Pointer engineering leadership digest

October 13th, 2026 | Read online Tuesday 13th October issue is presented by Unblocked The Context Layer For Agentic Software Development Your agents know the code. Give them the rest of your organizational context. Unblocked reasons across your code, conversations, issues, docs, and production systems so agents can complete work correctly with less human intervention. Try For Free Today Why Your Engineering Team Is Slow — Alex Piechowski tl;dr: “After years of codebase audits, the same five signals keep showing up, so I finally put them into a scoring rubric: The Codebase Drag Audit. Five signals, scored 0 to 2. If you hit 4 or above, the code needs direct investment before anything else will help.” Management CodeQuality TechDebt “You Didn’t Do It Right” — Jason Cohen tl;dr: “Four sincere attempts at OKRs, four failures, and every time: “you didn’t do it right.” Maybe the framework doesn’t fit you — so how do you find one that does?” Management GoalSetting [Webinar] How To Stop Rewriting Your Agent’s Code — Brandon Waselnuk tl;dr: You write the rules files, maintain the skills, and paste in the Slack thread your agent missed. But hand-curated context goes stale, and when the sources disagree, your agent can’t tell which is right. Join us live on Oct 28 (FREE) to see how a context engine helps agents get it right the first time. Promoted by Unblocked Event AI Agents I Don't Want The Details — Michael Heap tl;dr: "At first I thought ""I don't want the details"" sounded dismissive. How can they make informed decisions without understanding the details? Then I realised that ""I don't want the details"" wasn't being dismissive. The executive assumed that we were competent, and was saying ""I already believe you. Now let's talk about what happens next”. Leadership Communication “It is not the manager’s job to prevent risks. It is the manager’s job to make it safe to take them.” — Ed Catmull Don't Diagnose Your Opponents — Sean Goedecke tl;dr: “When you disagree with someone, there are two paths forward. The first is to try to engage with what they’re saying: what their reasons are, whether their position is true, what evidence could be brought to bear, and so on. The second is to diagnose them: to engage with the second-order question of why they’re saying it.” Leadership Communication How Do You Evaluate A Senior Engineer In The Age Of AI? tl;dr: When AI can accelerate execution, traditional signals of seniority don’t tell the whole story. This 30-point checklist gives engineering leaders a practical framework to score senior-level readiness. It includes a ready-to-use interview questionnaire, so you can see if your hiring criteria have kept up. Promoted by Assuresoft Guide Hiring AI How To Effectively Debug When You No Longer Understand The Code — Cindy Sridharan tl;dr: “I consider this an emergent skillset that’s different from coding or traditional debugging, but like any other skill, it’s one that can be honed with enough effort. While I’m no leading expert in this area, the general contours of how these skills can be actively cultivated are beginning to stand out in sharp relief. By putting my own experiences in writing, I’m hoping to hear from fellow practitioners their thoughts on this topic.” CodeQuality Debugging 38 Things We've Learned About Building AI Products — Ian Vanagas tl;dr: “We’ve built 10 different AI products at PostHog, including PostHog AI, our install Wizard, Replay Vision, Scouts, and more. They’re used by nearly 100,000 people every month. This is what we’ve learned.” CaseStudy AI Product Grieving The Loss Of Details — Alisa Sireneva tl;dr: “I’ve been thinking about where I stand in respect to the current state of the industry. This is more of a journal note than a post, apologies for that. I usually leave this stuff private, but I thought I’d post this as a trial in case someone relates to this experience and feels less alone.” Career IndustryTrends Most Popul