A few tips I picked up but rarely use:

1. Embrace nuance & complexity (hard)
2. Avoid fallacies (harder)
3. Be skeptical (easy)
4. Keep an open mind (easy)
5. Focus on form & content (hard)
That's all for now. Remember, these pointers are for ideal conditions but the usual way philosophizing is done is completely random, at least for me.

I argue with myself - out loud. I pace up and down in my living room, arguing both sides of a proposition, to try and achieve synthesis. There's something about expressing an idea out loud that tells you immediately if it's reasonable.

I think that looking at problems from various perspectives and angles helps, rather than being locked into one specific point of reference, helps one avoid being too narrow.

arguing both sides of a proposition, to try and achieve synthesis — counterpunch

A half-bottle of scotch helps there because the best solution is to forget the distinctions.

A half-bottle of scotch helps there because the best solution is to forget the distinctions. — magritte

A half bottle of brandy, actually, doesn't help - because my drunken debates can become violent! I'm very passionate about philosophy, even when arguing against myself.

It is important to compare my conclusions with the feelings it produces. Conclusions that produce good happy feelings are closer to the truth and inspire more creation than ones who produce negative, helpless, and sad ones.

Innatism/Nativism as exemplified in Russell's An Outline of Philosophy and Tallis' The Knowing Animal.

Though neither are innatists as such.

These are some interesting approaches, but interestingly they are different. :)
I may just make a post on addressing the process learning fundamentally and consider the various methods of philosophy or other learning methods to see what transitions well.

Then discuss further. -u-

When I immerse myself into philosophical contemplation, I follow the instruction sets in "Stockwell's and Furchtwanger's Guide to Contemplative Philosophical Immersions" to a tee.

I hide under the bedclothes and pray God to make it stop.

I think that looking at problems from various perspectives and angles helps, rather than being locked into one specific point of reference, helps one avoid being too narrow. — Jack Cummins

Rather, we should be adoxastoi (without views), aklineis (uninclined toward this side or that), and akradantoi (unwavering in our refusal to choose), saying about every single one that it no more is than it is not or it both is and is not or it neither is nor is not — Pyrrhos of Elis

I wouldn't mind someone explaining Pyrrho's statement above. Anyone?