Tax considerations
The tax treatment of any sale proceeds (whether received on completion or in the future) and of any holdings in the new structure will directly impact how much value you will end up with as a result of the transaction. You will most likely want any transaction to be structured to attract the minimum rate of tax available. It is important to note that tax structuring may not be possible shortly before the transaction and generally may not be implemented with retroactive effect.
Consideration structures
Your individual tax position will depend on the type of consideration you receive, the method of calculating it and the timing of any payment. You may receive any combination of the following types of consideration: cash, shares, or loan notes, and your tax position may be complicated by any entitlements to receive consideration post-sale, possibly by way of an "earn out".
Particular care should be taken by individuals in transactions where "rollover" or "earn-out" mechanisms are included in the drafting. Although they are useful commercial tools to incentivise founders and senior management staying on in the business (particularly in a private equity context) and bridge valuation gaps between buyers and sellers, they can result in unexpected tax consequences.
You should seek tax advice as early as possible on the appropriate way to structure such entitlements.