Programming

You point to Valve as a success story, but the "pick the work you want" also lead to less deliverables and focus and they had to refocus that approach. Free pick and experimentation is fine until you get to a point where you want to get something out the door - when it's a bigger thing, and you need more and focused people, to bring it to the finish line.

I can't speak how it would be elsewhere and everywhere, but I can speak from personal experience how my workplace is set up.

We're relatively small, work for various customers, some continuous and some contract-scoped. Developers work and speak either directly to and with customers, or have at most one person "in between" that is part of usually our team.

We have an agile and collaborative mindset, and often guide our customers into productive workflows.

Being on relatively small teams, with opportunity for high personal impact, and with agency, I was able to take initiative and work in a way I am very satisfied with. I am able to prioritize myself, collaborate with my customer to understand their needs, understandings, and priorities, and then make my decisions - explicitly or implicitly. Two-week plannings give good checkpoints to review and reassess intended priorities - which are only guides. Stuff comes up that takes priority anyway, be it from the customer, or improving code when you stumble upon it.

I'm glad to be on my current team where the customer pays monthly for how much we worked, so no repeated contract work estimation. I can and do decide on what makes sense, and we communicate on priorities, planning, and consequences. Either I decide or we discuss whether one or another solution makes more sense considering effort, significance, and degree of solution or acceptableness. One person from the customer is our direct gate to them, participates in meetings, planning, tickets, prioritization. They block all of their requests to us, and communicate to and with us on what they deem important enough. And they are our gateway to asking the customers roles and people regarding usage, functionality, needs, etc.

For me, this environment is perfect. It allows me to collaborate with the customers to match their long term needs.

I think it needs good enough developers though. There's those that are mindful and actively invested, but also people who are not. Some become great productive workers with guidance and experience, but it doesn't always fit. I feel like a lack of proactive good development given the environment and agency isn't a given, but I don't think "management" improves that. You're putting a manager on top in hopes they're a person like that. But why couldn't that be a team member in the first place?

Managers and more strict role splitting becomes more necessary or efficient the bigger you scale. I feel like smaller projects and teams are more efficient and satisfactory. You have less people and communication interfaces. And as a developer, you probably know that interfaces [between systems] are one of the biggest issue causers.

For context, I am Lead Developer (became when we introduced those roles explicitly), and our team size was 2 for a long time, but has now been 4 for a while, and is now 3 developers +1 now in semi-retirement working only half of the year.