Another issue could be the type of steel? Some of the "steels" you get are just knife rooters plain and simple, they won't do anything any good. I keep mentioning fine cut (#4, #5 etc) Cambrian brand steels or the modern equivalent, can get them as a 450mm or a slightly shorter version but they were a revelation for me with regard to steeling up edges. One of those steels with a handful of swipes and the knife's edge is as good as it ever was.
The best thing is as well, my stoning intervals on the Scary Sharp have gone from every few months to once or twice a year so the knife blades are going to be lasting a lot longer just with the change to this type of steel.
What i was finding prior was similar to what you describe from your mate, the edge of the blade rolled back and the clean stoned bevel no longer present.
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