Long time ago, when I was new to stringing, I made a mistake of starting without poking at the holes first. I put a new grommet in, and did not need an awl at all. It just fell into place. No effort was required on my part. Then I strung the racquet. Then, for a tie off, I needed to stuff 2 strings through the same hole! This is where I *wished* I had done what your stringer is doing.
Some 3 hours later, after a lot of cursing and pushing the second string in, with various objects, I finally got it in. As soon as I pulled it tight, the original string broke. The one that was there first, the main.
... I had to start all over again ....
After that episode, before each and every stringing, I now *always* poke awls into any hole which may potentially be a tie-off, and then at their neighbors. The way I string, I do not always end in the "designated" tie-off location, and I do not want any more repeats of the story above.
Your stringer probably have had an experience similiar to mine in the past 3 years.
