Unless you and the player have discussed this as an option already, I would make sure I had his permission to proceed with a session like this; if it's not presented right it could seem like you are arbitrarily throwing a wrench into the usually smooth workings of raising the dead that the players might expect. I don't know how your group have been playing this subject so far.
But! Assuming everyone is into it, then you WILL want to present a story-based reason (in-game) for changing the "usually smooth workings of raising the dead". Why is there suddenly a possible impediment to his coming back from the dead?
Possible reasons for the potential obstruction:
-- a power grab by the evil gods or spirits in the heavens, that want to hold on to (or intercept) the spirits of the recently departed, for their own ends, and don't want to see them return to the physical plane;
-- a magical doodad that is erupting and interfering with the normal flow of spiritual affairs;
-- a necromancer getting uppity in the region, grabbing onto recently departed spirits, which again interferes with the normal flow of death and life, etc...
With something like that as the motive for the extra-ordinary challenges in returning to the world of the living, I would also then use a spirit-guide friendly to the PC, to explain some of what is happening and what the PC must do to overcome the interference.
With that, the actual challenges can be presented to the PC by this spirit totem, wild spirit guide or whatever. For simplicity's sake for you the GM, I would present only a trio of challenges, representing the overall challenge of balancing the head, hand and heart. Some sort of combat challenge to exercise the Hand; a skill challenge to exercise the Head aspect of the character; and some roleplaying challenge to show off the Heart of the PC.
The Skill challenge should cater to the character class of the PC, so that his best skill would be used to win the day. The combat can be anything but I would try to use the PC's most hated or feared monster that he must overcome. And the roleplaying challenge might take the form of the PC confronting his own god's avatar or representative to petition his right to return to the physical world.
Ultimately it should be clear that the PC must succeed on at least two of the three challenges in order to win his way back to real life. And if he does ultimately succeed while failing one challenge, then I would want to "be-quest" the PC on some holy crusade or other to reclaim his honor in the real world after failing that test in the spirit world.
