To get things started, I imagine one non-human perspective is that represented by "big history", where "good" is more complex, and bad results from failures to maintain or increase complexity
If you are trying to train yourself to have an intuition on the sizes, you can use visualization tools, and there are two main ones at present:
If you want someone else to have an intuitive grasp of the size of an effect you're discussing, you can refer to lists of benchmarks. My height example comes from Cohen (1988's Statistical power analysis for the behavioral sciences), but more modern examples can be found here and here.
In your case, a run-of-the-mill productivity coach, who focuses on good habits, may not be ideal: It would take a lot of effort for small gains (due to diminishing returns).
But you could try coaches who aim to help you in mid- and long-term planning and strategies, and/or with clarifying values and thought patterns that influence those larger decisions. To give you two examples from within the EA/rationalist community (more names here), Lynette Bye has written about how you can prioritize projects on her blog and Pamela J Hobart introduces herself as a "philosophical life coach who helps intellectuals to clarify their thinking and values". Depending on your line of work, consider looking into consultants to get radically different viewpoints on longer term planning because being extremely efficient in the small scale of hours or days won't matter if you're working towards the wrong goal (or the right one with the wrong strategy).
About your two last questions: Some people are happy to meander through existence to chance upon an interesting self-discovery. Based on your question, my guess is that you are not one of them, and therefore randomly meeting coaches will just feel like a frustrating waste of time. So if you're not sure what you'd gain from a given coach and/or you don't resonate with their public materials, this is a great way of discarding their names when doing your coach search!