Do you think maybe it could be a generational thing? Or an introvert vs. extrovert thing? Or maybe in the workplace, it's more a matter of the type (i.e. job category) of employee, i.e. professionals would expect to have more scope and leeway in HOW they do their work as long as the work gets done, so they would lean more towards the "guess" culture.
Whatever the case, your post made me realize that a lot of my job dissatisfaction was down to the fact that I was a "guess" person stuck in an "ask" culture where the HOW of doing the job had to be distilled down to the fussiest, most minute procedural details. But I also find that many of the younger people seem to have a high need for positive feedback on the job, even when they are floundering or seem not to have a very good work ethic. I suppose the best work environments are those where the team leader and individual team members all have compatible workstyles (that would be the utopia) or at least (going back to the real world) are able to adapt their workstyles as needed and communicate what they prefer without fear of repercussions!