Why you can't have it all: "The Three Pillar"-trade-offs (3 of 5 in series)

Make sure you read the previous article: The Three Pillars refined; leadership, product, team (2/5)

So here's where it gets interesting. In the previous post, I talked about how each pillar can have structural dysfunctions, teams that seem cohesive but are actually united by a common enemy, strategies that are creative but lack discipline, leaders who are present but not actually strong.

But I've been wondering if something else is going on here. What if this isn't about structural problems? What if it's inherent to how organizations build themselves, or how complex systems operate?

I think maybe it's a focus problem. In my experience, optimizing for two of these areas often means the third takes a hit. But I've been thinking about why this happens, not just that it does.

It would be easy to assume it's just an outcome of resource allocation limitations, but I think it's more fundamental than that. When you optimize for change, you're creating feedback loops. Those feedback loops reinforce each other, and my observation is that only two of the three can be a part of the loop, while the third gets less reinforcement. Over time, the gap widens. It's like technical debt, it doesn't just sit there, it compounds over time.

Leadership + Team

You get deep alignment, fast decisions, resilient culture. But strategy drifts, and product-market fit can lag. I've seen this in early-stage startups with amazing founders and tight-knit teams, but ones that built "cool" tech that users didn't really need.

The inward focus problem

What's happening here? When leadership and team are strong, you get high internal coherence. Decisions happen quickly because there's trust. But that same coherence can create an inward focus. The team becomes so aligned internally that external signals, what customers actually want, get filtered through the internal lens. You're not ignoring the market, but you're optimizing for internal harmony over market truth.

I saw this in a fintech startup. The founder was brilliant, the team was tight-knit, decisions happened fast. They built a feature for automated portfolio rebalancing that the team was excited about. The engineers loved the algorithmic challenge. The product team thought it was innovative. The founder believed it was the future. They shipped it in two months.

But here's what happened: Customer interviews showed users wanted simpler transaction tracking, not complex rebalancing. The team dismissed this feedback. "They don't know what they want yet," someone said in a planning meeting. "We need to educate them." They were so aligned internally that they filtered external signals through their own lens. They weren't ignoring the market, but they were optimizing for internal harmony over market truth. Six months later, they had to deprecate the feature and rebuild what customers actually needed.

The dependency risk

And here's an additional real risk: if your competence is driven by leadership rather than the team itself, you end up building for collapse. When the leader leaves or makes a bad call, the whole system falters because the team's strength was dependent on that person. The trust and alignment were real, but they were anchored to one person rather than distributed across the team. That's when you see what looked like a strong Leadership + Team combination actually reveal itself as just strong leadership with a compliant team.

What I find fascinating about this pattern is how it reveals itself over time. The inward focus doesn't happen immediately. It's a gradual drift. The team becomes so good at aligning internally that external signals get filtered. It's not malicious or intentional. It's how the system adapts to its own success.

Leadership + Strategy

Bold moves, investor momentum, rapid iteration. But team burnout creeps in, onboarding lags, and trust starts leaking. In scaling SaaS companies, I've watched visionary CTOs drive killer roadmaps, but high churn among senior engineers who felt like cogs.

Speed vs. sustainability

The dynamic here is about speed vs. sustainability. Strong leadership plus clear strategy creates powerful momentum. You can move fast, make bold bets, iterate quickly. But momentum requires energy, and that energy comes from people. When you're not actively investing in team health, trust-building, psychological safety, sustainable pace, the system burns through its human capital. People leave not because they disagree with the strategy, but because they're exhausted.

I watched this happen in a scaling SaaS company. The CTO had a clear vision: expand into enterprise features, integrate with major platforms, build AI capabilities. The roadmap was ambitious and the strategy was sound. They moved fast, shipped features every two weeks, raised funding based on momentum.

But here's what I saw: A senior engineer who'd been there for two years pulled me aside after a sprint planning. "I'm working 60-hour weeks," they said. "Every sprint is a new emergency. We're not fixing technical debt, we're just piling on features. I haven't had a real break in six months." Three months later, they left for a company with better work-life balance. Not because they disagreed with the strategy, but because they were exhausted. The system was burning through its human capital. Over the next year, more senior engineers left for similar reasons.

The compliant team problem

And here's another pattern I've seen: this is also the classic case where your compliant startup team becomes problematic. In the early days, you had follower-willing developers who executed well because they trusted the leader's vision. They followed directions, shipped features, and the company succeeded. But now they're confident, not because they developed leadership, or vision, skills, but because the leadership's strategy worked. They start becoming more opinionated, but they never actually learned how to lead because they were strictly delegated to. They were executors, not decision-makers.

I saw this exact pattern in a startup that grew quickly from 10 to 100 people. In the early days, the founder made all product decisions. The engineers executed, technically mediocore but features were going out. They shipped fast, the product worked, the company succeeded. But when they needed to scale, the founder couldn't make every decision anymore. So they started promoting their best engineers to lead different teams.

Here's what happened: Even the engineers that was actually technically brilliant but had never learned to lead turned out to be horrible managers. In a team meeting, when two engineers disagreed about an architecture approach, the "new" manager couldn't facilitate the discussion. They defaulted to: "What would [founder] do?" They'd never developed their own judgment because they'd always been executors. When they tried to make a decision, they second-guessed themselves constantly. Eventually, their confidence took over and they just made a call, a horrible call, but with confidence from the success of their founder. The team that worked perfectly at 10 people started breaking down as they scaled. The engineer was rewarded for following, not for leading, and now the system needed leaders, at least until the team could be confident in themselves. Something they had no chance of becoming with their overly confident and incompetent leaders.

Strategy + Team

Sustainable pace, reliable delivery, low drama. But growth stalls, innovation slows, and you can drift into "comfortable mediocrity." I've especially seen this in teams with solid product fit and collaborative vibe, but stagnant growth without bold direction.

The comfortable mediocrity trap

This one is tricky because it feels good. The team is happy, the product works. But without strong leadership pushing for growth or challenging assumptions, the system settles into equilibrium. There's no one breaking ties, making unpopular calls, or pushing beyond comfort zones. The team's collaborative strength becomes a weakness when it needs to be disrupted.

I observed this in a very mature company. The team was collaborative, the product had solid market fit, delivery was reliable. But growth had plateaued for two years. A competitor launched a community-native version of their product, and the team discussed it in a planning meeting. "Should we pivot and build community?" someone asked. The discussion went in circles. Some wanted to stay on current focus, others wanted broader community, but there was no one to break the tie or make the call. The team's collaborative strength became a weakness: they couldn't disrupt themselves. Six months later, the competitor had captured 30% of their market share. The team was still discussing. Without strong leadership to make the unpopular call, they'd settled into comfortable mediocrity, for both product and technical capability, while the market moved on.

The weak area doesn't just lag behind, it creates ripple effects. Like a memory leak in your codebase, it slows everything down over time. But more than that, it undermines the other two pillars. A weak strategy makes even great teams question their work. A weak team makes even brilliant strategies fail in execution. A weak leader lets even strong strategies and teams drift.

But here's what I'm starting to wonder: maybe this isn't a permanent state. Maybe organizations don't just pick two pillars and accept that the third will always be weak. What if the pattern itself is dynamic? What if you're supposed to rotate through these combinations, strengthening different pillars at different times?

This rotation happens because complex systems adapt. When one pillar weakens enough, it forces attention back to it. An organization strong in Leadership + Strategy eventually hits team burnout, shifting toward Team + Strategy. Once the team stabilizes but growth stalls, Leadership + Strategy becomes critical again. The cycle continues.

Why leadership changes feel so disruptive

When you swap out leadership, you're often getting someone who optimizes for a different pillar combination. The previous leader focused on Leadership + Strategy, driving growth and making bold bets. They get replaced by someone who prioritizes Leadership + Team, rebuilding culture and slowing down to build trust. Suddenly, those strategic initiatives feel like wasted effort because the new leader is optimizing for something else entirely. This isn't about right or wrong. The loop is forcing a different focus.

Have you seen these patterns? Which configuration have you lived through? What broke first?