Part I: The Management Quiver

1. Don’t Be a Prick Be a human

a great manager is someone with whom you can make a connection no matter where you sit in the organization chart.

Every single person with whom you work has a vastly different set of needs.

• They are chaotic beautiful snowflakes.
• Fulfilling these needs is one way to make them content and productive.
• It is your full-time job to listen to these people and mentally document how they are built.

This is your most important job. I know the senior VP of engineering is telling you that hitting the date for the project is job number one, but you are not going to write the code, test the product, or document the features.

The team is going to do these things, and your job is managing the team.

The CEO believed that these spreadsheet-laden, all-hands meetings were all the connection he needed to build a relationship

You need to remember that what worked one day as a motivational technique will backfire in two months because human beings are confusing, erratic, and emotional. In order to manage human beings in the moment, you’ve got to be one.

2. Managers Are Not Evil: Start with a basic understanding of where managers come from and what they do

“What, exactly, do you do?” – This basic what-do-you-do disconnect between employees and managers is at the heart of why folks don’t trust their managers

managers who were great at the pride part, but turned into jerks when the panic started.

Likewise, new leaders and lessons showed up during the panic—leaders who were quietly getting their work done during the pride.

These are genuinely evil and mean people who put themselves before their team, who lie, and who have absolutely no ability to lead

because you don’t understand what they do, you are automatically biased against them.

Anyone outside of your head is a mystery because they are not you.

seven critical questions that you need to answer in order to figure out if this guy is capable of looking out for number one—you.

1. Where Does Your Manager Come From?
   • second most common complaint I’ve heard from frustrated employees is, “My manager has no idea what I do.”
   • that’s the risk of having a covert job. No one knows your value, which puts you first in line when it’s time to trim the workforce.
   • 15 minutes at the whiteboard with flowcharts. This is what I do and this is why it matters.
   • Right this second, someone you don’t know is saying something great about you because you took five minutes to pitch your boss on your work. Your manager did that. You gave him something to say.
2. How Is He Compensating for His Blind Spots
   • I ask the same question in every interview I have: “Where do you need help?”
   • A manager’s job is to take what skills they have, the ones that got them promoted, and figure out how to make them scale.
   • A manager’s job is to transform his glaring deficiency into a strength by finding the best person to fill it and trusting him to do the job.
3. Does Your Manager Speak the Language ?
   • “Why can’t he talk like a human?” He’s not talking to you. He’s talking to other managers and he’s saying some very Rands-like things, like “Commitments matter!” and “The team is smarter than the individual!”
   • the job at hand is to spread information across the organization as efficiently as possible. And a local dialect of managementese is the best way.
4. How Does Your Manager Talk to You?
   • first piece of advice to all new managers is: “Schedule one-on-ones with direct reports, keep them on the same day and time, and never cancel them.”
   • simple rule, “You will always learn something in your one-on-one.”
   • Whether it’s a one-on-one or a random hallway conversation, your manager should always be in active information acquisition.
5. How Much Action per Decision ?
   • The act of delegation is a slippery slope for managers. Yes, you want to figure out how not to be a bottleneck in your organization and, yes, you want to figure out how to scale, but you also want to continue to get your hands dirty.
   • Pure delegators are slowly becoming irrelevant to their organizations.
   • The folks who work for pure delegators don’t rely on them for their work because they know they can’t depend on them for action.
   • The question you need to answer for your manager is simple: does he do what he says he’s going to do? Does he make something happen?
6. Where Is Your Manager in the Political Food Chain ?
   • turns out the engineering managers were playing a lot of roller hockey and, while they played, Mike the New Guy was working it. He was chatting it up with the execs, getting to know the relevant players, pawns, and free electrons in the organization
   • Mike the New Guy was hungry. He was driven, and after six months of incessantly demonstrating this hunger, the execs gave him the keys to the executive washroom.
   • The difference between a manager who knows what’s going on in an organization and one who is a purely politically driven slimeball is thin. But I would take either of those over some passive manager who lets the organization happen to him.
   • The organization’s view of your manager is their view of you.
   • your manager is a passive non-communicator who doesn’t take the time to grok the political intrigue that is created by any large group of people. I see him as a non-factor and you’re living in the shadow of a non-factor.
7. What Happens When They Lose Their Shit?
   • Do they take care of those who got them there? Do they have a plan for what’s next?
   • Your manager is not a manager until he participated in a layoff.
   • There is no more pure a panic than a layoff, and you want to see who your manager will become because it’s often the first time he sees the organization is bigger than the people.
   • Panic backs a person into a corner and their only means of getting out of that corner is relying on skills that have worked for them in the past.
   • This is how a normally friendly manager can turn into a backstabbing asshole when it comes to a layoff. See, they were an asshole before; you just weren’t there to see it.

The Big Finish: When the first layoff hit Borland, senior VP of applications walked around the building, gathered the product team up, and then told us the straight dope about the layoff… in the hallway. This is what the layoff is about, this is who is affected, and this is when it’s happening.

Still, I think fondly of the guy because during a time of stress, he illuminated. He didn’t obfuscate.

Question #1: Where did I come from? Being able to relate to those you manage comes from intimately understanding their job. It allows you to speak their language.

Question #2: Where am I going? A plan for your manager’s next big move is his incentive. It puts him in the uncomfortable position of trying to discern the murky political motivations of the major influencers of your company.

You care because his [manager’s] success is your success.

3. Stables and Volatiles: There are two builders you need in the build

The birth of 1.0 initiates a split of the development team into two groups: Stables and Volatiles.

Stables are engineers who:

• Happily work with direction and appreciate that there appears to be a plan, as well as the calm predictability of a well-defined schedule.
• Play nicely with others because they value an efficiently run team.
• Calmly assess risk and carefully work to mitigate failure, however distant or improbable it might be.
• Tend to generate a lot of process because they know process creates predictably and measurability.
• Are known for their calm reliability.

Volatiles are the engineers who:

• Prefer to define strategy rather than follow it.
• Have issues with authority and often have legitimate arguments for anarchy.
• Can’t conceive of failing, and seek a thrill in risk.
• See working with others as a time-consuming and onerous task, prefer to work in small, autonomous groups, and don’t give a shit how you feel.
• Often don’t build particularly beautiful or stable things, but they sure do build a lot.
• Are only reliable if it’s in their best interest.
• Leave a trail of disruption in their wake.

Volatiles believe Stables are fat, lazy, and bureaucratic.

Stables believe Volatiles hold nothing sacred and are doing whatever they please, company or product be damned.

Bad news: everyone is right.

while all your leadership instincts are going to tell you to negotiate a peace treaty, you might want to encourage the war.

The birth of a successful 1.0 is a war with convention and common sense.

• handful of Volatiles who believe that “We can bring this new thing into the world,” and no one believes them.
• intimately aware of what it cost to get here, and they want to protect it.

Volatile transforms into a Stable.

• eager to make sure the team does not return to a war-like state
• They hire more people and they become a moderate-size, well-run engineering team.
• They hire people who are familiar, they hire engineers who are predisposed to be Volatile.
• Unintentionally, they plant the seeds for the next war.

The arrival of the second-generation Volatiles is the source of an amazing amount of organizational discontent.

your job as a leader is to nurture this disruption.

you have a choice: coast and die , or disrupt.

As a leader, you need to figure out how to invest in disruption, which is counterintuitive because disruption, by definition, is destructive.

years ago, some Volatile thought, We are not a seller of books, we are builders of technology. (Amazon AWS)

Your Stables bring predictability, repeatability, and credibility to your execution, and you need to build a world where they can thrive.

Volatiles who consider it their mission in life to replace the inefficient, boring, and uninspired.

create a corner of the building where they can disrupt.

constant negotiation of a temporary peace treaty between the factions.

4. The Rands Test: Take a brief test to understand the health of your team

“The Joel Test: 12 Steps to Better Code” – It’s his own, highly irresponsible, sloppy test to rate the quality of software. But… start here.

Growing rapidly teaches you one thing well: how communication continually finds new and interesting ways to break down.

A growing group needs to continually invest in new ways to figure out what it is collectively thinking

The Rands Test: 11 Possible Points

1. Do you have a one-on-one?
2. Do you have a team meeting?
3. Do you have status reports?
4. Can you say “no” to your boss?
5. Can you explain the strategy of the company to a stranger?
6. Can you explain the current health of business?
7. Does the guy/gal in charge regularly stand up in front of everyone and tell you what he/she is thinking? Are you buying it?
8. Do you know what you want to do next?
9. Does your boss?
10. Do you have time to be strategic?
11. Are you actively killing the Grapevine?

Do you have a consistent one-on-one where you talk about topics other than status? (+1)

• when it hits the fan, the last thing you want to do is reschedule one-on-one time
• conveyance of status is not the point of a one-on-one; the point is to have a conversation about something of substance.

Do you have a consistent team meeting? (+1)

• standing agenda item for all team meetings that reads “gossip, rumors, and lies,”
• next measure of a team meeting is, Did we make tangible progress on something of significance?

Are handwritten status reports delivered weekly via e-mail? (–1)

• e-mail-based status reports are one of the clearest and best signs of managerial incompetence and laziness.
• what I really want is your high-level assessment of the week. Three things that are working, three things that aren’t, and what we’re going to do about it.
• I can do a strategic assessment of the week, but why don’t we just put that at the beginning of the one-on-one?
• we can have a big fat debate.
• Status reports usually show up because a distant executive feels out of touch with part of his or her organization, and they believe getting everyone to efficiently document their week is going to help. It doesn’t.

Are you comfortable saying “no” to your boss? (+1)

• leaders who think they’re infallible slowly go insane with power created by the lie that being wrong is a sign of weakness.
• I admit I fucked up, because then I can figure out what I really did wrong, and that starts with someone saying “no.”

Can you explain the strategy of your company to a stranger? (+1)

• Moving away from communications, this point is about strategy and context.

Can you tell me with some accuracy the state of the business ? (Or could you go to someone somewhere and figure it out right now?) (+1)

• independently judge your company the same way that Wall Street does: your company is either growing or dying.
• have a defensible opinion regarding the state of the business,
• If you have a map of what the company intends to do, it’s easier to understand whether or not it’s doing it.

Is there a regular meeting where the guy/gal in charge gets up in front of everyone and tells you what he/she is thinking? (+1) And are you buying it? (+1)

• Gives everyone access to the CEO Allows him/her to explain their vision for the company Hopefully allows anyone to stand up and ask a question
• does the CEO’s version of the truth match yours,

Can you explain your career trajectory ? (+1) Bonus: Can your boss? (+1)

• can tell me your next move.
• It’s a simple statement, not a grand plan. “One day, I’d like to lead a team.”
• Does your boss know what you want to do next?

Do you have well-defined and protected time to be strategic? (+1)

• Can you point to time on your calendar or even just in your head where you are growing toward your goal?
• Busy feels great, but busy is usually tactical, not strategic.
• If you have time in which you’re investing in yourself while at work, and your boss is cool with

Are you actively killing the Grapevine ? (+1)

• no way you’re going to prevent folks from randomly talking to each other about every
• The thing you can change is the quality of the information that’s wandering around the company.
• In the absence of information, people make shit up. Worse, if they at all feel threatened, they make shit up that amplifies their worst fears.
• Rumors hate to justify themselves, so give yourself a point if you make it a point to kill gossip.

The point of the Rands Test is not the absolute score.

Your course is dependent on what you care about, and the Rands Test points out good places to start.

5. How to Run a Meeting Tips: for developing your meeting culture

Anything goes when it comes to a conversation.

Alignment vs. Creation

• alignment meetings are tactical communication exchanges that rarely dive into the strategic. have a weekly cadence,
• Creation meetings—diving into solving a hard problem—involve, well, more creativity.

Each hard problem requires a unique solution, and finding that solution is where creation meetings can go bad.

A meeting has two critical components : an agenda and a referee

• the agenda exists in everyone’s head. Everyone can answer the question, “What do we need to do get the hell out of here?”
• A good referee not only makes sure the majority of the attendees believe progress is being made, but they’re aware of anyone who doesn’t believe that progress is being made at any given moment.
• for everyone in the room: if their attention is elsewhere, they aren’t listening.
• responsibility of the referee to constantly surf the room visually to determine who is and isn’t engaged.

few small tips

• steer the conversation toward them and ask them a question relevant
• Reset the meeting with silence.
• Change the scenery.
• stand up.
• writing stuff on the whiteboard?

There is a point where the referee becomes the dictator and owns the meeting. abuse of the dictator role eventually results in everyone shutting down,

Improvisation . The solution to whatever the hard problem might be is going to show up via one of two things: random brilliance or grindingly hard work.

A good referee knows When the meeting is nowhere near the stated agenda, but everyone in the room is showing all the nonverbal signs of progress

When this person who appears to be rambling and wasting everyone’s time is onto something that might lead to random brilliance

The glaring danger signs for a meeting that is doomed, whether it’s a lack of preparation, the absence of a key player, or the fact the team is wound up about another issue entirely.

The courage it takes to stop this meeting five minutes into the scheduled hour because there is no discernible way to make progress.

A Culture of Meetings

• Meetings must exist, but meetings cannot be seen as the only solution for making progress.
• the definition of a successful meeting is that when the meeting is done, it need never occur again.

6. The Twinge: Listen all the time and use your experience to detect disasters before they occur

The question I want to answer here is how in the hell an SVP who isn’t even part of this project, who was invited as a courtesy, and who has never even see the project proposal finds the biggest strategic gap in our thinking after staring at our slides for 13 minutes? She had a Twinge.

Twinge Acquisition

• you manage both yourself and your team,
• “There is no way you’re doing it all. You need to trust and you need to delegate.”

• Built on Experience

• The building of things scratches an essential itch for engineers.
• Management is a total career restart
• the approaches they used for building products aren’t going to work when it comes to people.

A Manager’s Day : Full of Stories

• All day, you’re hearing stories from different people about the different arcs that are being played out
• need to always be asking: do you believe this story?
• First, this story is incomplete, and you’re OK with that.
• you need to trust that those who work with you are capable of synthesizing a story.
• Second, and contradictorily, know that for any story you’re hearing, you’re getting the version that supports their chosen version of reality.
• the opinion of the storyteller is affecting both the content and the tone.
• Their agenda dictates what they are choosing to tell you.
• malevolent forces are not necessarily driving the storyteller. They are hopeful and they want to succeed, but this story needs judgment,
• Sniffing around is often interpreted as micromanagement, a passive-aggressive way of stating, “I don’t believe you can do your job.”

I could spend my entire day trying to understand, and I’ve got two other projects of equal size that are running hot.

Do you remember every success and failure? No. However, this doesn’t mean you don’t remember the experience.

My belief is that my experiences drive my sometimes subconscious instincts, and this is why I’ve come to trust the Twinge.

Your failure to heed your Twinge is a management failure.

one of your jobs is to listen to the stories and map them against your experience.

And when there’s a Twinge, you ask questions,

when the story doesn’t quite feel right, you demand specifics.

7. The Update, the Vent, and the Disaster: The rules for a good 1:1 and the types of 1:1s that show up on your doorstep

Your job in a one-on-one is to give the smallest voice a chance to be heard.

Start with a question: “How are you?”

basic rules

• Hold a one-on-one the same time each week:
• weekly reminder that you are here for them—no matter how busy.

Always do it:

• each time you bail on a one-on-one, the person you’re managing hears, “You don’t matter.”
• Give it 30 minutes, at least
• people don’t work for you; you work for them.

How Are You?

• It’s a softball opener.
• Do you understand the answer isn’t the point, either? The content is merely a delivery vehicle for the mood, and the mood sets your agenda.

one of three buckets regarding the type of one-on-one we’re about to have:

• The Update (all clear!) The Vent (something’s up . . .) The Disaster (oh dear . . .)
• A one-on-one is not a project meeting. A one-on-one is not status report.
• A one-on-one is an opportunity to learn something new

take it on myself to find a meaty conversation, and if I don’t find it in the first 15 minutes, I’ve got three moves:

• Three prepared points: talking points collected over the week
• The mini-performance review: I see you’ve got a handle on your bugs, but one thing we talked about at your last annual performance review was getting a better handle on the architecture. How’s that going?
• My current disaster: if you’re leading with status and I can’t find an interesting discussion nugget, let’s talk about my current disaster. The point of this discussion is not to solve my Disaster; the point is that we’re going to have a conversation where one of us is going to learn something more than just project status.

while tactics are progress, the real progress is made when we get strategic

A productive one-on-one is one where we talk strategically about how we do stuff, but more importantly, how we might do this stuff better.

The Vent

• When the Vent begins, you might confuse this for a conversation. It’s not. It’s a mental release valve, and your job is to listen for as long as it takes.
• Don’t problem solve. Don’t redirect. Don’t comfort. Yet.
• They don’t want a solution; they want to be heard.

There is a point where you need to jump in, but these conclusions and your actions vary.

• It’s done: Vent starts to lose steam. Begin the triage
• It’s a rant: let them go another round
• The Vent that wants no help is a rant.

The Vent is motivated by emotion. That’s the key difference between the Update and the Vent.

Emotion is a slippery slope, and what can start as a Vent has a chance of spiraling into a Disaster.

The Disaster

• If a Vent feels like a speech, a Disaster feels like an attack.
• when I see the Disaster approaching, I carefully tuck all of my emotions in a box, lock the box, and magically transform into a Vulcan.
• if you so much as blink improperly, you’re contributing to the escalation of this situation.

tips on recognizing and handling the Disaster:

• The person you’re talking to isn’t him- or herself.
• a bizarre emotional version of the person
• Shut up. Really.
• you start defusing by contributing absolutely nothing.
• It’s not about the issue anymore.
• You’re experiencing the employee’s emotional baggage regarding the problem.

There will, hopefully, be a point when the majority of the emotion has passed, and the aggrieved will be willing to having a rational discussion.

A Disaster is the end result of poor management. When your employee believes totally losing their shit is a productive strategy, it’s because they believe it’s the only option left for making anything change.

Assume They Have Something to Teach You

The cliché is, “People are your most valuable resource.” I would argue that they are your only resource.

other tools only support your one and only resource: your people.

weekly opportunity for you to see where dissatisfaction might quietly appear.

weekly preventive maintenance while also understanding the health of your team.

place to listen for what your employee isn’t saying.

The sound that surrounds a successful regimen of one-on-ones is silence.

Your reward for a culture of healthy one-on-ones is a distinct lack of drama.

8. The Monday Freakout: Strategies for dealing with the unexpected

As a rule, the earlier on Sunday that you think about Monday is an indication of how much you neglected to do on Friday.

Rands Rule of Software Management #27 : If someone is going to freak out, it’s going to be on a Monday.

Don’t Participate in the Freakout

• simply listen and maintain eye contact.
• Listen. Nod. Repeat.
• Give the Freak the Benefit of the Doubt
• Chances are, your freak really does have something to say, but maybe they’ve lost perspective spending every waking moment stressing since last Friday at 5 p.m.
• In any freakout, there is normally a very noisy preamble which is designed to get your attention.

Hammer the Freak with Questions

• if it’s been a couple of minutes and all you’re hearing is preamble, it’s time to grab the reins.
• Ending the preamble and starting the conversation starts with a question.
• Properly timed and well-constructed questions lead your freak away from emotion because they force them to the other side of their brain
• Get the Freaks to Solve Their Own Problems
• side effect of attacking freakouts with questions is that you discover the freak is often already close to a solution.

You Still Have a Problem

• freakouts are a normal event in passionate engineering teams.
• It’s still a management failure.
• It’s great that your freak has chosen to freak out. The alternative is that they’re not saying a thing

But you screwed up.

once you successfully defuse the situation, you know two things.

• First, there is a problem that needs to be solved.
• Second, and more importantly, someone believes the best way to get your attention is by freaking out.

9. Lost in Translation: Communication strategies for disconnected personalities

Early on in your mastery of a complex thing, you are going to catastrophically overestimate your ability.

The sensation of the Fall is disproportionate to the size of the lesson.

In a normal getting-to-know-you situation with an employee, the first question I want to be able to answer is, “What do they want?”

Your first job isn’t understanding core motivation , it’s basic communication.

Whenever I say something that might be ambiguous, I ask, “What did you hear?”

when I’m listening, and the topic or intent is not abundantly clear, I restate: “OK, what I heard was . . .”

It sounds like this:

• Me: . . . and new requirements came in this weekend, but Jennifer still wants to see an initial spec by Thursday. Wallace, what did you hear there?
• Me: Yes, a spec on Thursday. And what does that mean for your work?
• Me: What I’m hearing is that you’ve got a pile of work that will need to be rescheduled, right?

With practice, you’ll learn the unique rules of engagement . You’ll discover the words and the ideas that people use to describe both their happiness and their displeasure.

when communications are down, listen hard, repeat everything, and assume nothing.

10. Agenda Detection: The first step in getting out of a meeting is understanding why it exists

agenda detection is the ability to discern

1. Typical meeting roles and how meeting participants assume them.
2. Explanation of what these distinct meeting roles want out of a meeting.
3. How to use this understanding to get the hell out of the meeting as quickly as possible.

Meeting Bail Tip #1: Identify the Type of Meeting

Chances are you’re either in an informational meeting or a conflict resolution meeting.

Information meeting:

• Roles and agendas in these meetings are simple. Talkers are talking and listeners are listening.
• There is no problem to be solved other than the transmission of information. The quicker it happens, the sooner everyone is back to work.
• Folks are here to nod, not solve problems.

At a conflict resolution meeting, some problem needs to be solved.

• Apparently, it could not be resolved via e-mail, instant messaging, or hallway conversations, so some bright fellow decided to convene a face-to-face meeting where the bandwidth is high and the time wastage is significant.

Meeting Bail Tip #2: Classify the Participants

two major types that you need to identify: players and pawns.

• players want something out of the meeting. They’ll be leaning forward, actively nodding, barely able to hold themselves back from spilling their agenda all over the table.
• Pawns are either silent or instruments of running the meeting. In either case, they’re adding very little to the meeting and can be removed from strategic consideration.

Meeting Bail Tip #3: Identify the Players

• you can assume all the engineers are players.
• product-management person is also a player as she represents the sales folks in this meeting.
• Program managers in these meetings are pawns.

If you’re sitting in a meeting where you’re unable to identify any players, get the hell out. This is a waste of your time.

Unfortunately, if you’re new to a group, you need to get burned by the windbags a few times before you learn to avoid these totally fucking useless meetings.

Meeting Bail Tip #4: Identify the Pros and Cons

• figure out each player’s position relative to the issue on the table.
• The pros are the players who are currently on the winning side of the issue. They’re getting what they want and are not incented to negotiate.
• The cons, clearly, are the ones who are being screwed. They’re likely the ones who yelled loudly enough to get the meeting set up in the first place. they’re expressing some degree of pissed-off-ed-ness.
• The specific pro does not need to be in the building, but they must have a designated proxy, or the cons will bitch, heads will nod, and nothing will happen.

common tactic of a good pro is to not acknowledge that they’re the pro.

Meeting Bail Tip #5: Figure Out the Issue

• now all you need to do is figure out what the whos want.

Meeting Bail Tip #6: Give the Cons What They Want

• The cons need a plan, some assurance that will somehow address whatever the issue is.
• Someone needs to synthesize everything into constructive next steps and communicate that to the cons, and then you’re done. You’re out the door.
• Doesn’t need to be a great plan, or an honest plan, or even a complete plan.

Meeting Bail Tip #7: Figure Out the Issue

• If it’s 30 minutes in and you still can’t figure out what the issue is, it’s time to go: too many issues.
• Someone who cares more than you needs to distill this chaos down to a coherent statement so the pros and cons can argue about one thing.
• Conclusion Meetings are always going to be inefficient because language is hard.

Meetings give us the opportunity to include other organizations with other accents. This makes the language chaos complete.

Now, you don’t care. You don’t need to know what they’re saying because with agenda detection, you can figure out who they are, what they want, get it for them, and get the hell out.

11. Dissecting the Mandate: Understanding when and how to insist on strategy

In your quiver of management skills

• There’s the annual review, where you take the time to really explain, in detail, what a given employee needs to do to grow.
• the layoff? That’s when you get asked who stays and who goes.

• there’s the mandate. The mandate is when you gather the team together and calmly say, “This is the way it is.”

• Most folks have learned to despise the mandate.
• We had a good solid week of organizational disarray and then we got back to work.
• “I’m the guy who’s telling you the way it is.”
• It is just as easy to convey, “Shut up and get moving,” as it is, “This is the move and I’m the guy you can blame if it’s a bad call.”
• move the team forward without hurting morale.

There are three distinct phases to the mandate: Decide, Deliver, and Deliver (Again).

Decide

• Every so often, a big decision comes along. Doesn’t matter what the content is, what matters is that some portion of your team is on one side of the decision and another group is on the other side. And they’re arguing.
• Rule of thumb : When the debate is no longer productive, it’s time to make a decision.
• My management style is to allow the team to argue as long as possible.
• This means that decision-making in groups that I manage tends to be slower because I’m busy cross-pollinating.
• Consequently, I’m certain it means our output is higher quality because we’ve taken the time to consider what the hell we’re doing.
• for every person on the team who has a strong opinion regarding the decision, there are probably four other coworkers who just want someone to make a decision so that they can get back to work.

Mandates are the friend of the silent majority. Even if you really annoy the concerned parties, the silent majority will appreciate the peace and quiet once you’ve delivered your verdict.

Deliver

• do a good job of explaining the decision, but they fail convey that this is the decision and further debate is not necessary.
• A good sign of poor mandate delivery is when the delivery degrades into another debate of the issues.

The team has got to leave the room knowing the decision has been made.

Deliver (Again)

• each person walking out of meeting has one of three distinct opinions: Yay: You are a great motivator. The winners will have this opinion of you and you still you need to deliver (again). Boo: You are a tyrant. Commonly held by those who’ve been screwed. You must deliver (again). Yawn: What took you so damned long? Silent majority here. Don’t sweat them.
• Delivering (again) is taking the time to individually express your reasoning to the concerned parties—both the winners and the losers.
• Expect more venting. In fact, insist on it. If you’re sitting with someone who was on the losing side of the decision and they’re still nodding their head, they don’t believe the battle is over. They’re sitting there figuring out their next move to erode the mandate.

Delivering (again) is not going to quench discontent in your team, but it’s going to give everyone involved a chance to speak up,

Foreign Mandates

• This is a mandate that occurs way outside of your sphere of influence.
• Regardless of what your opinion is, you must figure out the justification behind the mandate.

You are going to look lame when you relay the mandate without a clue as to why the mandate showed up.

12. Information Starvation: Each piece of information that arrives has a

proper home or homes

One of your many jobs as manager is information conduit, and the rules are deceptively simple: for each piece of information you see, you must correctly determine who on your team needs that piece of information to do their job.

Perhaps the biggest loss of essential information is when managers rely on their brains as to-do lists.

It might feel like you’re passing on useless information, but the rule of thumb is that you never know what your team is going to care about.

Simply because an e-mail or thought makes sense or has some interesting context in your head doesn’t automatically mean the insight is going to be obvious to anyone else.

taking the time to give each piece of information that you’re passing on a bit of your personal context never hurts.

Whether it’s gossip, rumors, staring, pacing, or yelling, your team is always telling you what they need to know. This means your job is not just to be an information conduit; it’s also to employ a policy of aggressive silence.

13. Subtlety, Subterfuge, and Silence: Three leadership approaches for traversing complexity and making progress

read The 48 Laws of Power; There’s some pretty evil shit documented there as well as some basic truths

Management is chess. When you’re presented with a problem, you sometimes need to sit back and take a look at the board, figure out the consequences of each of move, and, most importantly, pick a move.

the move and how you pick it does not involve 48 laws, but only three words: subtlety, subterfuge, and silence.

Subtlety

• the point of a performance review is not the review itself but the conversation that stems from it.
• Subtlety starts with humility.
• Sometimes your approach needs to start small, humble, and in a place in which you admit that you don’t have all the answers.
• Subtlety finishes with elegance.

It’s that you solve it in an ingenious, novel way that builds and refines your management aptitude.

Subterfuge

• Relative to management, subterfuge does not mean “deceit, dishonesty, cheating, fraud, or fraudulence.” It’s everything else.
• skunk works took us three weeks, not one, but when we showed off our work, the VP of engineering and VP of marketing were impressed and wanted to see us finish the work.

The use of subterfuge for good means keeping the intent honest.

Silence

• This guy’s personality totally and completely clashes with yours and he’s in his second hour of rambling about something you don’t understand.
• Shut up and listen.
• While all this talking is going on, I sit quietly and nod while learning what all these yammering people are about and carefully file it away for future reference.

Remember this: in most businesses, everyone’s basic agenda is visible after they’ve talked for about 30 seconds.

Asking for what you need is a good strategy in business; it’s called collaborating.

The 48 Laws of Power are the real deal, but they are focused on war, not business. Go buy the book if you want to know more, but read wisely.

there is one law—not in the book by Greene and Elffers—that is true: if you’re only interested in building power, you’re going to lose.

14. Managementese: The language you use defines your leadership

snippet of his conversation: “I think it’s a key decision and I’m asking you to think outside of the box . . .” I cringed. Management speak.

Well, it means something like “Don’t restrict your thinking to conventional avenues,” but that’s not what your team hears when you say it.

• What they hear is, “Hi, I’m a manager, and I’ve stopped thinking and am using throwaway phrases that obscure what I mean.”

Managementese is a language that is learned, evolved, and spoken by managers.

• For communication between managers, it’s a convenient, high-bandwidth means of conveying information.
• There are unique spheres of language that exist in each part of the corporate organizational chart.
• In each of these groups, there are managers who must speak their native language, as well as be able to translate between spheres in order to get the job done.
• The main issue folks have with managementese is not that they don’t understand what is being said; their issue is that they don’t trust it.

when you’re talking to individuals, talk to them using the familiar language of a friend.

15. You’re Not Listening: Look them straight in the eye and never look at the clock

start with the most basic rule of listening: If they don’t trust you, they aren’t going to say shit.

a good conversation starts with the ability to listen.

Let’s start… Open with innocuous preamble. In most discussions or one-on-ones, you have an agenda. There is a question that you really want to ask. Don’t start with this question. In fact, start with something small and innocuous. Crap openers like, “How are you?” or “What’s up?”

Your preamble states your intent: “Outside of this door, it is professionally noisy. Inside of this room, we are going to talk and listen.”

Look them straight in the eye and don’t look at the clock.

Eye contact is the easiest way to demonstrate your full attention, and it’s also the easiest way to destroy it.

Be a curious fool. Assume they have something to teach you.

early on in establishing the attention contract, they’re going to be nervous. They’re going to assume that you’ll be talking and not listening,

Keep asking stupid questions based on whatever topics arrive until you find an answer where they light up.

When you understand what they really care about, you’ll be better equipped to have bigger conversations, and that is where trust is built.

Validate ambiguity, map their words to yours, and build gentle segues .

maintain the conversational flow.

repeat their last sentence, “What I hear you saying is . . .” and then I repeat my version of their thought.

The goal is to make it clear to the other person: “I know you just said something complicated and I am directing my full attention at understanding what you said and what it means.”

discover how to move from one topic to the next.

Pause. Like, shut up

• The conversation is not headed where it needs to go, so you’re going to disrupt with silence.
• No matter how empathic or smart you believe yourself to be, the story they’re telling themselves is vastly different than the story you’re telling yourself.
• In these awkward silences, I find people volunteer the part of the story they really want to tell.

If They Don’t Trust You, They Aren’t Going to Say Shit

Listening is work, and the difference between listening well and making them feel like you’re selling them a car has to do with intent.

16. Fred Hates the Off-Site: A meeting designed to help you set or reset strategy

The reason an off-site exists is simple: you, the leader of the people, need certain essential work to occur that cannot easily occur now under normal conditions within the building.

• When it was only 20 of you, each of the three different off-sites I’m about to describe would just happen . . . organically.
• At an organizational size that varies for every team, natural cross-pollination and communication activities that used to happen organically, that allowed for cultural and strategic work to get done, and that allowed for big decisions to be made, can no longer occur.
• Random hallway error correction doesn’t happen, because the right folks aren’t bumping into each other.

We Need to Understand Who We Are

• You need an off-site not to solve a strategic product problem, but to give the team members time away from their hurry to get to know each other.
• The need for a team to understand itself is a cause worthy of an off-site all by itself.

We Need a New Direction and/or Fewer Disasters

• Either disasters are occurring and the normal processes of detection and correction aren’t working, or everything appears to be working but we’re not achieving success—for
• The purpose of this off-site is deep brainstorming

We are Embarking on an Epic Journey

• This off-site is an alignment meeting . Strategy can be discovered as part of this meeting, but that isn’t the primary goal. You are collectively pointing folks in the correct direction

A Meeting with Certain Characteristics

• By Definition, you can’t Invite Everyone
• the team has grown to a size where they are consumed by hopefully essential tactics. They don’t have time to step back and think about it later,
• You need to be able to look around the room and think, “These are the people who will solve the problem.”

An off-site is not an opportunity to ignore opinion; an off-site is a chance to select a group of folks who are going to best represent the company on whatever huge problem we’re solving.

Everyone Presents, or at Least Speaks

• rule of thumb is that each person at the off-site has a deliverable, and that usually means that they need to step up and present.
• First, if I can’t think of something I’d want this presenter to talk about given the problem at hand, then why are they invited?
• Second, I start to see duplication.

It’s Not in your Usual Building

• need a sense of elsewhere. They need to be far from the tactical distractions of the office because people need a new view.
• create grounds where people feel comfortable speaking heresy.

There’s Someone Responsible for Flow as Well as Action

• two roles you need to designate before the festivities begin: a Master of Ceremonies and a Taker of Notes, and they are usually not the same person.
• Master of Ceremonies is the person responsible for not just moving the day along, but also knowing when to stop and pivot.
• Taker of Notes reads like an administrative job, but it’s the most important gig in the room.
• you only find three new ideas that you act upon.
• immense burden of the Taker of Notes to not only find them, but assign them to the people who can and will drive them forward.

Each time your company doubles in size, it needs to reinvent how it communicates, and each subsequent transformation is increasingly radical and foreign.

No Personality Tests, No Trust Falls, and No Outsiders

• Avoid personality tests: while, yes, they now have convenient labels for each other, they haven’t really figured each other out—they’ve cheated. You’ve bypassed the learning process via a set of clever labels.
• If you want to understand someone, my advice is to sit next to them and solve a very hard problem together.
• Avoid trust falls: you’re putting the team through an uncomfortable and irrelevant social or strategic exercise because you’re attempting to build trust, why not make it relevant? It builds trust faster and you get actual work done.
• Avoid outsiders: they couldn’t give a shit whether you solve your problem or not.
• They don’t know the culture, the problem at hand, the politics, or the personalities. They’re simply not qualified to participate
• They Need to Sleep on It

There’s a moment I like each person to have as part of an off-site, and I call it the bright-and-shiny inflection point. They finally let go of all the tactical things they need to do and allow their brains to jump into the creative soup

An off-site must be at least two days long. You need one evening where everyone gets away from what is hopefully a high-bandwidth conversation regarding whatever it is that ails the company, and gets a chance to process this conversation in the back of their heads.

each person we add to do more work strategically slows us down. Each additional person levies a communication tax,

The successful off-site is one that maps the discoveries of the off-site to the reality of the work.

Bright-and-shiny inflection points are full of energy, but unless that energy is carefully channeled back into the building and immediately acted upon, all an off-site represents is a frustrating opportunity to dream, but not to act.

17. A Different Kind of DNA: A design and architecture meeting with teeth

a flat organization is one with as little hierarchy as possible to encourage the individual voice. What’s not to love?

• The flat religion’s answer to this development is rebranding of the role: the lead or manager is no different from the individual.
• the curse of Silicon Valley is that great engineers are often promoted to leadership for their hard work. While many succeed in this role, an equal part fails because the skills required to lead are vastly different than the ones required to be an engineer.
• we don’t have a good idea how to systematically grow engineers outside the traditional management hierarchy.

But I do not yet understand how this idea scales.

We need leads and managers as a means of scaling responsibility and communication, but we need to dispel the idea that their roles are also the exclusive owners of decision-making.

DNA stands for design ’n’ architecture.

DNA suggests, these engineers are responsible for deep analysis regarding decisions and directions core to the product.

DNA makes the informal formal and it has five kinds of win:

1. It shines a light brightly. DNA meeting is scheduled when something technical is going down. Something big. Something of magnitude.

2. Bring respectable firepower. not talking just about those with ability, but also the folks who go out of their way to teach

• DNA team is not only the set of engineers who are the best candidates to vet the big idea, but those who have ability to talk about how to make it better, can constructively criticize, and are distinctly drama- and politics-free.

1. It has teeth

• First, the rule for all attendees in a DNA meeting is, If you don’t contribute, you won’t be invited back.
• an active and healthy debate about a bet big enough
• Second, it needs to be culturally understood that if you don’t bring your A game to the DNA meeting, the team is authorized to mentally kick the shit out of you.
• They don’t rule by mandate, they influence by being great at what they do.

1. DNA has absolutely nothing to do with management (and everything to do with leadership).
   • Pure managers are not considered
   • DNA is about cultivating technical leadership

influential engineers who don’t want direct reports, but want to lead.

1. DNA is achievable and aspirational.

You build a DNA meeting to remind the team that all forms of leadership matter.

18. An Engineering Mindset: On the topic of whether you should still code

Rands Management Rule Book

• stay flexible
• Stop coding.
• you must learn to trust those who work for you to take care of the job of coding.

Too bad I’m wrong

you should be worried about your job because the evolution of how software development occurs might be moving faster than you are.

advice for maintaining an engineering mindset:

1. Use the development environment to build the product.
2. Be able to draw a detailed architectural diagram describing your product on any whiteboard at any time.
3. Own a feature. make it a small feature,
4. Write unit tests. there is no reason that a manager shouldn’t be participating in this massive global cross-pollination information cluster-fuck

If you want to be a good manager, you can stop coding daily, but . . . Stay flexible, remember what it means to be an engineer, and don’t stop developing.

19. Tear It Down: There are three leadership roles

“Would you rather be managed or be led?”

• believe in the power of the individual, but I also believe that in order to build epic shit at scale, a colorful tapestry of talent and degrees of experience is essential.
• when I say colorful, I mean people who often don’t get along precisely because of this diversity.

Three Leaders

1. The Lead: The Lead of Leads The Director
   • The Lead is at the beginning of their career of not doing the work, but rather leading the work.
   • The Lead is tactical, but is showing the first glimmers of strategy.
   • beginning to understand the power of delegation,
   • wrestling with the idea that they have authority.
   • beginning to understand that there are different domains out there with different rules, and a new aspect of their role is interfacing with these foreign elements.
2. The Lead of Leads’: obvious defining characteristic is that they are responsible for multiple leads,
   • not the most important characteristic. In my experience, the Leads of Leads are running the company.
   • no longer has any hands-on responsibility.
   • equal parts tactics and strategy.
   • They see the complete game board. They see all the pieces, so they can be credible strategists. Sometimes.
   • these folks who are ridiculed for being “middle management,” they are the people and process machinery that keeps the machine running efficiently.
3. The Director: primary focus is outward. The Director’s job is to figure out how the company fits into and interacts with the rest of the world.

20. Titles Are Toxic: Titles place an unfortunate absolute professional value on individuals

is it a job or a title? A job is a well-defined thing that has a clear and easy-to-understand set of responsibilities. A title often has neither.

Titles allow leadership to bucket individuals into convenient chunks so as to award compensation and measure seniority while also serving as labels that are somehow expected to give us an idea about expected ability.

This is an impossibly tall order and is at the root of title toxicity.

21. Saying No The single most powerful arrow in your professional quiver

There are managers out there who are absolutely punch drunk with power, and if you’re working for one of these folks, I’m really sorry.

• Managers don’t start crazy. It’s a learned trait,
• Managers lose it when they are no longer questioned in their decisions.
• Saying no is saying “stop,” and in a valley full of people who thrive on endless movement, the ability to strategically choose when it’s time to stop is the sign of a manager willing to defy convention.

“With great power comes great responsibility.” As a manager, you are responsible for making great decisions and the best way to do that is to involve as much of the team as possible in every decision.

Your team is collectively smarter than you simply because there are more of them. More importantly, by including them in the decision process and creating a team where they feel they can say no, you’re creating trust.

A team that trusts you is going to look out for you.

Part II: The Process is the Product

The Process is the Product

• People screw up. Every single one
• To prevent these screw-ups, the more organized members of the team create process.
• Process creates a delectable, healthy tension between those who measure and those who create.

22. 1.0: The hardest thing to build

Understanding 1.0

• you’re going to be screwed at some point. My advice is keep thinking, don’t yell, treat those you work with decently, and you’ll be fine.
• Most startups fail.

Figure 22-2. Rands 1.0 Hierarchy

                                   /-- Self-Actualization --\
                                  /--       Esteem         --\
                                 /--         Love           --\
                                /--         Safety           --\
                               /--       Physiological        --\

Do not trust charts ‘n’ graphs, but don’t let that lack of trust blind you to the intent of the story.

Pitch

• At the top of the hierarchy, there’s Your Great Idea. I’m calling it “pitch”
• If you don’t have the idea, you don’t know who to hire,

Fact #1: You’re in a hurry. Don’t forget it.

People

• With your pitch in hand, you’re going to find the people to build your idea. These are your founders.

Fact #2: No one is indispensable.

Your first three hires are your kindling. Their job is not to define the product roadmap, their job is to get things moving,

Fact #0: Startups almost always fail.

Fact #3: Process defines communication

Process

• agree how you’re going to share information.
• If your engineers aren’t arguing about the way they develop software all the time, they’re becoming stagnant, and that trickles down to your pitch and trickles up to your product.

Fact #4: Each layer shapes and moves those near it.

Product

• Folks who say “I like change” are not currently working at a startup.
• A neutral party doesn’t care about the pitch, your people, or any of the pyramid shoving you’ve been up to; they just care whether the product is useful.

Fact #5: You don’t have a company until you have a product.

Fact #6: The lower the failure, the higher the cost.

Building Culture

• what you’re really building in 1.0. A lasting, interesting culture that, if you’re lucky, continues to produce great products.

23. The Process Myth: Process is a seven-letter word that begins with P that engineers hate

Engineers are creatures who appreciate structure, order, and predictability, and the goal of a healthy process is to define structure so that order is maintained and predictability is increased.

Engineers don’t hate process. They hate process that can’t defend itself.

At Apple, there is a creature called an Engineering Program Manager (“EPM”). Their job is process enforcement.

• 70 percent of them are crap, because while they are capable of keeping the trains running on time, they don’t know why they’re doing what they’re doing.

Healthy Process Is Awesome

• With a small team, mostly you don’t need process because everyone knows everything and everyone.
• Hidden among all this work are essential parts of your company that everyone knows, but no one sees: your values and your culture.

at some magical Dunbar number, you pass two interrelated inflection points.

• First, the number of new hires arriving exceeds your population’s ability to organically infect culture and values.
• Second, because of the vast swath of preexisting people, the arriving individual erroneously believes that they as a single person can no longer influence the cultural course of the company.

1 The Old Guard.

• They understand the culture and the values because they’ve been living and breathing them.

2 The New Guard.

• they spend a lot of time confused about these topics because no one has taken the time to sit them down and explain them, and the folks who are qualified to do so are busy keeping the ship pointed in the right direction.

the Old Guard can’t conceive of a universe where everyone doesn’t know everything, Eventually, meetings are convened…

• They document the process. When you think of process, I want you to think of this moment, because it could be a noble moment. Process is being created not as means of control; it’s being built as documentation of culture and values.
• documentation of how rather than the essential explanation of why.
• Process should be written by those who are not only intimately experiencing the pain of a lack of process, but who are also experts in the culture.

Healthy process is awesome if it not only documents what we care about, but is also willing to defend itself.

24. How to Start: A nuts and bolts analysis of the time before you start

believe three things:

• Your brain is smarter about thinking than you think. many states of preparation are your brain cleverly and proactively trying to help you begin.
• Preparation, in its variety of forms, often gets a bad rap.
• Stress is a creativity buzz kill.

The risk of morning is exuberance . Unbridled exuberance

• Mornings have the gift of optimism because nothing has screwed up your day, yet.

Evenings are dark, repetitive reminders that no matter what you do, time is going to pass and you’ve likely wasted some of it.

• this mental state, the creativity dial easily moves to the depressingly lowercase “uninspired and listless,”

work the logical side. I give myself a task such as, What is the smallest piece of research I can do relative to the project?

25. Taking Time to Think Are you reacting or are you thinking?

Reacting vs. Thinking

• the “necessity is the mother of invention argument”; but, seriously, if your hair’s on fire, are you going to take the time to seriously consider all hair-dousing techniques, or are you just going to stick your head in the nearest convenient bucket
• Panic is the mother of the path of least resistance.
• one half is the creative brain. the source of inspiration.
• half of your brain is your reactive loves it when the sky is falling because it gets to move so gosh-darned quick.

reactive brain doesn’t actually like to think because thinking is messy.

• involves slowing down and actually soaking in a problem,
• thinking is hard to pull off at work—it doesn’t fit nicely into the daily course of business

examples:

• you never know when you’re done.
• Doing more thinking always pays off, but time is money and you’ve got 27 other meetings
• more people you include in the thinking process, the more genuine ideas you’ll find, but the process of finding those ideas will linearly slow down with each person

Everyone thinks differently.

• The time to kick off your deep thinking is right after your last major release.
• They’re exhausted, but they have hope because they know they can fix it in the next release.

I was a fan of kicking things off with an offsite meeting.

• The problem with this is that while everyone loves a field trip, the day is an illusion.
• create a thinking-conducive environment in your natural setting.
• Start with two meetings a week. The first is a brainstorm meeting and the second is a prototype meeting
• Make sure there is time between the brainstorm and prototype meeting.
• time to stew on the results of the brainstorm
• don’t want to wait too long to see a prototype because you’ll forget the context of the initial brainstorm.
• paradox here. Structured thinking kills thinking, but unstructured thinking leads to useless chaos.

Your meeting driver must be able to swerve the conversation back and forth between the two extremes, but generally keep it in the middle.

Whom to invite?

• If you invite every single person on the team, you’ll get nothing done
• You’ve got to start small and let the momentum build.
• one of the best signs of a productive design process is that the players change.

One land mine you’ve got to be aware of in your attendee selection is obstructionists.

• folks who’ve fallen into a total react lifestyle.
• tendency to map every new idea against previous experience and then declare the idea “unoriginal.”
• creativity buzz kill and are not folks you want to invite

goal for the first brainstorm meeting is to start reliving the pain of the last release.

• walk out of your first brainstorm meeting with five hot topics that folks want to address.

second meeting is your prototype meeting

• see the results of the last brainstorm

paper . . . code . . . wireframe . . . bulleted list. It doesn’t matter as long as there is documented evidence

things you can look for as the weeks pass:

• Are decisions being made?
• Are decisions being revisited?
• Are decisions constantly being revisited?

Reviewing decisions to date is a good way to find structure and move forward.

• Are the players changing?
• diversity of thought sitting outside of the room must be brought into the conversation.
• Are basic truths about your design showing up?
• Is it therapy or work?

team is going to spend the first brainstorming meetings venting.

• That’s OK, they need it.
• week three and you’re still on the vent, it’s time to make changes.

Are holy shit moments occurring?

• Is the to-do list growing or shrinking?
• early on in the design phase, it should be growing. If you’re getting close to the end of your design phase, it better be getting smaller.

Better is the enemy of done

rule of thumb is if you aren’t staring at one hard decision per meeting . . . you might be wasting your time.

26. The Value of the Soak Let your mind stumble and strike out in random directions

in creating a startup, you’re going to be faced with a thousand seemingly inconsequential decisions.

• five decisions that actually matter.
• believe it’s next to impossible to figure out which decisions matter and which ones do not.
• start with the most infuriating e-mail you’ve ever received.

soak is when you plant the seed of a thought in your brain and let it bump around

• soak is a protected activity that will rarely occur during your busy day because you’re busy reacting
• active soaks are activities that you can direct and usually involve gathering content,
• passive soaks are activities when you just point your brain in a random direction and pray.
• Passive soaks are where the real work gets done—provided you laid the groundwork with an active soak.

Active Soaking

• Ask dumb questions.
• Soaking starts out uncomfortable, but with each ignorant question you ask, you’re adding content to that managerial brain of yours.
• asking any question of your team is a handy way to indirectly say, “I care about what we’re doing enough to ask you what you think.”
• Pitch a stranger.
• Lots of nodding? Great, it’s coming together. Blank stare? Oops, time for more dumb questions starting with the person you just pitched.
• Write it down, throw it away, write it down again.
• Seeing the words on a piece of paper or flat panel monitor will, once again, expose gaps you can’t see in the picture in your mind.
• gaps prove you’ve got more dumb questions, so go ask them, write it down again, and then throw it away.

Passive Soaking

• Once you’ve done all your active content acquisition,
• Sleep on it.

Soaking Takes Time

• the soak is sometimes pretty thin.

If your boss is waiting for you to weigh in on a critical decision, I am not advising you to say, “I have no clue what to do, I’m going to go ask dumb questions, pitch a stranger, write it down and then throw it away, and then forget everything I did.”

any big decision, any big problem, deserves time and consideration.

27. Capturing Context: Storing the thoughts that made your ideas bright

another verb, let’s call it wow, and let’s have it mean, “I’ve done something significant to my project and I want to capture the context of that change.”

while having the code safely in version control is good, understanding what is happening to the project on a day-to-day basis is even better. It’s called a status report

I finally found my technology angle on killing status reports. We need our tools to allow us to capture context at the moment we’re being bright, not Friday at 4 p.m. when we’re trying to get the hell out of work.

How much easier would your status report process be if all you had to do on Friday afternoon was ask your favorite app, “Show me all the wow for the last week”? That report alone is enough incentive for me try to remember to record my wow

28. Trickle Theory: Stop. Go do one thing. Now.

“People who talk fast are moving quickly to cover up the gaps in their knowledge.”

I know it feels great to get that impossible task on the to-do list. I know it feels like you actually did something, but what you’ve done is avoid conflict.

two types of impossible tasks.

• First, there are impossibly dull tasks
• other end of the spectrum are impossibly hard tasks

Oddly, attacking both boring and hard tasks involve the same mental kung fu where your first move is starting.

Begin. Go read the first bug. Don’t think about how many are left. Go to the next one and watch what happens. In just a few minutes, you’ll have made something resembling progress.

Progress + momentum = confidence

The second piece of advice is simpler than the first, which is hard to imagine. Iterate. Once you’ve kicked yourself out of stop, iterate becomes a little easier,

• If you’re working on an impossibly hard or impossibly dull task and you find yourself mentally blocked by boredom or confusion, stop and do something else.
• when you’re facing an uphill mental battle with yourself regarding the impossible task, it’s time to choose another battle . . . that isn’t a battle.
• Viewed as a whole, these tasks represent a lot of work. Viewed against the actual amount of entropy in play in my small part of the world, these tasks represent a futile effort.

I know there is no controlling the world, but I will fluidly surf the entropy by constantly changing myself.

Surfing entropy takes confidence.

29. When the Sky Falls: Concrete steps to prop up the sky

Step 1: The Situation in the War Room

• Your first job is to understand absolutely everything you need to know about the current state of the disaster—you
• want to be able to draw a complete picture for everyone about whatever the hell is currently happening. I need whiteboards—lots of them. I need a War Room.
• remember that this first step is data collection, not problem solving and not judgment.

Step 2: The “Bet Your Car” Perspective

• Vet your model with at least three qualified others.
• These are people who were not directly involved in step 1 and who are people who don’t need to understand the particulars of the disaster.
• throw the current version on the nearest whiteboard in the War Room with the folks who are responsible for the work

Directly Responsible Individual, or DRI.

• It’s not the Directly Responsible Group of People with Good Intentions Who Are Attempting to Feel Good by Building Consensus
• put a proper name next to each and every task, this name should not be yours.

someone in the War Room asks, “Hey, why isn’t your name on the list?” Your answer is, “Because I’m the one making sure this whole thing is moving forward and I’m the one who gets fired if it doesn’t.”

Everybody is talking to everybody else about the state of your sky-falling situation, which means the Grapevine is actively working against you.

• While all of this going on, your job is internal public relations.
• If you walk by the War Room, poke your head in, and ask, “What’s up, guys?” I add you to the distribution list. You’re going to get every update until you beg to be removed.

step 0.

• What, precisely, are you trying to do?

In the face of disaster, it’s the wise person who does not act until they know. Unfucking the situation is a bandage. Understanding what you’re truly trying to fix is a cure.

30. Hacking Is Important Encouraging disruptive acts

Facebook S1 filing: The Hacker Way is an approach to building that involves continuous improvement and iteration. Hackers believe that something can always be better, and that nothing is ever complete. They just have to go fix it—often in the face of people who say it’s impossible or are content with the status quo.

Zuckerberg’s letter: “Done is better than perfect,” “Code wins arguments,” and “Hacker culture is extremely open and meritocratic.”

Hacking is disruptive,

Reasonable people are often scared by the new. This is because reasonable people are not barbarians, and they are not hackers. They appreciate the predictable, profitable, and knowable world that comes with a well-defined process,

What’s not documented are the nine spectacular failures the hacker survived before they built one success.

The well-intentioned people who arrive after the initial success of the hack don’t know of a world without it.

the people who grow the company are not the same people who founded it.

A healthy product company is, confusingly, one at odds with itself. It has a healthy part that is attempting to normalize and to create predictability , but it needs another part that is tasked with building something new that is going to disrupt and eventually destroy that normality.

31. Entropy Crushers Chaos-destroying machines

you’re approaching the dreaded moment where you don’t know the name of someone on your team. This is the first of many warnings that the team needs to evolve.

• project manager is responsible for shipping a product,
• product manager is responsible for making sure the right product is shipped.
• program manager is an uber-mutated combination of both that usually shows up to handle multiple interrelated projects

Project, Product, Program

• project = ship the product
• product = ship the right product
• program = ship many interrelated products,

rule : the addition of each new person on your team increases the cost of each of the following:

• Communication.
• Decisions.
• Error Correction.

Gantt charts are great at showing the order of operations for building software, but never in history of ever have they effectively been used to measure when to ship that software.

What your team, and your culture, needs out of a project manager is entirely dependent on the people, the team, the culture, the projects, and this moment in time.

The arrival of project managers (or whatever you end up calling them) needs to coincide with a clear and present danger to the product or the team. They are here to help with X because if we don’t solve X, we are screwed.

• There are project managers who go crazy with this power and become political.
• They’re using information to control rather than to illuminate. My advice: fire these people as quickly as possible.

good project manager’s job is to decrease chaos by increasing clarity.

As a lead, you have three jobs—people, process, and product —and you get to choose how to invest in each of those roles.

Part III Versions of You

• Your team is populated by a unique set of individuals that are distinctly not you.
• bored people quit.
• Inwards, outwards, organ¬ics, NADD, free electrons, bellwethers, incrementalists . . . I clearly have name-calling issues.

32. Bored People Quit How to detect and fix boredom before it’s a resignation

when someone quits they are effectively saying, “I no longer believe in this company.” What’s worse is that what they were originally thinking was, “I’m bored.”

three techniques for detecting boredom:

1. You notice any change in daily routine:
2. You ask , “Are you bored?”:
3. They tell you. And you listen:

What was “I’m bored” grew roots and became “I’m bored and why isn’t anyone doing anything about it?” and sprouted “I’m bored, I told my boss, and he . . . did nothing,” and finally bloomed into “I don’t want to work at a place where they don’t care if I’m bored.”

A Boredom Plan of Action

1. Where are they going?  
2. What are you currently doing to get them there?

• Francis wants to be a senior engineer, and we’re getting him there by giving him increasingly more responsibility.
• Ronald wants to build his own company, so I’m going out of my way to include him in meetings where he can learn how the sausage is really made.
• Brooke has no idea what she wants to do, so I’m throwing curveballs at her until she hits a home run.

Let them experiment

• Remember they can only take one for the team for so long
• Protect their time
• Aggressively remove noise
• Tell them what the hell is going on
• Don’t Forget What It’s Like to Build a Thing

My gig is the care and feeding of engineers, and their productivity is my productivity.

33. Bellwethers Defining an interview beyond the technical

Hiring anyone is a risk.

• You’re not going to know whom you hired for months.
• Interviewing is a team sport and failing to get everyone’s perspective regarding a candidate is not only a lost opportunity in terms of gathering some random piece of perspective, but it also sends an implied message to the team when Dave gets excused. The message is, “Dave’s opinion doesn’t matter.”

other key interview group is trickier. This is your go-to set of interviewers that you trust.

Your bellwether team is where you gather the most perspective. Three key bellwethers:

• Technical: Find a technical bully.
• Cultural: First, cultural fit within the team, and second, cultural fit within the company.
• Vision: (Strategic or Tactical?) Their job is to figure out the trajectory of the candidate. Are they up and coming? Do they want to change the world? Have they carved out a safe little corner of technology

Team Consensus: have an interview feedback meeting.

34. The Ninety-Day Interview Eight steps to following during your first ninety days

When you accept a new job, you don’t know who you are going to work with, what you are going to be doing, and how much (or little) you’re going to like it.

1. Stay Late, Show Up Early
2. Accept Every Lunch Invitation You Get
3. Always Ask About Acronyms
4. Say Something Really Stupid
5. Have a Drink
6. Tell Someone What to Do
7. Have an Argument: how does the organization value conflict? First, how does this group of people make a decision? Second, you’re going to have a better taste of their passion and their velocity.
8. Find Your Inner Circle

35. Managing Nerds: A leadership checklist for those who build

We know that it is an inherent property of complex systems that they will contain both our best work and our worst guesses. I call this state of mind the Nerd Burden

A Worst-Case Scenario

• to get mentally limber regarding nerds is with the Nerd Handbook.
• nerd treasures consistency
• nerd also treasures efficiency

Chasing the Two Highs

• The First High: When nerds see a knot, they want to unravel it.
• The Second High: Complete knot domination. The

If the First High is the joy of understanding, the Second High is the act of creation.

• You obsessively protect both your nerd’s time and space.

The road to either High is a mental state traditionally called the Zone.

1. The almost constant quest of the nerd is managing all the crap that is preventing him from entering the Zone as he searches for the Highs.
2. Every single second you allow a nerd to remain in the Zone is a second where something fucking miraculous can occur.
3. As explained in “A Nerd in a Cave,” Chapter 37, your nerd has built himself a cave. It might not actually look like a cave, or maybe it does. The goal around its construction is simple: protect the Zone so we can chase the Highs.

What is your nerd’s hoodie?

• They know when I reach to pull the hoodie over my head that I’ve successfully discarded all distractions on the planet Earth and am currently communing with the pure essence of whatever I’m working on. It’s irrational and it’s delicious.

Also, understand the interesting, potentially negative, byproducts of all this nerdery, such as . .

Not-invented-here syndrome

• When a nerd says “We can build it better,” he’s saying, “I have not devoted the necessary time to understanding the existing solution, and it’s more fun to build than to investigate someone else’s crap.”
• ask him to prove it. Make the Problem the explanation of why building new is a more logical and strategic approach

The bitter nerd : Another Snark from nerds is a leading indicator that I’m wasting their time, and when I find it I ask questions until I understand the inefficiency so I can change it or explain it.

The disinterested or drifting nerd :

• OK, it’s shiny. But is it too shiny? Is your nerd outside of the comfort zone of his ability?
• when a nerd appears stuck is pairing him with a credible technical peer—not a competitor, but a cohort.

Build calm and dark places where invoking the Zone is easy. Perform consistently and efficiently around your nerds so they can spend their energy on what they are building and not worry about that which they can’t control. Help them scale by knowing when they’re stuck or simply bored. And let them chase those Highs, because then they can amaze everyone.

36. NADD: Multitasking as art

NADD: “nerd attention deficiency disorder”.

this isn’t multitasking. This is an advanced case of nerd attention deficiency disorder

Anyone can multitask. NADD sufferers multitask with deft purpose. They’re on a quest of high-speed information acquisition and processing.

37. A Nerd in a Cave: The purpose of a cave is not to insulate, but germinate

Once I’ve successfully traversed my morning routine and have entered the zone, I am off limits.

Intruding into the cave and disrupting the zone is no different than standing up in the middle of the first-ever showing of The Empire Strikes Back, jumping up and down, and yelling, “Darth Vader is Luke’s father! Darth Vader is Luke’s father!”

Yes. When you successfully penetrate the zone, there is a chance I’ll be an asshole. In fact, I might snap.

Try as I might, I don’t always make it to the zone.

I’ll slightly adjust the five essential objects on my desk and I’ll begin . . . playing World of Warcraft. This is not the zone . . . this is the place.

38. Meeting Creatures: The humans you will meet

The Anchor; Slogan: “It’s all about me.”

• Meetings are power struggles between those who want something and those who don’t want to give it to them.
• A clear agenda that anoints the anchor right out of the gate is the best way to make sure everyone knows who the decision maker is.
• Second, you’ve got to know what to do when there is no anchor present. You’re wasting time.

Laptop Larry; Slogan: “Pardon me, what?”

• he brings his computer so he can work. Turns out he doesn’t work because he’s spending half his time half-listening to the meeting
• net negative when it comes to productivity.
• If notes must be taken, designate one person

Mr. Irrelevant; Slogan: “I’m just happy to be here.”

• figuring out who invited this guy to the meeting. What were they trying to do?
• If you uninvited him, he’s not going to be pissed, but the question is, who is going to be pissed?

Chatty Patty; Slogan: “I don’t shut up.”

• getting her talking is no issue. Your job is to figure out whether the signal-to-noise ratio is acceptable.
• Rather than ask, “How is QA?” you ask, “Patty, I’ve read your test plan, your current test results, and I understand you have a brief assessment for us regarding the quality of the product. Could you please give us a brief assessment?”
• giving Patty a well-defined space to wander in, you’re also saving time
• Don’t ever, ever argue with Chatty Patty in a meeting
• she already doesn’t know how to end a thought. Throw some emotional in there and she might never stop.

Translator Tim; Slogan: “I know every acronym ever. FTW!”

• essential when you’ve got groups of folks who come from very different parts of the organization.

Sally Synthesizer: Slogan: “What he’s saying is . . .”

• Sally grabs the conversation, no matter how messy it might be, and derives the basic truth of what was just discussed.
• She knows who the anchor is, she knows how to shut Patty up, and while it might appear that she’s just stating the obvious, she’s providing essential forward momentum to the meeting.
• Sally can get drunk with power because her skill is invaluable. When she starts to think she’s an anchor, you’ve got a problem.

Curveball Kurt: Slogan: “The sky is pancakes.”

• Kurt is easy to identify. You have no clue what he’s talking about.
• Your absolute worst situation is when your anchor is a Curveball.

The Snake: Slogan: “I’m actually the anchor. Ssssssh!”

• Fortunately for everyone, the snake move only works a few times within a company before word gets out who the real anchor is.

39. Incrementalists and Completionists: Realists at war with the dreamers

e-mail is never ever ever never ever the right way to resolve controversy.

Incrementalists are realists . They have a pretty good idea of what is achievable given a problem to solve, a product to ship.

Completionists are dreamers . They have a very good idea how to solve a given problem, and that answer is to solve it right.

This isn’t a battle of wrong versus right; it’s the battle of right versus right.

• use the simplest trick in the conflict resolution book : finding common ground.

Incrementalists Need Vision

• Your goal with incrementalists is to get them to define or see the plan from soup to nuts.
• This is a big deal for them because they normally can’t see past the next meeting.

Completionists Need Action

• for any given technical or product problem, there’s a completionist who knows exactly what to do. Problem is, not only can they see the immediate solution; they see the two-year solution and the five-year solution. By the way, the five-year solution drastically changes the immediate solution, which is why everyone else has a problem with it.
• completionists often lack common corporate and people sense
• they have nary a clue how to start pushing that agenda with the 12 different people who need to get on board

Two Different Coffee Addictions

• Getting lost in this addiction means that incrementalists never finish a thing.
• They have no concept of “done,” because done would mean no more motion
• warning signs you’re looking for here are that when an incrementalist is facing a hard problem, they’re constantly coming up with new ways to tackle the problem rather than actually tackling the problem.
• A quiet completionist doesn’t mean they don’t have anything to say—they’re just unlikely to speak until their plan is fully formed. Your issue is when your completionist has slipped into creative strategic nirvana, where actually finishing something is less important than considering it.

See It Yet?

Your job as a manager is to find and marry these personality types in your organization, because when they understand each other’s strengths, you’ve got a complete strategically tactical product team.

40. Organics and Mechanics: Moving forward methodically or simply all over the place

three buckets:

• I love this guy. Best manager ever.
• Mostly harmless . This guy doesn’t really challenge me, but then again, he’s not really slowing me down.
• Worst. Manager . Ever. This guy makes my life a living hell.

With coworkers, you speak the Truth. You speak it because each of you are slogging it out in your respective trenches,

With managers, you speak the Way. The Way includes the things we shall do to achieve organizational enlightenment. figure out how they acquire information, and chances are, they gather it either organically or mechanically.

The Itch Perspective

• Mechanic : “An itch. Well. This itch seems familiar. In fact, I scratched this type of itch in January 2001.
• Organic : “Wow, an itch. Hmmmm . . . well, this sucks. Hey Frank, we’ve got an itch . . . whaddya think? Yeah, that’s what I was thinking. You know, this itch seems familiar . .

An organic and a mechanic are staring at each other across the desk and are thinking the following: Mechanic: “This guy is walking chaos.” Organic: “This guy is totally uptight.”

If You Work for an Organic . . .

• Don’t confuse an extremely open mind with cluelessness.
• have a more complete picture about what is going down because they are better networked.
• Organics miss detail as they hurry from place to place.

If You Work for a Mechanic . .

• You must overload your mechanic with data in order to satiate their structured brain.
• and none of your responses appear to be the answer, it’s time to counter with, “I really don’t know what you are asking.”
• mechanics don’t trust you, and you’re right; they don’t. You will build trust by acting like a mechanic with them.
• you just need to speak mechanic long enough to soothe your mechanical manager.

Look Out For . . .

• Organic mechanics are frightening. They have extreme depth of knowledge, but there is no obvious organic thread that ties it all together.

The Answer Is in the Middle

• “A purely mechanical organization lacks inspiration. A purely organic organization is total chaos.”

Organics fill mechanical blind spots with their intuition and their passion while mechanics create a healthy, solid home where nutty organics can run into things at speed.

41. Inwards, Outwards, and Holistics Flavors of leadership

three distinct classes of managers

• first line manager , middle manager , and executive or senior manager

The Vision Hierarchy: one of three directions.

• Inwards : These types of managers are responsible for a small team of folks working on a single product or technology.
• Holistics : Traditionally, holistics make up the middle layer. Whereas the inward’s vision is pointed down at the individual team, the holistic is staring across the organization. likely managers of managers knowing what the hell is going on everywhere in the organization.
• Outwards : These are the senior managers. VPs, CEOs.

The well-being of the company is the responsibility of the holistics.

The outward’s vision is focused on the outside world. They care about the public perception of the company, the company’s relationship with its customers, That’s why they’re never at headquarters, they’re off telling other people what a great job all those holistics and inwards are doing.

Micromanagement is often a result of a manager jumping from one management class to another. Maybe it’s an outward who is getting panicky at the end of a result cycle, so he starts acting like an inward. Problem is, everyone knows he’s an outward.

My preference is to stock my team with holistic managers and inwards geared to become holistics. While an experienced, steady inward is a reliable manager, I prefer the enthusiasm of employees who are ready for the next thing, especially when the next thing for them is my job.

42. The Wolf The single most productive engineer you’ll meet

Like a Volatile, the Wolf moves fast because he or she is able to avoid the encumbering necessities of a group of people building at scale.

the influence earned by the Wolf can never ever be granted by a manager.

The Wolf doesn’t really need me.

43. Free Electrons Care and feeding of the highly productive

each time he’d fix something we’d discover another fundamental problem with the feature. small, incremental progress was being made with each bug fix, but Jerry was in a losing situation because his basic architecture was crap.

It’s a two-step fix process. We needed to make a Jerry adjustment and then we needed a miracle. I’ll start with the easy one.

1. The engineering manager sat Jerry down and told him we need to focus on quantity. There were scads of trivial little fixes all over the place that had been ignored, and Jerry could handle those.

2. You need a free electron.

   • single most productive engineer that you’re ever going to meet.

two classes of free electrons, senior electrons and junior electrons . Both have similar productivity yields, but the senior versions have become politically and socially aware.

junior electrons represent the single best hire you can make as a hiring manager. If you get two in 20 years, you’re doing something right.

Care and Feeding

• Keep them engaged.
• While the free electron is eminently capable of doing development, their value in the organization is research.
• Misdirected free electron intensity can yield odd results.
• Free electrons sometimes will not engage and they won’t explain why.
• high-functioning and have strong opinions about everything . . . but they may never tell you those opinions.
• If you’re asking them to do something that they don’t believe in, they aren’t going to do it.

It’s a team. All of this advice is directed at your free electron, but you need to remember even though they’re incredibly productive, they’re part of the team.

no need to call attention to the fact that you’ve got a free electron on your team. Trust me, everyone already knows it.

44. The Old Guard The cultural bellwether of the company

Dunbar’s Number is a favorite blunt diagnosis for the pains that affect rapidly growing teams.

• However, I think there is a more interesting emergent behavior during rapid growth, and it’s led by The Old Guard.

They Won

• A small group of inspired people has an idea, and just about everyone tells them the idea is really stupid,
• Each day, this small group is learning who they are as part of their struggle to survive.
• And then the Old Guard starts winning.

The New Guard

• After years of struggling , the dream that became the idea becomes the business.
• the question changes from, “Are we going to survive?” to “How are we going to scale?”
• Most everyone still believes they are on the brink of disaster. That’s mainly because they’ve lived in this world so long.

The organization of the Old Guard is instinctively flat.

• This is because they’ve got a near-complete mental catalog of the people, their knowledge, and their abilities.
• The Old Guard’s instincts are well earned and essential, but instincts don’t scale without help.

New Guard Friction

• new hires are a cure to a disease that the Old Guard both created and loves.

A Culture Quandary

• The largest battles that I’ve seen between the New Guard and the Old Guard at prior companies exist because the Old Guard has not effectively documented and shared the values that the company embodies.
• dialog : Old Guard: I feel this process is heavy. New Guard: I’ve seen this process work at a great many companies and here are the metrics to prove it. Old Guard: Yeah, something doesn’t feel right. New Guard: What the hell does feel have to do with it?
• when they say “It feels off . . .” what they are poorly articulating is “This process that you’re building does not support one (or more) of the key values of the company.”

45. Rules for the Reorg: Traversing massive change

Rule #1: Figure Out Your Role

• Even if this particular reorg doesn’t involve your team, it doesn’t mean that you can’t pitch your boss on fixing a long-standing organization problem in your group.

Rule #2: People Are Paranoid

• You’re going to walk out of that meeting thinking, “He doesn’t actually know what’s going to happen,” and you’re right.
• The fact that no one actually knows what is going to happen tomorrow creates a culture of paranoia and that means you need to start listening carefully.

Rule #3: The Grapevine Gone Mad

• Outside of the reorg, I put a lot of faith in the grapevine because I find there is less mutation of information
• patient, journalistic policy, where you confirm tidbits of information with independent sources before you believe anything.

Rule #4: Reorgs Take Forever

• going to be four times as long as you think.
• A reorg isn’t over until someone important has printed out a new organizational chart and presented it in front of the entire company.

Rule #5: Most Folks Love Reorgs (But Hate to Admit It)

• Reorganizations represent opportunity to those who are unhappy with the state of the current organization.
• For some reason, conversations about reorgs sound a lot like conversations about infidelity.
• People are incapable of shutting up.

The Only Rule: Patience

• very large groups of people working together barely looks like working because they move so slowly

46. An Unexpected Connection: The act of obsessively understanding in order to find connections

Nerds are fucking funny.

The processing of relevancy has three steps, and it’s the third where the magic happens:

• Collect the relevant.
• Research and index if necessary.
• Connect the relevant in efficient and entertaining ways.

Discovery of structure in a chaotic world means less chaos, and while we’re happy to make you laugh, the idea of a more orderly, structured, and knowable world is what drives us and keeps us warm in bed at night.

47. Avoiding the Fez: Investments in avoiding irrelevance

If you worry about career development once a year, you’re screwed.

• When you’re assessing an employee, you need to assess against their job, not the work they’ve done over the past two months.
• spending an hour a month jotting down reflections of the team for the past 30 days.
• What stands out in my mind? What’d we do? Who rocked? Don’t get hung up on documenting every single event or talking about every single person . . . just type.

Skill vs. Will Plus Epiphanies

• It’s a simple graph.
• One axis is skill—how much skill does the employee have to do his job? Is he qualified? Overqualified?
• other axis is will—this is where we measure the employee’s desire. Does she like her job? Really?

management style that shows up in every personality test.

• either ask assertive, meaning that you ask in order to get stuff done,
• or tell assertive, which means you tell to make progress.

An annual review is a discussion, not a speech.

• Rule of thumb: If you’re delivering big bad news, schedule two meetings. At the first meeting, you’re presenting the review, not the objectives.

some high-level thoughts about the extremes on the Skill/Will graph:

• High skill, low will: Boredom is imminent—needs a change of scenery and responsibility.
• High will, low skill: Needs training, needs mentorship. Needs management. The good news is they really, really want it. Savor this because as soon as the skill kicks in, they’re going to start wanting your job. This
• Low will, low skill: Boy, did you screw up. It takes a fairly concerted effort to ignore the needs of your employee so long that (a) they no longer have the skills necessary to do their job, and (b) they don’t want to do it.
• High skill, high will: Great job but, ummmmm, guess what? No one can maintain this for very long.

tell everyone I hire the same thing: “I hired you because you’ve got enough skill and enough will to have my job one day . . . whether you want it or not.” This statement tells those I work with that I expect them to succeed and reminds me to keep moving

48. A Glimpse and a Hook: Design your resume to be a consumable glimpse

The First Pass

• Your name . It’s simple. Do I know you?
• Company names . Do I recognize any companies that you worked at?
• Job description and history . Here I’m looking for history and trajectory. How many jobs have you had and for how long? How long have you been in your current role? Where’d you come from?
• Other interests and extracurriculars . Yeah, this is part of the first pass. I’m eagerly looking to find something that makes you different

the parts of your résumé I didn’t look at and never will.

• Professional objective . This is likely your lead paragraph and I skipped it.
• Skills . I skip the skills section not only because this is information I’ll derive from your job history, but also because this section is full of misinformation.
• Summary of qualifications

Differentiate, Don’t Annoy

• Design your résumé to downgrade. Your résumé needs to withstand some formatting abuse. Go get your résumé right now and convert it to plain text.
• Never include a cover letter
• Embrace honest buzzword-compliance
• it’s going to be passed through a couple of different recruiters

Sound like a human.

• Give me specifics and give them to me in a familiar tone.
• Include seemingly irrelevant experience

49. Nailing the Phone Screen: How to prepare for an important 30 minutes

The Purpose

• The question is, what questions do I have? Guess what—your job is to figure that out.
• Your Job Is to Prepare
• Do your research. Google me.
• If you have a product name or technology, repeat the same process. What is the product? Is it selling well? What do other people think about it?
• find a couple of compelling questions, because at some point during the phone screen I’m going to ask you, “Do you have any questions for me?” and this is the most important question I’m going to ask.

Back to the Beginning

• Can we communicate? I’m going to lead off with something simple and disarming.
• These pleasantries appear trivial, but they’re a big deal
• A couple of clarification softballs
• you should have your résumé sitting in front of you because it’s sitting in front of me
• What’s your story?
• see how you explain a complex idea over the phone to someone you don’t know and can’t see.
• I’m not looking for the quick, clean answer; I’m looking for a story that shows me more about how you communicate and how you think.

Your turn: show me what you’ve got.

• “Do you have any questions for me?”
• if you don’t have a list of questions lined up for me, all I hear is: You don’t want this job.

The Close

• Long, awkward pauses.
• Adversarial interactions.
• How’d it feel?
• Specific next steps.

50. Your Resignation Checklist A checklist for the final days

• Rule #1: Don’t Promise What You Can’t Do
• Rule #2: Respect Your Network
• Rule #3: Update “The Crew; list of each person that I’ve worked with in past 20 years that I would hire if I began a startup.
• Rule #4: Don’t Take Cheap Shots
• Rule #5: Do Right by Those Who Work for You and with You; Provide a written review to all my direct reports in my last two weeks.
• Rule #6: Don’t Volunteer to Do Work After You Leave (or, if You Do, Make Sure You Get a Lot of Money for It)
• Rule #7: Don’t Give Too Much Notice

51. Shields Down: A glimpse of a potential different future

Resignations happen in a moment, and it’s not when you declare, “I’m resigning.”

The moment happened a long time ago when you received a random email from a good friend who asked, “I know you’re really happy with your current gig because you’ve been raving about it for a year, but would you like to come visit Our Company? No commitment. Just coffee.”

52. Chaotic, Beautiful Snowflakes: On the necessity of leadership

Humans—engineers especially—significantly underestimate the cost of getting things done in groups of people.

Engineers have a well-deserved reputation for regularly being off by a factor of three in their work estimates, and that is partly due to the fact that we are really shitty at estimating the non-linear chaotic work (and fun) that exists in keeping a group of humans pointed in the right direction.

There are a slew of good reasons to hate crap leadership. There are leaders who hoard the information they discover. There are leaders who have crap judgement and perform awful analysis and make precisely the wrong decisions. There are leaders who are genetically bad at communication. And there are those who are simply a waste of air and space;

A portion of every leader’s day is the detection, triage, and resolution of work we never planned.

speaking as a leader, I can confidently say that it’s 9:23am and I have a full calendar of meetings, but I don’t actually know what I’m going to do today. It’s an essential part of the gig.