Fast forward 17 years: Habib is entering his eighth year of teaching, six of them at Gunn — and all of them in English.
"Gunn was just an amazing place to integrate into American society and get all the skills I needed to be successful in college in just four years," Habib said.
"There are definitely colleagues out there who used to be my teachers, and they're incredible people."
Hebrew was the first language of Habib, a native of Israel. And French — he lived in Brussels from age 8 to 14 — was his second, instilling a global outlook even before his family arrived in the Bay Area for his father's high-tech job.
"To see so much at such a young age was a big privilege. To learn another language, about cultures and stuff was quite special," said Habib, who still has a grandfather, aunts, uncles, cousins and friends in Israel.
Habib has taught math, accounting, history and economics.
He particularly loves teaching the history curriculum developed by the nonprofit, Boston-based Facing History and Ourselves. The program asks students to imagine themselves in historical situations, such as events leading up to the Holocaust, and then to relate those situations to choices they might face in the present.
"Facing History just understands what makes the teenage brain tick," he said.
"We take these case studies and learn about the steps it took to get to those events, and the actions or inactions people took when they were faced with different conditions.
"Then we can look at our own lives and see how we'd behave in certain conditions — try to take case studies from history and apply them to things that occur in school. For example, if there's a fight in school, what do you do?
"A lot of people, when they're honest, find that their actions would not necessarily be that clear."
Students get hooked by Facing History, Habib said, because "they start to see that history doesn't just happen, that it occurs because of actions people like them decide to take."
Habib won't be teaching history this fall but rather two AP economics courses, with the rest of his time spent as Gunn's "technology lead" — helping colleagues integrate technology into their teaching.
While not required for good teaching, technology "can make a great teacher even better and really add significantly to the curriculum and the teacher's professional growth," he believes.
For example, "screencasting" apps for the iPad have enabled students in his economics classes to divide into small groups to create short videos to teach one another the material.
"In microeconomics and macroeconomics there's a lot of material for the kids to know, and when we review for the tests it's always rushed," Habib said. "I feel like technology allows us to take a little more time to learn, gives the students more access to the material.
"When a kid creates something and sees that other kids are learning from it, it's pretty powerful, and there's a huge collaborative environment that's created because of that.
"I think collaborating effectively will be one of the most important skills of the 21st century, and technology allows kids to be active participants in the learning process."
As a student at Gunn in the '90s, Habib remembers feeling academic stress but admits "it might be a little bit worse" today, despite myriad school initiatives to address it.
Kids feel societal pressure to take difficult courses, he said, quickly adding, "That's not pressure that comes from the school.
"This is a greater societal issue — not just in Palo Alto but in our country as a whole, and certainly in very affluent areas."
Adding to that, high school is a time when students move toward being assessed mainly on performance, he said.
"I certainly express how effort is extremely important, and I mostly praise effort, not performance. But when it comes down to your evaluation on how well you understand the material, at the end of the day it comes down to your performance, whether you actually get it," he said.
"I'm a nice person, but I have very high expectations for my students."
Habib advises kids to surround themselves with positive influences — adults as well as peers — and not be afraid to seek help or to ask questions, even questions that seem stupid.
Students need exercise and rest and should try to strike a "healthy balance between social life, academics and just learning for the sake of learning.
"This could be whatever — playing a sport, listening to music, drawing, whatever. And help others. That's very important," he said.
Having been a student and a teacher at the school, Habib, not surprisingly, is a Gunn booster.
"Gunn is a freakishly amazing school on many levels — primarily the students," he said.
"The quality of the people, the quality of the students — it just doesn't exist in other places."