Just like some of the scubaboarders has mentioned, if he can equalize on the surface then he will surely be likely to do so underwater. I tend to agree that it depends a lot on the instructors. When I am taking students for discover scuba diving, I will try to understand my students and their level of comfort with water. You will be surprised to know that this will make a huge different. If you're friend is comfortable with water, first thing first have it checked with ENT before go and try again. If the ENT clears, then he should be okay to equalize.
When doing discover scuba diving, it is important that the instructor should not force the participants to descent too quickly, sometimes I will have to constantly remind them to equalize when descending. This is because some people are just very new to scuba diving and the excitement (sometime fears) can make them forget to equalize, this happens all the time.
Another thing that also helps is to student to equalize even before the descent, that is blow the nose slowly then start to descend, then I would often hold their hands or bcd and descent really really slow, and have them equalize as often as possible, sometime even every 15cm or so, this make a lot of different, once they pass around 5-7 meters mark (each individual is different), things got a lot easier.
I hope your friend will be able to descend and equalize and enjoy the beautiful underwater world.