When greeting someone at church on a Sunday morning, it's inevitable that I will be asked "How are you, James?". I try to avoid saying "Fine. How are you?" (let's refer to that phrase as IFHAY for short).
Why do I avoid IFHAY? Some who know me will accuse me of bringing my non-conformism into these situations, and I must admit, there's something to that. But that's not the primary purpose for not using that tired phrase. My problem with IFHAY is that it's a little too safe. Someone can have this mini-conversation several times on a Sunday morning, and never get any closer to anyone by day's end. By relying on IFHAY, you convince yourself that you have checked in on people and let them check in on you, but you get to keep your shield up, and you have managed to avoid challenging others to let theirs down, as well. Ultimately, you have done nothing worthwhile in any of these conversations.
The genuine Christian life includes transparency. Calling yourself a Christian while refusing to ask others to open up (or opening up yourself), is like a Toyota calling itself a car after its wheels have been removed. It's true by the strictest definition, but renders the car ineffective for both its owner and for anyone else.
When I was a home group leader, we ended each meeting with a prayer request time. One thing I learned was that transparency doesn't come easy, and I could gain insights into our closeness as a group by the types of requests that were brought up. It turns out there are 3 levels of transparency in that environment: (1) Requests to pray for someone else I know; (2) Pray for me for non-spiritual issues; (3) Pray for me for deeper issues.
When we first started meeting, the members, not knowing each other well, would offer up prayer requests for their aunt, their neighbor, or some story they read about in the news. When we knew each other better, some got a little braver and asked for prayer for their own situations: job, finances, kids' illness. At this point, there's still a shield up. Nobody dares to ask someone to pray for their marriage, any sin they are struggling with, their lack of prayer life, etc. I knew our group was where we should be when people started bringing these types of requests before the group. This doesn't happen unless there's a real connectedness. It goes beyond comfort. It's a complete trust that your friends will feel the things you feel about the thing you are requesting prayer for. It's knowing that they won't just throw unsolicited advice at you (again, that's a way of making yourself believe you have contributed to a fellow believer's well-being while still remaining in a "safe" place). It's knowing that they rejoice when you rejoice, and weep when you weep.
In my observation, when members are willing to take that brave step out of their comfort zone and go head-first into the deepest level, it's because one of the following events has occurred: (1) transparency has been modeled for them by someone else in the group; (2) desperation; (3) enough time has passed and the group has reached a comfort level with each other.
Going backward, the third on the list is the least desirable option. Why wait for years for closeness to occur to the point that members can share deep personal prayer needs? How much damage can the enemy do in the meantime?
The 2nd item is also something that you don't want to have to resort to. I know of one marriage that nobody knew was in trouble until great damage had been done by one of the spouses. We got together and prayed with both of them, but the breakup had essentially been set in motion already, and a heartbreaking divorce was the result. If only we had known about the factors which started the smaller cracks in the relationship! But prior to the exposure of the problems, all we heard was: "I'm fine. How are you?" Nobody saw through IFHAY. There was no transparency.
The first one is best: a Christian is going to feel they can be open when someone has gone before them. This is where the group leader can do his/her greatest work, by being the first to be truly transparent. The group I'm in now (not led by me) is headed by just such a leader. When you think about it, that's what a leader does: leads. Goes first.
I implore any Christian reading this to do two things: Be willing to open up with some other believer you can trust will pray for you. And when on the other side of that conversation, refuse to accept IFHAY. Don't be afraid to press in, and don't worry if you offend the person. The times we are living in demand it.