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Leadership Philosophies and Styles

Leadership Philosophies

This topic comes first, because the following articles offer great frameworks/definitions for leadership.

  • 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."

  • 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.

  • Failure as a Service - by Rich Armstrong. What it means to be a leader. Takeaways: Servant-leaders shouldn’t make decisions that should be made by the folks closest to the problem), unless they can’t be answered with readily-available or easily-collected data, and there’s no consensus on the solution. "When the people you manage bring you a tough call, and you choose right, they get the credit. When you choose wrong, you get the blame. And it’s OK, pookie. That’s what you’re here for."

  • 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 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."

  • 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."

  • 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.."

  • 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.

  • A Model for Leadership - A political article, but it provides one the most complete leadership frameworks we’ve seen. Values are the linchpin in the model, but important things precede and flow from values:

    • Experience: the total knowledge extracted from yr life i.e. understanding, wisdom, etc.
    • Judgement: ability to make considered decisions or come to sensible conclusions.
    • Values: your principles or standards of behavior. What you believe is important in life.
    • Vision: ability to articulate an ambitious and seemingly unattainable goal.
    • Strategy: ability to explain the steps necessary to achieve that vision.
    • Tactics: decompose a strategy into a series of logical actions that will achieve each step

  • 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."

  • 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."

  • 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.

  • 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.

  • 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.

  • 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."

  • 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.

Famous Leaders

  • 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."

  • 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.

Leadership Styles

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."

  • 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.

  • 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.

  • 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.

  • 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 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."

  • Your Most Important Skill: Empathy - by Chad Fowler. Takeaway: Includes a long-ish list of compelling reasons why empathy truly is your most important skill as a leader, and several suggestions on how to practice empathy: listen; watch and wonder; know your enemies, and choose the other side. "We all have friends and loved ones that complain to us about how they have been treated by other people. It’s human nature to complain and it’s the duty of a loved one to listen sympathetically. The assumption is that the listener is on the side of the complainer. A supportive friend or loved one almost always is, instinctually. Try practicing (internally) taking the opposing view point. Don’t go with your default reaction immediately. Start on the other side and work your way back."

Quotes on Leadership

  • “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

Research on Leadership

Themes Common to Both Google and Facebook

Based on articles/findings in previous section.

  • Coach/care: Help with career development, provide opportunities for growth
  • Empower the team: hold team accountable for success, recognize outstanding work, has key skills to advise team w/o micromanaging, and provides resources to team
  • Two-way communicate: listen and share, provide frequent actionable feedback
  • Have vision: has vision/strategy for team, be results-oriented, help team prioritize work