Best of LeadershipMay 2025

  1. 1
    Article
    Avatar of devsquadDev Squad·1y

    I'm the CTO now

    This post humorously narrates the author's unexpected rise to CTO amidst chaos in a failing startup. With most of the team quitting, the author becomes the CTO not out of ambition but exhaustion. They struggle with managing an inherited mess of tech and responsibilities, highlighting the burnout and absurdity in the tech industry. The narrative illustrates the often unplanned path to leadership and the challenges that come with sustaining a sinking ship.

  2. 2
    Article
    Avatar of workchroniclesWork Chronicles·52w

    (comic) I need you to be agile

    A humorous comic highlights the challenges and expectations in adopting agile methodologies within workplace dynamics, emphasizing the gap between management's demands and practical implementation.

  3. 3
    Article
    Avatar of techleaddigestTech Lead Digest·1y

    How To Get Good at Strategy

    The post emphasizes the importance of developing effective strategic thinking by understanding the core challenges in a situation and designing coordinated actions to address them. It highlights principles such as simplicity, coordination, specific challenge identification, and working with obstacles. Additionally, it warns against common strategy pitfalls like mistaking goals for strategy, analysis paralysis, and ignoring implementation.

  4. 4
    Article
    Avatar of itnextITNEXT·1y

    What does a Technical Lead do?

    The post explores the role of a Technical Lead, highlighting their responsibilities in guiding the technical direction of projects, mentoring team members, and ensuring alignment with business goals. It discusses the importance of technical ownership, project execution, cross-team communication, and quality oversight. Additionally, it touches on the concept of an Uber Tech Lead, who oversees multiple projects or teams and contributes to strategic decision-making.

  5. 5
    Article
    Avatar of swizecswizec.com·51w

    You're a business

    Treating your job like a business leads to increased autonomy, responsibility, and strategic influence. This mindset shift transforms your role from executing specific tasks to achieving broader goals and eventually to identifying needs and making things happen independently. The approach offers the benefits of business ownership while avoiding many of the associated burdens since others handle administrative aspects.

  6. 6
    Article
    Avatar of github_updatesGitHub Changelog·51w

    Introducing Copilot Spaces: A new way to work with code and context

    GitHub introduces Copilot Spaces, a new feature that centralizes project context including code, documentation, and custom instructions to make Copilot more knowledgeable about specific projects. Teams can create shared spaces to distribute expertise across organizations, with files automatically staying up-to-date from repositories. The feature is currently in early preview for all Copilot users, with billing changes taking effect June 4th, 2025.

  7. 7
    Article
    Avatar of swizecswizec.com·51w

    Software architecture IS Conway's Law

    Conway's Law states that organizations design systems that mirror their communication structures. When working solo, developers often create messy, tightly coupled code because there's no need for clear boundaries. However, when teams collaborate, they naturally create cleaner architecture by defining clear interfaces and splitting work into components. The key insight is that breaking down work into smaller steps, whether solo or in a team, leads to better architecture and more maintainable code.

  8. 8
    Article
    Avatar of thedevcraftThe Dev Craft·1y

    Entropy in Teams: The Silent Productivity Killer

    Software teams naturally deteriorate over time due to entropy, where processes that once worked efficiently become bloated and ineffective. The solution involves constant maintenance through entropy-focused retrospectives, regular documentation updates, and dedicated improvement budgets rather than waiting for major interventions. Success comes from consistent small actions that prevent disorder from accumulating.

  9. 9
    Article
    Avatar of collectionsCollections·1y

    Recognizing and Overcoming Hero Traps in Engineering Management

    Engineering managers often encounter 'hero traps' where well-intentioned behaviors hinder team development. Key traps include fixing problems personally, shielding teams from organizational issues, and overprotecting teams. Managers can overcome these obstacles by promoting autonomy, gradually withdrawing from direct problem-solving, and balancing advocacy.

  10. 10
    Article
    Avatar of dhhDavid Heinemeier Hansson·1y

    Have you tried the exact opposite?

    Exploring the opposite of current strategies can be a valuable way to challenge assumptions and validate beliefs. Businesses should regularly test their core beliefs to adapt to changing circumstances, maintaining intellectual humility and creative flexibility. The practice of embracing opposite approaches provides insightful lessons and can affirm better strategies.

  11. 11
    Article
    Avatar of programmingdigestProgramming Digest·1y

    Getting to Staff Engineer

    Becoming a staff engineer requires more than technical prowess; it involves changing your operational approach. Key aspects include supporting and mentoring others, owning significant problems rather than a codebase, and making behind-the-scenes impact visible. Staff engineers must prioritize organizational needs, lead without formal authority, and communicate effectively with different levels within the company.

  12. 12
    Article
    Avatar of staysaasyStay SaaSy·1y

    Setting Startup Policies

    Executives at startups need to set robust policies to prevent chaos and maintain order. Effective policy setting is akin to product management, requiring review, transparency, and evolution. Common pitfalls include secret exceptions, policies punishing adherence, and inadequate evolution in response to changing circumstances. It's crucial to limit the number of policies to avoid excessive friction and inefficiency.

  13. 13
    Article
    Avatar of collectionsCollections·1y

    From Developer to CTO: A Practical Five-Step Guide

    Transitioning from developer to CTO involves mastering skills beyond technical expertise. Key steps include translating technical issues into business insights, mastering context switching, influencing team culture, building trust, and designing systems for resilience. This guide helps navigate the journey while maintaining work-life balance.

  14. 14
    Video
    Avatar of seriousctoThe Serious CTO·1y

    No Degree. No Network. Still CTO.

    Transitioning from a junior developer to a CTO doesn't require a degree or a large network, but rather the right mindset and actions. Important steps include becoming a builder by solving real problems, leading without waiting for titles, building a personal brand as a tech leader, and choosing the right environment over titles. Experience, proving your value, and owning outcomes are key to success in a tech leadership role.

  15. 15
    Article
    Avatar of staysaasyStay SaaSy·52w

    AI Makes Bad Managers

    AI tools can be helpful in management, but relying on them for performance assessments can hinder the development of critical managerial skills. Effective management involves practicing communication, empathy, and strategic thinking, particularly in processes that require human judgement. AI is beneficial for repetitive tasks, but critical judgment roles should remain human-driven to cultivate management skills.

  16. 16
    Article
    Avatar of techleaddigestTech Lead Digest·52w

    Why People Really Quit — And How Great Managers Make Them Want to Stay

    Micromanagers and absentee managers contribute to employee turnover, while managers who practice thought partnership keep employees engaged. Thought partnership involves empowering and collaborating with team members. Effective management requires actively partnering with employees, listening, goal-setting, and seeking feedback. In contrast, ignoring top performers or excessively overseeing tasks can harm team dynamics and mental health. Managers should strive to balance involvement with empowerment to foster a supportive work environment.

  17. 17
    Article
    Avatar of communityCommunity Picks·1y

    The magic of software; or, what makes a good engineer also makes a good engineering organization

    The discussion explores the tension between software engineering and computer science, highlighting their differences and the unique magic that software brings. It argues that engineering vision and understanding are intertwined in a bidirectional relationship, which is crucial for innovation. The post critiques the widespread use of abstraction layers, suggesting they can stifle creativity and deeper understanding. It also likens large engineering organizations to abstraction layers, pointing out their limitations in driving radical changes and innovation due to siloed structures.

  18. 18
    Article
    Avatar of managingdevManaging Dev·1y

    Eyes on the road ahead

    Managers are reminded that while reflection on past mistakes is important, focusing on future opportunities and improvements is crucial for progress. It's essential to identify what to let go from the past and what to focus on for the team's clarity and success.

  19. 19
    Video
    Avatar of TechWithTimTech With Tim·1y

    NEVER hire this kind of person for your startup

    In early stage startups, hiring visionary executives who only offer guidance without participating in hands-on tasks can be detrimental. Such individuals might require additional resources to implement their strategies, which is ineffective during the initial phase where practical contribution and direct involvement are crucial for respect and success within the team.