IT Horror Stories with Jack Smith

Jack Smith

Details

IT Horror Stories with Jack Smith tells real stories from the world of IT: outages, failed migrations, broken infrastructure, cybersecurity incidents, software failures, networking disasters, cloud problems, Shadow IT, and the occasional decision that seemed like a good idea at the time. Jack Smith talks with the people who were there about what happened, how they got out of it, and what others can learn from the incident. Stories are anonymized where needed, and the focus is on technology, processes, and organizations rather than blaming individuals. New episodes weekly, with Jack's Rants in between. You are one of us.

Recent Episodes

OCT 19, 2026
Wrong Person, Right Skills : Technical Hiring Failures and Why Companies Mismanage IT Talent
Companies complain that they can't find the right technical people. Technical people complain that companies have no idea who they're actually looking for. This time, Jack crosses to the other side of the table with Ashley Randall to find out why both might be right. We look at how organizations turn operational problems into job descriptions, why they search for impossible unicorns, and what happens when the person they hire has the right skills for a job that doesn't actually exist as advertised. From HR screening and mismatched expectations to KPIs, management workshops, organizational silos, and the eternal question of whether HR is really there for you, we explore what happens when technical specialists and the business speak very different versions of the same language. Sometimes the problem isn't the person you hired. It's the job you thought you were hiring them for. To find out more about Ashley Randall and Aspiring Redirection, visit: Ashley Randall: https://www.linkedin.com/in/ashley-randall7/ Aspiring Redirection: https://www.linkedin.com/company/aspiring-redirection/ Want even more info ? Read our show notes and related blog post related to this episode : https://blog.ithorrorstories.eu/episode-27-wrong-person-right-skills/ 00:00 Introduction 00:43 Business Perspective 02:03 Hiring Challenges 04:48 Evaluating Talent 07:02 Structural Issues 08:52 Role Mismatches 13:24 Miscommunication Effects 17:15 Improving Processes 24:00 Culture and Metrics 33:43 HR and Employee Relations 39:23 Conclusion
44 MIN