Bears can generally be found near water. Generally speaking the need a good amount of water to digest their food. So creeks, rivers, lakes and riparian areas are all good bets for finding bears nearby.
As a total novice bear hunter, I'd advise you to take a drag and drive the dirt roads,during the day/evening, cleaning them of tracks, and then starting early morning, looking for fresh tracks. This should give you a good idea of the bears utilizing the area your hunting. It should also give you a decent idea of at least some of their travel routes, and any concentrations of bears utilizing a specific area. From there, I would concentrate on the heaviest used areas.
I have no idea what the regulations are for bear hunting in Montana, but if baiting is permitted, you may then want to bait the area(s) most heavily used. Here in Ca, baiting is a no go.
Here in Ca, in May, the bears can generally be found out and about feeding during the day, in areas with little to no pressure. So your plan of glassing, given the same conditions exist, is sound if you can overlook large areas. Generally in Ca, during May, the bears are primarily eating grasses and forbes, although they may still target fawns. I imagine the same conditions apply in Montana during May.
So in short, try to identify areas that multiple bears utilize, and then concentrate on those areas. Spend a little time identifying areas of concentration will significantly improve your odds, and it will be time well spent; providing you the opportunity to spend the remainder of your time hunting productive areas.
Best of luck!
