Working with Challenging Personalities

I recently got the following email inquiry from a friend who is part of forming community [note that I've lightly edited this correspondence and modified the names to obscure the identity of the group]:

We are at a juncture that is both exciting and extremely challenging. We have identified and made an offer on two adjacent properties that are in the target area we have been looking at and are affordable. Together, there will be eight units available for members, plus a common space, which will suit well our desire for a compact, urban community. But even if these properties fall through, our challenge will not go away.

As you know, our group has a multi-year history with bumps in the road, and we have shrunk to three active members—Dale, Chris, and myself (Lee). We also have two long-term members, Adrian and Evan, who are not currently active in the group yet are seriously considering stepping back in and are willing to invest money in this particular property.

Here's our dilemma. We have lost a lot of money over the years, and now have very little in the bank. While most of us have some additional money we can invest in this project, it won't be possible unless Evan contributes $120k, which can be used as a down payment. While Evan is willing to do this, here's the bomb: For various reasons, Evan does not feel she can live in a community this small with Chris living there as well.

Without Evan we cannot buy this property, and it is unlikely we can buy any property, especially one that Chris can afford to live in—as smaller properties will cost more per unit to rent.

We are at wits end. I know I do not feel I can last much longer in trying to create a successful group. I think we all feel the same, and have begun to discuss the possibility of dissolving the group at year's end if nothing is created before then. We care about Chris, enjoy him, and respect his contributions throughout the years. But it's looking like we can't have a successful community that includes Chris given our financial situation, Evan's discomfort at having Chris as a member of such a small community, and some feedback/concerns we've had from other potential partners in the past.

These are notes from a recent meeting of Dale, Chris and myself:  
"Chris is the designated big personality right now. New people are scared about committing, mentioning concerns about Chris. We're scared we can't recruit anyone new. It's putting the group and Chris into a weird situation. We want neutral, positive ways to shift whatever is putting people off, and to maintain good relationships with each other, without screwing over the group as a whole (if we can't recruit new members, this project will never work financially)."
  
Chris wants me to ask: "When other people talk to Dale I think it doesn't only create problems for all three of us, there's an extra unhelpful dynamic of Dale telling me (Lee) about the problem (when she does). I don't think that's working well, because Dale has her own feelings, and we have some problems in our relationship at this point, so the information about what other people are reporting comes across with a particular twist, which I then have my own reaction to. I'm not sure what to do about that, since I also want to know if somebody has a problem. I think they should be talking to me directly as much as possible, yet that's something to ask Laird about." 

So I am. While I think speaking directly with the person concerned makes sense, Chris' question also showcases some strain in Dale and Chris' relationship.

What to do?  We're in a horrible situation, where money is reigning over a long-term, hard working, committed member, and where without that money, we may have no community at all (where, unfortunately, money isn't the only problem).

Here's my response:
 
This is certainly a tough spot.

o  The three of you (Chris, Dale, and Lee)) are weary of the many years with so little progress toward manifesting a community.

o  You now have found property that you like and can afford, but only if Evan invests.

o  Evan will not invest if Chris is in the community.

o  Chris has been involved for a long time, and has demonstrated a significant dedication to the project, yet a number of others have also found it difficult to work with her.

So the situation presents as a choice between:

Option A: Sticking with Chris and trying to either: a) figure out a way to replace Evan's money; or b) look for a different property that is either more affordable or one that is large enough that Evan would consider living with Chris.

Option B: Proceeding with the current opportunity, and asking Chris to step out.

Let's walk through each option.

Analysis of Option A
I know virtually nothing about what you've attempted to identify potential sources of money that could replace Evan's $120k. While I think it's possible that you could solve this problem, it likely comes with (at least) two price tags: 
—You'd have to spend time and energy locating the money, and it may come with strings that will be more complicated than simply assigning equity to Evan. 
—You'd lose Evan as a member.

Passing on this attractive property and continuing the search is unattractive. Your group is tired and there's a sense of either this is it or it's time to fold your tent and let go. That is, you may not have sufficient reserves (in terms of energy and motivation, as well as money) to keep searching. Further, there is probably the sense that you'll still need to deal with the tensions for which Chris is a lightning rod, so it may as well be now.

Analysis of Option B
What's the analysis of Evan as a potential member? In particular, I'm wondering about Evan's willingness to work through tensions with others. Has Evan made a good faith attempt at understanding Chris and resolving tensions with him? This is relevant in that if you agree to Chris' terms, what will happen the next time Evan is in tension with someone?

Taking this another step, have you seriously labored with Evan about the basis for having drawn a line in the sand about Chris? Do you respect how Evan got to that conclusion?

If you ask Chris to leave the group, Dale & you will need to be able to live with that decision. While everyone is not meant to live together, and there are definite limits to how far groups can stretch to include everyone, you two need to feel that you've made enough of an effort to work through tensions with Chris and are convinced that the effort is too great relative to the benefits to continue. If you're not at peace with that, you'll feel guilty and it will undercut the joy you had meant to get out of starting a community. The community will become a poisoned apple. 

• • •

Whichever way you go, you'll want to feel that you're being realistic and that you're proceeding in a way that strengthens the resolve and capacity of the remaining group to work on tensions as they arise—with or without Chris.

Apropos Chris' question about how critical feedback is handled in the group, you'll want to proceed in such a way that you've done your best to handle any challenges about living with Chris (as a specific example of issues that might come up about living with anyone) as compassionately and authentically as possible—since that's your highest intention for how your community will function. If you don't feel you're handling that well, then I urge you to address that first.

I am not making a recommendation about whether Chris should be part of the group. Rather, I am making a recommendation that you look hard at how you deal with tensions and identify the limits of when you've tried hard enough and it's time to let go. These are not easy questions, but you have to face them.