Kenfu was the oldest son of Amhara noblemen Hailu Wolde Giorgis, the governor of Qwara by Woizero Walatta Tekle.
In the early 1830s, Kenfu was frequently allied with Dori Gugsa, or with the rising Wube Haile Maryam during conflicts.
In 1838, French traveller Antoine Thomson d'Abbadie carried two letters from Emperor Sahle Dengel to Queen Victoria of Britain, and Louis Philippe of France.
Kenfu Hailu is mentioned in the letters as one of the three most powerful lords of Ethiopia, the two others being Ras Ali, and Wube Haile Maryam (with a notable absence of the strongman of Shewa, Negus Sahle Selassie).
[3] As a child, Kassa Hailu received church education at the convent of Tekla Haymanot, between Gondar and Lake Tana.
He managed to escape a massacre that saw his fellow students killed by a defeated Oromo chieftain taking his vengeance on the children of the victors.
Kenfu took Kassa into his court as retainer, this being a way to train young members of the nobility in administration, etiquette, justice and politics.