At some point in your leadership career, you will feel ready for a different kind of challenge. You’ll get the urge to embark on a new adventure with another company.

Hypothetically speaking, let’s say you’ve reached that point already. Let’s say your work experience, certifications, great recommendations, and excellent showing at the interview have landed you a perfect new job. You even got a well-deserved raise and a better title.

You know this is a step in the right direction for your career, and you are confident about the move. You are eager to pick up in the new company where you left off in the previous one.

But on day one of your new job, the honeymoon is over. You quickly find out that your hard-earned trust factor did not follow you to this new company. You are back to square one. You have to build your reputation all over again, from scratch — and the expectations are even higher than before.

You are the new sheriff in town.

With a new company come new rules, new processes, new methodologies, new tools, new team members, new stakeholders, new constraints, new — well, you get the picture. You suddenly feel exactly like you felt before you embarked on your very first project — except for one key difference. You are no longer a rookie leader. This isn’t your first time playing ball. This is just a different league, where nobody knows your name. Yet.

Nobody cares how great you were in your past job. Even the manager who just hired you has already forgotten all of your previous accomplishments and awards, as impressive as they were. The only thing that matters now is how well you do going forward. It is imperative for you to hit a home run on your first task, and the bigger the task, the quicker you’ll build your reputation back up. Trust will be lurking just around the corner from there.

Success is built one milestone at a time. Your first order of business is to break your task down into smaller phases. Make them unofficial phases if you have to. Plan the very first phase in such a way that it’s a slam dunk — something at which you are guaranteed to succeed. Then, build on that accomplishment.

Look for low-hanging fruit, like a quick fix to mitigate a pain point or bottleneck, a simple tool or process improvement to streamline team communication, or a resource that furthers the knowledge of the team. Don’t be overly exuberant about making big changes — now is not the time. The last thing anyone needs is the new guy or gal disrupting his or her comfort zone. What you’re looking for is a string of positive outcomes. You need to demonstrate your competence early and often. Your addition to the team needs to feel good to everyone. You need to win people over, and they need to feel safe in your hands.

Key Points

• When leaders join a new organization, their past reputation does not transfer; trust must be rebuilt from zero

• The fastest way to build trust is by delivering small, visible wins early

• Breaking large responsibilities into low-risk phases increases early momentum

• Avoid making major changes too quickly; stability builds confidence

• New leaders should focus on earning trust before driving transformation

My first management job came by way of an internal promotion. My manager at the time probably saw some redeeming qualities in me, and he handed me my first project to lead.

My project was highly experimental in nature. Our company’s technical support department was looking for ways to speed up the time it took the support staff to resolve a customer problem over the phone. I was to explore how we could leverage a new tool called a “web browser” to that effect. The year was 1995. I had to learn a new programming syntax called “HTML” in the process. I was a team of one.

As far as projects go, they couldn’t have come any simpler than this. It was the perfect size for a rookie manager like me. We were a very process-oriented company, so I had to run my project like any other. I learned how to write all the project documents, held frequent status meetings and reviews, nurtured the relationship with the stakeholders, and managed to hold things together. The project finished on time and on budget.

I delivered a small intranet to the technical support team. It was nothing but a series of HTML pages, all linked together like a clickable flowchart, that pulled data on the fly from the company’s impossible-to-navigate and poorly organized knowledge base. I even had to give a demo in front of a large audience — my first public speaking gig. I finally got to wear the one tie in my closet.

Everyone loved the tool. It was simple to use, accessible from anywhere, and it zeroed in on customer issues more quickly than the old method. I got a pretty nice pat on the back. Because the internet was so new and foreign to most at the time, I was perceived as “the internet guy.” This helped open doors for career advancement within the company.

It is vital for you to hit a home run on your first project. Here’s how and why I succeeded:

1. The project made use of brand-new technology that no one else in the company had any knowledge of or experience with. HTML and intranet were foreign concepts at the time. I was given time to learn, and my peers couldn’t second-guess my work because I knew more than they did.

2. The project was experimental in nature and non-strategic. Expectations were low, so I didn’t feel any real pressure. I was free to set a timeline that gave me enough time to learn all I needed to learn and implement something concrete.

3. I was a trained computer scientist with expertise in software engineering and object-oriented languages like C++ and Java. HTML was super easy for me to learn because it was well within my wheelhouse.

4. HTML pages, by nature, are highly visual and interactive. What I delivered looked shiny and had a wow factor. I received a lot of “ooohs” and “aaahs” during my demo.

When choosing your first project, look for a combination of the following: low complexity or pressure, non-strategic or experimental, sufficient time to deliver, something new that very few people know or understand, and something highly visual and sexy.

An early success means you’ll earn respect in your new leadership role. You’ll be on your way to building your reputation. With reputation comes trust, and trust is everything when you are assigned another project with higher stakes, more vested stakeholders, and new team members.

For your first project, come out swinging like you’ve never swung before. Introduce yourself to the world with a bang!

Key Points

• A first management project often sets the foundation for long-term trust and credibility within an organization.

• Early leadership success is about choosing the right project.

• Delivering something visible and tangible helps create early momentum and positive perception.

• Trust earned on small projects often results in larger responsibilities, higher stakes, and broader influence later on.

I love climbing mountains. Growing up, I was fortunate to live close to a decent-sized hill. My dad and I used to walk together to the top every chance we got. When I was around 10 years old, I started doing the hike by myself. Soon after, I was jogging up and down that hill like it was a small mound. In the years that followed, I upgraded to a number of small rocky mountains.

My 20s saw me conquer many peaks in the 6,000+ foot range. In the beginning, I always climbed with a group of friends. Later on, I felt confident enough to do some hikes on my own. I eventually ventured out in the dead of winter, with snow and ice on the ground, to perform more harrowing climbs.

With each experience, I learned something new. I felt equipped to handle more challenging climbs, pushing the envelope a little more every time and growing in confidence as a result.

Then came the big one: Mount Fuji. Armed with no special gear and only a flashlight, I took a nine-hour trail up the 12,000-foot beast at night in the middle of an ice storm. The wind gusts were so strong I had to duck down the second I heard them howl, lest they pick me up and toss me down the flank of the mountain. At a certain point, I became disoriented from altitude sickness. I suffered, and I endured. I managed to make it to the top.

To many people, attempting this ascent in such conditions may seem like a stupid idea. But there was no gamble there. I knew I’d be challenged, but my gut told me I was capable of overcoming whatever I would face. I was confident. It felt right.

A project or area of responsibility is no different from a mountain you need to conquer.

Every manager has the experience of being handed his or her first project. It’s an exciting moment. You feel the adrenaline rush, and you ride an emotional high for quite some time afterward. But what you do next can make or break your career in management.

Do not, under any circumstances, get yourself into a project or area of responsibility you’re not ready for. It is shocking how often I’ve seen people dive head first into something they were not prepared to handle, only to fail miserably. Luckily, this mistake can easily be avoided.

Before accepting a new responsibility, regardless of where you are in your career, it is absolutely critical for you to do some due diligence. Meet with your manager and find out everything you can about the project. Pay special attention to the “what,” “why,” “who,” “how,” and “when.” Your goal is to get a good handle on the scope and complexity of the work ahead, the challenges you might face, and the expectations you must meet.

When meeting with your manager, ask the following types of questions:

• What impact will this project or responsibility have on the company’s bottom line?

A high impact means more pressure.

• Who are the stakeholders?

The higher the stakeholders are on the corporate food chain, the more you’ll be in the spotlight. Are you ready for prime time?

• Have the project charter, project initiation, or project planning documents been written already?

An undefined project can spell chaos and stress for you.

• Has funding been approved?

Time and resource constraints are your enemy.

• What is the scope and duration of the project?

Marathons are harder than they look!

• Is what’s being built within my subject matter expertise?

The more you know about what’s being built, the better equipped you will be.

• How many people will be on the project team?

You need the right number of people. Too few or too many will give you a guaranteed headache.

• Will the team members be dedicated to the project? If no, then what percentage of each person’s time can I count on?

Ideally, you want team members to be fully committed to your project. Shared resources mean the squeaky wheel always gets the grease.

• Are the team members local, or will they be geographically spread out?

It’s not fun dealing with geographically spread out groups, unless you enjoy daily status meetings at 6 a.m. or midnight.

• Do I have a balanced team in terms of competence and experience?

This will make or break the project.

• Are there outside consultants, vendors, or teams involved?

The more moving parts you have, the harder the project is to manage.

Ultimately, the big-picture question you are trying to answer is: Can I handle this project or responsibility?

This is by no means a yes or no proposition. It’s a gut feeling. Be honest with yourself. You want to feel challenged, and yes, you should be pushed to the limits of your competence — but you must feel confident in your ability to deliver. Otherwise, you are setting yourself up to fail. At the very least, you’re in for a very unpleasant experience.

If your gut tells you to walk away, politely decline the opportunity and explain to your manager that you are simply not ready for a project of this size or scope. Passing on a challenge at work may sometimes reflect negatively on you, but that setback will likely pale in comparison to the damage a failed project will do to your reputation. A tarnished image within a company often leads you straight to the active job seeker pool.

Properly saying no does take some finesse. You should always make every effort to offer a suitable alternative. It never hurts to find out if you could take a lesser role on the project (like an understudy) or to volunteer to be in charge of a different, smaller project.

A good friend of mine successfully hiked to the top of Mount Everest in 2012, a feat that has inspired me greatly. However, were he to invite me on his expedition the next time he attempted to tame a 20,000+ foot monster, I would politely decline without much thought. Why? Because there is only one outcome for me, regardless of how rigorously I train for the hike: I will die with 100 percent certainty. I am simply not mentally equipped for something of this magnitude, nor have I ever been tested at anything above 12,000 feet. The next level for me is around 15,000 feet, not 28,000! I would be stretching my competence level beyond my ability to cope with the inevitable unknowns.

To put it simply: I feel that I would fail, and without confidence, I surely will.

So start small and work your way up. Smaller projects and a smaller area of responsibility mean smaller mistakes. Build up your confidence through incremental successes until you feel ready for something bigger. Size matters.

Key Points

• Career growth happens through progressive challenges, not sudden leaps to the biggest responsibility available.

• Early management roles can accelerate or derail a career depending on the size, scope, and complexity of the project accepted.

• High-impact projects come with greater visibility and pressure, especially when senior stakeholders are involved.

• Confidence is a critical success factor - managers should feel challenged but capable, not overwhelmed or uncertain.

So you want to be in a management role, huh?

“How hard can it be?” you ask yourself shortly after shaking your manager’s hand in acceptance of your new role.

Your hard work over the years has finally paid off. You have been promoted, and “team leader” definitely seems like the next logical step in your career. You now sport a shiny new title, of which your loved ones will no doubt be proud. If you’re lucky, you got a slight bump in your salary, too (but I doubt it).

On your way home that evening, you swing by your local bookstore and load up on a bunch of leadership books. The electronic versions of these books are much cheaper, and many resources are free online, but you like how the physical copies look on a shelf. You’ll probably never read them anyway — and you know it — but that doesn’t matter. They will be there for “reference,” you tell yourself, conveniently choosing to forget Google or ChatGPT exists. You’re feeling good right now.

You show up at work the next day only to find your world has turned completely upside down. You are now the point person for your project, which means you’re responsible for meticulously following every one of the company’s obscure process mandates. If you’re lucky, all the documents of the project up to this point have been properly written, reviewed, and approved. More likely, a few are missing, and your friendly process police will be more than happy to remind you of that.

You notice a lot more emails in your inbox, all tagged “Extremely Urgent” — you know, the ones with the red exclamation points next to their subject lines. Soon, you find yourself spending a solid five hours of your day in meetings. Every day. Your universe begins to revolve around chasing people for information and continuously putting together status updates. You are now responsible for everything, and yet no one seems to be accountable to you.

If this sounds like a bad dream, then you should not be a manager. If, on the other hand, you thrive on sustained pressure, find chaos and uncertainty stimulating, and love to get noticed in an organization, then there is no better professional rite of passage than being a manager. This position allows you to demonstrate your leadership and communication skills, as well as your ability to handle pressure and manage risk. I can’t think of a better way to announce yourself to senior and executive management.

You’re either wired to be a manager, or you’re not. It’s as simple as that. Can anyone do it? Sure, but that doesn’t mean they’ll be good at it. I can buy some highly rated boots, crampons, and rope from an outdoor store, but that doesn’t make me a mountaineer. Can I learn how to be one? Definitely. However, if I am not cut out for the physical rigor of mountain climbing, or if I get dizzy from heights, then engaging in this activity will be very uncomfortable for me. It’ll be against my DNA, and I’ll never be good at it.

Do not, under any circumstances, do something you don’t feel you can excel at. You’ll only be setting yourself up for failure. Or unhappiness. Or both. It will bring you down mentally, emotionally, and physically, and it will impact the quality of your life. You deserve better.

Before you let the allure of a more glamorous job title or higher salary cloud your judgment, take a moment to look in the mirror. Take a day or three if you have to before accepting that new promotion. Your manager can wait. It’s time for you to do some soul-searching.

Remove the job title and the salary from the equation. These might seem attractive in the beginning, but a few months from now, you won’t care about them one bit.

Ask yourself if being a manager is what you’ve always wanted to do, or if this job will take you one step closer toward becoming the person you want to be. If the answer is yes, and if you feel ready for the challenge and are willing to endure the trial by fire that it entails, then embrace this opportunity with open arms.

If you don’t feel this is the right role for you, then figure out a polite and diplomatic way to decline the generous offer. Explain why in very personal terms. No one wants to see you fail, least of all your manager. He or she will understand, assuming your approach, your tone, and your reasons all come across as genuine. If your manager doesn’t understand, start updating your resume. You don’t want to work for this type of company anyway.

I never once thought I wanted to be a manager when I was growing up. I’m not sure anyone else has either. Ever. In the whole world. What I have always known is that I would someday run my own company. From an early age, I have also been interested in building things. As a child, I would obsessively collect anything I could lay my hands on — scrap metal, wires, batteries, corks, empty plastic casings of broken pens, torn pieces of aluminum foil. You name it. I was the most eager scavenger the world has ever known. I dumped everything in a huge box, and I spent my spare time figuring out what I could make with the stuff I had. I learned about resource constraints very early on.

Growing up, I was always the one organizing activities with my friends — where and when to play soccer, whom to coax so we had enough players, who was responsible for bringing a ball, and who had the ball pump last. We had all chipped in to buy a soccer ball (my idea), and the ownership of and responsibility for the ball was shared by everyone involved on a rotating basis (also my idea). Then, one day, our cherished ball was punctured, which meant it had to be inflated multiple times during the course of a game. In came the communal pump. It took me a lot of planning, discipline, commitment, and effort to make sure the ball, the pump, and all the players in the neighborhood showed up for the game on time. We played every Sunday morning at 7:00, but I was always the first one up at 5:00. No short order for a 9-year-old.

As a teenager, I was in charge of choosing the restaurants where we’d eat and which movies we’d see when planning afternoons out with that very same group of friends. I was the one chasing people for any money owed, and I made sure everyone paid their fair share.

Clearly, I was cut out to be a team leader, even if I didn’t know it then. When my first professional opportunity to manage a team came about, I took a week to think about it. I looked long and hard in the mirror, and I said, “Yes.”

After all, management was in my DNA.

Key Points

• Being promoted into management often feels rewarding at first, but the day-to-day reality is far more demanding than most people expect.

• New management roles come with full accountability and limited authority, especially early on.

• Thriving in management requires comfort with pressure, ambiguity, visibility, and constant decision-making.

• Accepting a management role you are not suited for can lead to stress, unhappiness, and long-term career damage.

• Before accepting a promotion, it is important to separate the appeal of the title and salary from the reality of the work itself.

Throughout my career, I’ve worked with a few people who were clearly just … coasting. You probably know the type. Always outside on smoke breaks, stretching lunch a little too long, or somehow disappearing right when a deadline is approaching.

My personal favorites were the clock watchers — a special breed with an almost supernatural ability to know exactly when it’s 5:00 PM. The second that clock hits the hour, they’re already halfway to the parking lot.

Let’s be honest: those people don’t go very far. If that’s how someone shows up at work, they’re not getting promoted. And if that sounds like you, it’s time to wake up — because when restructuring hits, you’ll be one of the first ones on the chopping block.

Before you can be noticed by your manager, you have to perform. I’m a big believer in quality of work over the “butt-in-seat” mindset — productivity matters more than simply being present. That said, you do have to be visible when it counts. Nobody values someone who gives off the impression that they’re just floating through the day. Not your manager. Not your teammates.

If you’re expected to be at work from 9 to 5, show up a bit earlier. Leave a bit later. Go slightly beyond what’s asked of you. Not every day forever — but enough that it’s noticed. And if smoking or vaping is your thing, save it for lunch. There’s nothing more frustrating for a manager than seeing half the office empty every hour because everyone’s outside. It kills productivity.

If you want your career to move forward, you have to drive it. Pay attention to the pace around you, then push just a little harder. Be the person who’s there when something needs doing. Switch gears when required. Deliver consistently.

Do that, and you will get noticed. I can guarantee it. Within a year or two, that visibility and reliability usually turn into a first real opportunity — leading a small team, owning a project, or stepping into a supervisory role. And once that happens, your career starts moving a lot faster.

How do I know? Because I’ve seen it happen. It happened to me, and I later watched it happen with people who worked for me. When I was a manager, I gave first breaks to the people who showed those habits.

When I started my first job as a software engineer, I didn’t even have a car. I had to figure out how to get to work, so I used our company’s internal bulletin board to find people to commute with. The person I rode in with in the mornings arrived very early. The person I rode home with left quite late. Without planning it, I ended up spending long hours at the office.

I was usually in the office before my manager showed up, and more often than not, I was still there after he’d gone home. In the mornings, I’d pass by his office on my way to get coffee (on purpose) and give him a quick nod or a casual “morning.” Later in the day, when the office had mostly cleared out, I’d purposefully run into him near the water-cooler or on his way out. We’d exchange a few words. Eventually those quick hellos turned into short conversations. “How are things going?” he’d ask. And from there, it just felt easy to talk. The ice broke on its own.

After about a year of that, my big break came. What my manager saw wasn’t necessarily raw talent or brilliance. It was commitment. And that made all the difference.

Key Points

• Career stagnation is more often caused by coasting behavior.

• Consistently appearing disengaged - excessive breaks, clock-watching, or low visibility - signals low reliability to managers and teammates.

• During restructurings or layoffs, employees perceived as coasting are often the first to be cut.

• Performance alone is not enough - visibility and presence at critical moments play a major role in career advancement.

• Small, consistent behaviors - arriving slightly earlier, staying a bit later, being present when needed - compound into trust over time.

Most professionals are taught the same lesson early in their careers: work hard, and success will follow.

Yet inside most organizations, this advice does not always work.

Every company has talented people who consistently deliver — but remain overlooked. At the same time, others advance faster, gain influence sooner, and receive opportunities that appear disproportionate to their effort.

The Rookie Manager explains why.

Career progression inside organizations is shaped by more than performance alone. Visibility, trust, perception, and timing play a far greater role than most professionals realize — and these factors are rarely taught or understood.

The guidance in this Substack is written for high performers and experienced professionals — individuals who are strong at what they do and who have been selected to lead a small team or project for the first time. This moment often represents a first real test: one that quietly determines how much trust they will earn, how visible their work becomes, and how far — and how fast — they will grow within the organization.

The Rookie Manager is about understanding and applying the unwritten rules that determine who gets recognized, trusted, and promoted.

It is a practical framework for professionals who want their contributions to be clearly understood, valued, and supported by decision-makers. It’s about not screwing up when you finally get your big break at management.

Here, you will learn how to:

• position your work so it is visible

• build trust with senior managers and stakeholders over time

• avoid common career-limiting mistakes

• become someone higher-ups rely on and advocate for

• accelerate your career from within, without changing who you are
  

If you have ever felt that your work speaks for itself — but no one seems to be listening — this Substack is for you.

It’s not about hard work. It’s about getting noticed.

Key Points

• Hard work alone does not guarantee career advancement inside organizations.

• Many high performers remain overlooked while others progress faster due to visibility, trust, and perception.

• First-time leadership opportunities often serve as a critical inflection point that determines future growth and credibility.

Imagine this: You are sitting behind the wheel of a car in the middle of nowhere. There is nothing around but a maze of roads. You know there are hazards and treacherous terrains ahead, but you do not know where they are. There are no maps.

Fortunately, you are not alone. You have a few passengers with you, each with their own personality and tolerance level. Each person has a different view of the best road to take and feels very strongly about his or her opinion. There isn’t enough gas in the tank to take you the distance, but it is your duty to defy the odds.

Oh, and that car you’re in? It completely falls apart when it moves, unless everyone holds it together in perfect unison. If your group fails to reach safety by nightfall, the blame will be yours alone.

Sound familiar? This is what it’s like to be a manager, supervisor, or team leader. I honestly do not know why anyone would want to do this for a living. We must be a crazy bunch indeed.

Yes, I count myself as a battle-tested leader — and I have the scars to prove it. I’ve run projects of all sizes and complexities for internet startups, medium-sized companies, and one of the largest corporations in the world. Some involved only a handful of people and had a small impact in the scheme of things. Others affected tens of millions of customers and required close collaboration between geographically dispersed teams spanning multiple continents. I’ve had the plug pulled on a project or two after a long and tortuous road that took years off my life. There were times when I nearly suffocated under the weight of overbearing outside consultants and hands-on stakeholders.

I’ve also accomplished the seemingly impossible. I once turned around an entire department with many millions of dollars at stake. My reward? The privilege of managing more (and bigger) projects at once!

I think management is one of the hardest jobs on the planet. It’s no doubt one of the most gratifying, too. Companies everywhere owe a lot to their managers. Without managers, nothing substantial would ever get built. The world of business would come to a grinding halt. It’d be anarchy everywhere.

At least, that’s what I’ve often told myself at night so I could wake up the next day mentally prepared to face the certain chaos that awaited me at work.

I’ve taken the car many times to safety — mostly on time, but also a few metaphorical days later once in a while. I’ve also taken the wrong road more often than I care to remember. However, I’ve learned some very valuable lessons along the way. Not the kind you’ll find in a reference book, but those you can only learn through hard knocks. With each lesson, I’ve become a better manager. My title may have changed over the years, but one thing hasn’t: I still manage multiple projects at once, and I love every minute of it.

Do I still make mistakes? Absolutely! But the impacts of my mistakes are far less consequential than they used to be. I can also spot those mistakes more quickly than I used to. If I’m too late to prevent them from happening, I’m very efficient at fixing them. Realistically speaking, that’s the best a manager can hope for.

Many of my anecdotes and tips are straightforward no-brainers, but it’s surprising how many managers get caught in common pitfalls. Certain mistakes will doom your project from the start. Watch out for those! In today’s ultra-competitive business environment, costly errors can deal a severe blow to your reputation and career growth. I hope this Substack helps you avoid at least one of them.

If you enjoy The Rookie Manager, it would mean the world to me if you invited friends and colleagues to subscribe and read with us. If you refer someone, you will receive benefits that give you special access to The Rookie Manager.

How to participate

1. Share The Rookie Manager. When you use the referral link below, or the “Share” button on any post, you'll get credit for any new subscribers. Simply send the link in a text, email, or share it on social media with friends.

Refer a friend

2. Earn benefits. When more friends use your referral link to subscribe (free or paid), you’ll receive special benefits.

• Get a 1 month comp for 3 referrals

• Get a 3 month comp for 10 referrals

• Get a 6 month comp for 25 referrals

Visit the leaderboard

To learn more, check out Substack’s FAQ.

Thank you for helping get the word out about The Rookie Manager.