Should I Manage People?
Key Considerations for Making the Leap to Leadership
Are you at a crossroads in your career, contemplating a shift into a management or leadership role? Perhaps you’ve been offered a management position, or you’re actively seeking one. Deciding whether to manage people is an impactful choice that requires careful thought and consideration. In this article, we’ll explore critical factors to consider before taking on a management role, drawing from my two decades of experience in leadership and management roles. Through a series of thoughtful questions I recently posed to a colleague, I’ll try to share the insights & observations I’ve gathered to help you make an informed decision about whether management is the right path for you.
Management is one of those topics in industry that is often discussed but rarely understood, especially by “outsiders”. Many professionals grapple with the decision whether to transition from individual contributor to manager, sometimes diving in without fully weighing the implications. Management isn’t just a step up the corporate ladder; it’s a profound shift in responsibilities and mindset.
A colleague recently approached me with questions about whether to accept a management role, prompting me to reflect on my own journey. I’ve held various leadership and management positions, often stumbling into them without much forethought. Now, with years of experience—learning from mistakes and striving for constant improvement—I want to share what I’ve learned to help you approach this decision with clarity.
The Most Important Consideration for Aspiring Managers
The first question, like most of these questions, is only partly about you:
“Can you find fulfillment in improving the lives and careers of others?
This is the cornerstone of management. Transitioning to a managerial role means your success is no longer tied solely or even predominantly to your individual performance but to the success of your team. If you’re motivated by helping others achieve their goals, enhance their skills, and deliver value, management might be a good fit. However, this shift isn’t always smooth. For some, leadership comes naturally, but for others — like me, with an engineering background, direct demeanor, and natural inclination for quick problem-solving — it can be a challenging transition.
(This would be a good place to pause and think of a time when you’ve already mentored someone, improving their work performance, career, or life. What feelings did that spark inside of you?)
When I became a manager, I found that for me, it wasn’t at all intuitive. I had to identify the skills I lacked and actively work to develop them. As someone who dislikes being mediocre, I was determined to excel, but it required effort to pinpoint my weaknesses and seek out role models.
If you’re not prepared for a potentially rocky transition, you might want to reconsider. Getting into management isn’t “arriving” so much as it is beginning an entirely new game that you’ve never played before.
Are you prepared to experience that “beginner” phase all over again? The bad news is that this can feel uncomfortable, and depending on how far you’ve progressed in your career to this point, it could have been a long time since the last time you felt this.
That said, it’s a different type of “beginner stage,” as you enter equipped with all the skills and wisdom accrued in your career to this point. In reality it feels similar to a musician learning a second or third musical instrument, or an accomplished athlete trying out a new sport: Uncomfortable, with hints of familiarity.
The Rewards and Challenges of Management
The Rewards of Managing People
One of the most fulfilling parts of being a manager is watching individuals and teams come together to tackle complex & daunting challenges, and knowing that you played a role in that cohesive execution. My first leadership opportunities came 6-7 years before I formally managed people, and I found immense satisfaction in seeing teams solve big problems collaboratively.
As I entered my late 20s, I began valuing others’ success over my own achievements. The most rewarding moments for me were (and still are) when someone thanks me for mentoring them, offering a new perspective, or helping them navigate a tough situation. Each instance of helping someone grow—whether by advancing their career, boosting their confidence, or helping them achieve a personal goal—outweighs any individual accomplishment I’ve had building product or writing code. The gratitude from others and impact you can have on their lives can be profoundly fulfilling, almost addictive, and far more meaningful than personal milestones.
The Challenges of Managing People
I won’t sugarcoat it: managing people is messy and complex, because people are messy and complex. By all accounts, managing people is quite similar to parenting: You’re leading individuals and trying to help them grow, while establishing boundaries and structure that perhaps didn’t already exist. Mistakes will be made, and you’ll need to accept that reality.
As an individual contributor, errors usually have a limited blast radius … but as a manager, your mistakes can affect a larger group’s performance, morale, and careers. This increased responsibility absolutely requires both humility and resilience on your part. You must accept that you’ll make mistakes—whether it’s giving poorly received feedback, being late with a performance review, or overlooking a team member’s needs—and be willing to apologize and correct course.
Another challenge is that you yourself might not receive adequate support developing leadership skills. Many companies, especially the smaller ones, often thrust new managers into roles without sufficient guidance. I was extremely fortunate to have mentors who taught me critical skills, like using 1-on-1s to build and strengthen rapport.
“Managing people is messy and complex, because people are messy and complex.”
The boss who first made me a manager advised me to connect with team members on a personal level—asking about their lives, families, or interests—before diving into work-related discussions. To some folks this may seem obvious, but it certainly wasn’t to this Engineer-brained manager at the time. My boss’s advice transformed how I approached things as a new manager, but not every organization provides even that level of mentorship. If you’re in an environment without strong leadership role models, you must seek out external guidance to identify and develop the necessary skills to becoming a good manager.
The final few sections of this post should help get you started.
Expectations vs. Reality in Management
What Are Your Expectations of People Management?
When I first moved into management, my expectations were shaped by a naive assumption that my technical expertise would make the transition seamless. I quickly learned that management required a completely different skillset as well as a different mindset.
Another key factor is whether you are assuming a Full-Time position as a Manager, or if “Manager” is an additional hat you’ve volunteered to wear along with your existing responsibilities.
The Player-Coach Reality
Remember how I mentioned earlier that smaller companies are notorious for placing people into leadership roles with little to no guidance and support? Well, unfortunately it’s also all too common for companies to give someone management responsibilities in addition to the demands of being an individual contributor (sometimes called an “associate” or something similar). I loosely refer to this as the Player-Coach model, which I’m sure anyone with a team sports background can understand. Wearing multiple hats isn’t unique to management, but it can be one of the most challenging situations to juggle effectively, both in scheduling and in adjusting your mindset.
When you first get into management—whether full-time or Player-Coach—you may not be thinking much about the state of your IC (individual contributor) skills, because all that’s new about managing people will monopolize your attention. Here’s something I don’t see mentioned often that is important to say explicitly: You should expect that the progression of your IC skills will (at best) slow and stall, and most likely will get a bit stale at first and fairly quickly lag behind former colleagues who are still full-time ICs. This is a tradeoff you have to accept, as there simply isn’t enough time in the day to aggressively progress both groups of skills.
When I became a formal Dev Team Lead and Dev Manager, I knew I'd be writing code less. But I didn't realize how much less time I'd actually spend coding in the player-coach model, especially splitting my time three ways.
Juggling all three proved more challenging than expected. What suffered most was the coding itself and maintaining my individual contributor skills. As I managed more people and recognized I needed to improve as a manager, those responsibilities increasingly became my primary focus, leaving less time for everything else.
I realized that being a good manager to even a handful of people can be a full-time job. To do it well, I had to relinquish the death grip of my inner control freak when it came to the other aspects of the player-coach dynamic. My expectations were that it would be easier, less involved, and less time-consuming than it actually was, but ended up taking far more of my time than anticipated.
The good news? I fell in love with two things, which made the transition easier and helped me let go of what I needed to leave behind:
Helping others achieve great things in their careers
Tackling an entirely new category of challenges and skill acquisition
The reality of management is that it’s less about technical expertise and more about fostering relationships, guiding growth, and handling ambiguity. It requires patience, emotional intelligence, and a willingness to grow alongside your team. For those considering management, understand that it’s a journey of continuous learning, not a destination you arrive at fully prepared.
Developing Your Management Skills
How do you develop your skills as a manager or leader? With an engineering background, I take the approach of: learn something, apply it, learn from that, then apply it again and again.
Learning as a self-taught engineer, I understood that reading something in a book is different from actually seeing it in action. Developing leadership skills followed the same pattern—constant practice, constantly absorbing and consuming as much as I could, and seeing how it worked with what I'd already learned and practiced.
When promoted into a management role, you start with some advantages. You're more relatable and respected given your years of experience in your field. If you were a great salesman who becomes a sales manager, or a good engineer who becomes an engineering manager, people will have baseline respect for you. But this baseline reputation is just the starting point—you need to maintain that mindset of continuous learning and application, not thinking that reaching a management position means you've "made it." This is the beginning of where you really start to learn, grow, evolve, and dramatically increase your potential impact.
“Getting into management isn’t ‘arriving’ so much as it is beginning an entirely new game that you’ve never played before.”
One mistake I've made multiple times is consuming too much information—constantly reading books, watching YouTube videos, taking courses—but not applying much or any of it. You have to actually apply what you're learning to determine if it's something you can use, if it fits your style and approach, and if it's working.
There are so many great frameworks, styles, and systems for leadership and management. You might learn about one, apply it, try some things, and realize it's not right for you. But inevitably, you'll find what works for you and fits your personality and unique style. You can't just consume without application, or you'll set yourself back weeks or months. It's better to learn something, recognize its value, and try it in your next one-on-one for a specific reason. Observe what happens and determine if it feels good, if it's something you could improve, if it's something to try again. The best way to develop your skills is through practice and application.
Essential Resources for Aspiring (and current) Managers
What resources—books, blogs, courses—are most useful for someone looking to be in a management role? There are so many, that the sheer size of this market makes it even more confounding why so many companies toss their new leaders into the proverbial deep end.
If I showed you my personal library, at least 20% of the books are directly on leadership, and another 20-30% focus on adjacent topics like emotional intelligence, influence, behavioral economics, philosophy, etc. And that doesn’t even cover the countless podcasts, courses, intensive events, and other resources I've consumed to better understand people so I could better lead them.
(This is a good moment to pause and point out the obvious: Good leadership requires dedication to the craft. IF you’re willing to be as dedicated to building and leading others as you’ve been to building the skills that have gotten you this far, then you may already have your answer on what you should do next.)
Either way, while my recommendations may not resonate with everyone based on your industry or individual background, the following are pretty universally revered and worth your time.
Extreme Ownership
The number one resource I'd recommend to anyone interested in leadership is the book Extreme Ownership by Jocko Willink and Leif Babin. Jocko also has an amazing podcast called the Jocko Podcast. In the nineties and early two thousands, Jocko and Leif essentially rebuilt the Navy SEAL leadership training program from the ground up.
This book is fantastic because it outlines principles using actual special forces scenarios in Ramadi during the Iraq War, as well as other conflicts. It then explains how the same principles & lessons have impacted real businesses through Willink & Babin’s consulting company Echelon Front and their work with various corporations.
A key lesson from Extreme Ownership is essentially that responsibility flows uphill—if something fails, it's not just that person's fault or team’s fault, but their manager's fault, their manager’s manager’s fault, and so on up the chain. Leadership is not about passing blame down to the boots on the ground. It's about taking responsibility and ownership of failures at a management, executive, and senior leadership level, then determining how to respond to those failures.
Perhaps counterintuitively, I love the idea that if my people take a loss — whether in a minor or a spectacular fashion — it's because there's something I didn't do to help them. Maybe it’s information I didn't provide, context they needed, or course correction I could have offered. Just because I accept responsibility doesn’t mean they don’t feel the L. If you hire the right people, they will absolutely hate to lose, and their leader accepting responsibility gives them the cover they need to learn and improve.
This book shifted my mindset on what good leaders do. They don't pass the buck. They don't blame others. They don't find scapegoats. They take responsibility for every step of the mission, and they focus on everyone getting better and doing things better the next time.
When I think about management and leading teams, I can't think of a better example of high-performing elite teams than the Navy SEALs. If you want to manage people and lead teams that do great things consistently, you won’t find a better lead to follow than the men who rebuilt Navy SEAL leadership training. I've easily gifted this book to a few dozen direct reports and colleagues across a number of organizations over the past decade, and it's practically my bible on sound leadership principles.
The Six Human Needs
The other resource I'd recommend for someone getting into management or leadership for the first time, is looking up human needs psychology — you might Google "Tony Robbins six human needs."
My brain works as an engine looking to identify patterns & systems. I thrive on having systems, patterns, rules, and models I can overlay onto people's behavior to (hopefully) better understand those behaviors.
Roughly a decade ago, I attended a Tony Robbins' event where he went deep on the fundamental six human needs. The idea is that every single thing anybody does, they do to meet one or more fundamental human needs. We all have these needs, we all do things to meet them, and we all do so in different ways.
Those six human needs include the need for
Certainty
Uncertainty (or variety)
Significance
Connection (and going deeper than connection, Love)
Growth
Contribution
I recommend you study six needs and memorize them. Years ago, when I used to lead regular “Dev Lead” training sessions at a previous company, the most impactful concept I ever presented and reinforced was this concept of the Six Human Needs.
(Here’s a brief intro and a longer TED Talk to get you started)
When you're managing or leading people, it can catch you off-guard how often people will surprise you with their behavior.
They'll respond to your emails in weird ways.
They'll do things that make you wonder why they did that thing, when you asked them to do something else.
Having a basic understanding of these six needs and human needs psychology will help you understand the irrational “machine” that is a human being — the complex, confusing, often illogical system that is the person you're managing.
Having a baseline understanding of these needs will help you brainstorm and think: maybe they didn't do what I asked because they needed to feel variety — i.e. they got sick of working on the same thing repeatedly.
Or maybe they did something else because it would get them recognition, and they sought to feel significant. Just having a baseline sense of these possibilities will help you understand behaviors a little better. It won't be a silver bullet, and it won't solve every problem, but it'll help you tremendously.
Final Thoughts: Should You Make the Transition?
We've covered the core questions around why you should or shouldn't get into a management position. There are many more questions we could cover, but I wanted to ensure you got value from this rather than just answering every question under the sun.
Inevitably, the one question I haven't directly answered is: would I recommend making the transition? I can't make that decision for anyone else—it has to be your call. But I hope what I've shared will help you more easily make the decision for yourself.
That said, while I can't make this decision for anyone else, I would advise you to consider it if you've got the opportunity. Consider it if you want to apply whatever analytical, creative, or problem-solving skillset you've developed in your life and career to an entirely foreign, unknown, and new area.
Consider it if you're patient enough to work in a situation where you can create broader, deeper, and more meaningful impact—but where that impact might take weeks, months, or even years to come to fruition. Admittedly, this timeline is something I struggle with. As a software engineer, I can see the results of my work almost immediately. As a manager, you have to wait and see if things pan out… but the pure joy of seeing a person, team, or organization excel based on your involvement is indescribable.
So absolutely consider leadership if you're interested in creating that broader, deeper, and more impactful change, and if you're patient enough to allow things to unfold. Consider it if you're not looking to be on Easy Street, but if you're looking at the challenge of solving some of the greatest, hardest problems of your lifetime and leaving a lasting impact that will continue long after you’re gone.
Share your thoughts: Share a lingering question or fear about becoming a manager in the comments, and let’s discuss to bring you closer to a decision.
