A response to the "small group questions" for the 20 October 2019 message at First Pres, Boulder. 
But, as it is written,“What no eye has seen, nor ear heard,nor the heart of man imagined,what God has prepared for those who love him”—
these things God has revealed to us through the Spirit. For the Spirit searches everything, even the depths of God. For who knows a person's thoughts except the spirit of that person, which is in him? So also no one comprehends the thoughts of God except the Spirit of God. Now we have received not the spirit of the world, but the Spirit who is from God, that we might understand the things freely given us by God. And we impart this in words not taught by human wisdom but taught by the Spirit, interpreting spiritual truths to those who are spiritual.
The natural person does not accept the things of the Spirit of God, for they are folly to him, and he is not able to understand them because they are spiritually discerned. The spiritual person judges all things, but is himself to be judged by no one. “For who has understood the mind of the Lord so as to instruct him?” But we have the mind of Christ.
excerpt from the English Standard Version of Paul's first Epistle to the Corinthians 
Religion has been described by some as a human striving upward to discover the divine. In contrast, Christianity has been described by others as God’s descent downward in revelation to humanity. What do you think about this statement?
I think it's reaching to say this is a contrast of statements from "some" and "others." In my experience, I have only ever heard Christians make either of these statements. I don't necessarily disagree with the sentiment; though I do worry that it betrays a certain ignorance of the perspectives of non-Christians; that it serves more to bolster our own pride rather than to proclaim the gospel.
Why was Paul careful not to use eloquence or wise words and persuasive speech in proclaiming the gospel to the Corinthians (1Cor.2:1–5)? What did Paul use instead?
Paul did not want the Corinthians faith to "rest in the wisdom of men but in the power of God."  Even if Paul used eloquent words to spread Truth, the eloquence itself might be used to undermind himself in pride, or to undermine the Truth by misdirecting attention. By sharing the Truth simply, there are no distractions.
What type of wisdom did Paul speak?
"Not a wisdom of this age or of the rulers of this age [but] a secret and hidden wisdom of God, which God decreed before the ages for our glory." 
Jesus said in John 16:13 that when the Spirit of truth comes he will lead you into all the truth. How is Paul saying something similar?
Paul says that "no one comprehends the thoughts of God except the Spirit of God" and that "we have received [...] the Spirit who is from God, that we might understand the things freely given us by God." Further, that "we have the mind of Christ." 
I find this particularly interesting in relation to other studies that I am working through; because sometimes we are exhorted by modern teachers and traditional theology that, because God's ways are higher than our ways, we cannot question where theology draws conclusions that seem counter to our understanding of good. Here Paul encourages us that, if we are in Christ, we should be able to understand what is good (and Christ also seems to expect the same of the people he ministers to.)
When have you sensed the Holy Spirit was guiding you or leading you in your life? What were signs of this?
I think the Holy Spirit guides us at all times; the question is whether we prioritize that Spirit or what remains of our flesh. As a result, I feel the Spirit's leading most in retrospective meditation, when I see all that God has done in my life, against all likelihood.
What helps you listen to the Spirit? What hinders you?
Prayer. Meditation. Calm. And just acknowledging the Truth of what is good to myself.