I think you are mistaken, because you have made a category error. The work of a personal secretary or an assistant isn't merely to book you an airline ticket or manage your calendar. These are part of it, yes, but not the entirety and even in those you are missing the nuance of it. Their job is to understand you, and act on your behalf in the matters you delegate, knowing what outcome you would choose yourself. This is a force multiplier in the way that Outlook will never be.
I started work in that era. That secretary booked an airline ticket by calling her contact at the same airline, regardless of price savings.
She typed his messages; that task is obviously done by the boss himself these days (Obama's blackberry addiction is a case in point). Voice-to-text handles her job while I'm driving; NO ONE did that job back then.
In the middle of the night, I can set an appointment that just occurred to me. Again, that's not something 1980s me could do.
Technology is a force multiplier you are ignoring. As bad as Outlook seems, it is better than most secretaries could be.
A large part of the force multiplier is just that she would sit on hold for you. Web sites rarely get so slow that you can't book the ticket yourself when it occurs to you.
Note again that I'm using "she" intentionally. When females are considered unable to do "real work" we don't value their time and so it is a force multiplier for the men who don't have to sit on hold, and we ignore all of her time that is wasted. I agree with those who are glad such days are over.
I think it's odd to devalue the time of someone who is helping you achieve more. That's definitely not a charitable way to treat people, nor is it the way I think about secretaries and assistants, regardless of their gender. While rank and file employees are no longer entitled to assistants, there are still thousands of people across corporate america in these roles and they are in many ways the most critical people to getting things done in many companies, and I have the utmost respect for them.
It is societies attitude toward women that is in question here. Most individual assistants were valued by those they were assisting. However many assistants would be even more valuable if they were doing something other than assisting, and so by having so many female assistants we devalued females who were able to do better work if allowed (they probably couldn't get the needed education, and glass ceilings were in play).
Of course in 1950 we didn't have computers able to do many of the things assistants did. As such we needed them to manually do various tasks that today computers do better. However the sexist making it females who are doing the job harmed the better female who could have done something better, and also the less capable males who couldn't do anything more complex anyway. (though there are a lot of jobs that those males could do that are even less complex)
> Their job is to understand you, and act on your behalf in the matters you delegate, knowing what outcome you would choose yourself.
And that works very well even today when you are high enough to get a personal secretary. For the engineer who always shared the secretary with several others she didn't know you as well, and in any case their preferences were not important enough to consider (you don't get first class options).
Even for my boss, outlook is a force multiplier over a secretary because he (happens to be he today, has been she in the past, and likely will be again in a few years) doesn't have very many things where knowing preferences matter and doesn't have such complex scheduling needs that a human needs to do it. The ability to schedule his own meetings is much more powerful than asking someone to do it - while it might take more time to do it he can see that by not inviting one person the meeting can be had sooner and that is a much greater multiplier than the time saves by having someone else who not knowing those details delays the meeting until everyone can be there.
Yes when your situation is such that a secretary can "understand you, and act on your behalf in the matters you delegate, knowing what outcome you would choose yourself" it is a force multiplier. However most of us are not really that different from anyone else and even where we are we are not allowed the level of differentiation. We also don't have nearly the ability to delegate things, much less enough things that someone else can delegate them on our behalf. And so for most of us outlook is a force multiplier over the secretary we would get.
