What Makes a Good Personal Assistant?

One of my mentors from years ago — who was one of the smartest people I’ve known — had a great deal of admiration for personal assistants. The human kind I mean. Through him, I gained an appreciation for them, too. By personal assistants I mean anyone who directly helps someone else do their job or perform a similar sort of function.

A personal assistant, like other employees, works for their boss. You can say that all employees are extensions of their boss and broadly-speaking they help their boss achieve the goals of her/his organization. But most employees have specialized jobs to do that apply to particular aspects of the organization they are part of. A personal assistant is different in that their job is to help their boss do his/her job more efficiently or effectively. They take on tasks that their boss can’t do due to time or other constraints, doesn’t want to do, finds value in having someone help with, etc. They remove roadblocks, take care of details, keep things organized and stop things falling through the cracks, and sometimes even act as roadblocks themselves — preventing other people from distracting their boss or wasting her/his time. In numerous ways they augment the value and productivity of their boss and make his/her life a little bit easier.

A good personal assistant is a natural, almost seamless extension of their employer. They have a deep understanding of the organization, its goals, resources and constraints, and the nature of the tasks to be done. They understand their employer’s role in the organization, her/his motivations and his/her opinions of other people inside the organization and externally in partner, customer and competitive organizations. They know who can be trusted and who to ‘go to’ for specific needs. They are perhaps their boss’ most trusted employee, a confidant.

Really good personal assistants anticipate their boss’ next requests and are prepared to respond to those as soon as the boss gives even an indication. They know the set of possible options/next steps and the likely decision criteria that would trigger one versus another. When something unexpected comes up, they know to alert their boss. They are honest and open with their boss (but not necessarily fully open with others, as they need to know when to protect their boss and her/his interests). They don’t necessarily need to be told explicitly when to do something or what to do. They can often read between the lines or recognize triggers for actions they should be taking. They can be entrusted to represent their boss and to make appropriate decisions on their boss’ behalf, when needed (and at the same time not overstep the boundaries of their authority and responsibility).

So how does a personal assistant become capable of contributing so effectively to the execution of tasks — some more mundane, some more important — that their boss otherwise would be doing? It’s all about context. A personal assistant knows the background for tasks and decisions. They know the history. They have strong domain knowledge. They know their boss’ preferences. They know how ‘outsiders’ (anyone but them and their boss) are likely to behave in certain situations, who to trust and who to keep an eye on. Some of this information they have been told explicitly by their boss. Some of it they have picked up just from working closely with their boss for some time. They need to know the limits of their own skills and knowledge and who to bring into the process (often on their boss’ behalf) to achieve the goal. They know where and when to ‘ping’ their boss and get additional direction, clarification or confirmation.

All of this is relevant to my interest in semantics for the following reason: if we want to develop virtual personal assistants — intelligent software agents — they will need similar knowledge and capabilities. That will have to come from somewhere, and it seems unlikely or at least inefficient if all that knowledge has to be hand-curated and all that logic has to be hand-coded. Some of it at least will need to be machine- learned/generated and then validated, based on existing knowledge and through learning loops (i.e., by trial and error and/or explicit feedback loops).

Think about the so-called personal digital assistants that exist today. Do they have these capabilities and knowledge? Not the ones I’m familiar with. They do a decent job of interpreting my explicit voice commands for a relatively fixed set of tasks, such as search, creating a meeting event or calling someone from my contact list. More complex tasks, if handled at all, involve a constant series of back and forth questions between the personal assistant and me. Human personal assistants might do this early in a task to establish the framing criteria, but part of their productivity-enhancing abilities lies in the fact that they can do many things autonomously or semi-autonomously (knowing when to come back to me with questions, or to discuss options or problems). Can you imagine if they behaved like their digital counterparts do today, simply echoing back much of your input and making you connect most of the dots and orchestrate most of the workflows through repeated questions derived from some sort of decision tree? Those aren’t true personal assistants, those are at best ‘helper apps’. But you have to start somewhere I guess.

We have a long way to go to get to where we have real virtual personal assistants. I think the basic technology components exist for the most part today to at least get started. But there is much work to do to put them together in the right way and create apps that do even a little bit of what Corporal ‘Radar’ O’Reilly did for the Colonel on M*A*S*H [Note: if you don’t know that reference, by all means Google it! He’s the kind of personal assistant I want to have in automated form].


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