Everything but the coffee: The evolution of the automated secretary

By Nathan Zeldes

It seemed to make sense at the time…

I remember the early optimism. It was the mid-90’s: we had just made the move to IBM PC’s (replacing our trusty VT220 VAX terminals), and had deployed Microsoft’s Office suite across our organization. Everyone could now type and print their own memos; everyone could process their own mail… and it didn’t take long before it dawned on the powers that be, that we could dispense with the age-old role of the secretary. The new software allowed managers to do everything a secretary was supposed to do for them… we were all to become free, self-sufficient, able to do it all by ourselves. Hallelujah!

Of course, we should have known this was not the whole story. The PC’s of the day had an 80386 microprocessor with some 300,000 transistors. The secretaries they presumed to replace had wetware processors with 100 billion neurons. Surely something might get lost in the transition?

Admittedly, the new technology did take over many office functions. With a word processor on every desk, it no longer made sense to have a secretary take dictation and type memos (with 3 actual carbon-paper copies). And email, whatever our love/hate relationship to it, did replace interoffice paper memos. But there is one software tool that was particularly hailed back then as a secretary-buster, and that was the email-integrated calendar. This, we were told, allows everyone to organize meetings and invite attendees directly. How cool is that?

Not very cool, of course, as people soon found. Finding a good time slot for half a dozen busy managers to meet – even once, much less recurrently – was a true Mission Impossible, requiring superhuman powers – and we had such superhumans in our midst until the mid-nineties: they were called secretaries. With them heading for extinction, we had a problem.

What was the problem? Two issues: first, the simplistic view that all you needed to do was share free/busy calendar information ignored the fact that the seemingly free slot on someone’s calendar may mean he’s on a business trip on the other side of the earth (hence, “free” – but asleep), or she may be driving back from a customer’s facility, or he may indeed be free but his wife alerted him he may need to take the kid to the doctor if that cough doesn’t clear up by then… or she just needs a few more days to have the required analysis ready, so she’d rather not meet this week at all. And in any case, they may show two free slots, but may have a strong preference to use one and not the other. Availability is a black and white parameter in Outlook, but it has countless shades of gray in real life. A human secretary knew how to navigate those shades of gray.

The second issue was that the key to getting those attendees to agree on a time is negotiation. You need to discuss their constraints and preferences, and get them to change their willingness, as in “Look, Jane, I realize you’ve blocked Monday afternoon to write those reviews, but that’s the only time everyone else can attend… can you perhaps do the reviews in the morning? Oh, you promised Joe to do the QA data analysis that morning? How about if I call Joe and ask him to change that?” Outlook can’t do that for you – but a network of secretaries, each in control of one calendar and talking to the others on the phone, can make miracles happen.

That is why the first generation of calendaring tools had failed. People, being ingenious, found ways to work around the problem. Optimists would gamble: just set a meeting and hope people will accept. Pragmatists like myself would try to do the secretary’s job and negotiate, which in my case I did by applying the only method that would work. I’d email attendees a list of a few time slots, and ask them to mark next to each one BEST, OK, or NO WAY. Then I’d tabulate the responses, choose the best time for most people, and inform all attendees of the winner. This is far from failsafe, notably because many of my coworkers would totally ignore he instructions and just mark their one favorite slot… but on the whole it worked much better than just relying on Outlook, because it put the people in the loop and gave them 3 rather than 2 levels of preference. And I’m pretty sure that’s what those secretaries of old used to do over the phone.

And that’s where things stood for a while, until the second generation of calendaring tools arrived, and lo and behold, they duplicated my system to a tee! Take Doodle: it creates an online table of time slots and asks attendees to mark them with their level of preference, then it tabulates the responses and informs… exactly the same method I’d devised. Of course Doodle has the advantage that people can’t ignore the instructions to mark every slot, and its integration into Outlook allows it to automate the rest of the process flow. It pulls in the people for just the part that a computer still can’t do: expressing their true wishes. We humans command, the computer does the grunt work. Right!

What I find encouraging is that there is a general trend towards advanced productivity software that is designed to “replace the secretary” more effectively than those first generation tools. For example, in my area of focus, dealing with information overload, we see a growing lineup of new email clients, apps and add-ons that are designed to handle email in the context of an overloaded work reality: tools that prioritize the flood of incoming messages, that analyze the content to figure the work required on each message and facilitate doing it, and so on. There are even tools out there that intercept incoming phone calls and decide based on what you are doing whether to pass the call through or move it to voice mail… the famous secretarial role of protecting the manager’s need for thinking time.

If this trend continues, maybe this time we’ll really be able to harness the computer to give us optimal administrative assistance.

Except for the coffee… that we’ll have to procure for ourselves.

Nathan Zeldes helps people and organizations reduce Information Overload and improve Knowledge Worker Productivity, a subject he blogs about at

1 comment on “Everything but the coffee: The evolution of the automated secretary

  1. Pingback: How Software Failed to Replace our Secretaries – and how it’s Getting Better -

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