Good morning, Stern~
Here is how I did it on my Sneakbox:
When I am under way, my pushpole lays on the starboard deck. I poke the top of the pole through the bail up forward of the cockpit. The bail is heavy galvanized wire wrapped in decoy line to prevent chafing.
Then drop the bottom end into a chock on the stern deck.
It is important that the forward bail be large enough so I can easily put the pole through it while standing in the cockpit. Similarly, I can put the other end in the chock quickly.
I lost one pole on a long run because the wake caught my duckbill. I subsequently added a line so it can be lashed into the stern chock for long runs.
It'll stay in place while trailing - because the belly strap keeps it in place - but I normally use the pole as a ridge pole for my canvas cockpit cover.
Hope this helps,
SJS