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  "description": "Weekly, hand-picked engineering leadership nuggets of wisdom",
  "path": "/the-managers-guide-141/",
  "publishedAt": "2026-06-09T12:14:09.000Z",
  "site": "https://the.managers.guide",
  "tags": [
    "PJ Evans",
    "Verification Debt Is Your Next Headache",
    "Say the Thing You Want",
    "The difference between Manager and Director",
    "Startup Engineering Team Organisation",
    "Three Bad Managers"
  ],
  "textContent": "> STRESS TEST your email server by ordering a single item from AliExpress.\n>\n> PJ Evans\n\n* * *\n\n### Verification Debt Is Your Next Headache\n\n  * 🔍 A different kind of debt: The concept of “verification debt” goes beyond standard technical debt — it specifically refers to the growing, hidden burden of manually testing and validating software due to a lack of proper automated systems.\n  * 🐢 The illusion of speed: Skipping automated tests initially makes an engineering team feel like they are moving fast. However, this creates a dangerous trap — every new feature exponentially increases the time it takes to manually verify that the entire system still works.\n  * 📈 Compounding consequences: Just like financial debt, verification debt compounds over time. As a product scales, the manual regression testing phase becomes a massive bottleneck, leading to painfully slow releases and a higher likelihood of “unexplained” bugs slipping into production.\n  * 💡 Automation is an enabler: To escape this vicious cycle, teams must shift their mindset and prioritize paying down this specific debt. Automated testing isn’t a tax on delivery — it is the essential infrastructure that allows teams to maintain their velocity and confidence as they grow.\n\n\n\n### Say the Thing You Want\n\n  * 🗣️ **Say what you want out loud** — Keeping career desires to yourself gives them no \"surface area\" for others to help you achieve them\n  * 😰 **Fear holds us back** — We stay quiet because asking feels presumptuous, risky, or too exposing — but these fears prevent growth opportunities\n  * 🎯 **Managers can't read minds** — Your manager has multiple reports and their own priorities; they can't send opportunities your way if they don't know your direction\n  * 🗺️ **Get a career roadmap** — When you voice your goals, managers can provide specific feedback on gaps and concrete steps to get there\n  * 🪞 **Self-assessment has blind spots** — You need external perspective to understand your strengths and weaknesses; thinking harder about yourself won't close these gaps\n  * ⚡ **Speaking makes it real** — Saying your goals out loud gives them weight and makes you start making different choices and taking different actions\n  * 🎲 **The risk is worth it** — If expressing career ambitions gets you punished, that's valuable information about your workplace; three years of hinting is worse than one honest conversation\n  * 💬 **Simple phrases work** — Try \"I've been thinking about the path to senior. Can we talk about where I stand?\" or \"I'm interested in leading a project. What would I need to show you?\"\n  * 🚪 **Next 1:1 is your chance** — When your manager asks \"anything else?\" — just say the thing instead of rationalizing why you shouldn't\n\n\n\n###\n\n### The difference between Manager and Director\n\n  * 🎯 **Core Evolution Model** : Leadership growth follows a \"What → How → Why\" progression — early career focuses on tangible outputs (What), management emphasizes processes and team effectiveness (How), and director level prioritizes strategy and purpose (Why)\n  * 👥 **Role Responsibility Shift** : Directors become strategic filters between business and tech, co-creating company direction rather than just consuming it — they evaluate and prioritize incoming work based on strategic alignment rather than executing all requests\n  * 📊 **Distance from Work** : Directors operate further from day-to-day execution and must develop new ways to collect signals about team health — using metrics, visual management tools, and periodic deep-dives across people, product, platform, and process dimensions\n  * 💪 **Power Transition** : Leadership power evolves from expertise (knowing the answers) to influence (relationships and trust) — authority from titles is the weakest form, while influence becomes everything at director level\n  * 🗣️ **Communication as Multiplier** : Communication skills become increasingly critical and can be the biggest growth blocker — directors need to influence peers, shape strategy, and build other leaders through clear communication\n  * 🎭 **Emotional Rewiring Required** : Each transition demands redefining personal impact — from tangible code/features (IC) to team delivery (manager) to abstract business outcomes (director), with longer feedback loops at each level\n  * ⚠️ **Common Anti-Pattern** : Directors who remain stuck in \"What\" mode by coding themselves or micromanaging implementation details — this shows lack of trust and prevents strategic thinking\n  * 🚀 **Proactive Development Advice** : Engage with all three dimensions (What/How/Why) early in your career — build relationships with Why and communication skills before the role demands it to ease future transitions\n\n\n\n###  Startup Engineering Team Organisation\n\n  * 🏗️ **Team Structure Evolution** — Startup engineering teams follow predictable patterns as they grow, each solving previous problems while creating new ones\n  * 💻 **Technical Teams Trap** — Organizing by tech stack (frontend, backend, mobile) creates silos where every project becomes a cross-team coordination nightmare\n  * 🎯 **Squad Success & Failure** — Business-domain squads improve product focus and team dynamics, but technical debt piles up as \"core\" engineering work gets deprioritized\n  * 📚 **Chapter Conflicts** — Adding technical chapters (communities of practice) helps with knowledge sharing, but creates constant battles between product priorities and technical maintenance\n  * ⚙️ **Core Team Complications** — Dedicated platform teams solve technical debt but create a \"two-class system\" where product engineers stop caring about technical quality\n  * 🎲 **Project Approach Problems** — One-shot technical projects seem clear but suffer from scope creep, timeline extensions, and knowledge loss when teams disband\n  * 👑 **Staff Engineer Solution** — Senior autonomous engineers plus ~20% chapter time provides flexibility, but puts huge pressure on staff engineers and requires rare skill combinations\n  * 🔄 **No Perfect Answer** — Every organizational structure has tradeoffs — the key is recognizing when current limitations outweigh benefits and being ready to evolve\n  * 📈 **Scale Matters** — What works for 18 engineers won't work for 50 or 5 — team structure must adapt to current size and challenges\n\n\n\n### Three Bad Managers\n\n  * 🎨 **The Artist** — A brilliant creative leader who valued art over people, couldn't engage with human management challenges, and required extensive written documentation to even sometimes pay attention to team dynamics\n  * 👑 **The Dictator** — A passionate but bulldozing leader who dominated every conversation, ignored expert input, and made terrible decisions because they couldn't stop \"litigating\" issues that were already solved\n  * 🗡️ **The Knife** — An inexplicably successful yet completely disconnected manager who pulled actual knives out during meetings, talked about unrelated topics, and was impossible to understand or influence\n  * 📊 **Success vs. Management Skills** — All three were objectively successful leaders who generated significant shareholder value, proving that leadership ability (strategy/vision) and management ability (operations/people) are completely different skill sets\n  * 🔄 **Everyone is an Adjustment** — The core lesson is that you must adapt your communication style, preparation methods, and approach for each person you work with — you don't get to pick your bosses, only how you respond to them\n  * 📝 **Adaptation Strategies** — With The Artist, detailed written explanations worked sometimes; with The Dictator, doing extensive homework and showing you \"care deeply\" earned respect; with The Knife, staying out of the way was the only viable approach\n  * 🎯 **You Can't Change Bad Managers** — The more senior the leader, the less you can influence them, so focus on adapting yourself rather than trying to fix them\n  * 🧠 **Intelligence ≠ Good Management** — All three were highly intelligent people who simply had no business managing humans, despite being effective at leading organizations toward goals\n\n\n\n* * *\n\n# That’s all for this week’s edition\n\nI 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.\n\nSee you all next week 👋\n\nOh, and if someone forwarded this email to you, sign up if you found it useful 👇\n\n## Sign up for The Managers' Guide\n\nYour guide to engineering leadership\n\nSubscribe\n\nEmail sent! Check your inbox to complete your signup.\n\nNo spam. Unsubscribe anytime.",
  "title": "The Managers' Guide № 141"
}