I get a number of shares in the company for which I work every year, so I have a number of shares that had various values when I acquired them.
When I sell a portion of my shares, I have various options over which shares to sell first.
I can only think of one scenario that would make me care about the order, and hence it seems to me that there are only two orders in which it makes sense to sell shares:
- You're selling a large amount of shares and might incur capital gains tax, so you want to sell the shares that had the highest value when acquired first to minimise or avoid tax.
- You're not selling that many shares, so you want to sell the shares that had the lowest value first, so you have the greatest opportunity to minimising tax in the future should you want to sell many shares.
Is there anything else that I've not considered that would affect the order in which to sell the shares?