Good boss, good product, good team: pick two

There's a running joke I keep hearing about work: you can have a good boss, a good product, or a good team. Pick two.

I've heard versions of it over drinks, in Slack threads, and during late-night coding sessions. People laugh because they recognize the choice. I kept wondering why it sounded so familiar across such different workplaces.

Over the past year, I've spent a lot of time with management theory and tried to put it to work. I've run Five Dysfunctions retros with my team and used Working Genius assessments. I've read Lencioni, Extreme Ownership, Jim Collins, Simon Sinek, and plenty about systems thinking.

The frameworks helped me name things I had seen, but I kept returning to that joke. In companies I knew, progress in two areas often coincided with a third getting worse. Sometimes nobody paid much attention until it began to interfere with the work.

Giving the three parts names

"Good boss" is too dependent on whether you happen to like your manager. I use Leadership for something broader: creating clarity, making difficult calls, and earning people's willingness to follow.

"Good product" becomes Strategy and Product: deciding which customer problems to solve, then checking whether the product actually solves them.

"Good team" becomes Team and Organization: people who can rely on each other's work and deal with disagreements, in an organization that helps them do both.

Those definitions matter because all three can look healthy from a distance. A decisive leader can create compliance rather than judgment. A busy roadmap can hide weak customer demand. A close team may be united by frustration with everybody outside it.

I explore those distinctions in the next post.

The question that stayed with me

Different leaders seem to reinforce different pairs. Some combine Leadership with Strategy and move the company quickly, while the team absorbs the cost. Others invest in Leadership and Team, but become less responsive to the market. Strategy and Team can sustain good delivery for a long time, until a decision arrives that nobody wants to own.

I've seen a new leader concentrate on a different pair and question the very things the previous leader was praised for. That may be part of why leadership changes can feel so jarring.

I don't know whether this is a hard limit of organizations. It may be a flaw in how I'm looking at them. But throughout my career, I've seen the neglected area eventually demand attention. I've also seen that shift arrive with a change of leader. I haven't yet seen many leaders recognize it and change their own focus while remaining in the role.

That's what I want to work through in this series. I'm interested in whether leaders can notice the neglected part soon enough to change their own approach, before somebody else arrives to do it for them.