Hiring is hard

Si and Neil compare notes on one of the most underestimated challenges in tech leadership: hiring well. From writing the job spec to navigating AI in the interview room, this episode covers the full journey, with plenty of honest opinions, personal stories and hard-won lessons along the way. Writing the Job Spec (03:16) - Where hiring goes wrong before it's even started. The laundry list problem, gender-encoded language, and why a backfill doesn't have to be like-for-like. Screening CVs and the Network Problem (17:43) - AI-generated applications are flooding inboxes. Is the CV even fit for purpose anymore, and what does leaning on your network really cost you? Side Projects and What CVs Can't Show (25:06) - Why both hosts have shifted away from using GitHub profiles and portfolios as a hiring signal, and what that says about privilege in the process. The Interview Process (29:21) - Take-home tests, live pairing exercises and the heuristic that ties it together: the interview should look like the work. Culture Fit vs. Culture Add (36:23) - Stop hiring a friend group. Why diverse thinking beats a room full of people who all get on brilliantly outside of work. Technical Assessment in the Age of AI (43:19) - When anyone can AI their way through a coding test, what are you actually testing for? Si's approach: hand them an LLM and watch how they use it. The Arms Race (49:32) - Candidates using AI to game hiring, companies using AI to screen it out. And a word on privilege: not everyone can afford a Claude Pro subscription. Connect with us Got thoughts on hiring? We'd love to hear them. Email: [email protected] Si on LinkedIn https://www.linkedin.com/in/sijobling/ Neil on LinkedIn https://www.linkedin.com/in/neil-younger/ Support Managing Engineers by contributing to their tip jar: https://tips.pinecast.com/jar/managingengineers Read transcript