OverBoard - Chapter 1.5

Be Careful About What You Wish


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Personal Drive

Not everyone on your team is there for the same reason. Understanding why someone shows up matters more than knowing how well they perform right now. A person optimizing for their paycheck behaves differently from one chasing reputation, and both behave differently from someone who is genuinely trying to learn.

Broad categories of what drives people:

None of these are wrong. The problem is when you assume everyone shares your drive, or when a project requires one type of motivation and you have staffed it with people running on a different one entirely.


Project Types

The type of project a person is on shapes their experience far more than most managers account for. Four broad categories:

Someone who has run a Greenfield project three times may find a fourth one unstimulating. The novelty is gone. They have made these decisions before. For them it is an Opening they have already played. For a junior engineer, the same project is a chance to finally build something from scratch, make real decisions, and own something end to end.

The mismatch between person and project type is where retention risk hides, and it almost never surfaces in a sprint review.


Retention

The people who want to stay and the people you want to retain may be different. That sentence sounds cynical. It is just accurate.

Want To Stay

The comfortable person. Making progress, no complaints in 1:1s, showing up, delivering, not asking for more. The silence is the signal. They are not engaged enough to be frustrated.

The project’s pace suits them, which is fine if the role calls for steady maintenance. The problem is when you need someone pushing and instead you have someone drifting. Comfortable conditions in a role that demands growth produce stagnation, not loyalty worth protecting.

In a Sustaining project this person may be exactly right. In a Greenfield or Improvement context, the same behavior is a warning sign.

Leaving Soon

The person you want to keep. They have opinions. They are frustrated, which means they care. They ask questions about other projects, about direction, about why decisions were made the way they were. They might be carrying more than their defined scope and feeling under-recognized for it.

In a 1:1 they engage, but there is an undercurrent of “I could be doing more than this.” They are outgrowing the current situation and they know it, even if they have not said it out loud.

The danger is that this person is easy to misread as difficult. Their frustration can look like a management problem when it is actually a signal. The moment they go quiet is the moment you have already lost them. Quiet does not mean resolved. It means they stopped expecting things to change.


The Information Problem

A manager typically only knows whether people are making progress or not. That is a delivery signal, not a health signal. It tells you the piece is moving, not whether it wants to keep moving.

Qualitative signals require someone close enough to the team to observe them and trusted enough to report honestly: a TL, TPM, or PM who has both access and credibility. Without that, attrition is a surprise every time. You find out when someone hands in their notice, not three months earlier when the warning signs were already there.

This is why the relationship with your TL matters beyond technical oversight. They are your ground-level read on who is quietly disengaging, who is frustrated in a way that could still be redirected, and who has mentally already left.

If you do not have that person, you are managing the board without being able to see half of it.

Chapter 3 of 5