Osborne completed his B Proc and LLB degrees (6 years) at both University of Limpopo, Turfloop in 1993 and University of KwaZulu-Natal, Howard College in 1995. In 1996, Osborne joined Norton Rose Fulbright Attorneys, Durban as a candidate attorney. During his time at Norton Rose Fulbright Attorneys, he was exposed to various aspects of legal practice that included employment and labour law. That is when he developed an interest in labour law, and from then it became his area of specialization. He later joined Webber Wentzel in Johannesburg as an Associate and, upon establishing his own legal practice, he was immediately promoted to a Senior Associate position.

For the period between 2002 until 2010 Osborne left practice and was exposed to working in a corporate business environment where he worked for Henkel South Africa as a Human Resource Manager and Executive during which he was also a member of the company’s EXCO. Osborne was later transferred to Dubai, UAE to concentrate on the company’s Adhesive Technologies for MENA (Middle East North Africa) Region. During this period, he worked as Regional HR Key Account Executive Manager providing HR Professional support to all Adhesive Technology units doing business in the MENA region.

He rejoined legal practice in 2011 and has since then been practicing as an employment and labour law practitioner. He has acted for some of the major corporate companies as well as State Owned Entities (SoEs), both in various dispute resolution disputes, CCMA, Labour Court, High Court matters as well as dealing with trade union collective bargaining and restructuring matters.