Why two strong pillars can weaken the third (3 of 5 in series)

After defining the three pillars, I started looking for them in companies I had worked with or observed.

The same pattern kept appearing. Two parts of the organization reinforced each other, and their visible success made problems in the third easier to explain away. By the time the weakness became urgent, it had begun to affect the strengths around it.

Leadership and team

A fintech founder I worked with had a tight-knit team and could make decisions quickly. The engineers enjoyed hard technical problems, the product group trusted the founder, and the company could move from an idea to a release without much internal friction.

They built automated portfolio rebalancing in two months. The founder believed it was the future, the product team considered it innovative, and the engineers liked the algorithmic challenge.

Customer interviews pointed somewhere much simpler. Users wanted better transaction tracking. In a planning meeting, somebody dismissed that response: "They don't know what they want yet. We need to educate them."

Six months later, the company deprecated the rebalancing feature and built what customers had asked for.

The trust inside the company was genuine. It allowed the group to move quickly, but it also made the shared view harder to challenge. Customer evidence had to compete with the confidence of people who already agreed with one another.

The fintech story left me with another question. If the leader supplies most of the judgment, a team can become very good at understanding and executing that person's decisions. Dependence may look like alignment until the leader steps away. That tension turned out to be less straightforward than I first thought, so I return to it in the next post.

Leadership and strategy

I saw a different kind of momentum in a scaling SaaS company. Its CTO had a clear plan: expand the enterprise feature set, integrate with major platforms, and add AI capabilities. The company shipped every two weeks and raised funding on the strength of that progress.

After one sprint planning session, a senior engineer who had been there for two years pulled me aside.

"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."

They left three months later for a company with better work-life balance. More senior engineers followed over the next year.

The strategy hadn't suddenly stopped making sense. The pace required to deliver it had consumed the people and maintenance work that could sustain it.

Growth can also expose how much judgment a leader has kept for themselves. I watched a startup grow from 10 to 100 people with the founder making every product decision. The early engineering group followed that direction and kept releasing features. The technical work wasn't exceptional, but the product worked and the company succeeded.

Once the founder could no longer make every call, the company promoted its best engineers to lead teams. Even technically brilliant engineers struggled. During an architecture disagreement, one new manager asked, "What would [founder] do?" They had spent years practicing execution and almost no time developing their own leadership judgment. Some second-guessed every decision. Others made poor calls with confidence borrowed from the company's earlier success.

By the time the company needed more leaders, its earlier way of working had mostly trained the engineers to follow.

Strategy and team

This pairing can remain comfortable for quite a while. The product works, delivery is reliable, and the group knows how to collaborate. Trouble appears when the market asks for a choice the team would rather keep discussing.

I observed a mature company whose growth had been flat for two years. A competitor released a community-focused version of its product, and the established team considered whether to respond.

"Should we pivot and build community?" somebody asked in a planning meeting.

Some people wanted to protect the existing focus. Others wanted to move toward community. The discussion circled because nobody would break the tie and accept the consequences of the choice.

Six months later, the competitor had captured 30 percent of the market. The original team was still discussing its response.

Collaboration had served that group well during normal delivery. Under threat, the same habits gave every concern another hearing and left the unpopular call without an owner.

Why the weak pillar returns

I first described these cases as resource allocation problems. That explanation felt incomplete. The strengths also produced evidence that each company should keep going as it was. The fintech team could point to its release speed, the SaaS company to its roadmap and funding, and the mature company to a thoughtful planning process. All of that remained true while the costs accumulated.

Eventually the neglected area interfered with the rest. Customer evidence undid the fintech bet. Exhaustion made the SaaS roadmap harder to sustain. The mature company's collaborative habits couldn't produce a response to its competitor.

This is still an observation rather than a rule. I am especially uncertain about Leadership and Team, because strong leadership can either develop a team's judgment or quietly replace it. The next post follows that tension through three teams.