According to the following article
https://msdn.microsoft.com/en-us/library/office/jj228679.aspx#ol15WhatsNew_AddinDisabling
Outlook uses the median time of 5 last runs and compares it to 1 millisecond (for add-in startup). This means that if I optimize my add-in and re-install it, I should run Outlook at least 4 more times to calculate the correct value of add-in startup. Does anybody know where this value is stored in Outlook (I guess registry)? I tried to remove my add-in's value from the following key: HKEY_CURRENT_USER\Software\Microsoft\Office\15.0\Outlook\AddInLoadTimes but it doesn't help, it still remembers it.