A response to the "small group questions" for the 17 February 2019 message at First Pres, Boulder. 
I always thank my God when I pray for you, Philemon, because I keep hearing about your faith in the Lord Jesus and your love for all of God’s people. And I am praying that you will put into action the generosity that comes from your faith as you understand and experience all the good things we have in Christ. Your love has given me much joy and comfort, my brother, for your kindness has often refreshed the hearts of God’s people.
That is why I am boldly asking a favor of you...
excerpt from the New Living Translation of the Epistle to Philemon 
What new insights did you gain from our study on the book of Philemon?
I was reading a commentary on Philemon  in my study tonight:
If the New Testament were simply a book of doctrinal teaching, this Epistle would certainly be out of place in it; and if the great purpose of revelation were to supply material for creeds, it would be hard to see what value could be attached to a simple, short letter, from which no contribution to theological doctrine or ecclesiastical order can be extracted. But if we do not turn to it for discoveries of truth, we can find in it very beautiful illustrations of Christianity at work.
Recently I've been trying to be more intentional about the way I profess my faith; not just to nonbelievers, but to professing Christians in my community. It's no secret that I have been forcefully frustrated and often discouraged by the discongruity between the teachings I was raised with and the behavior that I see from many that I once considered elders. In previous meditations I have reflected on the tone and heart with which I've approached such conversations, and purposed to be more charitable--in a sense, more generous--in such conversations.
Here, Paul (at least, as presented in our message today) presents an example of how better to exhort Christian behavior among believers. In a sense, it comes off to me as passive-aggressive: a tact that I very much try to avoid. However here, where presumably Paul is being genuine when he calls Philemon "beloved" whose "love has given me much joy and comfort." It speaks to a point made in the sermon: Paul is generous with his assumptions. He expects Philemon to act rightly, even if he is, it seems, guiding Philemon to do so.
I have much to learn from this.
This weekend, we explored four examples of what generosity looks like in the context of relationships: be generous with your words (v4-7) be generous with your time (v10); be generous with your resources (v18-19); and be generous with your assumptions (v21). What would you add to this list?
I hesitate to call the list complete; but I also don't have anything to add. I very much appreciate this insight into various aspects of generosity in our relationships with others (particularly as it relates to our relationships with fellow Christians); and I further appreciate that, during the message, these examples were called out with specific reference to passages in Philemon. (I have added these references in line with the questions.)
Considering the four examples listed above: in which area would you say you are the strongest?
I always struggle with self assessment, particularly when it comes to my strengths. I find that it is often when I think I am strong that I find my greatest weakness; because where I think I am strong, there I am overconfident .
But if I were to rank my strength in these four examples of generosity, I would at least put generosity of time and resources above words and assumptions. I would like to think that I prioritize time with others above most other concerns, even if I fail to seek or arrange it myself. And then, whenever I have been asked to help in some physical way, I believe that I have always been willing to share what we have, even if I am sometimes anxious beforehand (and I hope that this anxiety has never prevented anyone from asking for help). We have been blessed to embarrassment, and I have no pretense that what we have is the result of my hand, but God's in our lives. I only worry about my ability to discern between being generous and thinking of myself more highly than I ought.
Which one represents your greatest opportunity for growth?
If time and resources represent my strengths of generosity, than words and assumptions represent my weaknesses. If not my immediate assumptions, I am often quick to write-off the intent and heart of people who have disappointed me; and while I generally consider it a value that I am direct and honest with the people around me, I often loose sight of how my words will be received. At the very least, I should spend more time in prayer over what I will say, particularly if I pretend to look to the Epistles as my example.
Daniel, in his message this morning, exhorted us to "be liberal in our praise and conservative in our criticism." I relate this to the "robustness principle":
Be conservative in what you do, be liberal in what you accept from others.
Jon Postel, regarding the implementation of TCP
While I do try to be liberal in my praise, I often use this as an excuse to be equally liberal in my criticism; but I see value in trying to ensure that the one is more prevalent than the other.
What one relationship in your life could really benefit from some extravagant generosity at the moment?
I'll refrain from calling out any specific person here; though I will not pretend that the Spirit has not brought people to my heart.
I will, however, change context and admit that these principles of generosity--or lack thereof--apply to my relationship with Andi as well; and even my children, to a certain extent. Andi and I both often fail to be generous with our assumptions of each other; and I also often fail to be generous with my words, particularly failing to ensure that my praise outweighs my criticism.
What is one thing you will do this week to be more generous in that relationship?
I am often a critical person, and I mean this in the strict sense that I view the world through a lens of what could be made better about it. In my relationships at home, and particularly with Andi, I will endeavor to use my habit of criticism to prompt me to look for more charitable interpretations of what I experience, and to be more generous with the words I use, hopefully through prayer and the leadership of the Spirit.