How should the board handle discussion and negotiation of the superintendent's contract?
The board may not discuss, deliberate, negotiate or vote on the superintendent's contract in executive session. A sub-committee of the board, even if it is only two individuals, would also be required to have the discussions in public at a posted committee meeting if they jointly make their recommendations to the board.
The Attorney General's Public Records and Meetings Manual, page 114, says "... if the committee members are instructed to make individual rather than group decisions or recommendations, the 'meetings' of the committee are outside the scope of the meetings law. This unquestionably is a difficult area of interpretation, and governing bodies are cautioned not to misuse the committee appointment process or decision-making process to subvert the policy of the Public Meetings Law."
Some things you might consider:
Have the board hold a public discussion of the general parameters for the new contract. The board can then authorize the board chair to have a conversation with the superintendent privately about those parameters and report back to the board at a future public session. A single individual (the board chair in this example) is not considered to be a committee.
Hire your board's attorney to negotiate the contract using the parameters that you set as a board in public session.
The board will still have to deliberate and vote in public session to make the final decision.