Good boss, good product, good team, pick two (1 of 5 in series)

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. Then the conversation moves on.

I couldn't quite move on.

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. They also kept returning me to that joke. Organizations could make real progress in two areas while a third weakened, sometimes unnoticed. The pattern seemed to survive changes in company, method, and vocabulary.

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: a coherent bet on the future, grounded in what customers need and expressed through work that creates measurable value.

"Good team" becomes Team and Organization: trust, useful disagreement, accountability, and the structures that let people work well together.

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.

That might also explain why leadership changes can feel so jarring. A new leader often concentrates on a different pair, which recasts the previous leader's strengths as today's problems.

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.

So this series is an attempt to examine the joke instead of merely repeating it. Do organizations really have to choose two? If their focus moves over time, can a leader notice the movement early enough to take part in it?