I don’t have any rush or need to sell. I can do it now or I can do it in 10 years. When is it better though?
No body knows. I’d say at least diversify some percentage of it regularly. Your risk tolerance and goals should define that percentage.
Sell 65-70 per and diversify and leave the rest to ride further gains
Do not put all eggs in one basket. If MSFT stock goes down it usually means bad times for the company and a high chance for you to loose your job. Do you want to loose a job when most of your investments tanked as well? My approach is to sell employer's stock as soon possible, both RSUs and ESPP and buy SPY/QQQ instead to deversify if you do not need money in the nearest future.
Is it still a good idea to but msft stocks now
Sell company stock on vest.
What if MSFT hits 4T market cap in 3 years?
There’s plenty of unvested RSUs to capture that value. No need to correlate your employment with your investment account. There are more than 2000 equities out there. Don’t pick the one you work at.