plans and strategies and interacting with customers and other stakeholders. Allow yourself the humility to learn from their expertise.


Are you a first time manager? What have you found to be the biggest challenge in your new role? Let us know in the comments below. Also, be sure to check out our friends at When I Work’s first time manager handbook for more help tips and insights.

Special thanks to Emil Shour, Ryan Schneider, and Sean Kelly for contributing ideas to this piece!


Motivating & Managing Employees Resources:

141 Inspirational and Motivational Quotes for Work

21 Freakishly Effective Ways to Motivate Employees

11 Insanely Powerful and Motivational Videos For Your Team

Managing Millennials in The Workplace: Stop Making It Complicated

How to Run a Productive One-on-One Meeting

14 Essential Team Management Skills for First-Time Managers

Boost the Productivity of Your Meetings with These 26 Icebreaker Games

45 Insanely Fun Team Building Activities For Work

31 Things Successful People Do To Increase Their Productivity at Work


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