Asking Good Questions with Edward Roske

There are a few genuinely useful operator nuggets (shadow AI stats, Oracle migration difficulty, big-tech vs small-tech advice), but they're spread across long stretches of career anecdotes, diversity discussion, and Portland tangents.

“the free version of ChatGPT has over 20% critical data in it”

“There is such a tiny itty-bitty percentage that are successful coming off of Oracle”

Some framing is fresh (Peter Principle cycle in big tech, the 'where is the golden copy' point on vector storage), but much rests on well-worn metaphors—tools in a tool belt, AI won't replace humans, 'fall down 7 get up 8'—that circulate widely.

“You're not going to just throw away your hammer to build your house because you have a screwdriver now”

“that fall down 7 times, get up 8”

Genuinely senior practitioner: Oak Table Network member, AI lead at Silk, advocate/engineer at Redgate, Microsoft Oracle/Azure SME, multi-book author and board director—a real hands-on database operator at scale.

“one of the few women in the world to actually belong to the Oak Table Network”

“From her early Oracle days to leading AI at Silk, to her dual role as advocate and engineer at Redgate Software”

Some concrete data points (20% critical data stat, DB-Engines rankings, Blockbuster collapse, job-loss/creation figures), but many are loosely cited and much of the episode trades in general advice and personal stories rather than hard metrics.

“You'll see the numbers that back in about 2006, we're sitting about 1,400 on the ranking”

“they're saying 93 million jobs that will be cost by AI... There's another 143 million that will be created”

The host is engaged and asks open thematic questions with good rapport, but rarely pushes back or challenges claims; many questions are broad prompts and several are wrapped in jokey tangents that dilute depth.

“Are you seeing that drive to implement AI come from the technology side of the house?”

“Is there advice you'd give to a professional that wants to stay relevant”