We just let it happen… and that’s the beauty of this technique.

Bob Ross

The CTO's Hidden Notebook

• 📓 Beyond the Code — The article posits that a CTO's effectiveness hinges significantly on mastering aspects beyond pure technology. This “hidden notebook” contains the unwritten rules and implicit knowledge — strategy, people management, communication, and business acumen — often learned through hard-won experience rather than formal training.
• ❓ Prioritizing the “Why” — A core learning emphasized is the shift from how technology works to why it's being used. Effective CTOs, according to the piece, constantly link technology decisions back to business objectives, user needs, and overall company strategy, avoiding “technology for technology's sake”.
• 🗣️ Translation is Key — The ability to communicate complex technical concepts to non-technical stakeholders (like the board, CEO, or other departments) is presented as a crucial, yet often underdeveloped, skill. Influence and alignment rely heavily on this translation capability.
• 💡 Experience as Teacher — The “hidden notebook” metaphor strongly suggests that much critical CTO knowledge is tacit, built through navigating complex situations, making mistakes, and observing outcomes. It underscores the idea that failure and reflection are powerful learning tools in this role.
• 🧭 Strategic Foresight Needed — The article implicitly criticizes a purely operational focus, arguing that impactful CTOs dedicate significant effort to strategic thinking. This involves anticipating future technological shifts and understanding how technology can create long-term competitive advantages, not just solve today's problems.
• 👥 Culture & People First — While technology is the domain, the piece highlights that building, leading, and nurturing engineering teams and fostering a positive, productive culture are paramount responsibilities that significantly influence technological success.

Are 1:1s Worth The Time?

Spoiler: yes, yes they are, but...

• ❓ Questioning Default Value — The central theme challenges the automatic assumption that 1:1 meetings are inherently valuable. It suggests their worth is highly dependent on how they are conducted, rather than their mere existence on the calendar.
• ⏱️ Time Sink Potential — A key observation is that poorly structured 1:1s often devolve into inefficient status updates or routine check-ins, consuming significant time for both manager and report without delivering proportional benefit. The article implicitly asks if this time could be better spent.
• 🌱 Focus on Development & Blockers — Effective 1:1s, as argued, should prioritize deeper topics like career growth, skill development, addressing roadblocks, providing meaningful feedback, and building rapport — aspects often crowded out in less intentional meetings.
• 🔄 Shared Responsibility Crucial — The piece implies that the onus for a valuable 1:1 doesn't solely rest on the manager. Direct reports also need to come prepared with topics, challenges, and goals to make the conversation productive and tailored to their needs.
• 🗑️ Identifying Anti-Patterns — It highlights common pitfalls that diminish 1:1 value, such as lack of a clear agenda, frequent cancellations, superficial conversation, or using the time purely for task management best handled elsewhere.
• 🤔 Conditional Recommendation — The underlying learning is that 1:1s can be immensely valuable, but only if executed thoughtfully and intentionally. If they consistently lack substance or clear purpose, their continuation warrants critical re-evaluation.

How To Send Progress Updates

• 📢 Purpose Beyond Status — Updates are presented not just as status reports, but as crucial tools for alignment, building trust, ensuring visibility, and enabling asynchronous communication within and across teams.
• 🏗️ Structure Enhances Clarity — The article strongly advocates for a consistent structure (suggesting sections like “Accomplishments”, “Goals for next week”, “Blockers/Challenges”) to make updates predictable, scannable, and easier to digest over time.
• ✨ Focus on Impact, Not Just Activity — A key learning is to emphasize outcomes and progress towards goals rather than simply listing tasks completed. Quantifying impact where possible adds significant value.
• 👥 Audience Awareness is Key — It highlights the importance of considering who will read the update (e.g., direct team, manager, skip-level, stakeholders) and tailoring the level of detail and context accordingly.
• ⚠️ Proactive Problem-Solving — Updates serve as an essential mechanism for proactively flagging blockers, risks, or areas where help is needed, allowing issues to be addressed early rather than festering.
• ⏱️ Conciseness and Cadence Matter — The piece implicitly values respecting readers' time through brevity and clarity. Establishing a regular cadence (e.g., weekly) makes the update process routine and expected.

How To Stop People Pleasing At Work

• 🚫 People-Pleasing's Root — The article identifies people-pleasing less as genuine helpfulness and more as a behavior often rooted in fear — fear of conflict, rejection, or appearing unhelpful — which ultimately undermines personal well-being and effectiveness.
• 🛡️ Boundaries as Essential Protection — Setting boundaries (regarding workload, availability, types of requests) is presented not as selfishness, but as a critical mechanism for protecting one’s time, energy, and focus, enabling sustained productivity and preventing burnout.
• 📉 The Hidden Cost: Resentment & Burnout — A key observation is that failing to set boundaries frequently leads to internal resentment towards colleagues or the job, coupled with exhaustion from over-commitment, harming both morale and performance.
• 🗣️ Communicating Limits Clearly — Effective boundary setting requires clear, direct, yet respectful communication. This includes learning to say “no” without excessive apology, potentially explaining the reason (e.g., conflicting priorities), or offering alternative solutions where feasible.
• 🤔 From Pushover to Respected Peer — The piece implicitly argues that consistently enforcing boundaries, while potentially uncomfortable initially, often leads to increased respect from colleagues, as it signals self-awareness, prioritization skills, and reliability within defined limits.
• ⏳ Reclaiming Focus — A core learning highlighted is that boundaries are crucial for reclaiming control over one’s schedule and mental space, allowing for dedicated focus on high-priority tasks rather than constantly reacting to others’ demands.
• 💪 An Ongoing Practice — Setting and maintaining boundaries isn't a single action but an ongoing practice that requires conscious effort, self-awareness, and the willingness to navigate potentially awkward conversations for long-term benefit.

Intentions & Actions

• ❓ Intentions vs. Reality — The article starkly contrasts developers' good intentions regarding code quality (e.g., planning to “clean this later”) with their actual actions (e.g., committing messy code), arguing only the latter truly shapes the system's state.
• 📉 Actions Define the Codebase — It emphasizes that the cumulative effect of daily coding actions — tidying or neglecting to tidy — directly determines the software's maintainability and technical debt, irrespective of future plans or stated desires for quality.
• ⏳ The Cost of Inaction — Delaying tidying actions, even with the intention of returning, is framed as an active contribution to disorder. The immediate action taken (or not taken) has a direct, often negative, consequence on the codebase.
• 💡 Bridging the Gap — A core learning is the necessity to align actions with intentions by integrating small, tidying changes directly into the workflow (the essence of “Tidy First?”). This makes desired quality an outcome of consistent practice, not just aspiration.
• 👀 Observable Evidence Matters — The piece implicitly advocates for judging code quality, team discipline, and process effectiveness based on the tangible evidence of actions (the actual code, the commit history, the test quality) rather than accepting stated intentions at face value.

That’s all for this week’s edition

I hope you liked it, and you’ve learned something — if you did, don’t forget to give a thumbs-up, add your thoughts as comments, and share this issue with your friends and network.

See you all next week 👋