Management Challenges

The talk argues that engineers can boost their own impact by actively making their manager's job easier. It frames managing up as a set of four practical skills - curiosity, understanding the manager's role, building a positive relationship, and showcasing the manager's success. Each skill is illustrated with concrete anecdotes from the speaker's experience at Etsy, Flickr and dozens of startups. Curiosity is presented as the gateway: ask sincere questions instead of guessing intent. The speaker recounts a scenario where a teammate missed a deadline because no one asked the decision-maker why the date changed, and how a simple question would have clarified expectations. Understanding a manager means recognizing they spend most of their mental bandwidth on themselves and their boss, not on their reports. The talk highlights asymmetries like a manager's limited time for one-ons, the importance of knowing what the manager values - technology, product, or operational excellence - and how they are evaluated, whether on hiring, shipping, or OKRs. Building a positive relationship relies on genuine compliments and actionable help. The speaker shares how praising a CEO's clear strategy reinforced that behavior and led to better communication across the team. Finally, making the boss look good involves aligning with the team mission, delivering high-quality work, and equipping the manager to speak fluently about the engineer's contributions. This alignment drives resource allocation and career growth for both parties.