The Software Developer's Career Handbook
by Michale Lopp
Read Status: Completed 📕
Last Updated : 27 Dec 2021
22 min read ☕️
- Must-Read Sections
- Key Ideas
- Career Playbook
- You and Your Career Growth
- Deconstructing Management
- Your Daily Toolkit
- Your Next Gig
Most of the chapters in Being Geek originated from the blog posts of Michael's blog, Rands in Repose. As other reviewers have observed, the organisation of the book chapters is not the best. Nonetheless, there are numerous of wisdom that we can takeaway from Michael's rich experience in the tech industry.
- You and Your Career Growth
- Delivery Is Your Reputation
- The Culture Chart
- The Trickle List
- The Crisis and the Creative
Your career is defined by two tasks: what hard problems have you solved and whom have you joined in solving these problems?
You've had a small number of career-defining moments. ... Bad performance review? Time to become a manager? The company is collapsing? The urgency created by each of these scenarios varies, but understanding how they actually play out is an essential part of planning your next play.
The advice and this book begin with a contradiction: prepare for the unpredictable.
We seek definition to understand the system so that we can discern the rules so that we know what to do next so that we win.
We are fundamentally systems thinkers and believe that we can grasp the logic behind our world/career with enough time and effort. However, the world is unpredictable. We are surrounded by people who inevitably have flaws, biases, and emotions.
After an exhausting grind at work, you are sitting on the train back home. You reflect on the things you did for the day. That's what you're doing, but is that what you do? Are you dreaming about your next gig? Are you thinking strategically about your career?
HR and your boss are not responsible for your career growth. Only you are. You are the manager of your career.
The belief that your manager cares more about your growth than you is just a comforting illusion. Unfortunately. You are always second in line when it comes to growth with your manager. It is only human nature for your manager to put his interests before yours.
Your boss is not going to discover opportunity outside of the company. They're likely never going to say, "Yeah, we're doomed. Get the hell out."
Michael's career development and management philosophy can be simplified into a list of three items.
- Technical direction
Technical direction is a reminder to care daily about my work. Growth is actively watching my career and making sure that today is not a dull repetition of yesterday. Finally, delivery is my daily investment in my reputation. Keeping this list in my head keeps me asking questions and, more importantly, keeps me growing.
Michael believes that a manager's job is to forget. A common mistake of freshly minted managers is to attempt to know it all. Micromanaging drives your team crazy. Trust those that are closest to the problem to make the best decisions. This is how you scale as a manager. Your team members are not extensions of you.
Do you know of a person whom everyone goes to for technical help? The person delivers without a doubt. That is his skill and reputation.
So how do you measure your reputation? Any task, big or small that has landed on your plate and you failed to complete is eroding your reputation. A single failure to deliver isn't a disaster. Maybe it wasn't a big deal, but there was a brief moment they measured you. Your reputation of being a reliable team player dips.
When the boss is signing you up for failure, your move isn't laying down the no; your move is to tell the truth. Hey, I have no idea how to be successful here. I care about being successful, and so should you. Help.
Be maniacal about your reputation.
There are many reasons to leave a gig. Michael reminds us to always considers our new gig from a place of confidence.
If you're pissed, you're not in the mindset to make solid strategic decisions about your next gig. You're motivated by a single thought: I. Am. Out of here. ... you don't want to start a job change being pissed off. Nothing taints common sense more than being pissed off. ... You need to consider your new gig from a place of confidence. You don't want to be running from a mistake, but walking toward a new opportunity.
Ask yourself, what itch are you trying to scratch? A raise? You know you can get a raise just doing a good job where you're sitting right now, with people you know, in familiar surroundings. Switching gigs strikes me as a pretty radical change given all you want is more money. Your motivation around looking for a new gig should be commensurate with the confidence beating you're about to take. Take the beating, Michael advises. There is invaluable experience to discover in the chaotic flurry of new.
Lastly, in analyzing a potential new gig, you need to separate the new from the unique. "What is genuinely unique about this new job? Does this gig fit with your personal strategic direction? What is the opportunity to grow?" Finally, "Is it what you what to do?"
Chapters 4,5,6 are mostly general interview tips. What I found most interesting in this section is The Button.
While the interviewers need to learn about you, you need to learn about them. You need to figure out their Button. It is an opportunity for you to find out about their thoughts about their job and the company.
- Pissed Off Pete: Spend as much time to understand the situation. Find out why Pete is pissed. Might be a red flag.
- Chatty Patty: Huge source of information. Find out anything you can about the situation.
- The Poet: He has something he wants to tell you but only if you ask specifically. Notice where is he repeating himself. Poke him about that topic.
- Gotcha Greg: He think his job is to confuse you with a brainteaser. He likes to test whether you are mentally nimble. Demonstrate your thinking process, think out loud. When you are done, go on a button hunt. Greg likes to be on the offensive and he might be compensating for the fact that he don't really like a normal conversation.
- Slick Steve: He is going to ignore your attempts to find his button. Steve is probably not a part of the engineering team but the organization values him. He is here to vet something. The question is: What?
- Silent Bob: He is probably here to vet your technical and that's it. There is no button. Just show him what you got.
- The CEO: or the hiring manager's manager. Ignore your button hunt. Sell yourself and tell great stories. Put all the organization intelligence you got from other interviews to good use. The CEO is going to say that he isn't the decision-maker. He'll say that the hiring manager is, but if you do poorly with the CEO, it's unlikely that the hiring manager will contradict his boss.
The recruiter was asking you warm-up feeler questions like, "Why do you want to leave your current gig?" and "What's your ideal job?", when they slide in a casual, "So, what are you making now?"
Your inner dialog goes something like, "I'm making 64K, buuuut, I'm going to round up to 70k because, well, I'm worth it."
Yes, you are, but it's a lie and it's not a very good lie. You also broke the number one rule in negotiation: be informed.
"What are you making now?" Your answer: "I'm full-time and I'm making 64K. I'm getting a review in October, and my last raise was 4% plus a 2K bonus. I'd be walking away from 500 unvested options with a strike price currently 12 bucks under market, all of which are going to be totally vested in 12 months."
The structure of this answer is so much better than the one I tried to come up with myself.
Through the anecdotes from this book, I noticed that Michael has a keen ability to read people and situation.
In his words, "With time and experience, you'll learn there is a finite set of personalities walking the halls. Yes, they have their individual nuances, but these personalities and their motivations can be understood."
The culture chart is an unwritten representation of the culture of your company, and understanding it answers big questions that you must know:
What does this organization value?
Who created this value system?
Given this value system, who contributes high value?
Who is most aware of how value is being created?
In other words, tell me what it's going take to get you a promotion. what are the specific things do you need to do in order to be promoted?
It's your job to stay ahead of your manager. You're not going to get promoted by giving your manager what he wants; a promotion comes when you give him what he wants as well as what he does not expect but desperately needs.
There are other stories that you're going to hear over and over again, and inside each of these stories are the real corporate values. Each one, while designed to be entertaining, teaches a lesson about what this particular company values, and learning how to deliver that value is how you're going to get promoted.
The individuals who have the biggest impact on the culture and company aren't doing it for any other reason than they believe it is right thing to do, and if you want to grow in this particular company it's a good idea to at least know who they are and where they sit. You need to pay attention to this core group of engineers because as they do, so will the company.
Just because you've reverse engineered the development culture in your organization doesn't mean you've got a complete map of the overall culture. ... There's the been-here-forever network, the I-survived-the-layoff people, and the untouchable did-something-great-once crew.
I wasn't concerned when Netscape started losing market share to Microsoft. I didn't sweat it when the stock price stalled. The reason I started thinking about my next gig was, months before either of these two events occurred, one of the lunchtime bridge team left. ... one of those who had humbly done the work that defined the company no longer believed enough to stay.
First, just because you like your boss doesn't mean he's playing nice with others, and second, expect surprises.
Have 1:1 with your boss
One of the hats your boss should wear is that of mentor. He's likely seen more than you, which means there's a high likelihood that you can bring any random question, idea, or disaster to his desk and he can comment...hopefully valuably. The absence of a 1:1 is the absence of mentorship, and that means your need to gather your experience in the trenches.
Find out your boss's appetite for information
Understanding whether your boss is organic or mechanic is directional, not definitive, data ... Your boss is also a mix of both, and different aspects of his personality are going to manifest depending on different scenarios. My last boss was intensely organic until senior management started to lean on him, and then he went completely mechanic.
Understand your boss's perspective
He is living in a constant state of low-grade fear induced by being partially informed. This state began the moment he decided to no longer be an engineer and to jump into management. See, he believes what you believe, that the only truth is the code, but he doesn't code much anymore, so he's developed a semi-irrational fear—what's going on out there that I don't know and is it going to screw me?
The Leaper's skill lay in his ability to detect bullshit. Being bright, a former engineer, and familiar with the problem space, he could tell when he was being spun. He knew when he was hearing less than the truth.
There was one sure way to get him to leap: answer a question with an excuse.
An excuse has two parts: the content and the delivery. Your Antonio content may be spot on, but the reason The Leaper is going to leap on you is your delivery. It sounds like you're redirecting, it sounds like you're spinning. You're delivering the facts, but what's being heard is the emotion. OK, maybe it is Antonio's fault, but why'd he miss the date? Do you know? No, you're stuck on the fact he screwed up and by association screwed up you, and that's what you're conveying and that's what is being heard.
I know that feeling when someone in authority spends 30 seconds looking at something you've been working on for six months and immediately finds a painfully obvious flaw.
So, what are you going to do? Clearly, there's a reputation hit here, so what's the right move?
This is your opportunity to say something of value.
When your boss discover your screw-up, he may turn into one of the following archetypes.
While you're being grilled, I want you to remember this: the Interrogator is blowing off steam while asking the endless list of questions. This process of question and answer is laborious, but with each piece of data you convey, you have an opportunity to paint a more detailed picture of your fuckup and increase the chance he can help.There are Interrogators who don't actually have one question that they're driving toward, and these managers need managing. If you're 27 questions into your 1:1 with no clear direction and a total lack of context, it's time to dig in your heels and ask, "Hey, Boss, what are you really trying to figure out here? Are you just pissed, or are we trying to make progress?"
He wants to know everything that you're planning to do to resolve the fuckup, and if this list doesn't exist or isn't complete, you might as well reschedule the meeting, because there is no other way to satisfy the Prioritizer.
This is the manager who is going to swoop into the situation with good intentions, but he's mostly going to randomize the team with his endless good intentions. ... Your job as the minion of the Randomizer is to get back into the 1:1, close the door, and see if you can summon the Prioritizer. Your boss should be your strategic muse, not your tactical nightmare.
He is elegantly, calmly going to get you to realize the magnitude of the fuckup and also get you to suggest a reasonable course of action. In fact, you'll be proud of yourself halfway through the meeting when you slap your forehead and say, "Wow, this what happened and this is what we should do!"
If the Enemy shows up, your fuckup has now doubled in size. You've got a fuckup and you've got a manager who doesn't believe in you. ... You need to figure out why your manager doesn't trust you when he's freaking out.
Asking for the impossible is an advanced management technique, and it's one that is particularly abhorrent to engineers. Engineers are very clear on what is and isn't possible. ... There is an upside to pulling off the impossible. Not only is it a great morale booster, it can also be incredibly profitable, because all your competition thinks the impossible is, well, impossible.
Listen carefully to the actual request. Has your CEO done any preliminary work to actually figure out whether the impossible idea is achievable? What is his strategic intuition about this crazy idea?
There are managers and executives out there who can pitch the impossible on confidence alone.
Do I respect this person enough to tackle the impossible? Is he there at 3 a.m. on Sunday morning with everyone else, looking like he hasn't shaved in a week? Frequent impossible requests result in an erosion of respect and a decaying of credibility.
Maybe your CEO only has an idea and can only feel the possibility in what he's asking ... You're the person responsible for transforming the feel, the intuition, the glimpse of a plan, and the confidence into knowing and doing.
Different people cope with surprises in different ways.
Denial. That's the reaction. Doesn't matter if the surprise is reasonable, understandable, or well-explained. Dr. No's only reaction is a fighting "No."
let them react. The goal with Dr. No and everyone else in the room is to get their reaction out so that we can figure out what to do next.
The next time you chat, there will be residual No, but Dr. No knows that she's been heard and will be willing to brainstorm what to do next about the surprise.
Raging Bull wants to fight. you want to put the Raging Bull in a safe situation where he can react to his heart's content without afflicting psychological damage on others or sparking a mob mentality where he infects a mindless horde of mini-Raging Bulls.
Raging Bull will often continue to pick fights days after the initial surprise, which is why it's your move to get him thinking, as quickly as possible, about what's next.
she's just sitting there, but Still Water is taking it all in. She's not missing a thing, and in her complete silence, wearing her poker face, she is meticulously processing, evaluating all possible permutations, best- and worst-case scenarios, and potential impact on her day to day.
There's the true Still Water who is going to maintain the calm demeanor for the entire duration of the surprise. See, this Still Water's processing has resulted in a comfortable plan.
The second Still Water is mentally losing her shit. Sure, externally she looks calm, but internally her processing has resulted in increasingly loony nightmare scenarios regarding the surprise. Without quick action, Insane Still Water will find reason to become a Raging Bull.
you need to engage Still Water in the surprise and move the problem out of her head and onto the table where everyone can take action.
The Distiller attacks the surprise with questions.
You're going to feel you've got a good idea where the Distiller is at because of his endless questions, but now's a good time to explain that everyone comes down from a surprise in different ways, which is why everyone needs that personal follow-up.
The Handler is not surprised. In fact, she's fired up to handle whatever the surprise might be. Handler's coping mechanism is the illusion she's got it all figured out—that she's 10 steps ahead of everyone else. This is a convenient reaction when you've got the Raging Bull standing on the conference table challenging anyone to hand-to-hand combat, but the Handler needs help.
There will be a quiet moment in the middle of the night when the Handler realizes absolutely nothing has been handled, and then you'll see her actual reaction.
This flight reaction is one of accountability. My Bad's impression is that he's personally done something to incur this particular surprise.
My Bad needs to understand the actual cause behind the surprise. He didn't cause it, so he shouldn't feel it. The more he focuses on feeling responsible, the less energy and focus he has for making progress.
- Despair. the best way to attack this despair is with a project. Doesn't matter if the project is surprise-related or not, the geek needs something to do. They need the blissful distraction of building something.
You need to translate "I quit" into what she's actually saying: "I am very surprised, and I don't like being this surprised."
her knee-jerk reaction is a sign of a larger problem. I don't know what your surprise is, but I know if someone wants to quit, first, it's a big surprise, and second, she values her job second to her peace of mind.
I love it when the sky is falling. There is no more delicious a state of being than the imminent threat of disaster. During these times, I've done great work. There's a reputation you get after successfully performing the diving saves. You're "the Fixer".
Human beings provide mutual group therapy by endlessly talking about the crisis at hand.
everyone wants to know everything. Combine the communication vacuums and the group therapy creating a fire hose of additional questionable content and it's not surprising that everyone on the team wants to know everything. Before I proceed, I want total disclosure. I have something unique to add, and I better get a chance to do so.
There are three buckets of topics that I work through at my Staff, and they're increasingly slippery. We start with Operations (Where are we?), move onto Tactics (What are we going to do about that?), and finally, Strategy (No, really, what are we going to do about it?).
When my Staff meeting is done, I've not only taken a deep breath, I've also begun the process of calmly exhaling...I now know what we need to do this week.... This is generally where people screw up. They confuse the relief associated with the exhale with having a plan, with actual progress. You haven't done anything yet, except sit through three hours of meetings.
The "Look What We Built" meeting is the time to demonstrate progress, to show that even when the sky is falling, we know how to kick ass.
Geeks are motivated and find pleasure in completing tasks that are well-defined.
Once a geek has learned the game by discovering how to win, they become interested in advanced winning. They're interested in how their win fits into the rest of the world. They want to compare and measure and answer the social question, "Is my pile of win bigger than yours?"
We began to understand that achievement was not just becoming great at a game, but also being recognized for being great.
you don't wear a badge for yourself; you wear it for others to see.
Two painful lessons of hiring
Reqs vanish randomly, often without notice, without reason, and at the least convenient time.
People lose their flippin' minds during job transitions.
the strategy is simple: you consistently remind the candidate that they are wanted. In the mental chaos that is a career change, you and your gig are unchanging in your message. You're not coddling them; you're a constant amongst mental chaos.
This chapter may not be as relevant in a post-covid world.
There is a constant flow of information in your company. That means there are constant drips in the Pond, creating various-sized ripples traveling every which way, bumping into each other, and transforming each other into slightly mutated ripples.
It's what we do as curious humans; we receive information, digest it, alter it, and then send it on its way, tweaked to our own personal wavelengths. A remote employee is not in the Pond.
My most successful remote employee was a perfect anomaly. He wrote standards—protocols. The heart of his job was to define a structured means of communication where the primary goal was the removal of ambiguity. He was a phenomenal communicator. He went out of his way to completely and promptly answer every email. 24 hours a day. When he visited, he took the time to do a complete circumnavigation of the Pond, vetting all the ripples he could find. He instinctively knew that the skill in defining a protocol is creating a structure that is going to meet the needs of right now, but also the unimagined needs of five years from now. And he applied that not only to what he wrote, but also to how he worked.
The most valuable takeaway from this section is Michael's productivity system.
The Taste of the Day describes how I deal with tactics, identifying and recording tasks that need to be done. The Trickle List goes strategic and imparts direction for my day: what are the daily investments I want to make in my people and myself? The Crisis and the Creative is less a system and more a mental model for all of the work on my plate.
The curse of any effective task management system is that you get really good at capturing, prioritizing, and executing tasks. To the point that you start to believe that merely completing a task is helping your career. After a solid decade of rampant task management, I realized I needed to augment tasks with a system that would strategically guide and remind me that my job was not to do things, but to remember the interesting words in my title: manager, engineering, and products. That's what I do.
Trickle Theory. The argument was simple: you can do more than you think with small, consistent investments of your time.
Here's my current list:
People — Have a random chat with someone in the hallway
Write — Write something, anything
V — Take a vitamin
Biz — Learn a part of the business
Book — Reading something in a book
You're doing more than stuff and things with your trickles; you're designing moments of high potential.
Intentionally grow moments of randomness in your daily routine, you won't know what you may gain from the random encounter.
- This is any item I'm responsible for that is in Crisis.
- This is anything I'm responsible for that, by investing in or completing, means I'm growing, I built something, I took the team toward new.
- Items in the middle are the silent non-Crisis, non-Creative responsibilities that are my team just making it happen. It's all very important work, but it's work that occurs with very little investment from me because I've hired, manage, and work with competent people who excel at what they do.
The question I ask myself each morning as I stare at the day's selection of Crises is: "Am I going to play in the Crisis or the Creative?"
Check out chapter 29, 30, 32 for general presentation tips.
One of my common mistakes that I find myself repeating:
Time and time again I've watched eager engineers furiously clicking and dragging and sliding their demo all over the screen. Their enthusiasm is obscuring the entire reason we gathered in the first place. My rule of thumb is that when I get to the live portion of the demo, I set my head at half speed.
good program managers speak all the regional dialects of the company, so when engineering says, "It's done," they jump right in and translate, "Done pending function testing, production testing, and final documentation review," so that product management doesn't tell sales, "It's done," and they start selling something that actually isn't done.
Time. Quality. Features. These are common struggles of an engineering team. We can have both, but not all three.
Michael suggests that we can reframe this problem by identifying the most influential person behind each section: Bits, Features, and Truth.
You did a splendid job this year, and I think they should be throwing raises, bonuses, and stock your way. But it's even better if it's clear why you think you did a splendid job. Can you articulate it? And you might know, but does your boss? Can he explain to you, in detail, how well you kicked ass?
I didn't think so.
All of that ass-kickery is tricky to monitor, especially over an entire year. It gets even worse when one of your team members is not kicking ass. Legitimately or not, that's actually where a lot of your boss's attention is going. You read that right: someone else's failure is distracting from your phenomenal year.
The performance review is one of the only official documents of your career at this company. If you move, if your boss leaves, if there's a reorg, this is often the first document reviewed to understand the degree of your ass-kickery, and that means you want your boss to comprehend it.
The point of a review is the debate—to align your perceptions with those of the person who signs the checks—but even with all this structured healthy debate, there's still going to be a surprise.
My move is to keep a yearlong log of significant work as a task in whatever task tracking system I'm currently ignoring. Even if you haven't been paying consistent attention, you'll be surprised by what you can dig up in a weekend of considering your year.
A review not only forces the alignment discussion, it serves as a warning for the coming year: what do I need to do differently to avoid being blindsided when the next review arrives?
See Chapter 35 for considerations between choosing a startup or an established company.
Andy: "I'm leaving."
In a fraction of an instant, you are able to do all the political and social math regarding Andy's departure. You can see the complete set of unchangeable reasons he's leaving, you can predict who is going to follow, and you know that there isn't a damn thing you can do about it.
This is the Moment, and in that moment, you can see how it's all going to come crumbling down.
I've learned that often there is no preventing organizational fuckups of this magnitude, and sometimes the best you can do is either get the hell out or find a comfortable place to hide.
To understand how this exodus begins, you need to understand how information moves around your company. There are always two ongoing types of conversations in the building. One is tactical, and one is strategic.
- This is the daily conversation of the company. It includes the thoughts and opinions of everyone on the team. When everything is normal in the group, the tactical thread is kind of boring, but as we'll see, it changes when the sky is falling.
- This is what managers are talking about all day.
Whatever the underlying reasons are for this organizational collapse, they will first travel the strategic thread, as this is where early detection and triage will occur.
Michael explains that there are typical three waves in an exodus.
The First Wave
The first wave of departures consists of folks privy to the strategic conversational thread. They've heard what's coming, and they've done the political and social math, so they're out.
Without a single conversation, you can infer a lot simply from the starting location of the exodus.
In any exodus, there's a lynchpin departure in the first wave. This is the person perceived in the group or organization as absolutely essential to the business. If they leave, we're dead.
The troubling part of the lynchpin departure is that everyone knows this person is essential. Worse, everyone who's in on the strategic conversation knows this and they know the reasons why this person wants to leave and this person is still leaving.
The Second Wave
While randomness is part of doing business on planet Earth, most folks spend a lot of time insulating themselves from this randomness.
It's the tactical conversation thread that drives the second wave. The scary potential of the second wave is that the legitimate strategic reasons behind the first wave transform into crazy conspiracy theories based on people's core discomfort with a random world.
Management, at this point, has two options: Wait it out or stem the tide. Management may see acknowledgement of the disaster as a disaster in itself. Or Someone is going to stand up in front of the room and answer one question: "What are we doing to stop this random shit from happening?"
The second wave is when things just get weird. Half-true stories are being told in the hallways, and personalities have altered as people are shoved out of their comfort zones.
The Third Wave
The first wave is gone, the second is gone or about to be gone, and one morning you have a brief glimpse of normality. No one walks into your office with their Moment on their face. No one has resigned in a couple of days. It almost feels normal.
Not so fast.
Every talented person who hasn't left in the first two waves is going to be recruited by these annoying, happy former coworkers who dangle just one thing: you know where I am there's no disaster, right? The folks who have survived the multiple wave exoduses are tired, demoralized, and adrift, so the moment a familiar face shows up with good news about a bright future, they are susceptible.
You have to figure your next move
Are you the first one out? Or are you going to wait for your friends to throw you a lifesaver?
Here's the good news: you've just been through hell. You've just acquired years of professional experience watching the intricacies of your organization slowly collapse around you.
This rapid restructuring of your group will result in opportunities you would have never seen.
High tech is full of folks who are confusing success and fame with experience. They're thinking that showing up at conferences, giving interviews, and writing books about things they did in the past is experience. It's not. It's storytelling, and while it might be valuable storytelling, these people are slowly becoming echoes of who they were and moving further from the work they did that matters. They're confusing compliments for experience. ... Are you struggling to build something new or just easily repeating the success of your past? Success feels good, but you're not actually doing anything.
You are biased by the now. You are incapable of imagining what your professional life would be like if you were no longer doing it.
Are you also haunted by the mindset of mediocity? Just complete our work by following the rules of mediocrity. Do just enough. Don't rock the boat. Make yourself indispensable without being noticeable.
When inspiration strikes, Rands reminds us to trust our gut and charge forward. Start small. Just start.
Finishing this book is like a red pill moment to me. No amount of career preparation or reading up on career development books can prevent unpredictable moments from occuring in my career. Learning all of these from Rands' ancedotes can help in identifying the some storms before it happens, but misery, change and conflict will inevitably show up randomly throughout our career.