Soft Skills Engineering · Jamison Dance and Dave Smith

Episode 463: CTO w/ weak resume and I tried management and it was TERRIBLE

·27 min·2 clips

A CTO with nine years at one startup fears his resume is becoming worthless as the company sinks.

This episode of Soft Skills Engineering features hosts Dave Smith and Jameson Dance answering listener questions about software engineering careers. They address a CTO worried about his resume and an engineer who hated management. The first question comes from Albert Anonymous, a CTO at a five-engineer startup where he was the first employee and owns 10% after nine years. He enjoys the tech but fears the company will fail and worries his single-job resume makes him unhireable. He also mentions slacking off since having a child and feeling responsible for the company's survival. Dave suggests he could work fewer hours to keep the company afloat while starting something new on the side. Jameson believes the CTO will eventually leave and should act as a 10% owner to protect that asset. They propose he create a succession plan, possibly hiring a replacement to increase the company's value. Both hosts agree his lengthy founder-like role could make him seem risky to traditional employers. They suggest he might need to start his own company or accept a lower-level role elsewhere. The second question is from an anonymous engineer with nine years of experience who tried being a team leader and found it terrible. He describes constant pressure, pointless reports, and dreading pulling developers from refactoring rabbit holes. He took the promotion with no raise and easily demoted himself back to an individual contributor. He now feels lost, calling himself a "hyphen-shaped developer" with broad but shallow experience. Dave notes many disliked tasks are inherent to management, while Jameson relates to hating telling people not to do something they enjoy. They frame the experience as a positive learning outcome that eliminated one career path. The hosts suggest he could leverage his leadership skills without being a manager, like coordinating technical tasks. They also propose he might try going deep in a technical area or find a new product or team to reignite his passion. The tone is conversational and humorous, with the hosts joking about YAML, geese, and their patrons. They blend practical advice with empathetic support, often using metaphors and personal anecdotes. Software engineers feeling stuck in their careers or considering management would find this episode relatable. Listeners who enjoy candid, advice-driven discussions about workplace dynamics would appreciate it. Those seeking highly technical content or definitive answers might want to skip.

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