TBM 337: Pirates and Garbage Cans
News! I've started a YouTube channel. My goal is to get 100 videos up by the end of 2025. Most videos will be less than fifteen minutes.
On to this week’s post…
Why do problems fester for so long in companies? Why can it take so long for teams, managers, and leaders to work out their shit, by which point you have far fewer options?
Structured conflict resolution is common in legal disputes and international diplomacy but less common in internal business contexts. Why?
Admitting the need for help can be perceived as a leadership failure.
Blurred accountability and boundaries. There often aren't clearly defined "sides"—just overlapping interests with blurred boundaries.
Power dynamics make it risky to surface conflicts honestly.
Competition. The parties don't need to work or live together.
Leadership teams often read books like Crucial Conversations or The Five Dysfunctions of a Team. The implicit message is: "We should be able to navigate this ourselves, and if you can't, it is a personal flaw." Personal executive coaches are the norm; executive team coaches or facilitators (outside of isolated offsite activities) are the exception. Countries, unions, and communities perform conflict resolution in public—visibility is part of the process. Executives do their reckoning in private, lest cracks in their executive presence armor show.
When conflict is unavoidable and pretending isn't a viable option, humans tend to call in outside help. In business, the system often allows just enough room to avoid both the conflict and the discomfort of solving it. The cost of avoiding conflict is diffused—absorbed broadly as inefficiency, turnover, and passive-aggressive workarounds.
The Garbage Can Model
I am a big fan of the Garbage Can model that Cohen, March, and Olsen proposed. In this model, decision-making in organizations is not a rational process. Instead, it is a "mess" of problems, solutions, actors, and choice opportunities. The Wikipedia article has this wonderfully descriptive line describing the theory:
In situations of ambiguity, decision-making moves away from ideas of reality, causality, and intentionality to thoughts of meaning. Therefore, decisions become seen as vehicles for constructing meaningful interpretations of fundamentally confusing worlds instead of outcomes produced by comprehensible environments. As the complexity of decision situations increase so that they more closely resemble reality, they become meaning generators instead of consequence generators.
How does the model apply to our discussion of conflict resolution?
In diplomacy and legal contexts, there are defined parties seeking resolution, and formal structures exist to manage the process. In business, conflicts don't neatly map to specific problems with clear owners. They become floating problems in the garbage can. The people involved may lack the authority, interest, or clarity to address the issue head-on.
Formal conflict resolution requires intentional choice points (e.g., summits, negotiations, and legal proceedings). In business, conflicts linger in the organizational garbage can, waiting for the right mix of attention, participants, and urgency. Often, resolution happens by accident—when someone with enough power happens to care or when a crisis forces action.
The Garbage Can model challenges many existing theories on "rational" corporations. For comparison, we might compare your average corporation with a pirate ship.
Pirate Ship Necessity
Pirate ships had written articles ("pirate codes"), democratically elected captains and quartermasters, and systems for distributing the loot fairly. The captain had authority in battle. Outside of battle, decisions about daily life, punishments, and major choices were made collectively. The captain could be deposed if the crew lost confidence, and the quartermaster acted as a check on the captain's authority.
Compared to your average corporation, pirate ships had many more formalized mechanisms for conflict resolution. There was less need to hire consultants to say what no one else could say 😀.
With pirate ships, conflict was resolved because it had to be. The context was collective life-or-death. Pirates couldn't afford the luxury of unresolved conflict, while businesses often can (at least temporarily, because the consequences aren't as immediately existential). While pirates make decisions for survival, companies usually make decisions to sustain organizational narratives, even if that means avoiding conflict.
“Wartime”
These days, it is popular for leaders to talk publicly about reducing bureaucracy, cutting out middle management, "getting into the details," becoming more efficient, and "embracing wartime" (where wartime seems to be some combination of AI, international competition, higher interest rates, founder-CEO mid-life crisis, etc.).
This creates a wicked loop, as evidenced by this report from someone inside one of the FAAMG/MAMAA companies.
Everyone feels like they're on the chopping block. They know finding another cushy job like this will be hard because they've optimized themselves for this specific environment. Companies are cutting "fat," but in doing so, they're making people even more scared. That fear makes them act fatty. Only those who aren't afraid of losing their jobs are willing to take the risks needed to do meaningful work. And outside of the old-timers with "f you" money, that's a very small group. Which, in turn, cranks up leadership pressure. And the loop spirals. This is creating a massive execution gap. And I think this is happening everywhere."
The paradox: in their efforts to perhaps "embrace conflict," these leaders are creating conditions where actually resolving conflict is less likely. It is about facing conflict on their terms and in ways that protect their identity. But as this report points out, they face behaviors that confirm their beliefs! "It's not me," they think. People on teams are being evasive and playing politics, and I hate it!"
It's like a couple where one partner gets angry about "things being so complicated." In doing so, they create an environment where open, honest conversation feels risky. The partner's frustration about complexity ironically adds to the complexity because the other person starts walking on eggshells, carefully choosing words to avoid triggering another outburst. The very behavior intended to simplify and "just talk about it" makes genuine dialogue less likely.
Concluding…
So, back to our question:
Why do problems fester for so long in companies? Why can it take so long for teams, managers, and leaders to work out their shit?
The answer:
They can. A company's culture determines the norms and "meaning" that shape how conflicts are addressed, especially once they spiral beyond something more localized.
As a change-agent type—your average TBM reader—this is critical to internalize. You have to dance with this. You can't fight it. There's no magical epistemic crowbar.
Review Questions
Is work as high-stakes as we believe, or is that part of the issue?
At what point does a problem shift from something capable humans can reasonably sort out to something that might benefit from outside help?
How can you foster an environment where it's acceptable for teams to seek outside help when they get stuck?
Are escalations seen as a sign of weakness? If so, why? Where's the right balance between managers and teams working things out locally and escalating issues?
What are the norms in your company when it comes to dealing with conflict? Who do those norms serve? Who do they hurt? Are those norms still fit for purpose?
Assuming for a moment that the Garbage Can Model is true, how can you shape or nudge an environment so that the mix of actors, opportunities, problems, and solutions produces more likely congruent results?
Are there times when manufacturing a temporary crisis might be the only way to nudge people out of counterproductive loops before things spiral out of control?
Are startups like pirate ships or something else? Why or why not? At what stage of growth do startups start behaving like different types of organizations?
What's their knee-jerk reaction when people in your company get frustrated by a lack of coherence, bureaucracy, or politics?
What's a good experiment to run in your company? I recently met a company where people took a facilitation course and offered their services to other teams, providing an unbiased facilitator to help with team dynamics.
Great question! I'm lucky to be part of one of those rare internal team development consultants - there's 4 of us in the company I work for.
It's true that initially people tend to wait until things are on fire to get in touch with us, at which point (as you said) the scope of what can be done is much more limited.
The good news is that once people go through the process and emerge (relatively) unscathed, they tend to come back earlier on. We're even getting more requests where there's no issues, but people want to look ahead and think about how to seize future opportunities.
Sadly, the teams who need it most just don't ask for help, or even worse, they only do when forced by upper management (not a condition of success!).
I think bullets 1 and 2 are more pervasive reasons for why problems fester for long. I would add lack of spine as another pervasive contributing cause.