Employee share options and Black Economic Empowerment deals are financial instruments found in the South African market. Employee share options (ESOs) are issued as a form of non-cash compensation to the employees of the company in addition to their salaries or bonuses. Its value is linked to the share price and since there is no downside risk for the employee his share option is similar to owning a call option on the stock of his employer. Black economic empowerment (BEE) deals in this report refer to those types of transactions structured by listed South African companies to facilitate the transfer of a portion of their ordinary issued share capital to South African individuals or groups who qualify under the Broad-Based Black Economic Empowerment Act of 2003 (“the Act”). This Act requires a minimum percentage of the company to be black-owned in order to address the disproportionate distribution of wealth amongst racial groups in South Africa due to the legacy of Apartheid. These transactions are usually structured in such a way to allow the BEE partner to participate in the upside of the share price beyond a certain level but not in the downside which replicates a call option on the share price of the issuing company. The cost of both ESOs and BEE deals has to be accounted for on the balance sheet of the issuing company at its fair-value. Neither of these instruments can be traded and their extended option lifetimes are features that distinguish these deals significantly from regular traded options for which liquid markets exist. This makes pricing them a non-trivial exercise. A number of types of mathematical models have been developed to take the unique structure features into account to price them as accurately as possible. Research by Huddart&Lang (1995&1996) has shown that option holders often exercise their vested options long before the maturity of the transactions but are unable to quantify a measure that can be used. The wide variety of factors influencing option holders (recent stock price movements, market-to-strike ratio, proximity of vesting dates, time to maturity, share price volatility and wealth of option holder) as well as little exercise data publicly available prevents the options from being priced in a consistent manner. Various assumptions regarding the exercise behaviour of option holders are used that are not based on empirical observations even though the option prices are sensitive to this input. This dissertation provides an overview of the models, inputs and exercise behaviour assumptions that are recognized in pricing both ESOs and BEE deals under IFRS 2 in South Africa. This puts the reader in a position to evaluate all pricing aspects of these deals. Furthermore, their structuring are also analysed in order to identify the general issues related to them. A number of methods to manage the pricing issue surrounding exercise behaviour on ESOs have been considered for the South African market. The ESO Upper Bound-methodology showed that for each strike there is a threshold at which exercise will occur and the employee can invest the after-tax proceeds in a diversified portfolio with a higher expected return than that of the single equity option. This approach reduces the standard Black-Scholes option value without relying on assumptions about the employee’s exercise behaviour and is a viable alternative for the South African market. The derived option value represents the cost of the option. Seven large listed companies’ BEE transactions are dissected and compared against one another using the fair-value of the transaction as a percentage of the market capitalization of the company. The author shows how this measure is a more equitable way of assigning BEE credits to companies than the current practice which is shareholding-based. The current approach does not reward the effort (read cost) that a company has undertaken to transfer shares to black South Africans but only focuses on the amount that is finally owned by the BEE participants. This leaves the transaction vulnerable to a volatile share price and leads to transactions with extended lock-in periods that do not provide much economic benefit to the BEE participants for many years. Other inefficiencies in the type of BEE transactions that have emerged in reaction to the BEE codes that have been published by the South African government are also considered. Finally the funding model that is often used to facilitate these deals is assessed and the risks involved for the funder (bank) is reflected on.