Herman II was the eldest son of Lord Bernhard II and his wife, Heilwig, a daughter of Count Otto I Heilwig of Are-Hostaden. He was co-regent with his father, and succeeded him in 1196 as ruler of the House of Lippe. He was less belligerent than his father and brother, and often tried to act as intermediary whenhis neighbours had a dsipute.
In the dispute over the German throne in 1198, Herman supported the Guelph side. He switched sides to support Emperor Frederick II in 1214. He promoted the cities and gained the post of Vogt of the Monasteries Clarholz and Herzebrock.
His main opponent during this period was Engelbert II of Berg, who was Archbishop of Cologne.
Earlier in his career, Herman had supported Engelbert. In 1227, Herman II fought in the Battle of Bornhöved against Denmark.
