I would rule it slightly differently to most, which still creates the same outcome:
The Guard, with a 20 initiative, is surprised and cannot act, but has a turn. This means the first part of Assassinate does not count (ie there is no advantage).
The Rogue, with his 6 initiative, gets to attack the Guard. Based upon the "attacker unseen" rules, I would grant advantage if the situation allows an ambush-style attack (aka no more than 5' of movement in front of the Guard before the attack is unleashed).
This would mean the Rogue still gets the full benefit of Assassinate, in terms of a critical hit and a sneak attack, but the advantage is granted by a different rule.
If the Rogue went first in initiative, this means the Rogue would only get ONE sneak attack, because after revealing with the first Assassinate, the Guard has a turn in the surprise round (even if they cannot act) and so they wouldn't have Advantage on the second attack (unless granted through some other means). And since it'd be out of the surprise round by then, no auto crit either.
The Guard, with a 20 initiative, is surprised and cannot act, but has a turn. This means the first part of Assassinate does not count (ie there is no advantage).
The Rogue, with his 6 initiative, gets to attack the Guard. Based upon the "attacker unseen" rules, I would grant advantage if the situation allows an ambush-style attack (aka no more than 5' of movement in front of the Guard before the attack is unleashed).
This would mean the Rogue still gets the full benefit of Assassinate, in terms of a critical hit and a sneak attack, but the advantage is granted by a different rule.
If the Rogue went first in initiative, this means the Rogue would only get ONE sneak attack, because after revealing with the first Assassinate, the Guard has a turn in the surprise round (even if they cannot act) and so they wouldn't have Advantage on the second attack (unless granted through some other means). And since it'd be out of the surprise round by then, no auto crit either.