Good boss, good product, good team, pick two (1 of 5 in series)

There's a running joke I keep hearing: in any organization you join, you only get two of three things: a good boss, a good product, or a good team. Pick your poison.

I've heard this said over drinks, in Slack threads, during late-night coding sessions. It's one of those observations that feels true enough to be funny, but not serious enough to examine.

Over the past year, I've been deep in management theory. Not just reading it, but using it. Five Dysfunctions retros with my team. Working Genius assessments. Watching Lencioni's models play out in real time. Also digging into Extreme Ownership, Jim Collins, Simon Sinek, systems thinking.

What struck me: these frameworks keep revealing the same constraint. No matter how well you apply them, you can only optimize for two pillars at a time. And I keep coming back to that joke. It's starting to feel less like a joke and more like something real.

Refining the Terms

As I've dug deeper, I've found myself refining those original terms. "Good boss" becomes Leadership, someone who creates clarity, makes hard calls, and earns followership. "Good product" expands into Strategy/Product, a coherent bet on the future grounded in customer truth. And "good team" evolves into Team/Organisation, trust, psychological safety, and accountability that actually work.

I've noticed that different leaders naturally gravitate toward different combinations. Some excel at Leadership + Strategy. They drive bold moves but may let team health slide. Others prioritize Leadership + Team. They build strong cultures but can miss market shifts. This explains why leadership transitions feel jarring. The new leader isn't just different. They're optimizing for a different two pillars, which makes the previous leader's focus seem misguided or wrong.

I've also been thinking about how this pattern connects to what Lencioni talks about, organizational health, trust, clarity, the way systems reinforce themselves. The frameworks he provides are powerful, but I keep noticing the same constraint: you can optimize for strong leadership and a healthy team, but strategy drifts. You can have visionary leadership and killer products, but team health suffers. You can have solid strategy and happy teams, but leadership feels absent.

I'm not saying Lencioni is wrong; I have no merit for that, he's clearly pointing to something real. But I'd like to know if there's a limitation built into how organizations actually work. A constraint that's not about doing things wrong, but about the nature of complex systems themselves. Does complex systems just work out this way? When you optimize for two things, you create feedback loops that reinforce those two things. The third pillar doesn't just get less attention. It gets less reinforcement in the system's feedback loops.

Is this a cycle?

And here's what's been nagging at me: what if this isn't a permanent state, but a cycle? What if organizations don't just pick two and stick with them, but rotate through different combinations as they evolve? Maybe real leadership is the ability to spot these, and change as they go?

What I'm discovering is that organizations rotate through different combinations over time. They don't pick two pillars and stay there. The weak pillar eventually demands attention, forcing a shift. This creates a continuous loop where focus rotates as conditions change. But through my entire career I've only seen these transitions happen with leadership change, I've never seen a leader be a part of a focus change, which makes me wonder if thats just how it is?

What I want to explore

I'm writing these posts to get concrete with this observation. To put it into words and see if it resonates.

Have you seen this pattern? Does it match how you've experienced organizations? Or am I missing something?