The Art of Leadership By Michael Lopp
Juan Carlos Zambrano
Gerente de Finanzas @ Tecnofarma Bolivia | Coaching ontologico
Introduction
This is a book full of small things. Simple, memorable leadership acts and practices that I’ve gathered and refined over the years
Here’s my favorite: I’ve preached 1:1s, weekly recurring meetings with direct reports, for decades. I believe a 1:1 represents the simplest and most reliable way to build trust between you and your coworkers, by providing a weekly high-bandwidth conversation on current events affecting the team. 1:1s are the first meeting I schedule when I show up at a new gig and they are the last meeting I’ll reschedule or cancel during busy times. 1:1s have been my team-building go-to move for years.
I originally pitched this book as a set of leadership hacks. The title fit. Sort of. I’m an engineering leader. I am surrounded by talented engineers who often pride themselves on developing hacks. I spend a lot of time writing about leadership and packaging that wisdom, and the concept of a hack feels efficient and familiar.
Problem is: you can’t hack leadership
Leadership, like any complex skill, can’t be hacked; it must be thoughtfully and patiently built. Leadership is built on a set of practices, but the judgment of choosing when to use or deploy a certain habit is . One of the primary reasons there are not noteworthy university degrees in leadership is because leadership is a set of skills you must learn from the job.
At this point in our history as a species, we are unfortunately addicted to the idea of time-saving hacks—simple, clever ways to quickly achieve or know a thing. This is not that book. This is a book of repeatable practices that over time will combine to form sustainable, self-improving leadership.
Pick a small thing, practice it for three months, and discover for yourself how it will make you a better leader
Act I. Netscape: Manager
Management. I was a manager. It seemed like important progress, but for a job so critical to the growth of a team, organization, and company, I received precisely zero training.
Wait, who is my HR partner? What is a req? What is a staff meeting? How should I run one? Why was I invited to this meeting? What is my role here? What is a performance review? How do I write one well? How much do I involve my team in the performance review process? How do I grow my team? Wait, how do I grow my team when it’s unclear how to grow myself
The book (physical or digital) you’re holding in your hands is a direct result of my frustration with the lack of well-defined support during my first years of being a manager. The presumption that the optimal way to figure out the role was via osmosis and serendipity struck my engineering brain as horrifically inefficient
In our first act, let’s adopt the following perspective: you’re about a year into the new management gig. It’s been long enough that you believe you know what you are doing, but you’re still wondering about the importance of 1:1s, whether you need a mentor or not, how to think about managing performance…and, wow, there sure are a lot of meetings.
Chapter 1. Assume They Have Something to Teach You
The daily morning calendar scrub before work goes like this
More importantly, there are actually no marginal minutes. It is my personal and professional responsibility as a leader to bring as much enthusiasm, curiosity, and forward momentum as possible to every single minute of my day. When I find myself in a situation where the value is not obvious, I seek it because it’s always there.
Chapter 2. Meeting Blur
Too Much
As a leader, you have disproportionate access to developments in your team and company. Nothing surprising here. You are the representative of your team, so you get invited to a lot of meetings for representatives. These meetings contain synthesized information about what is going down in the company right now
Let’s forget for a moment why there are so many meetings2 and focus on your mental state. You’re a bright, emotionally intelligent human. You walk into a meeting and have a credible mental profile of each human at the table. Why are they here? What do they want? How do they feel about the topic at hand? All of this information is front of mind and readily accessible.
This is what leaders do. We compile every single moment into a vast internal story about the state of the company. We use this informative narrative for good, not evil
For me, Meeting Blur occurs when I can no longer compile these profiles. The amount of incoming data exceeds my ability to compile the story
On the Topic of Operational Excellence
When you reach Meeting Blur, a reset needs to occur
There are any number of time-saving moves you can pull off, but being in this position in the first place remains a leadership failure because you do not have a good internal measure for what you can and cannot do.
Leaders set the bar for what is and is not acceptable on their teams. They define this bar both overtly with the words they say, and more subtly with their actions. There are two scenarios that may play out when you’ve reached Meeting Blur: either you don’t change anything and do all of your work poorly, or you drop some of that work, which equates to a missed commitment. While the optics on both scenarios are bad, what is worse is that by choosing either course you signal to your team that these obvious bad outcomes are acceptable.
Chapter 3. The Situation
Capital-S Situations
For capital-S Situations, there’s no easy answer. A Situation is a complicated, never-seen-before beast, and the reason that everyone in the room is energetically quiet is that they’ve never seen this before and they’re wondering what the hell is going to happen
The following laborious workflow is how I make a decision regarding the Situation. Not every Situation demands all the steps. Some steps are repeated multiple times. The route through these steps varies as a function of the Situation as well as the facts, opinions, and lies I discover as I perform each step. These are the questions I ask myself
Am I the right person to handle this Situation? Is solving this Situation truly part of my job responsibility? No? Okay, who is the right Situation handler and how quickly can I get this on their plate?
Do I have complete context? Do I have all the essential facts, opinions, and lies surrounding the Situation? Have all relevant, affected, and interested parties who care about the Situation weighed in? Have I triangulated the facts? Have I discovered multiple different perspectives regarding the Situation? What has happened to the facts as I’ve looked at them through different lenses? What has this triangulation told me about my sources of information?
What are the track records of my sources of information? Do I trust the sources of information? If I have a past history with these humans, how does that color the information they’ve provided? Do I understand the nature of the biases of those providing the information? Am I clear on what they have to lose or gain by sharing this information? Did they acknowledge or volunteer those potential losses or gains during our discussions?
What inconsistencies in facts have been discovered, and do I understand the nature of those inconsistencies? I’m not looking for resolution of any inconsistencies, just the back story. He and she disagree on principle. They didn’t have all the essential facts, so it kinda looks like they’re lying
Can I coherently explain multiple perspectives on the Situation? What happens when I explain one perspective to a neutral party? How about when I explain a competing perspective? If I can effectively explain the Situation and its complexity from both perspectives and with a distinct lack of emotion, I’m making progress
Do I understand my biases relative to the Situation? If my role in this Situation is to make a decision, part of understanding involves understanding my bias.1 With this understanding in mind, is there someone better placed to make the call here?
Do I understand my emotional state relative to the Situation? Emotion is sure to affect my judgment. Like my biases, it is nigh impossible to separate my emotions from an issue, whether those emotions are positive, negative,2 or a bit of both. Am I clear on how emotion is affecting me relative to this decision? If it’s affecting me negatively, will some cool-down time help? No? Okay, who is a neutral party who can make a decision here?
Last thing, and it’s a repeat. Am I the right person to handle this Situation? After you’ve done all the work in the seven prior steps, do you still think you’re the best person to decide and to act?
Capital-D Decisions
When a Situation shows up, it’s full of energy. The humans are enthusiastically swirling around it, wondering Where did it come from? How’d we miss this? How screwed are we? and What are we going to do? It’s easy to get caught up in the excitement, drop everything, call an emergency staff meeting, and move into wartime leadership mode.
Most Situations do not require this amount of attention. Just because the Situation arrives with great urgency doesn’t mean you must always act with great urgency. The prior eight laborious steps are designed to give you context while also sending a calming dose of patience into the corporate bloodstream. Someone is working on it. Carefully
There are leaders who are world class at making real-time Situation-based decisions. They stare straight into a hot burning Situation and make a call right then and there. Their track record indicates either superior judgment or incredible luck
I’d rather be good than lucky
Chapter 4. Act Last, Read the Room, and Taste the Soup
Oddly, at work, you will find yourself sitting in a meeting where folks are going around the table and giving their opinion about some important topic—and for a great many situations, when it’s your turn to offer your opinion, the savvy move is to pass
Information builds context, and context is what forms the setting for an idea so that it can be understood. The more folks go around the table and weigh in with what they think about the idea, the more context you have, so the better you can shape your opinion before you share it.
My opening move in any presentation is to read the room. The slippery question I am answering for myself is, What mood is this particular set of humans in? Impossible to answer, right? What is the aggregate happiness or sadness of a group of 10 or 50 or 500 humans? How are they feeling? And why does it matter?
The reason you care about the ambient mood of a group of humans is that you have business with the folks—you have a talk to deliver, you have a 1:1 to complete, or you have an urgent topic to discuss at a cross-functional meeting. Their collective mood is a critical signal informing your approach path for getting your work done, and the sooner you’ve tested the mood, the sooner you have an approach vector.
Here are my opening moves for reading the room
For a talk, I almost always open with an audience participation exercise. Raise your hands. How many extroverts? How many introverts? Why do I care about the split of perceived personality types?
For a 1:1, I ask, How are you? I listen carefully to the answer. What’s the first thing they say? Do they deflect with humor? Is it the standard off-the-cuff answer?
Meeting—and to make it harder, let’s say it’s a meeting I am not running, but in which I have a role as a participant. Not being able to land the first question and set the tone makes the initial read harder, but all the signal I need is still in the room. Who is running the meeting? How do they open it? Who perks up? Who keeps their nose buried in their phone? As the topic changes, how does the demeanor of each denizen change? What do I know about each participant in the room, and how might that context inform my reading of their changes of mood depending on the topic?1
Taste the Soup
What do you hate about micromanagers? I’ll tell you what I hate. I hate leaders who believe that prescribing every single action without room for improvisation, iteration, or feedback is anything but demeaning and demoralizing. If I screwed up, if I failed on something critical because I failed to listen to your guidance, then sure…dictator it up. Until we arrive at that failure case, I don’t need to be told what to do; I need you to taste the soup.
In a meeting where an individual or team is presenting a complex idea or project, my job as the leader is soup tasting. It’s sampling critical parts of the idea to get a sense of how this soup has been or will be made
Leaders who default to micromanagement teach you nothing about the craft of building. Their tell-assertive style creates an unsafe environment where some of the best parts of being human, our inspiration and our creativity, cannot exist. Tasting the soup by asking small but critical questions based on legitimate experience creates an environment of helpful and instructive curiosity. Why did you choose this design? What is this metric going to tell us? What do you think the user is thinking at this moment?
The opposite of quiet is noisy, and business is noisy. It’s full of humans acting first, ignoring the room, and tasting none of the soup…and perhaps being annoyingly successful with each of these acts. Like all the advice you’ve ever received, mine is situationally useful, but it’s based on what I value as a leader
Chapter 5. Spidey-Sense
Understanding Spidey-Sense
Spidey-sense is real-time wisdom. You build wisdom through experiences, small and large. These experiences leave you with impressions, opinions, and lessons learned. When they’re shared with other humans, you’ll find differences of opinion on their value. However, these different perspectives expand your understanding and teach you lessons. You observe it all—the different approaches, attitudes, emotions, and words. You continue to learn, and carefully index and file away those lessons
As this corpus of knowledge grows, your brain discovers delicious patterns. When situation X occurs, I often observe that the resulting situation Y, weirdly, happens a month later. Huh. These collected, observed patterns compile nicely into judgment.1 Over time and with practice, you become comfortable rendering a decision based on this judgment when presented with a new situation. You can explain and defend your reasoning because you’ve seen this scenario 42 times before. You’ve seen these types of humans act in this type of situation, and you understand the possible outcomes. Your decision is defensible. You can clearly explain it. Are you right? Only time will tell, but in any event you observe the results and impact of your decision, learn from it, and the cycle repeats
The prior two paragraphs are the primary reason that universities don’t offer substantive degrees in leadership. Most of the essential skills required to be an effective leader are acquired and built by deliberately experiencing the seemingly infinite number of scenarios that play out during the workday…for years
Spidey-sense is a hunch that may be discovered at any moment, when you’re tasting the soup. It’s your experience speaking…loudly. A moment of inspiration. Of intuition. It feels like magic because the insight arrives instantly, appears out of nowhere—and that’s why you should trust it.
Spidey-sense is a feeling. That’s why we don’t initially trust it—because leadership is a well-defined set of concrete principles you follow to maximize your and your team’s effectiveness
Spidey-sense is a feeling. You might be hesitant to heed it because you can’t tell where it came from. You might attempt to ignore it because a feeling inspired by hard-earned wisdom and one inspired by an irrational emotion feel the same. They aren’t, but the only way you’re going to learn the difference is by first listening, then acting
Chapter 6. Your Professional Growth Questionnaire
The Professional Growth Questionnaire
The following is a large set of questions I think you should ask yourself multiple times a year. Furthermore, I recommend writing down your answers to these questions each time so that you can review them at a later date, because how your answers change over time is as interesting as the answers themselves
There are no right or wrong answers to these questions. There is no grade. The exercise is meant to stimulate thinking about your professional growth, to help you understand your level of satisfaction with your current gig, and to let you consider the possibilities of a future role
My expectation is that, when you’re done writing your answers, you’ll have at least one unexpected tangible follow-up for yourself or your manager
What are your strengths? How do you know that?
What do you need to work on? How do you know that? How are you working on this area? Is your company helping?
When was your last promotion? How was the promotion communicated to you? What is the one thing you believe you did to earn this promotion?
When was your last compensation increase? (Compensation = base salary + bonus and/or stock.)
Do you feel fairly compensated? If not, what would you consider fair compensation? What facts do you base that opinion on? Have you told this to your manager?
When was the last time you received useful feedback from your manager?
What compliment do you wish you could receive about your work?
Are you learning from your manager? What was the last significant thing you learned from them?
What was the last thing you built at work that you enjoyed?
What was your last major failure at work? What’d you learn? Are you clear about the root causes of that failure?
What was the last piece of feedback you received (from anyone) that substantially changed your working style?
Who is your mentor?1 When was the last time you met with them?
When was your last 360 review?2 What was your biggest lesson?
When did you last change jobs? Why?
When did you last change companies? Why?
What aspect of your current job would you bring with you to a future gig?
What is your dream job? (Role, company, etc.)
What is a company you admire? What attributes do you admire?
Who is a leader that you admire? What are the qualities of that leader that you admire?
Your answer to this question—to this opportunity—isn’t a simple yes or no. The answer is, How does this opportunity fit into my broader career plan?
Answering all of the questions in that list will help you paint a specific mental picture of both how you feel you’re doing in your current role and what you’re looking to do next. Hopefully, afterward you’ll have at least one tangible topic for a discussion with your manager in mind
While it is your manager’s job to identify and cultivate growth opportunities for you, forming this mental picture will help you listen carefully for opportunities that might arise at any moment and give you a better rubric for quickly assessing them.
Chapter 7. A Performance Question
The Checklist Sentence
Have you had multiple face-to-face conversations over multiple months with the employee where you have clearly explained and agreed there is a gap in performance, and where you have agreed to specific measurable actions to address that gap?
It’s a big question, and there are significant words and concepts in that big sentence that humans like to forget or ignore, so while you construct your answer I am going to call out the important points
Multiple conversations. Rushing it is the classic entry into performance management
Three substantive conversations, at a minimum, are needed with the employee. You need to give yourself time to explain the situation clearly, and you need to give them ample time to think about what you said and ask clarifying questions. Chances are, especially for new managers, that what you think you’re saying is not what is being said or heard, especially when the message is critical feedback. The second and third conversations are essential opportunities to correct any errors in communication.
Face-to-face conversations. Feedback about performance warrants two-way communication, and when you are uncomfortably sitting there delivering complex constructive feedback, you can see with your eyeballs how they’re hearing it. Email, Slack, and any other non-face-to-face mediums are avoiding the important educational work of bidirectional communication
Many months. Substantive changes to deep-rooted human behaviors are often necessary to correct issues with humans that lead to performance management, and that means talking about those issues. Repeatedly. In different contexts. For months
Clearly explained. The final clause—agreed to a specific measurable action to address that gap—is the most important because if the employee doesn’t agree with your description of the situation, they aren’t going to act. How are you going to tell if they agree? You ask. Is it clear what I’m describing, and how we can address it? Did that make sense? Do you agree with my assessment?
What if the employee doesn’t agree with your assessment? Great. Start the discussion. What wasn’t clear? What did you hear me say? What data do I not have? How do our facts differ? Is there a different approach we could use? You’ve begun a healthy and clarifying conversation where the stakes are not making a decision about whether to fire or not fire, but figuring out how to communicate and work better
What if, after you’ve clarified your rationale for the assessment, they still don’t agree? No problem. Let’s agree to table this discussion for today. Give ourselves a week to let the conversation percolate and pick it up next week in our 1:1. We’re not on a timetable. We are simply working on a project
What if, after percolation, they still don’t agree? I have to follow this path because one day you, as a leader, are going to find yourself two months into a conversation where either you’re not clearly explaining or perhaps they just don’t want to hear what you have to say. Performance management time, right? Wrong.
Try one more approach: write your feedback down.1 This might feel like a formal step toward performance management, but we’re still not there. We’re removing the interpersonal dynamics from the situation and focusing on the words, transformed into sentences, that are delivering a critical thought. Yes, there is a smidge of formality that comes with the written word, but in my experience it also comes with a higher chance of mutual clarity.
Reality Changes
The reality is that you’re always managing performance. Your very existence as a leader sets a performance bar. How you act, what you say, how you treat others, how you work, all of your attributes influence how your team performs because you demonstrate what you value as a leader
The performance management attitude I want you to avoid is the flip-a-switch approach with your team—Well, now it’s time to get serious—because in my experience it’s manager shorthand for How do I let this human go? rather than How do I make this human better?
There are very clear, obvious, and immediate situations where you do need to let a human go—for example, if they are stealing from you, you let them go. The vast majority of the situations surrounding performance, though, are coachable. The work is complex, uncomfortable, time-consuming, and often hard to measure, but it is during these hard conversations that you become a better communicator, you learn the value of different perspectives, you build empathy, you become a better coach, and you become a better leader
Chapter 8. Rands Information practices
Your most precious asset is your time, and this chapter exists to save you time. You can start adopting the following set of habits right now to give yourself hours of your life back. Equally importantly, these habits will substantially increase your productivity by reducing stress, increasing focus, and ultimately improving the quality of the things you build with your hands
Some of these practices pay immediate time-saving dividends. Some require small, consistent investment over time to achieve the desired effect. All require discipline. Some feel destructive
Browser
Brace yourself. Some of these will hurt
Make a copy of your bookmarks and store it somewhere safe
Start rebuilding your bookmarks from memory a bit at a time
No feed reader? Configure and pay for Feedly. Learn the keystrokes
Install an ad blocker
Pin your must-have browser tools
Use tabs in your favorite browser
Strive to have a single browser window open at a time
A win condition: The ability to scrub all your consumables in fewer than 10 minutes, and the absence of a long tail of cluttered bookmarks whose compounding/increasing stresses force you to declare bookmark bankruptcy every month and a half.
Phone
If your phone allows it, flag VIPs in your contact list
Turn on any episode of season 2 of The Office, sit somewhere comfortable, and turn off all noncritical notifications on your phone
Purchase and install a spam-blocking utility
Return to your comfortable place, turn on any episode of season 2 of Parks and Recreation, and delete any app you haven’t recently used on your phone
If the mail is from an external (nonwork) source and you don’t want to read it, do one of the following without fail
If the mail is from a work source and it’s generated by a robot
spend a morning learning how to filter these
If you haven’t already, learn the keystrokes for your favorite email application
A win condition: Using this protocol I’ve managed to get my work and personal inboxes to inbox zero and keep them there, every day. It took months of filter tweaking and unapologetic religious spam flagging, but for the first time in years, what I have in my inbox is mostly high-signal mails that I need, with little filtering fuss
Life
I am often asked how I prioritize my time, because there is a perception that I do a lot of work.2 First and obviously, I have precisely the same number of minutes of the day that you have. Second, I am ruthless about spending my time appropriately
Chapter 9. The New Manager Death Spiral
The starting gun fires, and when the starting gun fires, you run. You’re a new manager, and while the sound of gunfire is startling, you run because this is finally your chance. You’ve been promoted to the role of manager, you want this gig, and this is your chance to shine, so you run
I will now explain how your good intentions and well-trained instincts are going to erode your credibility, stunt the growth of your team, and reinforce the theory that most managers are power-hungry jerks claiming all the authority and making judgment calls with woefully incomplete data
It’s called the New Manager Death Spiral and, unfortunately, I can write about it effectively because I’ve performed parts of it. Over and over
It begins with a thought: I can do it all. I’m the Boss.
As a new manager, you want to prove yourself, so you sign up for everything, you work late, and you do your very best to kick ass and make a good first impression with your new set of direct reports. This is the approach that worked well for you as an individual, so, of course, it’ll work when you’re leading a team. This is where the Spiral begins, because the initial thought is actually, I can do it all myself. I’m the Boss.
You are used to having complete visibility and total ownership of your work because that is how it worked in your former individual contributor work life
The problem is your enthusiastic effort to prove yourself. You signed up for far more work than you could possibly do yourself, which leads to your first failure mode
This is where the Spiral gets painful. Remember, the Spiral represents every possible wrong decision stitched together
Management Is Not a Promotion
You’re promoted when you are successful in your current job. In many companies, the expectation is that you’ll have been performing at that higher level for a period of time before you are promoted, so there’s a good chance you’re equipped for the new gig
You do not start management equipped for the gig. Your first role in management is a career restart. Yes, you’ve acquired dealing-with-humans skills from being a part of a team, but the New Manager Death Spiral demonstrates how the very instincts that got you the new role are going to steer you in the wrong direction.
Here are three of the most important small things
Let others change your mind. There are more of them than you. The size of your team’s network is collectively larger than yours, so it stands to reason they have more information. Listen to that information and let others change your perspective and your decisions
Augment your obvious and nonobvious weaknesses by building a diverse team. It’s choosing the path of least resistance to build a team full of humans who agree with you. Ideas don’t get better with agreement. Ideas gather their strength with healthy discord, and that means finding and hiring humans who represent the widest possible spread of perspective and experience
Delegate more than is comfortable. The complete delegation of work to someone else on the team is a vote of confidence in their ability, which is one essential way that trust forms within a team. Letting go of doing the work is tricky, but the manager’s job isn’t doing quality work, it’s building a healthy team that does quality work at scale
At the heart of each small thing is the same essential leadership binding agent: trust. When you are actively listening, and when their ideas visibly change your decisions, you build trust. When diversity of opinion is valued and creates healthy debate, you create trust
Act II. Apple: Director
As a manager, I had to deal with the discomfort of not actually doing the practical and obvious work, but at least I could glance at the engineer’s monitor and get a glimpse of work happening. As a manager of managers, I had to take the word of other managers regarding how the work was proceeding. This distance is the primary challenge for the manager of managers. How do you
Gather and maintain context of complex projects at a distance?
Build high-trust relationships with your team and your peers to keep communication freely flowing?
Define the vision and strategy for an entire organization rather than a team?
Communicate that vision and strategy?
Adapt your organization to deliver that vision and strategy, or build an entirely new team to do so if necessary?
You know. The simple things
Just as the role of manager is preparation for being a manager of managers, the role of director is preparation for being an executive. I spent over eight years in various manager-of-managers roles at Apple. At the time I felt I wasn’t progressing quickly enough, but as it turned out, it was just right
Chapter 10. The Blue Tape List
Everything Is Broken
I’ve discovered that a simple fix is patience. In time, that which is different will feel normal. It’s why when a team member reports moderate concerns with a new hire, I always gently ask, When did they start? If the answer is less than two months ago, I suggest, If it’s not heinous behavior, give it another month. They’re still adapting to a new environment, and we don’t know who they are.
That might be good advice for a manager with a new direct report, but when you’re the direct report, when you’re in the middle of the second month and it all feels broken, Just a wait a bit longer is unhelpful advice. It’s also bad advice
You will notice my advice to new hires does not commit to fixing everything that feels off, but rather commits to addressing it. This could mean fixing the issue, but it could also mean responding and clearly explaining my reasoning why I didn’t think fixing the issue was the right move
It’s a surprise when a month passes, and discover how many items that seemed urgent at the time now seem entirely irrelevant. You are learning so much every single minute of a new gig; you are gathering so much context. You are continually updating your understanding of the team, your role, and the company. The context you’ve acquired after three months of work isn’t remotely complete, but it is exponentially more complete than at the end of month two
Make sure every item gets a response. If you’re planning on fixing the issue, explain how and when. If you’re not planning on fixing it, explain why. If you aren’t sure about the issue’s relative importance, think about how you might find it
Chapter 11. Delegate Until It Hurts
I have this list. It’s a list of leadership merit badges. You acquire one of these badges when you complete a task that requires significant leadership. Acquiring the badge is the least important thing. The most important thing is that you discover the lesson that awards it. It’s the most important leadership merit badge, regardless of role: Delegation.
Entrust
Let’s start with a definition. Delegate. Verb. Entrust (a task or responsibility) to another person, typically one who is less senior than oneself. The key word in that definition is entrust, but before we unpack that let’s first step back in time to those heady first days as a manager
Perhaps the most confusing part of the early days of leadership is the shift in responsibility. You had something that you were responsible for: an area, a feature, a technology…but now it’s more. Your responsibility encompasses all of the responsibilities of all the folks on your team
It is true that if something were to go sideways with one of your teams, leadership will be staring at you and looking for answers. When they’re staring, it sure feels like you’re responsible. But a far more productive mindset is that you’re accountable
While accountability implies responsibility, there’s an important distinction: accountability requires a willingness or obligation to justify (account for) actions and decisions. This means when it goes sideways and everyone’s staring at you, you need to be able to explain both how you got there and what is going to be done to fix it. How do you know these things? Your team has already told you…voluntarily
When things go sideways, when the sky falls, you’ll rush to find the humans who know about the problem area. They know you’re in a dire situation and they know you are moving with great urgency. They have a professional irrational fear and they are listening to every single word you say
At this moment, a manager who believes they are solely responsible for this situation will say I a lot. They are going to ask penetrating questions that indicate it’s their problem to solve because important people are asking them hard questions. They feel responsible, and hidden between the words they use and tucked nefariously behind the questions they ask is the distinct impression that they believe If I were the engineer running this, we would’ve never ended up in this situation
Watch trust erode
The reason Delegation is the most important merit badge is that earning it means you’ve learned important leadership lessons that will allow you to accelerate your leadership journey
Shush, Little Voice
The complete delegation of familiar work to another human is a clear vote of confidence in their ability, which is one essential way of forming trust within a team. Letting go of doing the hands-on work is a tricky and nonobvious win, but as a leader, you build yourself by building others
Another reason Delegation remains my essential leadership merit badge is because it is a skill that scales. You’ll need one version of it as a manager and you’ll need another as a director. Even better, the more advanced versions of delegation require the development of advanced skills on your side
Here’s an excerpt from a leadership career path I wrote at a prior company. This is how I describe the act of delegation at different levels of experience
Manager: Identifies and delegates small, well-defined projects to individuals within the team who require significant oversight
Sr. Manager: Identifies and delegates significant projects to individuals within the team who require some oversight
Director: Identifies and delegates large projects to teams or individuals who require little oversight
Sr. Director: Identifies and delegates large and complex projects to teams or individuals who require little oversight
Executive: Identifies and delegates large and complex projects to cross-functional internal or external teams that require little oversight.
You can see the three skills that you are developing as you grow as a leader
Measuring the amount of oversight provided to the team/individual
Assessing the magnitude and complexity of projects
Considering the composition and size of teams capable of doing the work
A common complaint I hear about managers is the classic, What do they do all day? You know what a good manager is doing? They’re giving away just about everything that lands on their plate to members of their team because their job isn’t building the product, their job is building a team that is capable of building the product
It’s confusing and challenging because you’re giving away the work that likely made you…you. That work you did gave you the experience to become a better leader. Delegation isn’t just how you’ll scale yourself—it’s how you’ll build leadership within your team
Chapter 12. How to Recruit
First Rule of Recruiting: Give It 50%
Let’s start with the rule. For every open job on your team, you need to spend one hour a day per req on recruiting-related activities. Cap that investment at 50% of your time
Seriously, 50% of my time? Yup. But we have a fully functional and talented recruiting organization. That’s super and will make your life better, but devoting 50% of your time to recruiting still stands. Why?
On the list of work you can do to build and maintain a healthy and productive engineering team, the work involved in discovering, recruiting, selling, and hiring the humans for your team is quite likely the most important you can do. The humans on your team not only are responsible for all the work the team does but also are the heartbeat of the culture. We spend a lot of time talking about culture in high technology, but the simple fact is that culture is built and cared for by the humans who do the work. Your ability to shape the culture is a function of your ability to hire a diverse set of humans who are going to add to that culture.
A Recruiting Primer
A good way to think about your recruiting work is to delve into the stages of the recruiting process itself
The stages here are:
Applications. Applied for a role or were sourced by an internal or external party.
Screens. Made it past a first-round screening process
Qualifies. Made it through a more critical screening process. Think coding challenge or technical phone screen designed to gather more signal
Interviews. Entered the formal interview process
Onsites. In the building for an interview
Offers. Received an offer
Hires. Accepted their offer
You first need to make sure you have two agreements in place with your recruiting team:
Agreement on the stages in your pipeline
With #1 defined, you now need to agree to make it ridiculously easy to access this information
With all this data in place and the process running smoothly, you can learn about the efficiency of the different parts of your recruiting process and you can ask informed questions
There are three states I consider as part of this unique pipeline: Discover, Understand, and Delight.
Discover
Discover, first, is the state of mind of any qualified candidate who does not yet know about the opportunity on your team and at your company. It is your job to find these humans and help them discover the desire to work with you at your company
Make a list of each and every person you’ve worked with who you want to work with again
In Discovery, you are making targeted strategic investments in your network. The reason these folks are on your Must List is that you have seen with your own eyes the work they can do
On to the Understand state. A candidate has passed through the very crowded top of the funnel and has reached the evaluation portion
The recruiting focus here is, Do they have the necessary skills? The interview process is designed to gather this information from the candidate. Your focus during Understanding is to again consider the candidate’s mindset. While they are getting peppered with questions about their skills and qualifications, they are also wondering, Who is this engineering team? What do they value? and Where are they headed?
Your responsibility is to make sure the candidates understand your mission, culture, and values.3 While they will organically pick up some of this during interviews, you need to make sure it’s one person’s responsibility to clearly tell the engineering story
There are two scenarios for a candidate passing through the Understand state. Scenario A: they receive an offer, and the time spent in Understanding paves the way to a rich offer conversation and allows them to hit the ground running when they arrive. Scenario B: they don’t get an offer, but they leave with a clear understanding of you, the character of your team, and your mission. Recruiters call the time spent interviewing the candidate experience, and I would suggest that whether they get an offer or not, Understanding is the cornerstone of an exceptional candidate experience
We’ve reached the Delight state. Congratulations! You’re making an offer to an engineer
They accept! Hooray! We’re still not done because they are still not sitting in that chair. Let’s welcome them. Let’s Delight them
The nightmare scenario is a candidate declining an offer they already accepted. I think it’s professionally bad form, but it happens more often than you’d expect
The offer letter is an important document. It contains the definitive details of compensation and benefits, and these are important facts—but during this critical time of consideration, I want these future coworkers delighted with a Real Offer Letter
During the post-offer-acceptance time, most companies send a note…a gift
The work of recruiting is a shared responsibility. Yes, you can be a successful hiring manager devoting less than 50% of your time to it. Yes, all of the funnel work can be completed by a recruiter; many of my best recruiting moves came from watching and working with talented recruiters.
The situation I want to avoid is a hiring manager who delegates the entire recruiting process to their fully functional and talented recruiting team. There are critical leadership skills you need to learn and refine during the Discovery, Understanding, and Delight stages. In Discovery, it’s understanding the power of persistent serendipitous networking. In Understanding, it’s understanding how to tell the tale of your company as well as being able to understand the tale of the candidate. Finally, in Delight, it’s the ability to discern the best way to delight this candidate at a time when their worry and risk aversion are the strongest
Chapter 13. Gossip, Rumors, and Lies
An Unacceptable Amount of Crap
I’m solidly on the record as believing 1:1s are the most important meeting of the week. A very close second is the staff meeting. I find that 1:1s beat staff meetings in two important categories: trust building and quality of signal. There are ongoing, compounding benefits to a regular well-run staff meeting, though: team building, efficient information dissemination, and healthy debate are three I can think of off the top of my head. There are more
Definitions first. I define a staff meeting as the correct collection of leadership gathered together to represent a team, product, company, or problem. Lots of words. A simpler and perhaps more immediately applicable version is, a meeting of your direct reports.
Great! You have directs, which means you should have a staff meeting, right? Maybe
The decision to start your first staff meeting requires judgment. Ask yourself the following questions
How many direct reports? Two? Yeah, no staff meeting necessary. Three or more? Keep reading
How many of your directs spend time working together? If it’s more than half, consider a staff meeting.
Do your directs have direct reports who are managers? Then you needed a staff meeting a while ago
How much has your team grown in the last six months? More than 25%? Have a staff meeting
How much of the crap that you’ve dealt with in the last month smells like it could have been resolved if people on your team were just talking with each other? If the amount of crap is unacceptable to you, have a staff meeting.
Did something recently organizationally explode? Have a staff meeting. No need for it to be recurring, yet.
A Well-Intentioned Hatred of Meetings
A first staff meeting is understandably a pretty quiet affair. It’s a delightful combination of unfamiliarity combined with a well-intentioned hatred of meetings. In our hypothetical opening example, Evan set a horrible initial meeting tone because he committed the worst meeting sin: no agenda.
Before I dive into these agenda topics, let’s talk about two essential meeting roles. In a well-run staff meeting, 95% percent of the activity is healthy conversation and debate. Key word: healthy. It’s a clear signal that a staff meeting is working when the majority of attendees jump into conversations and drive those conversations in unexpected directions. It’s a clear sign that no one is curating those conversations when those unexpected directions are not revealing insight or value. It’s time for a Meeting Runner
The Meeting Runner has two jobs: set the agenda and manage the flow. We’ll talk agenda shortly, so let’s first talk about managing flow. The Meeting Runner is responsible for making the following call throughout the meeting: When is this particular conversational thread no longer creating enough value? It’s a nuanced job, but without this human curating the conversation, a staff meeting can turn into a directionless heated venting session. Fortunately, as we’ll learn shortly, the Meeting Runner has an essential driving force at their disposal—the agenda.
Humans have complicated relationships with meetings. If they’re in the meeting and it’s not meeting their expectations, they’re mad. If they’re not invited to a meeting where they believe they should be present, they’re mad.
Meetings create power structures. Intentionally or not, they become a measure of status. Are you in that meeting? No? Well, I am. If you found sound reason to have a staff meeting in the list given earlier, I’m not worried about the first three months of this meeting’s existence. It’s during year two, when that good reason may have vanished and now you have this formerly important meeting purely out of habit, that things get tricky.
The rule is: in the absence of information, humans fill the gap with the worst possible version of the truth. Two years into your meeting when you’re not sharing the notes, the humans not in the meeting will be telling the most interesting and untrue stories about what happens in it. I guarantee it. This isn’t out of spite. They aren’t being malicious. They just don’t know what’s going on, so they’re going to tell their version of the story.
Share your notes. Every time. The act of doing so will force you to ask the following question before you share them: Is what we are doing here valuable?
A Three-Point Agenda
Here’s a starting agenda
The Minimal Metrics Story
Rolling Team-Sourced Topics
Gossip, Rumors, and Lies
Recommended by LinkedIn
The Minimal Metrics Story is the list of essential metrics this group must review on a regular basis, and I recommend leading with them because they frame the whole meeting
What are the key metrics this group is responsible for? Revenue? Application performance? Security incidents? Number of critical bugs filed? The list is endless, and it’s okay if your first meetings don’t have them clearly defined. But after a month, if these haven’t shown up, I’d be wondering why you pulled this group together. What problem are you trying to solve? I’m not saying you demonstrated poor judgment by calling the meeting, but if a concrete set of measurable things to review hasn’t shown up, why is the group meeting on a regular basis?
A Rolling Team-Sourced Agenda is the heart of your meeting. For the first iteration of this meeting, you’ll need to build the agenda yourself. This shouldn’t be hard because there’s a pressing reason for these humans to be together. Once, twice, or perhaps three times you can set the agenda for the meeting to address that pressing reason, but at the end of each of these meetings you should say, Here’s a document I’ve shared with everyone. Please add any agenda topics for next time.
You’re looking for two important developments over the course of the first three meetings:
Unexpectedly useful conversational detours
Unsolicited agenda items proposed by the rest of the room
Staff meetings are an hour. It feels like a lot of time, but when this meeting is working you’ll effortlessly fill the time
This final section of your staff meeting is a safe place for all participants to raise any issues, to ask any random questions, or to confirm any hallway or Slack chatter. Chances are, whatever seismic event caused this meeting to occur is still being organizationally digested, and often the stories being told are absurd. Gossip, Rumors, and Lies is time to get that important absurdity out in the open, so you can begin to construct a healthy response.
Meetings Are a Symptom, Not the Cure
The reason meetings have evolved as an acceptable first response is because they address one key issue: they give the team an opportunity to discuss their perceptions of the change. This feels good. The reason meetings are often hated is because while talking feels good, it’s not true progress.
Chapter 14. Rainbows and Unicorns
Duh
I’ll write about the two other rules and how they relate to good leadership and a healthy team another time. A compliment is a selfless, well-articulated, and timely recognition of achievement. To start to understand the value of a compliment, let’s go back to that Peggle video. Play it again.
When it comes to the motivation of humans, we’ve designed all sorts of communications tools and interesting cultural artifacts to help us move forward. Here’s a deadline that clearly tells us when we should be done
Peggle rewards you when you perform a simple task. It’s saccharine and over the top, but you can’t say that Peggle doesn’t own the compliment. The game’s developers want you to celebrate your achievement in the loudest, most ludicrous way, and it works
The Compliment Breakdown
Recognition is what you’re trying to provide, but how do you go about this? Is this a compliment you want to land 1:1 at the moment the achievement occurs, or is it the type of compliment that you want to tuck away so you can land it in front of the entire team for maximum recognition? I don’t know. There are so many contextual variables to consider here that it’s hard to give universal advice. Do they need to hear it? Or do others need to hear it about them? Understand what behavior you want to recognize, and why, and make a call.
Timeliness is the easiest attribute to understand. My default is to compliment as quickly as possible because I believe it’s the most effective way to reinforce behavior
Well-articulated is the attribute that is the hardest to define and the most important. Let’s start with what looks like a horrible compliment
The most nuanced part of a compliment is selflessness. This is also entirely context-dependent, but a good compliment is one that comes without perceived social cost or dependency. You know what doghouse roses are? They’re flowers you buy for your significant other because you screwed up. Yes, they are pretty, but all the recipient sees in those roses is your screw-up. It’s a thoughtless, empty gift that erodes trust. A good compliment contains nothing about you or what you want. It is entirely about the achievement of the other human.
A well-constructed compliment has an emotional payload. It is full of rainbows and unicorns. It’s this strange, unpredictable payload that makes us nervous about compliments. But when made selflessly and used for good, a compliment is an elegant and lasting way to recognize and reward when people are showcasing the best versions of themselves
Chapter 15. Say the Hard Thing
The Voice in Your Head
This voice works in your favor. It translates everything you experience into digestible constructs that you can understand, and it often biases these constructs toward your hopes and dreams. It is optimistic. This is well researched and normal. We are all the heroes of our own story. This voice tells the story of the world from your perspective, passed through the sum total of your experiences, translated into information, morphed into judgment, and often resulting in the creation of incremental wisdom
This voice is also often wrong or just misinformed, especially when you fail.
You’re embarrassed or ashamed when you fail. Maybe you’re mad, but after the initial emotion churn passes, you protectively rationalize. You find a narrative about the failure that is acceptable in the context of what you currently know. What did you learn? How will you proceed? What story will you tell others about this failure? All of this is defined by how you process your failure
Notice a pattern here? You are missing critical data when all you consult is yourself. It’s not that your inner dialog has a devious plan to prevent you from learning, it’s that it’s operating with an incomplete and biased set of data. The humans around you, watching you act, have the additional context and the experience required to make important observations about both your successes and your failures
How does this relate back to saying the hard thing? When we don’t want to say the hard thing we exacerbate the problem because we have the same voice in our head telling us, It would be hard for me to hear this, so I don’t want to say it. Worse, in the manager/employee relationship, the historic professional incentives are designed to prevent us from saying the hard thing. Your voice cautiously advises you, They write your review. They set your compensation. You cannot tell them that. They’ll be mad.
Let’s fix this. There are two practices: learning to say the hard thing followed by actively hearing the hard thing.
Saying the Hard Thing
A good place to start practicing feedback is with new employees. Once we’re past the getting to know you phase of a working relationship, a month or two in, I start giving feedback
Hearing the Hard Thing
The first time someone gives you critical feedback, it’s a test for everyone involved. The giver is taking a risk because you’re the boss and they’ve seen prior bosses lose their s—t when they’ve received feedback. Now, hopefully for well-intentioned reasons, they are giving you—the receiver—this gift, with the hope that it is useful.1
There are three classes of feedback:
No big deal feedback is no big deal. You hear it, you accept it, you update your priors, and you move along with your slightly altered worldview
Slow burn feedback feels like No Big Deal until you’re driving home from work and realize there was unexpected depth to the feedback
Just plain hard feedback is different. In many cases, I can tell when hard feedback is about to arrive. There could be a sudden change in the tone of the conversation; it might be a one-off meeting that doesn’t normally happen; or I might simply notice a strange new expression
Hard feedback, critical feedback, is distilled truth.2 In the days and weeks full of vapid How ya doings? Great jobs, and high fives, hard feedback represents a rarely seen report on the state of your ability. When the feedback is hard, there is another two-step process for making sure you don’t miss anything
Step 1: No matter how critical the feedback, listen and search for just a glimpse of understanding. Why only a glimpse? I’m glad you asked
Listen for what? One simple insight. One realization. Here’s one example: Why are they choosing to give me this feedback right now? The trick is to engage your rational brain, the part of your brain that likes to solve problems, as opposed to the part that wants to scream, because the part of your brain that wants to scream is exceptional at demonstrating tremendously poor judgment
Step 2: Repeat what you heard
You will be shocked by the usefulness of this simple advice. Even if you achieve the pure listening zen prescribed in step 1, you are still building your own version of the narrative
Your Goal in Life
Again, your goal in life is to make feedback in all directions no big deal. You and your team never start in this state; you work up to it. You start with small spoken observations that slowly turn into more useful feedback. You watch each other to see if you’re listening to the feedback, and eventually acting on it.3 Once everyone has seen that feedback is both shared and acted on, you begin to feel more comfortable sharing larger, more complex, and harder feedback. Why? Trust
Feedback is an incredibly valuable social transaction. It shows that people have taken their time to observe an aspect of you. They have other things to do, but today they are investing in you. You think you’ve got it all figured out, but you don’t. In turn, you take the time to clearly hear the feedback, ask clarifying questions, and hopefully adjust the way you work
Chapter 16. Everything Breaks
Provide A Clear Explanation of the Rules
The goal of your onboarding program is to get the new humans up to speed and productive as quickly as possible. Each of my past three start-ups has invested in onboarding programs, with the most recent being the most thoughtful. At each start-up, we should have invested five times as much
The challenge with investing in onboarding, as with most investments in the humans at your company, is proving a compelling and measurable return on that investment. Everyone agrees that onboarding feels like a thing we should invest in, but isn’t the first priority building and selling a product?
Your onboarding program has three sections
Our vision. What is the ambitious mountain we are climbing? Why are we doing it? And what is going to happen when we get there?
Our values. On this journey, how do we want to treat ourselves and others? Why did we pick these values? What do these values teach us? What do they look like in practice?
Our practices. What are the specific proven practices we use on this journey to get things done? How do we build together?1
Allow the Rules to Evolve in Unexpected Ways
Failure is an opportunity to learn. Yes, you should put out the failure fire as quickly as possible, but the moment the fire is out you need to begin a systematic, efficient, and familiar process of figuring out how it started so you can prevent it from happening again.
Play, Learn, and Repeat
An epic failure has the unique attribute that when it occurs, you have everyone’s attention. It is relatively easy to instigate change after an epic failure because everyone is staring at the sky, not blinking, prepared for it to fall once more. Learning from epic failures isn’t hard. Disciplined learning from all failures requires thoughtful work.
What is this fear based on? Depends on the failure, but it’s likely a combination of
Once they’re broken, and with ruthless and calming efficiency, you must set to the task of learning. What truly broke here? What is the best set of fixes? Who is accountable for leading those fixes? It won’t completely address the fear, but a culture of learning and acting on those learnings will signal to everyone that you take failure seriously and are eager to learn completely.
Chapter 17. The Org Chart Test
The Legibility Test
When you’re a small team—say, less than one hundred—the org chart isn’t that important because the humans can keep the state of the team in their heads. Nothing needs to be written down because communication is freely flowing. The communication tax of large organizations has not yet been applied. The humans know who is responsible for what. They know who owns different parts of the stack. They must. It’s a small company, and the ownership of things is changing all the time because…it’s a start-up. Chaos is the defining characteristic.
But at some point, someone on the team is talking to an interview candidate, and they realize they need to draw a visual representation of the team. It’s crude. It’s fast. And it’s the very first org chart. More on this in a moment, but first back to the test
Could your average employee, without any outside help, read your org chart and answer the following questions?
Management types take this artifact for granted because we live it. Our day is full of travels across the org chart. It’s our mental map for the humans and technologies within our teams, which means we both understand it and take it for granted. The vast majority of the humans in your organization do not have a daily need to comprehend the org chart, but when they do, your goal is instant maximum legibility
The Basics at Scale
A people-based org chart describes power structures. Who is responsible for whom? What do they own? How big is their area of influence? Whom do they report to? You cannot avoid these questions being asked, but you can set the tone for how you view your organizational structures. Product first? Technology first? Or people first?
I share this advice with you because it’s a mistake I made for years. Initial conditions set a tone that is nigh impossible to change
Chapter 18. A Distributed Meeting Primer
Remote
Let’s start with the word remote. Remote team. Remote worker. The word means situated far from the main centers of the population, which in the context of the workplace is usually factually inaccurate—a remote team or human is simply one that is not at headquarters. But it’s what most people think of when they say remote, and that’s the first problem
The Many People Meeting
In the many people meeting, you have two locations: host and distributed. Host is where the majority of the humans are located, and distributed is where we find the humans on the various other ends of a videoconference call.
I’ve already written about the rules for this type of meeting. I’d suggest reading that article and considering the following challenge: how do we make this meeting the same experience for all parties, so as to create the same amount of value for everyone?
My advice for leaders who regularly conduct distributed meetings falls into three categories: Pre-Meeting, During, and Post-Meeting.
Don’t chintz on audio/video hardware and networking
Schedule meetings at X:05 or X:35 and get there at X:00 to make sure all the technology is set up for a distributed meeting
Set sensible defaults in your audio/videoconferencing software
Check your background
Is the whiteboard in play? Great
Assign a spotter on the host side
Understand the acoustic attributes of a room
Encourage participants to hit mute if they are not speaking
When focus shifts to the whiteboard
The room with the most people disconnects last. Respect
For a first-time meeting with these humans or in this space, ask how it went for everyone. Fix things that are broken
You may learn that some distributed folks couldn’t hear well during the meeting. Invest in fixing bad audio in conference rooms
Given the likelihood that the distributed folks missed something during the meeting—which is a thing to be fixed—the distribution of the meeting notes provides a critical feedback loop for everyone who took part.
No Measurable Difference
Much of the leadership work I’ve done around distributed teams centers not on resolving concerns about how the audio/visual equipment works in a meeting, but on how a distributed team feels treated by headquarters. It’s never just one thing: it’s a long list of grievances that combine into the erroneous but very real perception that a distributed team is somehow less important.
Much of the advice I’ve given here is tactical—simple acts to facilitate better communication—but in combination it supports a broader goal. By making sure every human in the meeting has equal access to the communication and the context, we send a clear message that being distributed doesn’t matter. There is no measurable difference if you are in the host room or distributed.
Act III. Slack: Executive
This responsibility is accompanied by the toughest aspect of the executive role, which is that fires burn faster uphill. When something catches fire on one team, there is a manager there who hopefully competently handles the fire. Sometimes they can’t. The fire gains strength and speed, and it’s escalated to their director, who with their additional experience can often put out the now significant blaze. Sometimes they can’t. Sometimes the magnitude of the disaster is beyond the ability of your whole team, so they escalate it to you
As an executive, the majority of unexpected situations you’ll face are prequalified five-alarm fires. They are the worst possible version of the situation. And that’s just Monday.
Strange, right? So, what do executives do all day? Fight fires? Yes, but our primary job is fire prevention. What combination of people, products, and processes is necessary to build the highest-quality product? Figuring that out is the easy part of the executive’s job. Here’s the hard part: what combination of people, products, and processes is necessary to prevent fires from existing?
Chapter 19. Allergic to Wisdom
A Circus of Failure
Remember, management isn’t a promotion, it’s a career restart. And just like when joining a compelling new start-up, we begin with the following affirmation: I need to look like I know what I’m doing even though I’ve never done it before.
There’s wisdom there. Part of leadership is learning to demonstrate enough charisma and enthusiasm to convince the team that against impossible odds, we will succeed. This behavior is supported by the unspoken fact that your team initially assumes, The leader has a plan and even if I don’t understand it now, I have faith they know what they are doing.
My failures were vast. There were morale issues because no one understood the product strategy I produced. They went undetected. Vapid and unhelpful performance reviews were produced. By me. Weeks of lost productivity occurred because I leaked to the team news of a forthcoming reorganization that wasn’t done for another three months. Infighting occurred because I was a conduit for gossip.
The unintentional allergy a rapidly growing start-up has to preexisting wisdom is part ignorance and part pride. These start-ups are successful because they believe at their core that the impossible can exist. It’s my favorite part of the culture and it’s why I don’t say, Back at Apple, we did it this way. I just act without asking
Their enthusiasm for this business they brought into existence has spilled over into all aspects of the organization. Everything must be looked at through this innovative lens. Sure, I’m a firm believer that we must continuously evolve ourselves and our business, but the act of innovation is an expensive one. We stop. We stare at the problem set. We debate. We debate endlessly. We yell. We whiteboard. And then finally we come to a clever, thoughtful, and defensible decision on how to proceed, and we charge forward enthusiastically because we just brought this unique decision, this perceived invention, into the world
Every aspect of a rapidly growing, innovative company does not need to be processed through this innovation engine. In fact, you are going to lose valuable energy, momentum, and productivity doing so. There are a handful of company-critical decisions that need this level of attention, and for the rest we can rely on prior art.
Act Without Asking
As an executive, you’re in the unique position of being the human in charge of the entire organization. You have a boss. They’re the CEO, but they’re busy being the interface to the rest of the world and their expectations of you are something like, Productively run your business. Competently answer questions when I ask them. If you need help, ask.
My default operating model is sharing a vision for where we’re going. This means describing our ambitious future and all the strategic steps we’ll need to take to get there. I’ll want your opinion because I know ideas get better with eyeballs, but sometimes, rarely, we’re just going to go. See, I’ve been here before and by acting without asking, I’m giving us a strategic advantage, I’m saving us time and money, and I’m being a leader.
Chapter 20. The Guard
The Productive Team Teams
The core attribute of a productive team is so simple and obvious that we forget it—it’s like breathing, an act so essential that we forget we do it, though we can’t exist without it
A productive team knows itself
The team members know each other’s names, and they understand and appreciate each other’s respective strengths, weaknesses, and motivations. They are not strangers
With this essential understanding in place, and with practice, the humans in a healthy team effortlessly and without ego call on each other when they need help. They do not care who gets the credit for the work because they want the work to get done well by the most qualified humans with the best judgment
This is a team that trusts itself, and it is likely that you’ve spent most of your career not on this type of team. I’m sorry. Let’s talk about some of the reasons this hasn’t happened yet
Trust Falls for Everyone!
You know what the most-ridiculed team building exercise is for an offsite? Trust falls. The idea is that the team separates into pairs and each group performs an exercise where one person faces away from the other person, folds their arms, and falls backward—and hopefully, the other person catches them.
Trust falls are the rallying cry for the awkward offsite, but what makes them awkward? Why are they ridiculed? What about this exercise makes it funny? Trust? What’s funny about that? Nothing. We giggle about trust falls because we don’t really know the complex mechanics of building trust in a work setting
Chapter 21. The Culture Creek
An Unchangeable Culture
Most everyone is going to talk about how to build the culture, but the vast majority of the culture has already been built. No matter how many times a group of well-intentioned humans plasters a new set of values on the wall, the culture will not significantly change while the founding team is running the company. Really
Listen for the Stories
Your company’s values are painted in huge black block letters on the wall. Let me guess
We Value Transparency
Teamwork Makes the Dream Work
We Are the Customer
Be Kind
We Are Obsessed About <Something
Listen. Maybe it’s the first argument that you hear amongst the team. Perhaps it’s a complicated design decision. No one is going to raise their hand and state a value: We Are the Customer
These stories are the culture. Not the words on the wall. It’s convenient when the stories and the words support each other, but I’ve worked at companies where teamwork was preached as a core value—I heard about it during the interview process, it was an essential part of onboarding—but the first real story I heard over lunch was how the CEO was a horrific dictator.
The stories that define a culture are not a deliberate strategy. No one called a meeting to decide which stories mattered to the company. A core set of humans in the building retold the stories that mattered to them, over and over again, slowly carving a well-defined path in the consciousness of the company. With time, it becomes religion. When we’re in situation X, we tell the tale of story Y. Does story Y always apply to situation X? Maybe. I don’t know. It’s the story we tell.
Chapter 22. Anti-Flow
Weaponized Inspiration Generation
As I look at my work calendar, I see comfortable boxes of time designed to chunk my week into knowable bits of time. Those bits of time are meetings where I and humans I care about have structured our time with agendas. Crafted to focus on the problems at hand, agendas are run by humans and keep us on topic and within time. These boxes are valuable. Decisions are made. Work that matters progresses in a structured fashion
By design and with a lot of help, my week and my mind are on rails. There is essential unmeasurable work that needs to happen on a regular basis that should not just happen in the shower
Anti-Flow is the weaponized generation of inspiration. Anything can show up during deep sessions of Anti-Flow, from the mundane to the magical
Not knowing the source of this inspiration makes the concept of Anti-Flow at odds with a working day, which perhaps makes a bike ride a better place to Anti-Flow. It’s one of the reasons why when my wife asks me, Do you get bored on three-hour rides? I respond honestly, It’s when I do my most important work
You don’t bike. That’s fine. Think about the last time you had a non-shower a-ha moment. Cleaning the garage, knitting, driving to Monterey Bay. There were no internet distractions, and an intriguing idea appeared out of nowhere. Wherever you were, whatever you were doing, devise a reliable means to do it again. Every week. There is Anti-Flow to be had everywhere
Chapter 23. A Meritocracy Is a Trailing Indicator
Two Paths
There are two career paths1 in your organization: one that describes the growth of individuals and one that illustrates the growth of managers. These paths are readily visible public artifacts written by those who do the work. This means engineering writes the path for engineers, marketing writes the path for marketing specialists, and so on.
The contents of these artifacts need to reflect your organization’s values, culture, and language. For individual contributors, I humbly recommend the career path contain the following information:
A series of levels and titles
A brief description of the overall expectation of each level
A list of competencies that are required for each level
A definition of how each competency may be demonstrated, for each level
This suggested list is not definitive. You could easily add to this artifact items like a sphere of influence, ideal years of experience, or comparable levels outside of your company. And then do the whole thing over again for your manager career path
If you are feeling overwhelmed by the enormity of this task, you’re in good company. You can certainly find career paths online that can serve as starting points for creating these descriptions, but I strongly encourage your team to write their own because your culture is unique. The competencies you need are a function of the values of your particular collection of builders
Two Equal Paths
There are many good reasons for an engineer to want to move into management, but if their only reason is the perception that management is the best place to grow as a leader, then the leadership team has created the perception that leadership is not the job of individuals. This is a disaster.
The Growth Tax
During a period of rapid growth with only organic role definition, everyone is wondering where they stand because everything is changing all the time. Suddenly, these new managers appear who have the power to determine roles, and individuals ask themselves, What other powers are they going to grant themselves? And how do I get in on that action?
So, you wrote a career path for individuals in which you defined a clear set of competencies signaling the growth of the individual—but you forgot to make it clear that leadership comes from everywhere. If an individual doesn’t believe that they have the same ability to lead as a manager, then those who desire to lead will attempt to get on the manager path.
One of the bigger challenges during rapid growth is a thing I call the growth tax. It’s a productivity penalty you incur that increases as a function of the size of your team. Ask yourself these questions
How long does it take to make a hard decision?
How does a person find out a critical piece of information?
How do we figure out who owns what?
But these small communication taxes pale in comparison to the much larger taxes levied by defining cultural norms. By fostering the belief that the managers are the only leaders, you create hierarchy. We must go to a higher power to ask for permission. Hierarchy creates silos. We own this, and they own that. Silos often create politics. Their mission is the only mission. Our mission is lesser.
This is a disaster.
Leadership Comes from Everywhere
Are managers required as group size scales? My vote is yes. You might disagree, but I think having a set of humans responsible for the people, processes, and product is essential for scaling. One reason you might disagree is that you’ve seen managers who’ve done the job poorly. That sucks. There are good managers out there, and they are the ones who understand their job is to manage the health and advancement of their team, because without their team they have exactly no job
The definition of individual contributor leadership starts with defining a leadership competency in your career path—but you need to spend an equal amount of time defining clear places for individuals to lead. Here are two roles you can invest in: Technical lead, Technical lead manager.
A Trailing Indicator
My last piece of advice on career paths is the most complex and incomplete. As I wrote earlier, the manner in which you define leadership is as important as how you are applying it. A thoughtfully constructed promotion process provides a means of consistently and fairly demonstrating to the entire team how you value leadership
Chapter 24. How to Build a Rumor
Being a part of rapid-growth start-ups for the past 10 years, I’ve had front-row seats for watching rumor cultures grow. It is during rapid growth that communication structures are tested. Each new human who arrives needs to understand the company, its culture, and its values. I’m talking about both the values you paint on the wall and the silent values that exist as a part of each team.
Overt and covert values are more easily infected and corrected before the organism reaches a size where the relatively new hires (the New Guard) outnumber the Old Guard. At this inflection point, the culture starts to drift because the amount of entropy introduced by the New Guard exceeds the ability of the Old Guard to correct it. This is when the fascinating rumors begin
Rumors start in the gray space. This is the space created between rapidly growing teams that used to interact every day but are now sitting in different buildings. It’s the space created by communication vacuums. You neglected to explain your intent regarding a strategic product decision. A single sentence at an all hands was misinterpreted, and no one raised their hand to ask for clarification. The rumor began as a simple misunderstanding, and then it became something much stronger and more pervasive. How
The Severity of Nonsense
Your brain is trained to detect bulls—t. Evolutionarily speaking, I don’t know how we acquired this essential skill, but each human being can listen to a statement and make an initial assessment: Bulls—t or not?
The difference between bulls—t and a rumor is the severity of the nonsense. Bulls—t sounds so insanely bizarre that it’s easier just to ignore it, whereas a rumor often contains a semblance of truth that gives it a whiff of credibility. But whether it’s a rumor or straight-up bulls—t, your response is the same: discover the truth.
A better result is that you find a hint of the question being asked. It can be a solidly structured hypothesis or a wild-ass guess, but with this insight in hand, you respond, and you act. You answer the question either in a public forum or with a change in your behavior. You release a little bit of truth into the wilderness
Rumors Are a Function of Culture
Rumors are a function of culture. In this manufactured scenario, it was easier and safer to talk not to the originator of the situation, but to a distant observer. It was easier and safer to not stand behind one’s words, but to attribute them to an anonymous other
Chapter 25. Kobayashi Maru Management
A Proper Preparation
A useful piece on how to move into damage control mode and deftly handle this no-win scenario seems like a good idea, but wouldn’t it be better if this chapter explained how to not get into this situation in the first place?
My Kobayashi prevention protocol is, conveniently, the same process I follow for any significant change on the team. Let’s begin:
Frame the situation via a written artifact. You need to create a presentation or document that clearly explains what is going on, why it is happening, what success looks like in light of this change, how you are going to measure success, and how anyone can give feedback on this development. This is simply a draft, and it’s going to change a lot before you’re done.
Vet the draft plan with three no-skin-in-the-game trusted humans. Take your draft and give it to three humans who are not affected by this change and whom you trust to tell it to you straight. If there is only one piece of advice you should follow in this entire chapter, this is it. Unaffected trusted humans are the ones who are most likely to both see the obvious flaws in your plans and be eager to tell you about these flaws
Write down a list of all people and teams that you expect will be affected by the change. This exercise is the first step of building out a communication plan, but right now it’s a sizing exercise. Write the list. How many folks are on it? Five? Just five? Why are you still reading this article if we’re talking about five affected people? I’ll tell you why. You can smell the larger-than-expected impact. Your Spidey-sense is tingling. How many humans will really be affected? Not just directly, but indirectly? Humans who care about the directly affected humans. Humans who will have a strong opinion about the change. Humans who are going to raise their hands and speak. Yeah, put them all on the list. Then return to your three trusted humans and vet the list
Draft your communication plan. With your framing and vetted list in hand, it’s time to operationalize this program. It’s called a cascading communications plan because you start with the most affected humans and slowly work your way toward the less affected humans. Here’s the order of operation
A Prediction of the Unpredictable
No one celebrates when nothing happens. We all know when something significant goes wrong, because suddenly everyone’s rushing around with great ferocity. Heroes and heroines appear when something goes wrong. They work for three days straight. We award spot bonuses for this exceptional effort. There are no spot bonuses for averted disasters, because they are the result of capable leaders competently doing their jobs.
Chapter 26. The Signal Network
Critical Freshness
In thinking about all the listening I’ve done and information I’ve acquired, I discovered I have a mental model for classifying information
This grid has two axes. The vertical axis measures the criticality of a given piece of information
The horizontal axis is where this graph gets interesting. It measures freshness, which is a synthetic measure of how long it takes a given piece of information to get to the human who gets the most value from its arrival. Confused? Keep reading.
The interpretation of this graph is a very personal thing. You need to consider it as a thought experiment through a couple of different lenses. First, what is critical information to one human is irrelevant to another. Jake’s desire to quit is hugely important to his manager, but less relevant to someone outside of the organization. Second, and worse, if the information about Jake takes two weeks to get to Jake’s manager the information is not fresh, and Jake’s manager has less time to take proper action
Every single human in the organization has their own version of this graph, and my thesis is that the interpretation of the graph describes the health of your signal network
Your Signal Network
Your signal network is the combination of all the available information sources and all the information generated (or relayed) via those sources. The complete network is a combination of humans and robots, but for the sake of this chapter, let’s focus on human information sources. Back to the graph
If you think about your average workday, you are continually discovering pieces of information. Intentionally and accidentally. In meetings, in hallways, and in the cafe. Your working life is chock-full of rapidly arriving information, and your brain must quickly digest, parse, pattern match, and make a judgment regarding each piece of information. What is it? How critical is it? What am I going to do with it? Should I pass it along? And to whom?
Each quadrant of this graph describes a different assessment of a piece of information. Let’s walk through them:
Stale Slowness. The lower-left quadrant is the most boring one. The information here is not relevant and isn’t fresh, but who cares? It’s low-signal information, and it’s stale, so there is no need to act
Voluminous Spam. The lower-right quadrant is less annoying. You’re still dealing with less-critical information, but the more you move to the right, the fresher the information is. You’re sure learning lots of useless things quickly. At an extreme, it’s spam. An organization spends energy moving information hither and fro. If you’re seeing a lot of information falling into this quadrant, I am concerned about the overall efficiency of your team. If you’re seeing a lot of useless information on a day-to-day basis, what about the rest of your team? How much time is the team spending wading through the noise to find signal? How much time is it wasting looking for nuggets of relevancy?1
Critically Fresh. The upper right quadrant is your informations sweet spot. Critical information is getting to you in a timely fashion. Yes, id’d be super if all the information were further up and to the right, but the fact the information is in this quadrant is a win. The vibe her es a distinct lack of surprises. When a piece of information lands on your plate, it’s fresh. It’s clear someone just made this horrible decision, and you have simple time to coach them in the correct direction.
The Important Slow. The final quadrant, the upper left, is the danger zone. Critical information making its way slowly to the humans who need it the most is the source of much of your organizational consternation, and I need a whole section to explain why.
No Surprises
If you buy that ensuring the healthy flow of information is an essential practice as a leader, then you understand why I religiously hold 1:1s. It’s a regular meeting where I make it clear what critical information I care about and where I consistently share the critical information my team needs. It’s never a perfect transaction. I often incorrectly flag as essential information that is spam, and you will too. Over time, we will calibrate. In time, we won’t wait until the 1:1 to relay information because we’ll intuitively understand that for this given piece of information, the faster it lands in the right hands, the higher the value.
Your ability to effectively lead is a function of the collective quality of the decisions you make on a daily basis. You can take your time on many decisions. You can wait days or weeks until you’ve gathered all the relevant signal necessary. Other decisions must be made right now. At that moment, the health of your signal network, the amount of critical information that has arrived in a timely fashion, makes the difference between an informed decision and the flipping of a coin.
Chapter 27. A Precious Hour
The amazing set of skills we’ve built to compensate for this utter lack of context is impressive. You would not believe how many times your boss has walked into a meeting with absolutely no clue what is supposed to happen during that meeting. Managers have developed aggressive context acquisition skills. They walk into the room and immediately assess whose meeting it is, then listen intensely for the first five minutes to figure out why they’re all there while sporting a well-rehearsed facial expression that conveys to the entire room, Yes, yes, I certainly know what is going on here.
Like these context acquisition skills, we’ve also convinced ourselves that we have built a mental process that gives us the high that we’re missing in our interrupt-driven lifestyles. We’ve created the Faux-Zone
In the 45 minutes before my 8 a.m. meeting, I did not enter the Zone, but I am in the Faux-Zone. It is a place intended to create the same rewarding sense of productivity and satisfaction as the Zone, but it is an absolutely fake Zone—complete with the addictive mental and chemical feedback, but lacking creative value. In the Faux-Zone, you aren’t really building anything.
A Precious Hour
My deep-rooted fear of becoming irrelevant is based on decades of watching those in the tech industry around me doing just that—sitting there busily doing things they’ve convinced themselves are relevant, but that really are just Faux-things-to-do wrapped in a distracting sense of busy. One day, they look up from their keyboards and honestly ask, Right, so what’s Dropbox?
No matter what? Since I’ve started I’ve had roughly a 50% success rate in actually getting to my hour. The excuses are varied, but the data is compelling. Even at a 50% hit rate, I’ve written more, I’ve tinkered more, and, most importantly, I’ve spent over eight hours this month alone exercising the part of my brain I care about the most: the part that allows me to create
An Insidious Situation
There is a time and place for the purposeful noisiness of busy. The work surrounding a group of people building an impressive thing contains essential and unavoidable busy, and you will be rewarded for consistently performing this work well. This positive feedback can feed the erroneous assumption, Well, the busier I am, the more rewards are forthcoming. This is compounded by the insidious fact that part of being busy is that you aren’t actually aware that you’re busy because you’re too busy being busy. You have no internal measurement of the amount of time you’ve actually spent being busy
In my precious hour, I am aware that it is quiet. During this silence, maybe nothing at all is built other than the room I’ve given myself to think. I break the flow of enticing small things to do, I separate myself from the bright people on similarly impressive busy quests, and I listen to what I’m thinking
Chapter 28. Find a Mentor
What Could Go Wrong?
First-time director. I’d been promoted because I’d written a couple of leadership books and had developed a strong support network of bright humans within the current company. They were looking for fresh blood, but the role was poorly defined and not running an engineering team. What could go wrong? Quite a bit
While the leadership skills I’d built over the years were helpful, there was no way to quickly gather the immense domain context of a different job like, say, human resources. I was capable of leading, but the gaping hole in domain-specific experience caused the gig to go sideways within six months. I adopted the advice I’d readily given to many others, but had not yet followed. I hired an external human—who would eventually become my mentor—to do a 360 review of my performance
A 360 review proceeds as follows
Want to know why I preach about 1:1s? Want to know why I keep harping on the importance of feedback? It boils down to the moment I received the feedback from my first 360
Chapter 29. How to Rands.
North Star Principles
Humans first. I believe that happy, informed, and productive humans build fantastic products. I optimize for the humans. Other leaders will maximize the business, the technology, or any other number of important facets. Ideological diversity is key to an effective team. All perspectives are relevant, and we need all these leaders, but my bias is toward building productive humans
Leadership comes from everywhere. My wife likes to remind me that I hated meetings for the first 10 years of my professional career. She’s right. I’ve wasted a lot of time in meetings that were poorly run by bad managers. As an engineer, I remain skeptical of managers even as a manager. While I believe managers are an essential part of a scaling organization, I don’t believe they have a monopoly on leadership, and I work hard to build other constructs and opportunities in my teams for nonmanagers to effectively lead
I see things as systems. I reduce all complex things (including humans) into systems. I think in flowcharts. I take great joy in attempting to understand how these systems and flowcharts all fit together. When I see large or small inefficiencies in systems, I like to fix them, with your help.
It is important to me that humans are treated fairly. I believe that most humans are trying to do the right thing, but unconscious bias leads them astray. I work hard to understand and address my biases because I understand their ability to create inequity.
I heavily bias toward action. Long meetings where we are endlessly debating potential directions are often valuable, but I believe starting is the best way to begin learning and make progress. This is not always the correct strategy. This strategy annoys those who like to debate
I believe in the compounding awesomeness of continually fixing small things. I believe quality assurance is everyone’s responsibility and there are bugs to be fixed everywhere…all the time.
I start with an assumption of positive intent for all involved. This has worked out well for me over my career
I need you to know that sometimes we are in HIGH ALERT and things will get strange. There is an exception to many of my practices and principles, and that is when we are in a HIGH ALERT situation. HIGH ALERT conditions usually involve existential threats to our company. During this time, my usual people, process, and product protocols are secondary to countering this threat. If it is not obvious, I will alert you that I am in this state and give you my best guess of when we’ll be done. If I am constantly in this state, something is fundamentally wrong
Chapter 30. Be Unfailingly Kind
Clear communications, demonstrated expertise, clear and actionable feedback, and even-keeled temperament. I’m describing a set of solid leadership traits here, but I’m not even to the important part. See, I’ve seen all these behaviors before in a great many humans. What makes DJ unique is that: he’s always this leader. I’ve come to expect precisely this behavior out of DJ each time we’ve played—like clockwork. I aspire to be a good leader, but I have bad days. I slept poorly. I sat in that useless meeting where nothing of substance was contemplated for an hour, and I lost my faith in humanity.
Leadership in a volunteer organization is perhaps the best way to think about leading a raid. You have a set of humans that are hopefully dedicated to a common goal, and that are donating their time in support of this goal. Most volunteer organizations have a far nobler mission than the acquisition of epic loot, but the theory is that when you have a volunteer workforce of people donating their time out of the kindness of their hearts, you see a different leadership approach
I believe two things. First, an unfailingly kind leadership protocol seems like a solid approach for a volunteer organization. You don’t hire your team, and they likely come from diverse backgrounds with different motivations, so your ability to explain and guide is key. Your ability to convey credibility and become the expert as quickly as possible is paramount because volunteers leave…randomly. In the face of disaster, you must remain a calm and focused leader—this leadership trait is essential. Disaster is a strong word, but in a world where volunteers are doing work they are choosing to do rather than work they must do, unexpected situations are the norm.
Second, I believe being unfailingly kind is the best approach for every leadership situation. As you’ve been reading this chapter, you’ve probably thought of a leader who is precisely the opposite of what I’ve described. They’re a dictator, a micromanager, a yelling, driven, larger-than-life personality. You might believe they are successful because of these traits, and that might be true, but is that the leader you aspire to be?
Not me
Epilogue: The Way I Heard It Was...
We’re a team. There’s a mountain that no one has ever climbed before, but you—in your bones—believe we can. More importantly, you can stand in front of us, point at the mountain, and tell us the compelling story of how we’re going to climb that impossible peak
Your story is engaging, but light on specifics. We don’t care because we all desire to achieve the impossible and, more importantly, we just love the way you tell this story. We believe you. This belief washes away the perceived need for concrete next steps. We are emotional beings; your manner and delivery have convinced us to follow you on an impossible journey
This is vision. You are using all your leadership skills to describe a vision
There is still a mountain to climb. How are we actually going to perform this Herculean feat? Thankfully, we have you. Now you begin to plan
You start with questions: How big is the mountain? What obstacles are we aware of? Where is the top? What is the best path to climb to the top? Are there alternative paths? How many hikers do we have, and how fit are they? What are their respective strengths and weaknesses? What is the best configuration of humans to perform each task? What contingencies are we going to need to build for unexpected developments while hiking?
It’s an endless list of questions, so you first determine which answers are critical, which are important, and which are nice to have. Second, you hand the task of answering many of these questions to humans on your team. You do this by first reminding us of your vision, explaining the relative importance of the questions, and defining when you need to know an answer. Each time, without fail, you finish with I trust you to do this important thing.
You learn not just from the answers, but from how the team discovers answers. Their discoveries update your mental model of not only how we’re going to achieve this impossible task, but also the abilities and nuances of the humans you will need to depend upon
This is strategy. You are using all your leadership skills to define a strategy that supports a vision
The execution of the plan, the tactics, is the hardest part, but no one will believe this for a while. We’re optimistic, full of energy, and chasing an ambitious, compelling vision. We’re laughing, patting ourselves on the back, and climbing. We frequently look at the plan that we’ve built, read the signs, and follow the directions. Step after step.
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Financial Planning Manager - VIVA
1yGracias Juan Carlos