The following advice is anecdotal and is a very clear example of "other optimizing". So don't take it with a grain of salt, take it with at least a table spoon.

I've found that engaging people about their rationality habits is frequently something that needs to be done in a manner which is significantly more confrontational than what is considered polite conversation. Being told that how you think is flawed at a fundamental level is very difficult to deal with, and people will be inclined to not deal with it. So you need to talk to people about the real world consequences of their biases and very specifically describe how acting in a less biased manner will improve their life and the lives of those around them.

Anecdotally I've found this to be true in convincing people to donate money to the AMF. My friends will be happy to agree that they should do so, but unless prodded repeatedly and pointedly they will not actually take the next step of donating. I accept that my friends are not a good sample to generalize from (my social circle tends to include those who are already slightly more rational than the average bear to begin with). So if you want to convince someone to be more rational, bug them about it. Once a week for two months. Specificity is key here, talk about real life examples where their biases are causing problems. The more concrete the better since it allows them to have a clear picture of what improvement will look like.