In 2018, a senior engineer at a $40 million ARR SaaS company faced a critical decision on database architecture. He argued against a rushed implementation that would not scale, but product leadership pushed ahead. Frustrated by the lack of influence over technical decisions, he began interviewing elsewhere. Within 18 months, the company lost five senior engineers and faced significant performance issues, costing them roughly $1.4 million in recruitment and productivity losses. The root cause was a failure in communication. Information about engineer dissatisfaction did not reach executives until it was too late, due to filtering at various management levels. Hierarchies often suppress bad news rather than facilitate it. Information gets diluted as it passes through layers of management, with middle managers hesitant to escalate issues that may reflect poorly on them. For example, a software company’s engineers identified performance issues that went unaddressed for five months. By the time executives were informed, it seemed like an unexpected crisis. This communication breakdown means leaders operate on outdated and sanitized information, missing early signs of dissatisfaction and technical problems. The article critiques the norm of avoiding skip-level conversations, which prevents executives from hearing unfiltered truths directly from engineers. Instead of relying on reports, CTOs benefit from direct engagement with staff, gaining insights that can guide strategic decisions. For instance, a payments company’s new CTO instituted open office hours, uncovering critical issues that managers were unaware of. Addressing these problems quickly reduced voluntary attrition to near zero. Ultimately, engineers often leave not solely for better pay but due to a perceived loss of agency when their expertise is ignored in key decisions.