This topic comes first, because the following articles offer great frameworks/definitions for leadership.
Actions Reflect Leadership — Not Words - by Claire Lew. Takeaway: “Studies have found that the biggest reason for why people don’t speak up at work is because they believe it is futile. Employees don’t think anything will happen with their feedback … so they don’t give it … If you want honest feedback, you must act on the feedback you’ve gotten in some way. Prove to employees it’s worth their effort to be honest with you.”
Average Manager vs. Great Manager, Explained in 10 Sketches - by Julie Zhuo (VP Product Design, Facebook). Go look at these, they’re humorous and poignant. It’ll only take a minute.
Be Yourself, but Carefully - by Lisa Rosh and Lynn Offerman. Takeaway: “Sharing details about your life can be a valuable way to build relationships in the workplace. But self-disclosures can also lead to oversharing, which can do more harm than good in the office.”
The Best Leaders Are Constant Learners - HBR article by Kenneth Mikkelsen and Harold Jarche. Takeaway: “Leaders that stay on top of society’s changes do so by being receptive and able to learn.”
The Best Management Is Less Management - by Michael Useem and Harbir Singh. Takeaway: “[W]hen time is limited and stakes are high, the most effective leaders rely on their ranks to do what they do best. These leaders empower people to use their expertise to solve problems and achieve goals. They also enable managers at every level of the organization to think like CEOs, making decisions with a large degree of autonomy. There’s a clear system in place for monitoring progress, but it doesn’t impede people from getting the work done. This is strategic leadership at its best, and in a moment of crisis it becomes all the more critical.”
CEOs Should Stop Thinking that Execution Is Somebody Else’s Job; It Is Theirs - by Roger L. Martin. Takeaway: “1. Make only the set of choices you are more capable of making than anyone else. 2. Explain the choice that has been made and the reasoning behind it. 3. Explicitly identify the next downstream choice. 4. Assist in making the downstream choice, as needed. 5. Commit to revisit and modify the choice based on downstream feedback.”
Developing the Leader Within You 2.0 - by John C. Maxwell. Takeaway: “…leaders are not born, they’re made”; “Good leaders don’t just resolve the issue to get it off their plates quickly for the sake of their own comfort. They help create solutions that take their people and their organization forward and put them in a better position than they were in before they experienced the problem.”
The Difference Between Amateurs and Professionals - by Farnam Street. Takeaway: a series of bullet points identifying the differences. Examples: “Amateurs give up at the first sign of trouble and assume they’re failures. Professionals see failure as part of the path to growth and mastery; Amateurs don’t have any idea what improves the odds of achieving good outcomes. Professionals do.”
Don’t Try to Be the “Fun Boss” — and Other Lessons in Ethical Leadership - by Kimberly Nei and Darin Nei. Takeaway: Be humble, not charismatic; be steady and dependable; remember that modesty is the best policy, balance analysis with action, be vigilant — vulnerability increases over time.
Effective Leaders - by Brendan Ward. Takeaway: effective leaders set, communicate, and reinforce tangible goals toward broader impact. They set priorities and act strategically, share the opportunity to lead, and listen more than they talk. They are highly introspective, actively seek feedback, grow from their mistakes, and are constantly learning across a broad range of topics.
Effective Leadership Styles for Scrum Masters - by Ben Linders. Takeaway: This post provides an overview of many effective leadership styles that Scrum masters can learn from and apply when working in agile teams, so that their teams can deliver value. Servant leadership alone is not enough.
Engineering Leadership Principles with Oren Ellenbogen (podcast) - by Christian McCarrick. Takeaway: A chat with the editor of Software Lead Weekly/the author of Leading Snowflakes.
Etsy Lessons - by Lara Hogan. Takeaway: a collection of wisdom Hogan (now at Kickstarter) collected over her years at Etsy, about topics ranging from rethinking diversity hiring to how to deal with feeling shaky as a leader.
Flavors of Engineering Management - by Benjamin Encz. Takeaway: Encz has identified three types of leader — “tech lead engineering manager (typically technology stack focused team, still lots of coding, leadership via technical merits, good for recruiting); product team engineering manager (team spans multiple technology stacks, can touch on product management and project management, needs to think more about cross-functional interactions); people engineering manager (very focused on people aspects, has strong individual contributors who drive a lot of decision making, hiring, etc., can support larger team).”
From College Dropout to CEO of a Billion-Dollar Company: 3 Leadership Lessons from the Founder of Hootsuite - by Catherine Clifford. Takeaway: Start with the why, communicate often, and allow for facetime.
The Future of Management - by Esko Kilpi. Takeaway: “The future is accordingly described as goals and performance targets. Following this logic, the role of management is to control the movement into a chosen future. But what management really is, is about reduction of anxiety. Anxiety levels in the experiences of individuals most often depend on the perceived level of control people have over themselves and their environment. This drives our need to believe that someone is, or should be, in control.”
Good Leaders Are Good Learners - by Lauren A. Keating, Peter A. Heslin and Susan J. Ashford. Takeaway: “[R]esearch on leadership development shows that leaders who are in learning mode develop stronger leadership skills than their peers.” Being experienced helps, but isn’t enough.
Google Employees Weighed in on What Makes a Highly Effective Manager. Technical Expertise Came in Dead Last - by Michael Schneider. Takeaway: Tech expertise is worth little if a manager is not committed to communicating clearly/effectively, developing people and removing obstacles so they can get things done.
Hallmarks of a Good Technical Leader - by Brian Anderson and Camille Fournier. Takeaway: “Good technical leaders are capable of understanding systems through many different lenses. They understand that their companies are shaped by people and technologies and processes, and they’re capable of investigating each of these areas to understand how it contributes to the current success or challenges of the team. Good technical leaders have a strong sense of technical empathy, which helps them appreciate the challenges their engineers are facing, even if those engineers are working on problems that the leader has never personally written code to solve. Finally, good technical leaders have good technical judgment.”
High-Performing Teams Need Flexible Leaders - by Srikar Doddi. Takeaway: Offers insights into how to change your style based on the needs of the team. Takeaways: Always be explicit with how you expect each individual in the team to behave and the results you’d like them to achieve, and hold everyone accountable. That starts with you, and the example you set to everyone else. Having a well-articulated vision and expectation will enable flexibility of style and methods to reach a highly performant execution. See also, “Why the rise of Amazon means the end of Walmart.”)
How Do I Manage People? - by Lenny Markus. Takeaway: Based around questions posed in a Twitter thread kicked off by Charity Majors, this article offers a well-rounded view of all aspects of a manager’s duties, along with personal insights from the author.
How Much to Manage (“Management Energy Units”) - by Steven Sinofsky. Takeaway: Discusses the various level-directions of management (down to reports, up to your boss, sideways to your peers), as well as how much time an individual level should generally be spending on them vs “work”. Make sure you are spending the right amount of time managing in the right areas.
How Strong Is Your Leadership Toolkit? - by Alex Saez. Takeaway: Establish strong relationships, understand employee needs, and possess the appropriate “hard” and “soft” skills.
How to Lead a Team (podcast) - by Simon Sinek. Fun trivia: Joe Goldberg, the originator of this Awesome list, realized through this podcast that “You can’t manage people, you can only lead them. You can only manage processes.”
I’ve Interviewed Over 300 Entrepreneurs–Here’s Their Most Counterintuitive Advice - by Jenna Abdou. Takeaway: Specialize in more stuff than you think you have to; share what makes you tick, then have your team do the same; forget the competition, and let things happen instead of always making them happen.
In Just 8 Words, Uber’s New CEO Gave a Master Class in Leadership - by Jessica Stillman. Takeaway: Uber CEO Dara Khosrowshahi, who took over from Travis Kalanick, seems the reverse of his predecessor by expressing vulnerability. In his sign-off, he wrote to his team: “I have to tell you I am scared.” Vulnerability is an underrated leadership skill.
The Key to Employee-Empowering Leadership - by Ed Krow, an HR consultant. Takeaway: Empower people, let go, learn to take calculated risks, create incentives/compensation.
Lazy Leadership: Thinking of Your Org as a Machine - by Andrew Wilkinson. Takeaway: “It’s about spending time on what matters and what you’re good at, then leaving everything else to your team. Giving up on the idea that you have to drive yourself into the ground in order to run a successful company, and thinking about your business as a machine that you design and optimize, instead of becoming a worn out cog within.”
Lead at Your Best - by Joanna Barsh and Johanne Lavoie. Takeaway: A five-step approach that focuses on raising self-awareness to enhance leadership. Find your strengths; practice the pause; forge trust; choose your questions wisely; and make time to recover.
Leadership FAQ - Essay by Henry Ward that offers a concise list of essential questions with clear, thought-provoking answers. For example: “How do I give negative feedback? By being curious..”
Leadership Is a Quality That You Can Teach Yourself - by Christian Bonilla. Takeaway: “To be a successful leader, you have to learn to consider how your work affects others, and how to work with people to get things done. The higher up you go in any organization, the harder it is to get things done on your own. So invest in building relationships every step of the way, and you’ll have more people who want to see you succeed when your time comes.”
Leadership Nudges - by David Marquet. Takeaway: short, digestible videos about intent-based leadership, from being a “know all, tell not” leader to thinking long-term.
Love Being a Lead - by Mikio L. Braun. Takeaway: Love being a lead boils down to “Everything you do is about helping those whom you lead do their work.
Management Philosophy - by Gordon Radlein. Takeaway: A five-point philosophy: Trust above all else, feedback, give space to succeed or fail, find the right balance of process, and always have a vision.
The Most Important Metric You’ll Ever Need - by Barry O’Reilly. Takeaway: “ask your team what their rate of learning is”—this, as Software Lead Weekly’s Oren Ellenbogen notes, “is actually a great question to ask on your 1:1s and company surveys.”
On Being a Bad Manager - by Jason Fried. Takeaway: “Observation is no substitute for doing.”
On Being an Engineering Manager - by Rui Peres. Takeaway: Filter out the noise, be optimistic, prioritize company/team/individual, and other tips.
On Leadership vs Management - by dbsmasher. Takeaway: a “flight of ideas” about the ability of all members of an organization to be leaders, and what to do to cultivate that mindset (and what not to do.
Our 6 Must Reads for Scaling Yourself as a Leader - by FirstRound. Takeaway: Comes with outside resources that support six planks. Understand and engineer your calendar around your energy (physical, emotional and mental); say “not now, not ever” using “no” templates; avoid decision debt — create process and structure that doesn’t need you; challenge the “when” to make speed a habit; beat burnout with prioritization and communication techniques; and balance internal and external movitations to see yourself and decisions more clearly.
The Principles of Quantum Team Management - by James Everingham. Takeaway: “Setting up your team the way you would set up a machine can give you a ton of leverage — as long as you realize how complicated and unpredictable the people in that machine can be.”
Scale-up Leadership Lessons I’ve Learned Over 9 Years as HubSpot’s CEO - by Brian Halligan. Takeaway: Different skills are necessary when you’re leading a scale-up and not a startup. These are: using employee Net Promoter Scores as manager thermometers; Enterprise Value > Team Value > Self Value; be the Chief Pothole Prevention Officer and the Chief Explanation Officer; everything needs to work right almost all the time; you have to make decisions; make them the right decisions instead of the most popular ones; do things right instead of fast; balance the pressure for short-term results while making long-term investments; document strategy.
Self Leadership for Agility - by Ben Linders. Takeaway: a chat with Christopher Avery, who advocates the belief that “leading others starts with leading yourself.”
Simon Sinek: Leaders Eat Last (video) - For a detailed summary by Joe Goldberg, go here.
Six Crucial Behaviors Of Collaborative Leaders - by Carol Kinsey Goman. Takeaway: Silo-busting, building trust, aligning body language, promoting diversity, sharpening “soft” skills, and creating psychological safety are the six behaviors leaders need.
6 Lessons from Lara Hogan on Humanizing Management - by GitPrime. Takeaway: Recalibrate what success looks like; learn what makes the individual grumpy, and how to know when they’re grumpy, how your report prefers feedback and recognition, and the person’s goals and needs (from you, from their team, etc.); use her three-part feedback behavior path; manage through crisis; optimize for long-term relationships, and develop your managers.
Six Recipes for Software Managers - by Adam Buggia. Takeaway: covers six basics of effective leadership—1:1’s, team surveys, psychological safety, building resilient teams, informing your department, and self-improvement—and provides “recipes” to achieve them.
6 Things Great Leaders Do Differently - by Travis Bradberry. Takeaway: They’re kind without being weak or expecting something in return, strong without being harsh, confident without being cocky, stay positive but remain realistic, are role models not preachers, and will do anything for their teams.
A Tech Lead Manifesto - by Sam Newman. Takeaway: a very pithy summary of what a tech lead should and should not do. Newman believes tech leads should continue coding, but should not write all the “hard” code.
10 Principles of Strategic Leadership - by Jessica Leitch, David Lancefield, and Mark Dawson. Takeaway: Distribute responsibility, be honest and open about information, create multiple paths for raising and testing ideas, make it safe to fail, provide access to other strategists, develop opportunities for experience-based learning, hire for transformation, bring your whole self to work, find time to reflect, and recognize leadership development as an ongoing practice.
Ten Senior Leadership Lessons I Wish I Learned Sooner - by Julia Grace. Takeaway: “observations growing from a junior manager to a senior manager running a whole organization … For example: providing less guidance is often better. The more prescriptive you are, the less you allow people below you to grow.”
10 Things Great Bosses Do Every Day - by Dr. Travis Bradberry. Takeaway: from “respects your time” to “looks for and celebrates wins,” this list covers the bases.
Ten Uncomfortable Deeds that Will Pay off Forever - by Travis Bradberry. Takeaway: Get up early, accomplish an “impossible” goal, meditate, focus on one thing at a time, volunteer, practice public speaking, talk to someone you don’t know, bite your tongue, say no, quit putting things off.
This Is the Number One Thing That Holds Most People Back from Success - by Seth Godin. Takeaway: It’s your attitude.
3 Harmful Ideas About Leadership (and Shifts You Can Make) - by Karen Tay. Takeaway: “[G]ood leadership is less and less defined by subject-area expertise, and more and more defined by the ability to hire well and create the conditions for talented individuals to propel the business forward, such as trust and autonomy.”
[Unintuitive Things I’ve Learned About Management (Part 1) and (Part 2)(https://medium.com/the-year-of-the-looking-glass/unintuitive-things-i-ve-learned-about-management-part-2-7c22fc9d87ed) - by Julie Zhuo. Takeaway: You must like dealing with people to be great at management; having all the answers is not the goal—motivating the team to find the answers is; evaluate the strength of a manager by looking at the strength of their team; the most significant advantage a senior manager has over a junior manager is an expanded perspective; aligning on why is more important than aligning on how; sometimes a great person will not work out on a great team, and that is okay; you never regret moving a struggling person too soon—you only regret doing it too late; your team should respect you, but you don’t need them to agree with everything you say or do.
[We Need to Talk About Servant Leadership] (https://mfbt.ca/we-need-to-talk-about-servant-leadership-a719c4c05434) - by Johnathan Nightingale. Takeaway: Denying power inequities serves no one, and skims over the real existence of privilege that comes with power. “Own the authority of your role. If that authority is uncomfortable and you’re worried about wielding it poorly, then get educated. You can be a better boss than the ones you’ve had. Figure out when your duty of service is to the individuals on your team, and when it’s to the organization at large. Figure out how you want to act in the rare but real cases where those are in conflict.”
What Mistakes in Your Experience Does Management Keep Making? - by Hacker News commenters. A list/online discussion about the many ways that tech management goes awry.
What “S’Up”? Using Triads to Develop Tribal Leadership - by Daniel Doubrovkine. Takeaway: an exploration of Artsy’s weekly “S’Up” informal gathering of three randomly selected colleagues, which reinforces tribal leadership. “Stages of Tribal Leadership are often categorized by evaluating the number of connections and communication channels between team members, and triads are the most stable and valuable foundations, a building block of a Stage Four culture. S’Up is a tool we built that creates triads. The result can often feel inspiring and lead to durable communication channels at scale.”
Why Should You Want to Lead People? - by Amit Goldshmidt. Takeaway: Reasons why you should and should not want to lead others.
Why Tim Cook is Steve Ballmer and Why He Still Has His Job at Apple - by Steve Blank. Takeaway: “What happens to a company when a visionary CEO is gone? Most often innovation dies and the company coasts for years on momentum and its brand. Rarely does it regain its former glory.” Uses Microsoft and Apple as examples.
Why You Must Lead Differently as Your Team Grows - Forbes article by George Bradt.
How Charles Schwab Got His Workers To Produce More Steel - by Vivian Giang for Business Insider. Takeaway: chalk a number six on the floor and see what your employees/team members do.
How I Failed - by Tim O’Reilly. The founder of O’Reilly writes “a candid post about some of the things that kept me, my employees, and our company from achieving our full potential.”
DevOps Days Keynote - by Kelsey Hightower. Takeaway: a riveting, personal, and slide-free keynote in which Hightower underscores the importance of “giving a damn.”
10 Senior Leadership Lessons I Wish I Learned Sooner - by Julie Grace. Takeaways: Grace’s observations from growing from a junior manager to senior manager to running a whole organization (Director of Infrastructure Engineering at Slack). Less guidance is better, get comfortable with accountability, communication with peers/upper management/teams is key.
To Be a Great Leader, Rethink Your Default Behaviors - by Deirdre Cerminaro. Takeaway: Working with IDEO’s CEO Tim Brown reiterated the values to “act with humility,” not pride; “trust the intuition of others,” don’t be a skeptic; “encourage half-baked ideas,” don’t require them to be polished; “inspire, don’t instruct”; and “model behaviors, don’t dictate them.”
20 Years Ago, Steve Jobs Demonstrated the Perfect Way to Respond to an Insult - by Justin Bariso. Takeaway: Includes video of the 1997 exchange between a man in the audience who insults Jobs, and the latter’s calm and thoughtful response.
Vulnerability and Leadership (video) - by Brene Brown, researcher, author and storyteller. Takeaway: In this TED talk, Dr. Brown discusses connection/lack thereof, shame (the fear of disconnection and being unworthy of connection). Connection and being aware of its need results in more effective leadership because one can then reach/inspire/enliven people.
What It’s Really Like Working with Steve Jobs” - by Glenn Reid. Takeaway: Reid describes designing products with Jobs as a type of “cauldron”-like investigation in which ideas formed around an iteration and who thought up the idea didn’t matter. The process put more focus on the ideas and less on Jobs, specific others in the room, or ego.
Folks categorize leaders into N different types, or the job into M different activities.
An Inside Look at a Flat Organization That Serves Millions - by First Round Capital. Takeaway: When you boil it down, management is really about two things—trust and clarity. “Keeping a company flat is all about finding creative ways to achieve trust and clarity without the bureaucracy.”
“Build a Team That Doesn’t Need You” and Other Counterintuitive Strategies to Succeed as a Manager - by Ben Thompson. Takeaway: a profile of Heptio VP Engineering Kevin Stewart, who identifies and discusses the following leadership qualities: authentically caring about people on your team, preparing yourself as a leader and understanding your organization, rallying your team through empowerment and transparency/openness, providing context around decisions and disagreeing-and-committing if necessary, and getting out of people’s way.
Introverts Think They Won’t Like Being Leaders but They Are Capable - by Peter O’Connor and Andrew Spark. Takeaway: Introverted characteristics are prevalent in servant leaders. The challenge is to help introverts to be more confident about their leadership potential.
The First 90 Days: Critical Success Strategies for New Leaders at All Levels (book) - by Michael Watkins. Covers the essentials of transitioning into a leadership role, from making allies to avoiding common mistakes.
Key Traits for Best Team Leaders - by Francesca Fontana. Takeaway: “[R]esearch revealed four common traits of leaders who get the best collaborative efforts from their teams. The majority of respondents at high-performing companies said successful collaboration comes down to a few key behaviors: modeling collaborative action, building strong networks among employees, encouraging collaboration across departments and structuring work effectively.”
Mastering the Rockefeller Habits: What You Must Do to Increase the Value of Your Growing Firm (book) - by Verne Harnish. Takeaway: practical strategies for growing a business, including the importance of identifying the “x” factor—discovering, defining, and acting upon to create value.
The New Leader’s 100-Day Action Plan: How to Take Charge, Build Your Team, and Get Immediate Results (book) - by George Bradt. This book provides an onboarding plan for new managers and executives to adjust to their new roles. Chapters cover internal politics/understanding them; motivating teams using the BRAVE (Behaviors, Relationships, Attitudes, Values, and Environment) approach; handling crises, and more.
The New Technology Leader’s Plan - by Kate Matsudaira. A series of posts covering these topics: Understanding the Strategy; Conversations with the Team; Understand and Assess Technical Risks (Technical Risk Assessment); Focus on Early Wins.
Qualities of an Exceptional Engineering Director - by various. Takeaway: a lengthy Twitter thread in which contributors identify the qualities they believe a great engineering leader needs.
What Open Leaders Do - by Sam Knuth. Takeaway: Open leaders focus on supporting people to become successful, set vision and context, and seeking feedback about how people feel about their work and environment as well as whether they feel connected to/understand its purpose.
Team and Strategy - by venture capitalist Fred Wilson. Takeaway: Leaders should do only three (or six?) things. They are: Recruit/retain; build/evolve long-term strategy; ensure there’s money; maintain balance between departments; create a commitments system; talk to clients to keep market insight fresh.
The Three Types of Leaders The World Needs Most: Artistic, Scientific and Interpersonal - Forbes article by George Bradt. Takeaway: artistic leaders inspire by influencing feelings and perceptions; scientific leaders influence and inspire knowledge with their thinking and ideas; and interpersonal leaders “can be found ruling, guiding and inspiring at the head of their interpersonal cohort whether it’s a team, organization, or political entity.” They’re not mutually exclusive.
12 “Manager READMEs” from Silicon Valley’s Top Tech Companies - by Brennan McEachran. Takeaway: A collection of manager READMEs from leaders at Slack, Shopify, Forter and other companies.
Watch: Google’s Research on Making Managers Awesome - by re:Work/Google. Takeway: includes video and insights gained through Project Oxygen, Google’s research into management. Includes Google’s eight manager behaviors: 1) is a good coach; 2) empowers the team and doesn’t micromanage; 3) expresses interest/concern for team members’ success and personal well-being; 4) is productive and results-oriented; 5) is a good communicator; 6) helps with career development; 7) has a clear vision/strategy for the team; and 8) has important technical skills that help him/her advise the team.
What It Means to Be an Open Source Leader - by Jim Whitehurst. Takeaway: Red Hat’s CEO describes how one might apply open source principles to leadership. “Being an open leader means creating the context others need to do their best work.”
Why Good Bosses Tune in to Their People - by By Robert I. Sutton. Takeaway: Express confidence even if you don’t feel it, don’t be indecisive, give credit to your people, and when something goes wrong in your domain accept blame and learn from it.
Why Supercell’s Founder Wants to Be the World’s Least Powerful CEO - by Sonali De Rycker. Takeaway from CEO Ilkka Paananen: “My goal is to be the world’s least powerful CEO. What I mean by this is that the fewer decisions I make, the more the teams are making.”
Worry Is the Most Useless Emotion - by Claire Lew. Takeaway: Five things leaders can do to stop worrying, an activity that doesn’t necessarily improve or resolve things. “Instead of idling in indecision and mulling over every possible path and course of action, the question ‘What’s the most I can do with what I have right now?’ forces your hand. You must deal with the cards in front of you. And once you do, you’ll clear a path to move forward within the constraints you have. Now you can focus on what you can control.”
“Decisions in 10 minutes or less, or the next one is free.” - Included in this Microsoft article
“If you want to build a ship, don’t drum up the men to gather wood, divide the work and give orders. Instead, teach them to yearn for the vast and endless sea.” - Antoine de Saint-Exupery
“If your actions inspire others to dream more, learn more, do more and become more, you are a leader.” - John Quincy Adams
“Mistakes are expected, respected, inspected, and corrected.” - unknown
“No (wo)man is really defeated unless (s)he is discouraged.” - Bruce Lee
“No one is going to follow you anywhere, anytime until you have earned the right to lead.” - George Bradt
“What actually separates winners from losers isn’t talent, it’s attitude.” - Seth Godin
Facebook’s HR Chief Conducted a Company-Wide Study to Find Its Best Managers — and 7 Behaviors Stood Out - by Richard Feloni for Business Insider. Takeaway: Care about your team members; hold their team accountable for success; set clear expectations and goals, and four more.
How Do You Measure Leadership? - by Ali Rowghani. Takeaway: three traits of effective leaders, including “Clarity of Thought and Communication”; “Clarity of Thought and Communication,” and “Personal Integrity and Commitment.”
How Google Sold Its Engineers on Management - by David A. Garvin for Harvard Business Review. Takeaway: Google found eight common traits in their most successful managers, including coaching and communicating. They can all be summed up in one mantra: “Love your soldiers.”
Based on articles/findings in previous section.