Henare attended Napier Boys' High School and Utah Valley State College. He was part of the Tall Blacks team multiple times and competed for NZ at the U/16, U/18 and U/20 junior levels. He won two New Zealand NBL championships with the Auckland Stars in 1999 and 2000 and competed in the New Zealand NBL All-Star Game in 2001.
He was a part of the inaugural New Zealand Breakers team in 2003 and was a New Zealand Breakers co-captain for the 2004–05 season, before becoming the full-time captain for the 2005–06 season. He also played for the Hawke's Bay Hawks of the New Zealand NBL and Bandırma Banvit of the Turkish Basketball League.
In 2009, Henare won his fifth Dave Taylor Trophy while playing for the Christchurch Cougars. The award is given to the season's assist champion, and with his fifth in 2009, he moved two clear of the next best in Kenny McFadden who won the award three times.
Henare retired from professional basketball at the end of the 2010–11 season. He was honoured by becoming the first Breakers player to have his number (32) retired.
Henare coached the Hawke's Bay Hawks during the 2011 and 2012 NBL seasons. He signed to coach the Southland Sharks for the 2013 and 2014 NBL seasons. On 3 June 2013, Henare extended his contract with the Southland Sharks until 2015.
On 30 May 2014, Henare came out of retirement to be the temporary player/coach of the Southland Sharks after multiple players were suspended.
Following the 2015–16 NBL season, Henare was appointed the head coach of the New Zealand Breakers. He stepped down from the role in March 2018. In July 2018, he was appointed head coach of the Wellington Saints for the 2019 season. In October 2018, he joined Melbourne United as an assistant coach for the remainder of the 2018–19 season.
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