From engineer to head of engineering | Tales about Software Engineering

Stepping into a head of engineering role at a Middle Eastern fintech forced the author to confront imposter syndrome head-on while the organization wrestled with fragmented processes and a growing sense of dysfunction. The narrative shows how a background in agile at Equal Experts clashed with legacy waterfall mindsets, revealing the hidden cost of "process for process' sake" and the pressure to deliver quickly in new markets.

The author initially pushed agile ceremonies and OKRs as a cure-all, only to be perceived as a know-it-all. This misstep sparked friction with the incumbent engineering lead and highlighted how aggressive cultural change can backfire without careful listening. Real-world examples include endless steer-co meetings, water-flooded suppliers, and the tension between rapid product rollout and regulatory compliance.

Learning to step back, the writer adopted a quieter approach: one-to-one conversations, intranet news posts, and building a support network of former colleagues. By sharing insights through short, repeatable messages, he avoided hero-mode firefighting and let engineers own solutions while he set strategic direction.

The piece emphasizes that senior engineering leaders must balance strategic thinking with empathy, create space for cross-functional dialogue, and tolerate the discomfort of not having all the answers. It offers concrete tactics-use OKRs sparingly, prioritize meeting effectiveness, and communicate openly about failures-to help other leaders navigate similar transitions.

Ultimately, the story is a candid reminder that leading engineers is less about imposing frameworks and more about fostering an environment where the right processes emerge organically, allowing teams to ship value without drowning in bureaucracy.