Michael Lopp on Management

Book: The Art of Leadership: Small Things, Done Well
Author: Michael Lopp

Summary

Michael Lopp's book is about leadership, but it's really about management. There's nothing groundbreaking here, but considering it is from a practitioner in the field for the last two decades, its utility can't be questioned. The book is organized as a collection of strategies - techniques? - that the author suggests one pick and try for sometime, ideally three months. If you like it, do it forever and allow compounding to work its magic. The crux boils down to this: be kind, be reliable, and have a lot of 1:1s. That's not hard. Right? Right.

Notes

• Those years of building out the team taught me that management is fundamentally about uncovering information — roadblocks your team is facing, interpersonal friction, etc.— and then slicing through the BS to find the right way forward. Doing it well means getting good at both of those. On the information front, it means asking the right questions and designing an intentional culture that fosters truth telling. In terms of finding a path forward, it means learning about the universe of possible solutions and then choosing the best one for the particular situation.
• 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.
• 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 the art of leadership. 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.
• 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. Assume they have something to teach you.
• When it comes to complex political scenarios, you need to keep track of who knows what. Again, nothing nefarious. No ill intent. Just an honest attempt to shape the narrative productively.

Operational Excellence

• You sign up for things and get them done. Every single time.
• 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.
• Thinking I am being responsible and helpful, I sign up for things. I do this repeatedly and sign up for too many things. Over time, I realize I’m overloaded, so I back out on some commitments. Where’s the flaw? Because I could not initially correctly assess how much work I could do, I’m signaling to my team that it’s okay to back out of commitments.

Act Last

• You’ll be 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.
• 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. Who are the critical people? What are the critical parts? Which decisions matter? I don’t know. I do believe that a prerequisite for leadership is that you have experience.
• Let others share their thoughts. You never know when a great idea will appear. Understand that because you’re the leader, your team is going to be less likely to contradict your idea—which is another good reason to act last.
• Demonstrate respect to the team by asking great questions. Be curious. Your experience has taught you lessons, and your questions often share those lessons better than your lectures. Plus, you never know what kind of soup you’ll get to taste.

Performance

• It’s always performance season.
• How often should you review and revise your answers to these questions (about what you need from your career)? Four times a year? Five? Your call, but it needs to be more frequently than the company’s official performance season because professional growth occurs every single day. Most days that growth is not obvious; it’s the daily set of work on your plate that is predictable and understood. No surprises.
• If you’re going to say yes to the opportunity, it needs to be an informed yes. What is it about this opportunity that will allow you to grow?
• Give yourself months and months to discuss a gap in performance (of a reportee). Analyze it from different angles and make it about learning rather than a step on the road to performance management.
• 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 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.

Delegation

• 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.
• 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.
• 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.
• Just as the role of manager is preparation for being a manager of managers, the role of director is preparation for being an executive.
  • Politics, the good and the bad, is now part of your daily diet. Communication downward and upward has always been important, but now you must communicate sideways—and now it’s time to give away your Legos.
• 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.

Recruiting

• 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.
• There are two use cases for The Must List. First, whenever a new gig opens up on my team, I fire up the List and see if there is anyone on it who might fit the bill. Then I send them a friendly note. Hi. How are you? Got a gig and I must work with you again. Coffee? More often than not, if we haven’t spoken recently, this human and I will get coffee regardless of their interest in the role because these are dear friends.
• Every month or so, whether or not I have a relevant open gig on my team, I review the list and see whom I have not spoken with in the last 90 days. Time for an email? Okay: Hi. How are you? Coffee? Again, they’re rarely interested in switching gigs, but if they happen to be looking, I will move mountains to work with them again.
• 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.

Gossip and Lies

• 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.
• 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.
• 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. Combine this slippery situation with the fact that meeting efficiency devolves as a function of the number of humans greater than seven that are present, and you’ve got a maddening set of complicated constraints. The simple but perhaps controversial practice I recommend is that every single meeting have a Meeting Historian, and the work of that Historian be broadcast to the whole company.
• Politics are a natural development in a large group of humans working together. Corrosive politics give me rage. Taking credit for others’ ideas, hoarding information, not allowing the best idea to win—the list goes on and on, and when I discover this type of politics where I work there is rage.
• The fact is, in the absence of information, your team will make up the worst possible version of the truth, usually reflecting their worst fears. This deceptively simple rule is the reason for many of the rumors circulating within your team and at your company.

Say the hard thing

• On my short list of critical leadership skills, the ability to “say the hard thing” is right after “delegate until it hurts.” The majority of people-related disasters I’ve created have originated with my choice to not say the hard thing.
• Your job, the work you should value the most, is helping your team grow. Compliments and recognition are one way to highlight exceptional work, but saying the hard thing always gets their attention.
• 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. I keep it lightweight at first (“ In this meeting, you said this thing. Is this what you meant to say?”), and at the end of each 1: 1 I ask the same question, “Do you have any feedback for me?”
• 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.
• 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.
• These principles frame my advice for your growing company: Provide a clear explanation of the rules. Be prepared for the rules to evolve in unexpected ways. Play, learn, and repeat.
• At a start-up, “fail fast” isn’t good advice; it’s a way of life, and it’s the defining characteristic. It is up to you to make failure a competitive advantage.
• 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.

The first three months

• The first three months at a new job is a delicate time because you are in the “first impression zone” where, whether you like it or not, the judgment factor is impossibly high.
• 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.”
  • Part of leadership is learning to demonstrate enough charisma and enthusiasm to convince the team that against impossible odds, we will succeed.
• Your team’s first impression of your leadership style should not be, “My new executive is not going to ask my opinion. They like going rogue.” I would much prefer, “My new executive moves rather quickly and with intense and defensible purpose.”
• The first 90 days is a dangerous time. First impressions are hard to change. Your first few months set the tone. Simple acts as a leader will resonate loudly throughout the team and the organization.
• 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.

Misc

• Other than spending time with my family, my absolute favorite time of the week is Saturday morning. I sleep in a little bit, walk upstairs, start the coffee process, and wander over to the computer. There’s a Dropbox folder titled “Latest Rands Articles,” and right at this moment there are 65 articles in progress there. After a brief stumble through the internet, a precious time begins. I have precisely the right music on, in the center of my screen is a wall of words, and in that moment I’m decidedly not busy, I’m not working—I am building a thing, and I need this time every single day.
• 1:1 every week - This meeting is for discussing topics of substance, not updates. I’ve created a private Slack channel for the two of us to capture future topics for our 1: 1s as well as to provide a handy historic record of what we’ve discussed.
• 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 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.
• Clear communications, demonstrated expertise, clear and actionable feedback, and even-keeled temperament. All the time.
• 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.
• How do you interview for leadership skills? I hear this question a lot, and 9 times out of 10 the thoughtful but predictable response is, “Ask them about the last person they let go.