#337 – August 13, 2026
middle management teaches useful skills but won't make you a great executive
Middle management roles are a trap
3 minutes by Will Larson
Middle management teaches useful skills but won't make you a great executive. The habits it rewards, like pleasing stakeholders and avoiding micromanagement, actually work against the deeper skills executives need: domain expertise, driving execution, and building culture. Spending too long in middle management prepares you only for more middle management. A little time there is valuable, but moving on quickly gives you a better shot at executive success.
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ARR doesn't mean what it used to
8 minutes by Simon Wu
Investors no longer trust ARR because the term means different things to different founders. Some annualize a single strong month, others blend recurring and usage-based revenue, and many confuse bookings with actual revenue. The same problem shows up in gross margins, where compute or integration costs get buried below the line. Founders who clearly define their metrics upfront build more credibility than any growth chart can.
Tension in systems design
20 minutes by Fred Hebert
Two broad approaches shape how we design and manage systems. One breaks things down into parts to predict and control outcomes. The other accepts that complex systems resist that kind of analysis and focuses on shaping conditions for good behaviour to emerge naturally. Both have real limits, and switching between them carries hidden costs. Before changing how software teams work, especially with AI tools, it helps to know which approach you are actually using and what it quietly depends on to function.
Giving and taking credit in big tech companies
8 minutes by Sean Goedecke
Managers can't truly assess technical work, so they rely on trusted engineers to quietly judge your performance. Simply doing good work won't get you far — you need to tell people what you've done and why it matters. Sean points out that sharing credit with others gives them reason to support you, while hoarding it leaves you exposed when things go wrong. Credit is not a zero-sum game.
On managing your energy
11 minutes by James Samuel
Time alone doesn't determine how much you can get done. Energy matters just as much, and it comes in different forms: physical, mental, and emotional. Some tasks drain one type more than others. James suggests that structuring your day around your energy, not just your schedule, helps you do better work where it counts most.
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