Evil Wolf certainly had reasons to be happy.
No profession is easy, and as a guide, if you have the bad luck of encountering a group of dimwits, not to mention those who score high and perform low, it is the fear of unnecessarily attracting unwanted enemies. If you help, you might encounter danger; if you don't, and a client dies, who would dare do business with you again? You would end up being the one to clean up the mess.
What was supposed to be easy money ultimately became hard-earned money.
At first, Leon's aggressive behavior towards the Lizardfolk was indeed worrying, but after a few admonitions, he behaved quite well, especially just now when he somehow managed to enter the cave leading to the Dark Territory even before him, which was really surprising.
Evil Wolf felt that this mission was secure.