Is it cynical to do what your manager wants?
When I suggest doing what your management chain wants, people call me cynical. Is it cynical to deliberately work on things your company incentivizes and neglect things your company doesn’t reward? It might seem so on the face of it. However, I think this attitude is actually optimistic, not cynical. The real cynic is the person who says that you should ignore management incentives and just do the right thing for the customer.
The idea that “screw the managers, you should do the right thing for the customer” comes from a belief that your managers are all idiots (or at least enough of them are that good ideas don’t percolate through). They don’t care about the customer, they just care about making money. You - the pure engineer, not the slimy executive - are the only one who can be trusted to act in the customer’s best interests. This is a deeply, deeply cynical position!
Doing what your management chain wants is an expression of optimism. It comes from a belief that your company knows what it’s doing, and that the people it chooses to set strategy are basically competent. For large successful tech companies, that belief justified by the fact that the current company setup has attracted a lot of customers and made a lot of money, so it’s probably doing something right. In short, it’s a belief that your management chain aren’t idiots, and can be trusted to do their job without you second-guessing them.
Planting your feet and saying “screw the company, I’m going to do the right thing for my users” feels good. It feels righteous, particularly when you receive negative pushback for it. For some people, this feeling is enough to carry them through an entire career. But we should be honest about how cynical that attitude really is. The other approach - saying “I’m going to work with my management chain to help the company succeeed” - is less exciting, and in some cases probably does mean doing things that users won’t like. But it’s not inherently cynical.
Does working with your management chain make you a “yes man”? It depends on the company. Effective managers want their plans to actually work. They don’t want engineers saying “sir yes sir” about strategies that are bad ideas or are technically doomed. They want engineers who can work with them to find a way to achieve the company’s goals.
I’ve worked with incompetent managers, just as I’ve worked with incompetent engineers. But overall I have a good opinion of all my colleagues, whether executives or engineers. Executives in particular are highly incentivized to succeed: the higher up you climb, the less you can blame bad luck or bad strategy and the more accountable you are for actual results. I have never worked with an executive who was indifferent to the company’s success, but I’ve worked with many, many engineers who were.