There's a couple of factors here worth keeping in mind.
One is that classical conditioning continues to work, even when I'm concentrating on operant conditioning. So one result of this strategy is that my target will come to associate me with aversive stimuli, which will in turn reduce the effectiveness of my attempts at reinforcement. They will similarly associate the teaching sessions and math with those stimuli, which may be counterproductive.
Another is that a target consciously noticing my attempts at conditioning changes the whole ball game, in ways I don't entirely understand and I'm not sure are entirely understood. Sometimes it's a huge win. Sometimes it's a huge lose. Staying subtle is more predictable, if I can do it, but of course it's not always possible to avoid detection, and sometimes it's better to admit to my attempts at conditioning than to be caught out at them. The safest move is to first establish a social context where my attempts at conditioning can be labelled "manners," such that any attempt to call me out on them is inherently low-status, but that's not always possible either.
When using praise signals as reinforcers for systems, like some humans, who are capable of skepticism about my motives, it helps to be seen to use expensive signals. (Attention often works well, which is one reason Internet trolls are so persistent.) Of course, that typically means I have to invest resources into my conditioning efforts.
In general, the approach I endorse is to maintain (and adjust as needed) a consistent threshold of evaluation, ignore behavior that falls below that threshold, reward behavior that clears it, and resist the temptation to go meta about the process.
Part of the sequence: The Science of Winning at Life
Also see: Basics of Animal Reinforcement, Basics of Human Reinforcement, Physical and Mental Behavior, Wanting vs. Liking Revisited, Approving reinforces low-effort behaviors, Applying Behavioral Psychology on Myself.
Story 1:
On Skype with Eliezer, I said: "Eliezer, you've been unusually pleasant these past three weeks. I'm really happy to see that, and moreover, it increases my probability than an Eliezer-led FAI research team will work. What caused this change, do you think?"
Eliezer replied: "Well, three weeks ago I was working with Anna and Alicorn, and every time I said something nice they fed me an M&M."
Story 2:
I once witnessed a worker who hated keeping a work log because it was only used "against" him. His supervisor would call to say "Why did you spend so much time on that?" or "Why isn't this done yet?" but never "I saw you handled X, great job!" Not surprisingly, he often "forgot" to fill out his worklog.
Ever since I got everyone at the Singularity Institute to keep work logs, I've tried to avoid connections between "concerned" feedback and staff work logs, and instead take time to comment positively on things I see in those work logs.
Story 3:
Chatting with Eliezer, I said, "Eliezer, I get the sense that I've inadvertently caused you to be slightly averse to talking to me. Maybe because we disagree on so many things, or something?"
Eliezer's reply was: "No, it's much simpler. Our conversations usually run longer than our previously set deadline, so whenever I finish talking with you I feel drained and slightly cranky."
Now I finish our conversations on time.
Story 4:
A major Singularity Institute donor recently said to me: "By the way, I decided that every time I donate to the Singularity Institute, I'll set aside an additional 5% for myself to do fun things with, as a motivation to donate."
The power of reinforcement
It's amazing to me how consistently we fail to take advantage of the power of reinforcement.
Maybe it's because behaviorist techniques like reinforcement feel like they don't respect human agency enough. But if you aren't treating humans more like animals than most people are, then you're modeling humans poorly.
You are not an agenty homunculus "corrupted" by heuristics and biases. You just are heuristics and biases. And you respond to reinforcement, because most of your motivation systems still work like the motivation systems of other animals.
A quick reminder of what you learned in high school
What works
Example applications
For additional examples and studies, see The Power of Reinforcement (2004), Don't Shoot the Dog (2006), and Learning and Behavior (2008).
I close with Story 5, from Amy Sutherland:
Next post: Rational Romantic Relationships Part 1
Previous post: The Good News of Situationist Psychology
My thanks to Erica Edelman for doing much of the research for this post.