We surround hotel, not initially considering that (4)
I believe the answer is:
when
'considering that' is the definition.
(I've seen this in another clue)
'we surround hotel not initially' is the wordplay.
'surround' is an insertion indicator.
'hotel' becomes 'h' (phonetic alphabet).
'initially' says to take the initial letters.
The initial letter of 'not' is 'n'.
'we' enclosing 'h' is 'whe'.
'whe'+'n'='WHEN'
(Other definitions for when that I've seen before include "stop pouring the drink" , "As soon as" , "Over what period?" , "Say it when you''ve had enough" , "At what time?" .)