A great guide on how to be an effective technical leader with good and bad examples. The book goes through a lot of processes, mindsets, and values that might be considered common sense for a leader yet most don't have or do. Management as empathy, empowering people, and support.
The Manager's Path: A Guide for Tech Leaders Navigating Growth and Change
Citation (APA): Fournier, C. (2017). The Manager's Path: A Guide for Tech Leaders Navigating Growth and Change [Kindle Android version]. Retrieved from Amazon.com
1. Management 101
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One- on- one meetings (1- 1s) with your direct manager are an essential feature of a good working relationship.
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1- 1s serve two purposes. First, they create human connection between you and your manager.
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trust, real trust, requires the ability and willingness to be vulnerable in front of each other.
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Manson said it first. Jk.
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The second purpose of a 1- 1 is a regular opportunity for you to speak privately with your manager about whatever needs discussing.
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The second thing to expect from your manager is feedback.
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I encourage you to create and build a strong network of peers. One thing that early career engineers often don’t appreciate is how their current peers will turn into their future jobs. This peer group includes everyone from your schoolmates to your teammates to the people you meet at conferences and meetups. It’s OK to be a little bit shy, but most CTOs have to learn how to socialize with all sorts of people and create strong networks across companies.
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Whether you are brand new to the workplace or 20 years into your career, the onus of figuring out what you want to do, what you want to learn, and what will make you happy rests on your shoulders.
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Knowing yourself is step one. Step two is going after what you want. Bring agendas to your 1- 1s when you have things you need to talk about. When you want to work on projects, ask. Advocate for yourself. When your manager isn’t helpful, look for other places to get help. Seek out feedback, including constructive feedback on areas to improve. When that feedback comes to you, take it graciously, even when you don’t agree with it. When you are persistently unhappy, say something. When you are stuck, ask for help. When you want a raise, ask for it. When you want a promotion, find out what you need to do to get it.
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Your relationship with your manager is like any other close interpersonal relationship. The only person you can change is yourself.
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Especially as you become more senior, remember that your manager expects you to bring solutions, not problems. Try not to make every 1- 1 about how you need something, how something is wrong, or how you want something more. When you have a problem, instead of demanding that your manager solve it for you, try asking her for advice on how she might approach the problem. Asking for advice is always a good way to show respect and trust.
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Your manager can make a huge difference in your career. So, as much as you can, consider not only the job, the company, and the pay, but also the manager when you are evaluating job opportunities.
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Listening is the first and most basic skill of managing people. Listening is a precursor to empathy, which is one of the core skills of a quality manager.
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One of the early lessons in leadership, whether it is via direct management or indirect influence, is that people are not good at saying precisely what they mean in a way that others can exactly understand.
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When you’re face to face with another person, you also have to interpret his body language and the way he’s saying those words. Is he looking you in the eye? Is he smiling? Frowning? Sighing? These small signals give you a clue as to whether he feels understood or not.
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What you measure, you improve. As a manager you help your team succeed by creating clear, focused, measurable goals.
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While many people think creativity is about seeing new things, it’s also about seeing patterns that are hidden to others. It’s hard to see patterns when the only data points you have are your own experiences. Working with new people who are learning things for the first time can shed light on these hidden patterns and help you make connections you may not otherwise have made.
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Your career ultimately succeeds or fails on the strength of your network.
3. Tech Lead
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The tech lead is learning how to be a strong technical project manager, and as such, they are scaling themselves by delegating work effectively without micromanaging.
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Being a tech lead is an exercise in influencing without authority. As the tech lead I am leading a team, but we all report to the same engineering manager. So not only do I have to influence my peers, but I also have to influence up to my manager to ensure we are prioritizing the right work.
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The plan itself, however accurate it turns out, is less important than spending time on the act of planning.
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We think our management “gets” what we do as technologists. Just “read the code, man!” The software we live and breathe every day ought to seem obvious to anyone working in technology, right? But it is not. Technology managers hire the best people (hopefully), who solve very difficult problems. But they don’t “get” it all. I’ve always been surprised how grateful senior technical managers have been when I can explain some very basic modern ideas (e.g., what’s this NoSQL stuff all about, and why should I care?) to them in a nonthreatening and noncondescending way.
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premortem, an exercise where you go through all the things that could fail on the launch of this big project.
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Some of them don’t bother to tell you when they’re unhappy; they just get fed up and quit before you’ve noticed there’s anything wrong.
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When the company is doing well, and you have lots of money to pay, and there are plenty of exciting projects, life is great; but when things are stressful, you see how little power you have to make people happy.
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If one universal talent separates successful leaders from the pack, it’s communication skills. Successful leaders write well, they read carefully, and they can get up in front of a group and speak. They pay attention in meetings and are constantly testing the limits of their knowledge and the knowledge of the team.
4. Managing People
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How do you like to be praised, in public or in private? Some people really hate to be praised in public. You want to know this.
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Another approach that many experienced managers use is to help their new reports create a 30/ 60/ 90- day plan.
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For early- to mid- career hires, one aspect of onboarding will likely include contributing to the team’s onboarding documentation. A best practice in many engineering teams is to create a set of onboarding documents that are edited by every new hire as he gets up to speed. He edits the documentation to reflect processes or tools that have changed since the last hire, or points that he found confusing.
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One final piece of advice: get as much feedback as you can about the new hire’s perspective on the team in that first 90 days. This is a rare period, where a new person comes in with fresh eyes and often sees things that are hard for the established team members to see. On the other hand, remember that people in their first 90 days lack the context that the overall team possesses, so take their observations with the requisite grain of salt, and definitely don’t encourage people in this period to criticize the established processes or systems in a way that makes the existing team feel attacked.
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Regular 1- 1s are like oil changes; if you skip them, plan to get stranded on the side of the highway at the worst possible time.
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The default scheduling for 1- 1s is weekly. I encourage you to start with weekly 1- 1s and adjust the frequency only if both of you agree that this is more than you need.
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Be careful here. Some people assume that good relationships require very little attention, and spend all of their time on their bad relationships. But there are plenty of people, myself included, who feel a strong need for regular 1- 1 time even in good relationships. Just because you think things are going smoothly with this person doesn’t mean that she agrees. Don’t make the fatal error of spending all your time with your problem employees and ignoring your stars.
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Autonomy, the ability to have control over some part of your work, is an important element of motivation. This is why micromanagers find it so difficult to retain great teams. When you strip creative and talented people of their autonomy, they lose motivation very quickly. There’s nothing worse than feeling like you can’t make a single decision on your own, or feeling like every single piece of work you do has to be double- and triple- checked by your manager.
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delegation is not the same thing as abdication. When you’re delegating responsibility, you’re still expected to be involved as much as is necessary to help the project succeed.
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Practice looking for talents and achievements on your team, first and foremost. Good managers have a knack for identifying talents and helping people draw more out of their strengths. Yes, you’ll also want to look for weaknesses and areas for improvement, but if you spend most of your time trying to get people to correct weaknesses, you’ll end up with a style that feels more like continuous criticism.
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The 360 model is a performance review that includes feedback from, in addition to a person’s manager, his teammates, anyone who reports to him, and coworkers he regularly interacts with, as well as a self- review. For example, an engineer with no direct reports might solicit reviews from two other engineers on her team, the new hire she was mentoring, and the product manager she works with. Performance reviews take a long time because you need to give and receive feedback from many different people. As a manager, you then have to gather all that feedback together and summarize it for the person being reviewed.
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Use concrete examples, and excerpts from peer reviews Anonymize peer reviews, if needed. If you can’t use a concrete example to support a point, ask yourself if the point is something you should be communicating in the review. Forcing yourself to be specific will steer you away from writing reviews based on underlying bias.
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Spend plenty of time on accomplishments and strengths You want to celebrate achievements, talk about what’s going well, and give plenty of praise for good work. This goes not only for the writing process but also— and especially— for the delivery. Don’t let people skip over the good stuff in order to obsess over the areas for improvement, as many will want to do. Those strengths are what you’ll use to determine when people should be promoted, and it is important to write them down and reflect on them.
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It’s rare to see someone with true potential in a company and poor performance, though you may see slightly below middle- of- the- road performance. Often the solution to this problem is to move the person to a place where his potential can be realized.
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Don’t confuse “potential” as it might be described by a grade- school teacher with the type of potential you care about. You are not molding young minds; you’re asking employees to do work and help you grow a company. Potential, therefore, must be tied to actions and value produced, even if it’s not directly the value you expected to see produced. The sooner you can get over the disappointment that a high- potential person didn’t work out, the sooner you can identify the true high- potential stars on your team and develop them fully.
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One of the basic rules of management is the rule of no surprises, particularly negative ones. You need to understand what a person is supposed to be giving you, and if that isn’t happening, make it clear to her early and often that she is not meeting expectations. The ideal is that you know exactly what job she is supposed to be doing, and if she isn’t doing it, you can say, “You aren’t doing X, Y, and Z. Do more of those things.” Of course, like all perfect circumstances, reality is rarely so simple.
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Some managers will ignore the excuses at their peril, and lose employee after employee to an unwelcoming team that fails to onboard, coach, and give clear goals to employees. On the other hand, some managers will accept any excuse until problems can no longer be swept under the rug, and the team is furious at management’s inaction with regard to the lagging employee.
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A very good reminder to interview new employees, no matter who is in charge of their onboarding asking if they understand what they're supposed to do, know how to get help, and if their goals are clear.
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A final warning: don’t put anyone on a plan whom you wouldn’t be happy to lose. Most smart employees will take this formal warning as a sign that the organization is not a good fit for them, and leave as quickly as possible.
5. Managing a Team
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It turns out, being a good manager isn’t about having the most technical knowledge. The work of supporting people was far more important to management success.
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at this level, if you don’t stay in the code, you risk making yourself technically obsolete too early in your career. You may be on a management career path, but that doesn’t mean that you should wash your hands of technical responsibilities. In fact, I mention specifically in my engineering lead job description that I expect managers at this level to implement small features and bug fixes.
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Why bother writing any code if all you’re doing is small stuff? The answer is that you need to stay enough in the code to see where the bottlenecks and process problems are. You might be able to see this by observing metrics, but it’s far easier to feel these problems when you’re actively engaged in writing code yourself.
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stay technical until you feel that you have truly mastered what you want to learn for writing code and designing systems, and then decide if you want to switch careers into management. It’s hard to make up lost time when you stop writing code, and if you do it too early in your career, you may never achieve sufficient technical savvy to get beyond the role of middle management.
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Sometimes, teams aren’t shipping because the tools and processes they’ve been using make it hard to get work done quickly. A common example is that your team only tries to release changes to production once a week or less. Infrequent releases can hide pain points such as poor tooling around releases, heavily manual testing, features that are too big, or developers who don’t know how to break their work down. Now that you’re managing the team, start to push for the removal of these bottlenecks.
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You can make the situation worse by undermining your peers in front of your team, so even when you are frustrated with them, try to stay positive and supportive of their efforts in public.
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If your team isn’t working well together, look into creating some opportunities for them to hang out without it being all about work. Taking the whole team to lunch, leaving work early on a Friday afternoon to attend a fun event together, encouraging some PG- rated humor in chat rooms, and asking people how their lives are going are all ways to cultivate team unity.
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Developing customer empathy will also help you figure out which areas of the technology have the greatest direct impact on your customers, and that understanding will guide where you invest engineering effort.
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Agile processes usually have a retrospective meeting at the end of each two- week development sprint, where you discuss what happened during the sprint and pick a few events— good, bad, or neutral— to discuss in detail.
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Don’t rely exclusively on consensus or voting. Consensus can appear morally authoritative, but that assumes that everyone involved in the voting process is impartial, has an equal stake in the various outcomes, and has equal knowledge of the context. These conditions are rarely met on teams where each person has different levels of expertise and different roles. As when the team voted down Charles’s work, consensus can be downright cruel. Don’t set people up for votes that you know will fail instead of taking the responsibility as a manager of delivering that bad news yourself.
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As a manager, if you’re giving negative feedback in the course of a performance review, it shouldn’t be a major surprise to your employee. There may be nuances that you didn’t think through until writing the review, but if there are major problems with someone’s work, that person should know about them as soon as you notice them. If you don’t notice these problems yourself but learn about them during the review process via feedback from several peers, that’s not a good sign. It’s probably an indication that you are not paying attention, and not making space in your 1- 1s for your team to discuss problems they’re having with their colleagues.
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I was once given a test of a happy engineering team: “If you buy them pizza in the evening, will they stick around and socialize together, or will they race out the door as quickly as possible?” I have some quibbles with that. Employees with obligations that take them out of the office at a strict time every day are no more or less engaged than those who are willing to stand around and chat. The larger point, however, is still a good one. Most gelled teams have a sense of camaraderie that makes them joke together, get coffee, share lunch, and feel friendly toward one another. They may have obligations they respect, and passions outside of work, but they don’t view their team as something they’re eager to escape every day.
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The real goal here is psychological safety— that is, a team whose members are willing to take risks and make mistakes in front of one another. This is the underpinning of a successful team.
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All the evidence in the world can’t change a person who doesn’t want to change.
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Budget 20% of time for generic sustaining engineering work across the board By “generic sustaining engineering work,” I mean testing, debugging, cleaning up legacy code, migrating language or platform versions, and doing other work that has to happen. If you make this a habit, you can use it to tackle some of the midsize legacy code every quarter and get decent improvements. Cleaning up systems as you go keeps those systems easy to work in, which keeps your teams moving forward on new features.
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if you fill the schedule to 100% with feature development, expect that the feature development will quickly slow down as a result of this overscheduling.
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As you approach deadlines, it is your job to say no
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The popular doubling rule of software estimation is, “Whenever asked for an estimate, take your guess and double it.”
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it’s distracting and stressful for engineers to have a manager who’s constantly asking them for random project estimates. As the manager, you’re responsible for handling uncertainty and limiting how much of that uncertainty you expose to your team.
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Plan to work on at least a couple of features in your first 60 days. Take a specced- out feature and add it. Pair with one of the engineers on a feature he’s working on, and have him pair with you as you start working on a feature of your own. Get your code reviewed by a member of the team. Perform a release, and do a rotation of supporting the systems for at least a couple of days if support is part of the team’s responsibilities.
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How to onboard yourself
6. Managing Multiple Teams
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When you know that you need to say no, it’s better to say it quickly than to delay and drag out the process. If you have the authority to say no, and you don’t believe something should happen, do yourself a favor and don’t agonize over the process. You’ll be wrong sometimes, so when you discover that you were too quick to say no, apologize for making that mistake.
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For most engineers, the answer to these questions can be discerned by the speed and frequency with which they push code.
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In this modern era, frequency of code change is one of the leading indicators of a healthy engineering team.
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Incident management, when it becomes merely reacting to incidents rather than working to reduce them, can turn into a task that diminishes your team’s ability to do what they do best.
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It can be hard for new managers to create a shared team identity. Many of them default to an identity built around the specifics of their job function or technology. They unite the team by emphasizing how this identity is special as compared to other teams. When they go too far, this identity is used to make the team feel superior to the rest of the company, and the team is more interested in its superiority than the company’s goals. Rallying a team in this way is a shallow binding that is vulnerable to many dysfunctions:
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As a manager, be careful about focusing on your teams to the exclusion of the wider group. Even when you have been hired to fix a team, remember that the company has gotten this far because of some fundamental strengths. Before you try to change everything to fit your vision, take the time to understand the company’s strengths and culture, and think about how you’re going to create a team that works well with this culture, not against it. The trick is not to focus on what’s broken, but to identify existing strengths and cultivate them.
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What are Insync's strengths? - smart people. Seriously. - autonomy - travel and life friendly - we have a product people want and use Can build IWT to complement this by improving remote work processes. Allow people to get more done in less time, anywhere.
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“Faster” is about “the same value to the company in less total time.”
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Go home! And stop emailing people at all hours of the night and all hours of the weekend! Forcing yourself to disengage is essential for your mental health, believe me.
7. Managing Managers
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One thing that managers have to keep in mind is that part of their job is to ferret out problems proactively.
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The open-door policy is nice in theory, but it takes an extremely brave engineer to willingly take the risk of going to her boss (or especially her boss’s boss, etc.) to tell him about problems.
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The risk of relying on an open-door policy increases the further away you get from a team. This culminates in the most classic, clueless executive move of relying on office hours instead of meeting one-on-one and with teams directly, and wondering why the wonderful management staff isn’t managing to retain great talent or get things done.
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Some suggested prompts to provide the person you are holding the skip-level 1-1 with include:
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What follows are nice questions to ask anyone you're tasked to mentor/help actually.
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Whether you have experienced managers or first-timers reporting to you, there is one universal goal for these relationships: they should make your life easier. Your managers should allow you to spend more time on the bigger picture, and less time on the details of any one team.
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Spending quality time with your new managers is important, and you should expect this to be an up-front cost that pays long-term dividends for your organization.
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We talk a lot about culture fit for all hiring, but managers create subcultures, and a manager who creates an incompatible subculture can be a problem if you want your teams to work together well.
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Don’t compromise on culture fit, especially when hiring managers.
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You’re responsible for cultivating the culture of your organization, and especially when you’ve been at the company for a longer period of time, you should ensure that all of your managers respect and nurture the type of culture that you think is best for the team. If you want teams that operate with transparency, make sure the manager shares information. If you want teams that encourage exploration, make sure the manager schedules time and space for his team to explore ideas. Think about what your culture values, and help your managers embody those values while still respecting that every team will be a little bit different and every manager will have certain strengths and weaknesses that you’ll need to account for.
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The biggest difference between a management interview and an engineering interview is that managers can, theoretically, bullshit you more easily.
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The skills of a manager, as we have discussed at length, are pretty much entirely based around communication.
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Any manager you hire should role-play a few 1-1s as part of the interview process. One of the best ways to do this is by asking the people who would report to the new manager to interview her by asking her to help with problems they have right now, or have had in the recent past.
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a good manager — even without a full understanding of the people or projects involved — should have good instincts for questions to ask and suggested next steps that might improve matters.
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A good technical manager will know what kinds of questions to ask that tease out the core issues and guide the group to a solid consensus.
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Culture fit is so important in managers because they shape their teams to their culture, and they hire new people based on their cultural ideas.
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most new hires act in self-interest until they get to know their colleagues, and then they move into group interest.
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If you can screen for managers who naturally gravitate toward the cultural values that your company already possesses, they are more likely to make this shift quickly than managers who have very different personal beliefs.
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Do thorough reference checks for anyone you’re planning to bring on board, even if you’ve worked with that person before. Ask the references to describe the ways that the person succeeds as well as the ways she fails. Ask them if they would work with or for this person again. Ask them what they love about the person, and what drives them crazy.
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Ask the person to teach you about the work she does. Sit down with her and treat her as if she were your mentor, the person to teach you the ropes for this job. Whether it’s QA, design, product management, or technical operations, ask lots of questions, but in an open way. Make it clear to the person that your goal is to understand what she does so that you’re capable of appreciating it better.
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Managing teams is a series of complex black boxes interacting with other complex black boxes. These black boxes have inputs and outputs that can be observed, but when the outputs aren’t as expected, figuring out why requires trying to open them up and see what’s going on inside. And, just as sometimes you don’t have the source code, or the source code is in a language you don’t understand, or the logfiles aren’t readable, the black boxes of teams can resist yielding their inner workings.
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Good meetings have a heavy discussion element, where opinions and ideas are drawn out of the team. If the meetings are overscripted, so that no real conversation can take place, it stifles that creative discussion. If people are afraid to disagree or bring up issues for fear of dealing with conflict, or if managers always shut down conflict without letting disagreements air, this is a sign of an unhealthy team culture.
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Your presence changes the team’s behavior and may hide the problem you’re trying to find, in the same way that a log statement can cause a concurrency issue to be magically erased, at least for some time.
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Be Curious The pursuit of why when it comes to organizational problems is the thing that gives you patterns to match on, and lessons to lead with.
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Estimates are often useful even if they aren’t perfectly accurate because they help escalate complexity to the rest of the team.
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We can’t predict the future perfectly, but teaching our teams how to hone their instincts about complexity and opportunity is a worthy goal.
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Especially in smaller companies, it’s hard to get people to commit a year in advance to the work that will be done for the next year.
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Strategies for Handling Roadmap Uncertainty
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Think about how to break down big projects into a series of smaller deliverables so that you can achieve some of the results, even if you don’t necessarily complete the grand vision.
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Dedicate 20% of your team’s schedule to “sustaining engineering.” This means allowing time for refactoring, fixing outstanding bugs, improving engineering processes, doing minor cleanup, and providing ongoing support. Take this into account in every planning session.
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Managers who don’t stay technical enough sometimes find themselves in the bad habit of acting as a go-between for senior management and their teams. Instead of filtering requests, they relay them to the team and then relay the team’s response back up to management. This is not a value-add role.
8. The Big Leagues
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You’re capable of making hard decisions without perfect information and willing to face the consequences of those decisions.
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You’re capable of understanding the current landscape of your business, as well as seeing into its many potential futures. You know how to plan for the months and years ahead so that your organization is best suited to handle those potential futures and capture opportunities as they come along.
Highlight (yellow) - Staying Technically Relevant > Location 3251
You understand how to disagree with a decision and commit to deliver on it even though you disagree.
Highlight (yellow) - Staying Technically Relevant > Location 3258
The strong senior leader is capable of synthesizing large quantities of information quickly, identifying critical elements of that information, and sharing the information with the appropriate third parties in a way they will be able to understand.
Highlight (yellow) - Staying Technically Relevant > Location 3261
Reminding people of their commitments by asking questions instead of giving orders. It’s hard for a leader of a large team to forcefully guide that team in any direction, so instead rely on nudging members of the team to keep the overall organization on track.
Highlight (yellow) - Staying Technically Relevant > Location 3265
Taking conflicting perspectives and incomplete information and setting a direction, knowing that the consequences of a poor decision will impact both you and possibly the whole team. If making decisions were easy, there would be much less need for managers and leaders. However, as anyone who has spent a lot of time managing can tell you, making decisions is one of the most draining and stressful parts of the job.
Highlight (yellow) - Staying Technically Relevant > Location 3269
Showing people what the values of the company are. Showing up for your commitments. Setting the best example for the team even when you don’t feel like it.
Highlight (yellow) - Staying Technically Relevant > Location 3277
my job wasn’t to be the smartest person in the room. It wasn’t to be “right.” Rather, my role was to help the team make the best possible decisions and help them implement them in a sustainable and efficient way.
Highlight (yellow) - Staying Technically Relevant > Location 3279
A good leader shapes technology discussions to inject the strategic objectives and take into consideration the nontechnical implications of a technical decision. It’s not about being the lead engineer, chasing the latest language or framework, or having the shiniest technology. It’s about building a team with the tools and attributes to build the best possible product for our customers.
Highlight (yellow) - What’s a VP of Engineering? > Location 3339
Often a great VP of Engineering is described as having a good “ground game.” This person is capable of dropping into the details and making things happen at a low level. While some CTOs will do this, if there’s both a CTO and a VP of Engineering, the VP is usually the one pushing the execution of ideas, while the CTO focuses on larger strategy and the position of technology within the company.
Highlight (yellow) - What’s a CTO? > Location 3365
Let’s start by talking about what a CTO is not. CTO is not an engineering role. CTO is not the top of the technical ladder, and it is not the natural progression engineers should strive to achieve over the course of their careers. It’s not a role most people who love coding, architecture, and deep technical design would enjoy doing. It follows that the CTO is not necessarily the best engineer in the company.
Highlight (yellow) - What’s a CTO? > Location 3375
the CTO should be the strategic technical executive the company needs in its current stage of evolution. What do I mean by “strategic”? The CTO thinks about the long term, and helps to plan the future of the business and the elements that make that possible. What do I mean by “executive”? The CTO takes that strategic thinking and helps to make it real and operational by breaking down the problem and directing people to execute against it.
Highlight (yellow) - What’s a CTO? > Location 3383
the CTO must understand where the biggest technical opportunities and risks for the business are and focus on capitalizing on them. If he is focused on recruiting, retention, process, and people management, that’s because it’s the most important thing for the technology team to focus on at the time. I present this idea in contrast to the notion that the CTO should focus on purely technical issues, as the “chief nerd.”
Highlight (yellow) - What’s a CTO? > Location 3398
You can’t give up the responsibility of management without giving up the power that comes with it.
Highlight (yellow) - What’s a CTO? > Location 3427
“Wanting to be a CTO (or VP of Engineering) is like wanting to be married. Remember that it’s not just the title, it’s also the company and the people that matter.” Titles are definitely not everything.
Highlight (yellow) - Changing Priorities > Location 3444
Do you know what the top priority is? Do your teams know what it is? Do the developers on those teams know what it is? Sometimes the answer to this question is simply a matter of communication. You don’t know what the top priority is, or you didn’t communicate it clearly and urgently to your management team, and they didn’t communicate it clearly and urgently to their development teams. You didn’t explicitly go through the list of things in flight and kill or postpone work in order to make room for this priority. You need to do that, if it’s truly urgent. Saying something is top priority is one thing, but making the actual tradeoffs on the schedule to get people moving on it is completely different.
Highlight (yellow) - Changing Priorities > Location 3453
If you think that the team needs to finish their current work before shifting to the new top priority, you must communicate that clearly.
Highlight (yellow) - Changing Priorities > Location 3459
The more senior the management and leadership position you take in a company, the more the job becomes making sure that the organization moves in the direction it needs to move in, and that includes changing direction when needed.
Highlight (yellow) - Changing Priorities > Location 3464
never underestimate how many times and how many ways something needs to be said before it sinks in. Communication in a large organization is hard. In my experience, most people need to hear something at least three times before it really sinks in.
Highlight (yellow) - Setting the Strategy > Location 3494
Do a Lot of Research I started by considering the team, the technology we had currently built, and the company. I asked the engineering team where their pain points were. I asked several executives in various areas where they expected growth to come from in the future. Then, I asked myself several questions. I considered where the scaling challenges were now, and where they might be in the future. I examined the engineering team and found its productivity bottlenecks. I studied the technology landscape and wondered how it might change in the near future, especially as it pertained to personalization and mobile development.
Highlight (yellow) - Setting the Strategy > Location 3499
Combine Your Research and Your Ideas
Highlight (yellow) - Setting the Strategy > Location 3501
I used the data to come up with a rough idea for a possible future. I spent some time sitting alone in a room with a whiteboard or paper and drawing out the systems in place at our company, slicing and dicing the systems and teams across various common attributes.
Highlight (yellow) - Setting the Strategy > Location 3518
As a speaker, I’ve been trained to make slide decks that are sparse, in support of an audience that listens closely. This board needed a deck that was very dense with information. It’s not uncommon for company boards to read through the slide deck before a meeting, so that the meetings can be focused more on details than on presentations. I didn’t understand this at the time, so I wasted a lot of energy trying to make something that wasn’t informative on paper. Lesson learned.
Highlight (yellow) - Setting the Strategy > Location 3523
I like to describe technology strategy for product-focused companies as something that “enables the many potential futures of the business.” It’s not just a reactive document that tries to account for current problems, but it anticipates and enables future growth. If you’re in a product-focused business, this is the heart of your technology strategy. It’s not about actually deciding the product’s direction, but about enabling the larger roadmap to play out successfully.
Note - Setting the Strategy > Location 3524
Increase optionality of the business! Why not strive to make Insync antifragile?
Highlight (yellow) - Challenging Situations: Delivering Bad News > Location 3545
Don’t blast an impersonal message to a large group.
Highlight (yellow) - Challenging Situations: Delivering Bad News > Location 3547
the second-worst way to deliver this message, especially to a large group that you know won’t be happy, is with them all in a room at once.
Highlight (yellow) - Challenging Situations: Delivering Bad News > Location 3551
Do talk to individuals as much as possible. Instead of impersonal or group-based communication, try your best to talk to people individually about the news. Think about the people who are going to have the strongest reaction, and try to tailor the news to them. Give them space one-on-one to react, to ask questions, to get it straight from you.
Highlight (yellow) - Senior Peers in Other Functions > Location 3609
Senior leaders, more than any other group in a company, must actively practice first-team focus (introduced in Chapter 6). They are dedicated first and foremost to the business and its success, and secondly to the success of their departments as a way of contributing to the overall business success.
Highlight (yellow) - Senior Peers in Other Functions > Location 3615
So what does it feel like to work well with cross-functional peers? To start with, you let them own their areas, and they let you own yours.
Highlight (yellow) - Senior Peers in Other Functions > Location 3617
Giving her respectful deference when it comes to her turf is fundamental. If you disagree with her management style or application of her skill set in places where it isn’t directly affecting your team, you treat that disagreement like you would treat a good friend who happens to date people you don’t love. Unless she asks for your advice, try to stay out of it as much as possible, and certainly approach any disagreement you choose to discuss with kindness. Be willing to let those differences lie.
Highlight (yellow) - Senior Peers in Other Functions > Location 3626
In The Five Dysfunctions of a Team, Lencioni notes that absence of trust is a fundamental dysfunction. In this case, what’s missing is the trust that your peers are actively trying to do their best for the organization, that they are not trying to manipulate situations, undermine you, or otherwise get their own way.
Highlight (yellow) - Senior Peers in Other Functions > Location 3636
It can’t be said strongly enough: your peers who are not analytically driven are not stupid. On the flip side, we undermine ourselves when we fail to talk so that nontechnical peers can understand what we’re saying. Throwing out jargon to people who aren’t familiar with it — and who don’t even need to be familiar with it — makes us look stupid to them. We therefore need to figure out how to communicate the complexity of our work in a way that an intelligent but nontechnical peer can understand.
Note - Senior Peers in Other Functions > Location 3640
Highlight (yellow) - Senior Peers in Other Functions > Location 3640
The final element of this first-team trust and respect is the cone of silence. Disagreements that happen in the context of the leadership team don’t exist to the wider team. Once a decision is made, we commit to that decision and put on a united front in front of our engineering teams and anyone else in the company. It’s easier said than done — I’ve struggled frequently with hiding my own disagreements with my peers. Letting go when you don’t get your way, especially when you don’t feel that your objections have been heard, is hard, and it will have to happen from time to time.
Highlight (yellow) - Senior Peers in Other Functions > Location 3644
The middle ground, openly disagreeing with your peers, does nothing but make the situation worse for everyone.
Highlight (yellow) - The Echo > Location 3654
If you shift your mindset successfully, you will probably start to detach socially a little bit from the overall organization. When there’s a happy hour, you go for a drink and then leave the team to socialize. Closing down the bar with your whole organization will tend to have bad consequences for everyone, so I strongly advise that you avoid doing that with any regularity. Socializing heavily with your team outside of working hours is a thing of the past.
Note - The Echo > Location 3657
Remember this is only for super high level executives. This is kind of a necessary thing apparently but I don't like it.
Highlight (yellow) - The Echo > Location 3657
First, if you don’t detach, you’re likely to be accused of playing favorites. In fact, you probably will play favorites if you maintain very strong social ties with people who report up to you on the team. This hurts, but it is true.
Highlight (yellow) - The Echo > Location 3660
Second, you need to detach because you need to learn how to lead effectively, and leading effectively requires people to take your words seriously. The downside of leading at this level is that with a throwaway comment, you can cause people to change their whole focus. This is bad, unless you’re aware of that and actually make use of it appropriately. If you try to maintain a “buddy” image, your reports are going to have a hard time distinguishing between their buddy thinking out loud and their boss asking them to focus on something.
Highlight (yellow) - The Echo > Location 3663
Detaching also means being thoughtful about where you spend your time. As the senior leader, you’ll often suck all of the oxygen out of a room. Your mere presence will change the tone and structure of meetings you attend. If you aren’t careful, you’ll end up pontificating and change the direction of a project because you had a great brainstorm in a one-off meeting you decided to drop into. It sucks! I know! It’s frustrating that you can no longer be one of the team whose ideas are there to be evaluated and potentially rejected — but you are no longer that person.
Highlight (yellow) - The Echo > Location 3667
If you’ve ever worked with anyone who overlapped with Steve Jobs at Apple, chances are you’ve heard that person talk about “Steve” and the impact he had on some project he or she was working on. Apple employees used the specter of Steve to argue for and against decisions, as a moral compass for what the organization should be doing.
Note - The Echo > Location 3670
Companies echo values held by leadership.
Highlight (yellow) - The Echo > Location 3674
You’re going to be part of hard decisions that will impact the whole business, and these decisions may cause you a great deal of stress. It won’t be appropriate to discuss these decisions with other people at the company. It’s deeply tempting to rant to those people you consider friends in your reporting team about the challenges of your position, but this is a bad idea. As their leader, you can easily undermine their confidence by sharing worries that they can’t do anything to mitigate. Transparency that may have been harmless or even possibly helpful at lower levels of management can become incredibly damaging to the stability of your team at this level.
Highlight (yellow) - The Echo > Location 3682
As you grow more detached from the team, it can be easy to start to dehumanize people and treat them like cogs. People can tell when that’s happening, when their leaders stop caring about the individuals in the organization. They’re less likely to feel committed to giving their all, to taking risks and pushing through hard circumstances, if they feel that no one really cares about them personally.
Highlight (yellow) - The Echo > Location 3686
You’ll have to make hard calls as an executive, but your team deserves a leader who’s able to be kind even while making those hard calls.
Highlight (yellow) - The Echo > Location 3688
You’re a role model. What kind of leaders do you want to develop? What kind of legacy do you want to leave?
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3695
Michael is also a good leader: technical, charismatic, capable of making decisions and getting things done. He’s also good at keeping his cool. Instead of getting tense and angry, he gets curious when things don’t seem to be going well. His first instinct is to ask questions, and these questions often cause the team to come to their own realizations about what’s going wrong.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3705
People were afraid to take risks, and if you want to have an independent team capable of setting their own direction and pushing themselves, you need them to take risks.
Note - Ruling with Fear, Guiding with Trust > Location 3706
If your goal is a decentralized company full of independent, initiative-taking individuals, psychological safety is the best bet.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3712
Note - Ruling with Fear, Guiding with Trust > Location 3712
Small talk with people, ask about their lives. This is good because it's easy for me.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3717
Most people are scared to take risks in front of people they think will reject them if they fail.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3719
Apologize. When you screw up, apologize. Practice apologizing honestly and briefly. “I’m sorry, I should not have yelled at you and I have no excuse for my bad behavior.”“I’m sorry, I did not listen to you and I know I contributed to your frustration at this situation.”“I’m sorry, I made a mistake when I neglected to tell you about Bob.” Apologies don’t need to be drawn-out affairs. A short apology that takes responsibility for your role in creating a negative situation or hurting another person is all that is necessary. If you go too long, it often turns into an excuse or a distraction. The goal with apologizing is to show people that you know your behavior has an impact on others, and to role-model for them that it’s OK to make a mistake but that you should apologize when you hurt other people. You’re showing the team that apologizing doesn’t make you weaker — it makes the whole team stronger.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3726
Get curious. When you disagree with something, stop to ask why. Not every disagreement is an undermining of your authority. When you take the time to seek out more information about something with which you disagree, you’ll often find that you were reacting to something you didn’t really understand.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3730
When we attack, many people evade or shut down, and they learn that it’s a good idea to hide information from us so we won’t attack or criticize them. When you get curious and learn how to turn that disagreement into honest questioning, you can learn more about other perspectives on the issue because your team will open up. This is how you get the most information out and help everyone make the best decisions.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3733
Learn how to hold people accountable without making them bad.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3735
How do you measure success? Does the team have the capabilities needed to succeed? Are you providing feedback along the way?
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Think of the times you’ve made a person or a team out to be “bad” because they failed. Are you holding yourself accountable for setting them up for success? When everything is clear and you’ve all done your best, I bet you’ll find that accountability comes with far less character judgment, because you all clearly see what has happened.
9. Bootstrapping Culture
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3842
We don’t set up systems because structure and process have inherent value. We do it because we want to learn from our successes and our mistakes, and to share those successes and encode the lessons we learn from failures in a transparent way. This learning and sharing is how organizations become more stable and more scalable over time.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3848
it’s hard to learn if you don’t have a basic theory to test, and you don’t set out to prove or disprove hypotheses about that theory.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3868
One of the greatest writings about organizational politics is a piece called “The Tyranny of Structurelessness” by Jo Freeman. While the article is about early feminist/anarchist collectives, Freeman’s insights apply equally well to startup culture. Pretending to lack structure tends to create hidden power structures resulting from the nature of human communication and the challenges of trying to scale that communication. Interestingly, Freeman describes a set of circumstances in which the unstructured group can, in fact, work:
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3882
the number of interactions necessary to involve everybody increases geometrically with the number of participants. This inevitably limits group participants to about five, or excludes some from some of the decisions. Successful groups can be as large as 10 or 15, but only when they are in fact composed of several smaller subgroups which perform specific parts of the task, and whose members overlap with each other so that knowledge of what the different subgroups are doing can be passed around easily.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3890
Forcing the team to be collocated lowers communication barriers.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3900
Structure is how we scale, diversify, and take on more complex long-term tasks. We do it to our software, we do it to our teams, and we do it to our processes.
Note - Ruling with Fear, Guiding with Trust > Location 3901
This is a mind-opener for me, that structure enables scale.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3903
Nothing is more ridiculous than a small team with a rigid hierarchy.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3907
it’s more common in small companies to see structure come too late. The problems creep up slowly. One person gets used to making all of the decisions and changing his mind frequently. This strategy works fine when it’s just him and a couple of others. But when he keeps doing it with a team of 10, a team of 20, a team of 50, what you start to see is a high degree of confusion and wasted effort. The cost to change his mind becomes more and more expensive.
Highlight (yellow) - Ruling with Fear, Guiding with Trust > Location 3911
On describes the earliest startup as like driving a race car. You’re close to the ground, and you feel every move you make. You have control, you can turn quickly, you feel like things are moving fast. Of course, you’re also at risk of crashing at any moment, but you only take yourself down if you do. As you grow, you graduate to a commercial flight. You’re farther from the ground, and more people’s lives depend on you, so you need to consider your movements more carefully, but you still feel in control and can turn the plane relatively quickly. Finally, you graduate to a spaceship, where you can’t make quick moves and the course is set long in advance, but you’re capable of going very far and taking tons of people along for the ride.
Highlight (yellow) - Assessing Your Role > Location 3937
John Gall’s book Systemantics:1 A complex system that works is invariably found to have evolved from a simple system that worked. A complex system designed from scratch never works and cannot be patched up to make it work. You have to start over with a working simple system.
Highlight (yellow) - Assessing Your Role > Location 3948
Using failure to guide evolution lets you apply structure at the right level. If a failure is occurring in only one part of the system — say, on one team — you can try to address the structure on that team without necessarily changing the larger structure.
Highlight (yellow) - Assessing Your Role > Location 3966
When every new hire slows the team down for months because there is no onboarding process, that is a failure due to lack of structure. When people regularly leave the company because they have no path to advancement or career growth, that is a failure due to lack of structure. The third time you have a production outage because someone logged directly into the database and accidentally dropped a critical table, that is a failure due to lack of structure.
Highlight (yellow) - Creating Your Culture > Location 3974
Culture is how things get done, without people having to think about it. Frederick Laloux, Reinventing Organizations: A Guide to Creating Organizations Inspired by the Next Stage of Human Consciousness
Highlight (yellow) - Applying Core Values > Location 4023
reinforce your culture by rewarding people for exhibiting its values in positive ways. People can share core value stories at company all-hands meetings. At our technology department all-hands meetings, we would have people give shoutouts to each other for “keeping it dope” and going above and beyond.
Highlight (yellow) - Applying Core Values > Location 4027
The stories that we tell as a community bond us together.
Highlight (yellow) - Applying Core Values > Location 4037
Using the core values to coach people in areas where they are misaligned can help you articulate what otherwise may feel like just ambiguous friction.
Highlight (yellow) - Applying Core Values > Location 4038
use this as part of your interview process. Remind your interviewers of the values of the team, and ask them to look out explicitly for places where the interviewee seems to match or collide with these values.
Highlight (yellow) - Creating Cultural Policy > Location 4060
there comes a time for adding structure, and that time is usually when things are failing.
Highlight (yellow) - Creating Cultural Policy > Location 4082
What works for one company — a company that is creating a certain type of product or working in a certain industry — will not always translate well to another company, even if the companies have a lot of things in common.
Highlight (yellow) - Writing a Career Ladder > Location 4150
Senior management is generally a volume-driven need. You need enough managers to manage the people you have on the team.
Highlight (yellow) - Cross-Functional Teams > Location 4194
Call them what you want —“pods” or “squads” or “pillars”— but cross-functional product development groups are a popular structure for a good reason. By putting everyone who is needed to make a project successful together in one group, you help the members of those teams focus on the project at hand, and you make the communication for the whole group much more effective.
Highlight (yellow) - Cross-Functional Teams > Location 4197
Conway’s Law is often cited in discussions of this kind of structure. It states: “Organizations which design systems…are constrained to produce designs which are copies of the communication structures of these organizations.”
Note - Cross-Functional Teams > Location 4199
This is one of the big takeaways. Improve communication of an organization, the rest follows.
Highlight (yellow) - Developing Engineering Processes > Location 4253
Think of process as risk management. As your teams and systems grow, it’s almost impossible for any one person to keep the systems in her head. Because we have a bunch of people coordinating work, we evolve processes around that work coordination in order to make risks obvious.
Highlight (yellow) - Developing Engineering Processes > Location 4262
There’s a saying in politics that “a good political idea is one that works well in half-baked form,” and the same goes for engineering processes.
Highlight (yellow) - Developing Engineering Processes > Location 4340
The most important lesson I’ve learned is that you have to be able to manage yourself if you want to be good at managing others. The more time you spend understanding yourself, the way you react, the things that inspire you, and the things that drive you crazy, the better off you will be.
Highlight (yellow) - Developing Engineering Processes > Location 4342
Great managers are masters of working through conflict. Getting good at working through conflict means getting good at taking your ego out of the conversation.
Highlight (yellow) - Developing Engineering Processes > Location 4347
Learning to recognize the voice of your ego is one of the benefits of meditation,
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Some of my favorite resources include the podcasts on tarabrach.com and the writings of Pema Chödrön.
Highlight (yellow) - Developing Engineering Processes > Location 4352
One other trick I use to get away from my ego is curiosity. I also have a daily habit of writing a page or two of free-flow thoughts every morning, to clear my mind and prepare for the day. I always end with the mantra “Get curious.”