Author: Eric F. Savage

An area that user-focused software has gotten better at in the past 10 years or so is being aware, and protective of, the context in which users are operating. Things like autocomplete and instant validation are expected behaviors now. An area that software is really picking up steam is analytics, understanding behaviors. You see lightweight versions of this creeping into consumer software with things like Mint.com and the graphs in Thunderbird, but most of the cool stuff is happening on a large scale in Hadoop clusters and hedge funds, because that where the money is right now.

But where software has not been making advancements is in being proactively helpful, using that context awareness, as well as those analytics. If that phrase puts you in a Clippy-induced rage, my apologies, but I think this is an area where software needs to go. I think Clippy failed because it was interfering with creative input. We’ve since learned that when I user wants to tell you something, you want to expedite that, not interfere. Google’s famed homepage doesn’t tell you how, or how to search. They’ve adapted to work with what people want to tell it.

I’m talking about software that gets involved in things computers are good at, like managing information, and gets involved in the process the way that a helpful person would. We’ve done some of this in simple, mechanical ways. Mint.com will tell me when I’ve blown my beef jerky budget, Thunderbird will remind you to attach a file if you have the word “attached” in your email. I think this is a teeny-tiny preview of where things will go.

Let’s say you get a strange new job helping people manage their schedule. You get assigned a client. What’s the first thing you do, after introducing yourself? You don’t sit there and watch them, or ask them to fill out a calendar and promise to remind them when things are due. No, you ask questions. And not questions a computer would currently ask, but a question like “what’s the most important thing you do every day?”. Once you’ve gotten a few answers, you start making specific suggestions like “Do you think you could do this task on the weekends instead of before work?”.

Now, we’re a long way from software fooling people into thinking it cares about them, or understand their quirks, but we’re also not even trying to do the simple stuff. When I enter an appointment on Google calendar, it has some fields I can put data in, but it makes no attempt to understand what I’m doing. It doesn’t try to notice that it’s a doctor’s appointment in Boston at 9am and that I’m coming from an hour away during rush hour, and maybe that 15 minute reminder isn’t really going to do much. It would be more helpful if it asks a question like “are you having blood drawn?”, because if I am, it can then remind me the night before that I shouldn’t eat dinner. It can look at traffic that morning and tell me that maybe I should leave even earlier because there’s an accident. It can put something on my todo list for two weeks from now to see if the results are in. All from asking one easy question.

Now, a programmer who got a spec with a feature like this would probably be speechless. The complexity and heuristics involved are enormous. It would probably get pared down to “put doctor icon on appointment if the word doctor appears in title”. Lame, but that’s a start, right? I think this behavior is going to be attacked on many fronts, from “dumb” rules like that, to fancy techniques that haven’t even been invented yet.

I’ve started experimenting with this technique to manage the list of ideas/tasks I have. In order to see how it might work, I’ve actually forbidden myself to even use a GUI. It’s all command line prompts, because I basically want it to ask me questions rather than accept my commands. There’s not much to it right now, it basically picks an item off the list, and says, “Do you want to do this?” and I have to answer it (or skip it, which is valid data too). I can say it’s already done, or that I can’t do it because something else needs to happen first, or that I just don’t want to do it today.

If it’s having trouble deciding what option to show me, it will show two of them and say “Which of these is more important?”. Again, I’m not re-ordering a list or assigning priorities, I’m answering simple questions. More importantly, I’m only answering questions that have a direct impact on how the program helps me. None of this is artificial intelligence or fancy math or data structures, the code is actually pretty tedious so far, but even after a few hours, it actually feels helpful, almost personable.

If you know of any examples of software that actually tries to help in meaningful ways, even if it fails at it, let me know!