steering coupling??????

Thanks for the feedback everyone. When I bought the column, it was slightly collapsed and did not slide very well (had to be persuaded.) I believe the problem is the column and not so much the coupling. The shoes and spring clip sit in there very tight. I don't want to gouge my column. I filled the coupling up with grease and even greased the parts going into the coupling. I read somewhere in this forum to put locking pliers on the column and tap it in. I'm just looking for the best way. Thanks again everyone:)

I'm confused now... There are 3 separate things here (at least)
1. The splines need to engage till the roll pin hole lines up with the open area of the gear shaft. You can check that best with the coupler off the column.
2. The column shaft needs to be able to move in the coupler. But the shaft/column does not touch the coupler. It's the new shoes from the rebuild kit sliding in the coupler body that are the main issue. The shoes seat on the pin through the end of the shaft and should be able to pivot before inserting in the coupler body. The spring pushes the shoes out to the side 'tracks' in the coupler. Was the coupler body completely clean. So how would you gouge the column?
3. Last but definitely not least (and Redfish already mentioned)- COLLAPSED Column? Sounds like a big red flag to me...What are you referring to?