If you’re ever going to do epic sh*t, you’ll have to get comfortable with unreadiness. When you’re not ready is the best time to start.

The Crucial Difference Between Nice and Kind Leadership

• 👥 Being “nice” often means avoiding conflict and prioritizing short-term comfort, while being “kind” focuses on genuine care and long-term growth — a crucial distinction in leadership
• 🎭 Nice leaders tend to avoid critical feedback and tough decisions, essentially painting “shiny colors on a falling building” — while kind leaders practice “tough love” through honest communication
• 💪 Key traits of kind leadership include: providing timely feedback even when uncomfortable, making decisions based on what's best for the team (not personal popularity), and addressing issues head-on with compassion
• 📖 The author shares a personal story of managing a “brilliant jerk” — choosing the kind approach of direct feedback over being nice led to unexpected positive long-term outcomes, even after having to terminate the person
• 🌱 The fired employee later became the author's coaching client — demonstrating how prioritizing kindness over niceness can build lasting trust and respect, even through difficult decisions
• ⚡ Core takeaway: Leadership is a “relationship game” where trust and respect trump popularity — being kind requires courage but yields better long-term results than being merely nice

Stars and Guardians

• ⚖️ Organizations have a natural tension between “Stars” (who create value through risk-taking) and “Guardians” (who prevent value loss through protection) — like engineering vs. operations teams
• 🌟 Stars (e.g., sales, engineering, design) tend to say “yes” to new ideas and take risks, while Guardians (e.g., legal, security, finance) typically err on the side of caution or saying “no”
• 👻 Interesting dynamic: Guardians are invisible when successful and only noticed in failure — while Stars shine brightest in success and can hide in collective failure
• 🤝 Four key elements for productive tension between Stars and Guardians: shared long-term vision, relationships built during “peacetime,” full transparency, and shared credit for outcomes
• 🎯 Some teams (like product management and communications) sit at the fulcrum — their balance often indicates overall organizational health
• 💡 Key insight: Without a clear company vision, power naturally skews toward Guardians — contributing to the innovator's dilemma in successful companies

A Self-Care Checklist for Leaders

• 🧠 Despite increased focus on well-being since the pandemic, many leaders still struggle with self-care due to cultural, organizational, and personal barriers

• ⚡ The article presents a 5-part framework for leader self-care:

  • Body budget (sleep, diet, exercise)

  • Emotional health (regulation and relaxation)

  • Relationships (collaboration and support)

  • Choice points (autonomy and boundaries)

  • Growth and nourishment (learning and creativity)

• 💪 Key mindset shifts needed include: giving yourself permission for self-care, avoiding all-or-nothing thinking, starting small, and celebrating progress

• 🎯 Practical suggestions include: micro-workouts during the day, emotion regulation using the ABC framework (Awareness, Build intelligence, Communicate), and intentional relationship building

• ⏰ Leaders should take 15 minutes weekly to reflect on their health in each of the five areas, noting what's working and what needs adjustment

• 🌱 The article emphasizes that physiological well-being directly impacts leadership effectiveness — it's not just personal health, but “the smart leadership thing to do”

Status games

• 🧬 Status behaviors are deeply rooted in evolution (800M years) and manifest in subtle social cues — the way we stand, speak, look, and interact

• 🎭 The concept comes from theater training, where actors learned that “no action is motiveless” and every interaction implies status positioning

• ⚡ Status games are particularly dangerous in startups because they can derail the needed harmony and common objectives

• 🚩 Common harmful status-seeking behaviors in engineering teams include:

  • Building unnecessary things

  • Using unfamiliar tech stacks

  • Unnecessary rewrites

  • Claiming sole credit for team work

  • Making noisy but empty contributions

• 🛠️ Engineers can also play status games by lowering others' status through:

  • Shooting down ideas without reason

  • Making unhelpful code review comments

  • Blame-shifting for production issues

  • Escalating to managers unnecessarily

• 💡 Key to managing status games: shine light on them, discuss rationally, avoid escalation — while still maintaining healthy, evidence-based debate

Writing

Why leaders should take the time to write

• 🧠 Writing is crucial for clear thinking — as computer scientist Leslie Lamport states: "If you're thinking without writing, you only think you're thinking"

• 💡 Knowledge workers spend most time thinking rather than doing — even software engineers report only 15% of time actually writing code, rest is thinking and planning

• ✍️ Writing forces structured thinking by:

  • Clarifying ambiguous thoughts

  • Revealing gaps in logic

  • Uncovering hidden assumptions

  • Creating permanent, transferable records

• 🏢 Major tech companies highly value writing skills:

  • Meta's Distinguished Engineers all have "world-class" writing abilities

  • Amazon starts meetings with silent reading of "six-pager" memos

  • Writing is seen as core to effective leadership and decision-making

• 🎯 The author argues you don't "find time" to write — you make time because it's fundamental to:

  • Clear thinking

  • Effective leadership

  • Professional growth

  • Knowledge sharing

• 📚 Writing isn't just for leaders — it's increasingly essential across all tech roles for documenting, persuading, and organizing thoughts effectively

That’s all for this week’s edition

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See y’all next week 👋