Kifle was born in Adi Billai in Eritrea's Debub Region. He made his first international appearance for Eritrea at the age of 21, running in the 3000 metres at the 1999 IAAF World Indoor Championships. He finished in last place and was over twenty seconds behind the rest of the runners. His first international outdoor competition followed later that year and he ran in the heats of the 5000 metres at the 1999 World Championships in Athletics in Seville. In 2000 he came 61st at the 2000 IAAF World Cross Country Championships and made his Olympic debut with a performance in the heats of the 10,000 metres at the 2000 Sydney Olympics. He began to improve from the 2002 season onwards: he was eighth in the long race at the 2000 IAAF World Cross Country Championships, fourth at the 2002 IAAF World Half Marathon Championships with a time of 1:01:05 hours, and came sixth over 5000 m at the 2002 African Championships in Athletics. He also won the Cursa de Bombers 10K in Spain that year.