Roughly, yes, he does.
If he is directly directing or controlling the investment in any way, yes he does.
On the other hand, if he owns shares in a "technology contra fund" with independent fund managers, and that fund shorts in MSFT, then he doesn't. On the third hand, if the SEC or some pissed off MSFT investors think he is overinvesting in this hypothetical technology contra fund as a way to get around the reporting rules, then he has to report that too. There is no escape, and very few safe harbors.
If you work for a publicly traded company, and you are subject to the lock-out rules and disclosure rules, there will be someone in your HR's legal and investor relation groups who will explain this all to do you deep and exhausting detail.