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  • Writer's pictureMatt Gordon

Leading Bad Groups: A Lovelier Prospect

Updated: Feb 24, 2023

By: Matt Gordon

I was talking recently to another person. Conversations always seem to go best in this manner. She shared with me about a group she was leading that wasn’t going well. I’m not sure if you have ever been in charge of a group that isn’t going well, but it shapes up about like I think a hostage situation does, with you, the leader, playing the role of the chief negotiator and the groupmates becoming conspiratorial miscreants. Your first objective is just to get them talking—about anything. Their goal is not to rat to some cop about anything.

“So I thought we could go around and share our name and say one word—any word—out loud.”


“Okay, I’ll start. Matt. Cucumber. Next?”


“Great. Just want to make sure everyone understands what we are doing. You—meaning everyone who isn’t me—are going to take turns saying your name followed by any word of any language . . . at all. Okay, who’s up?”


“Doesn’t have to be your name. Can just be a name. Any name.”

Shuffling of a chair here; a sniffle there. Otherwise, silence.

“Did anyone do anything fun this or any weekend ever?”

And so it goes. It can happen when teaching a class, in a book club or church small group, managing a work team, even coaching an especially reticent youth sports team. For whatever reason, the experience can convert time into a transcendent hellish eternity.

This other person I was talking with recently was experiencing this in a group in which she had reached the halfway point in terms of meetings. She was a bit distraught, wondering aloud what she was going to do—how she was going to get through to the stubborn holdouts?

I think this is probably the plot of a lot of movies. Michelle Pfeiffer has to break through to the inner-city kids; Robin Williams must bestir the private school rigidity and adolescent groupthink to make Whitman relevant; Gordon Bombay must overcome a team’s loser mentality and his own checkered past to make the Ducks fly together.

It is always pretty easy in the movies, and usually is accomplished in about 90 minutes. Get Coolio to spit some songs, or have kids stand on their desks, or bring some eggs to hockey practice. The next thing you know the ice is more than broken—it is like it was never there.

Real life is different though. People are more stubborn and the feelings are real. That is what this hapless group leader was experiencing. She was stuck in a weekly fight and outnumbered 20-1.

So truly I was surprised by her next move. She fought.

The reason for my surprise is that I’m not sure that is the prevailing reaction these days—maybe any days? Sure, in films it is. But if our experiences were the subject of such films, I think the moral of the story would be less about getting kids to college or PeeWee championships, and more about running out the string. That is my first reaction when the odds are long. Just get through with as little carnage as possible. Do the bare minimum. Try to care as little as possible so you hurt as little as possible when you inevitably fail.

We can read all the self-help leadership books we want and watch all the moralizing films we can, yet the most modest of tests seem to cripple us. We have become a people of convenience, who will take what is allotted us, complain a bit, and then hope to avoid that scenario again at all costs.

The truth is that a bad group dynamic is not a hostage situation. It is a bunch of people collectively proving out my point. It is folks who are put in a spot they, for whatever reason, do not want to be in, and then doing what we have chosen to do in such situations: just run out the string discontentedly. Close our eyes and clench our hearts till it is over.

What happens when perseverance dies? When poetry decidedly sucks because there is no one willing to remind us of the sweet syllabic cadence of dancing dactyls? Many groups and teams have chosen comfort, holding out against the potential discomfort of better for the promise of passing time and getting along back to convenience. What happens when the leaders among us choose the same?

In my conversation with this aforementioned woman, I did not have to answer the question, for she came with pad and pen in hand. She came to tinker—to cry even!—toward a possible better. She was not content to leave hostages behind, even if by attempting to save someone from the doldrums of social isolation, she might herself take wounds. This person developed a tactical plan to draw the group out of themselves and invite them to make best use of the time they had together. In short, she chose to actively persevere rather than just wait it out and move along.

These are some steps she took:

  1. Care – She chose to care about excellence. Just getting by is not excellent. Settling and waiting for things to end is not excellent. She chose to care about her role to play in the world, and the role of the individuals in her group too. This might have only been a tiny piece of those broader roles, but in the precise moment of her group’s gathering, it is the only place any of them are. It is the absolute maximum of their existence. Where we are is where we are. The absolute only place we can be. What do we do with the places we occupy? We must keep asking ourselves and others that. In this way we care, and in that care, we cultivate meaning. We human.

  2. Target – This person wisely targeted the gatekeepers. I have never been to prison, but I imagine I would not be the biggest guy there. Unless they make specialized prisons for very tiny people, I would need a size that is not my own to spare myself from physical hardship. Recently, I heard an interview with a guy who found himself in prison and outsized. He used basketball—a thing he was good at—as a means to win favor with those bigger than himself. From those relationships came protection and even influence. Group scenarios are not prison, but the social economics of gaining influence are not much different. If you are the unpopular outsider, attempt to gain the trust of the popular insider. It expedites the process and scales better experience faster. In the case of my friend, she found the person who held the most sway in her group, and she reached out. She was vulnerable with him. She asked for help. And she won him over to the cause of better, winning others by proxy.

  3. Try – Why not? Well, I guess because we don’t trust that we will be successful. But what if we are constantly defining success wrong? Success, possibly, is in the trying. It is the crucible of character. It is the forge of integrity. It is the incubator for future strategy. How can we actually get better at navigating tough situations if we camouflage ourselves in apathy in every tough situation? No, it is in the fight that I learn to fight. As long as I actually fight. Not sure how many life lessons have come from the old cower-wail-and-wait tactic. When you are put in a situation that there is decidedly no way out of, trying is the pathway toward success.

  4. Maintain Perspective – When we think about what causes us deep consternation, how many of those things actually matter? When I think of group dynamics, the awkward silence comes to mind. “It was so awkward!” we lament. What? That ten seconds of no one answering your questions? Who cares. It is ten seconds. Not everyone will respond to us in life. Not everyone will like us. Not everyone will shower adoration on us. Not everyone is easily won. Not everyone speaks when spoken to or says “How high?” when we say jump. So why does it cripple us so? Well, probably because we lack perspective, eternally or otherwise. Also, because comfort is a god. But what if, with perspective, we took momentary discomfort in stride? What if we could shrug off a bad hour as just that? It is a bad hour. A bad hour! That’s it! And now that I call a spade a spade, I shrink the enemy. A bad hour is not some giant raining down taunts and threatening my village. It is a meager, measly thing, easily endured. Also, once I know what I’m in for—this is going to be a bad hour—it becomes a bit easier to strive realistically toward making it a little less bad. We tend to expect perfection on everything, and hence we are crippled by any threat to utopia. Likewise, if we expect moderate discontent rather than absolute dystopia, then it is a bit easier to be undaunted by and shrink challenging moments and to strive reasonably for marginally better rather than absolute (and mythical) perfection. Rather than being deterred by Heaven being prison or paralyzed by the chore of making prison into Heaven, we can be more realistic with our assessment: which tends to be more in-line with making something boring a little less so. How can I give Iowa just a splash of Chicago? How can I throw some paint on the walls of this basement? How can I plant a flower here or there? Steady care is not an overnight overhaul. It is a process of minute beautification. And that is almost a lovelier prospect.

I could go on. But instead I want to share one line of an email about the experience my friend had in her group this week. Same group that threatened to dementor her soul last week, mind you. She breathed, got perspective, made a plan, chose to care big, and here was her response this week:

Today was SUCH a good day. Highest participation and pretty conversational. My heart is still so full, and I’m not sure that’s going to go away anytime soon.

Reminds a bit of the old CS Lewis quip about it making all the difference in the world to YOU if you serve like Judas or like John. Yes, the group will benefit, but our own lot in life improves when we are caught up in the delight of dancing in meaning. It is not a song that plays in every room we occupy, but rather the tune we take with us into the rooms of our life. That is, if we choose to--if we bravely choose life over existence even in the small, quiet places.


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