Why two strong pillars can weaken the third

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

What struck me was how easy it was to explain away a problem while the rest of the company seemed to be doing well. These are the combinations I kept seeing.

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 team trusted one another and moved quickly. That agreement also made it easier to dismiss customers who wanted something less exciting to build.

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 roadmap still made sense on paper. Keeping up with it had meant 60-hour weeks and letting technical debt accumulate. The company was losing experienced engineers who knew how to deliver 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 the founder would 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.

They needed practice making decisions before the company depended on them to lead others. Shipping successfully under the founder hadn't given them much of that practice.

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% of the market. The original team was still discussing its response.

The team knew how to collaborate on delivery. They hadn't worked out who could end a discussion like this and commit the company to a response.

Success gave them a reason to keep going

I first described these cases as resource allocation problems. That explanation felt incomplete. Each company had reasons to keep working as it had before. The fintech team was shipping quickly. The SaaS company had raised funding. In the mature company, a way of working that served normal delivery had carried over into a decision it couldn't resolve.

I'm especially uncertain about Leadership and Team. Strong leadership can develop a team's judgment, but it can also leave people dependent on the leader's answers. The next post follows that tension through three teams.