Gladys Molefi Olebile was born in 1931 in the village of Modimola, Mafikeng, Union of South Africa.

From her maternal side, she belonged to the Tawana-a-Tshidi Mina Tholo royal family.

After graduating from Tigerkloof, she followed in her mother's footsteps by becoming a teacher for many years, firstly in her hometown of Mafikeng and later at Kanye, Bechuanaland.

Ambassador Horace Dawson, helped Olebile Masire establish Botswana's first charity.

[4] She was married to the late former President of Botswana Quett Ketumile Masire in 1958 and had six children.