[Political Interest]

In a lot of discussions I have on a range of subjects with many people I often encounter a lack of nuance. Often I will make a statement or an argument and someone will assume that because I take a certain position on one issue I must therefore take the same position on a different issue.

And often people think I am saying something different to what I am actually saying.

Is this inability to understand nuance a sign of intellectual weakness?

[Sivad]

Yeah, people are impossibly stupid.

[Wellsy]

Vague generalizations tend to be a necessity of a lack of content.
So to gain a nuanced perspective, one needs to have investigated/studied the relevant subject.
https://www.ethicalpolitics.org/ablunden/pdfs/The%20Psychology%20of%20Concepts.pdf

Tests (Margolis & Laurence 1999, p. 444) involving novices and experts in the sciences showed that the concepts of experts were fuzzier than those who actually knew nothing about the topic; the more developed the concept, the fuzzier the boundaries. All this goes to show that there is more to any concept worthy of the name than can be set down in a few dead words. This is not a problem of psychology, it is in the nature of concepts themselves. Concepts are not pigeonholes and concepts which conformed to expectations of these researchers would be very poor concepts.

But how often do people's interests and study necessarily coincide to have a discussion that is between equals in understanding.
In such a circumstance, one needs to find the point of shared interest, the shared object that motivates the discussion.

And difficulty in understanding someone is an issue of shared projects and as such, one might have no real shared ground on which to communicate with you, to make sense of your concepts.
https://www.ethicalpolitics.org/ablunden/pdfs/An_interdisciplinary_concept_of_activity.pdf

Secondly, Cole found (1997) that psychological work with experimental subjects could only succeed to the extent that both the researcher and the experimental subject shared a common aim (even if they had different motives). This could happen if an adult subject was part of a culture where scientific experimentation was widely understood and supported, but in many cases it could only be achieved by the researcher focusing on achieving something that the experimental subject wanted to achieve, in the hope that scientific insights would come as a by-product of the subject doing what she wanted to do anyway. For example, in order to effectively study a learning process, it was necessary to actually help someone learn something they really wanted to learn.

Generally speaking the actions and artifacts used in the scenario have to be indigenous to the culture of the experimental subject and the scenario must be either itself a normal part of the subject’s culture, or so constructed that the way in which it is construed within the subject culture is transparent.

Under these conditions it is possible for the two parties to share a common ‘project’. Otherwise ambiguity, misunderstanding and failures of communication prevail. Where subjects are not committed to a common project, one and the same action or artifact, for example an interview question, could figure in two different activities. This is the relevance of the ‘hermeneutic circle’: each action is interpreted by a subject on the basis of a presumption of the activity or project of which it is a part, but a project can only be perceived through the actions by which it is instantiated. This is how cross-cultural misunderstandings occur.

https://www.ethicalpolitics.org/wits/projects-context.pdf

TRADITION is the context in which a text is produced in the theory of Hang-Georg Gadamer, the founder of philosophical hermeneutics. This is a fine concept for the work for which it was designed – the interpretation of texts, but it translates perfectly well to understanding people’s action in some social context. Tradition has a meaning similar to ‘culture’ in the common meaning of that term, as the entirety of social mores, practices and ethos of some community. But for Gadamer, tradition has some important nuances of meaning. Firstly, tradition motivates, secondly tradition develops, and thirdly tradition restricts.

But also the assumption of crude positions is necessarily a stage in probing one's opinion on a thing.
Some people leave a lot implicit and so in trying to construct your idea of a person's position, you sometimes have to throw somethings at the wall and see what sticks. There is also the case that one might have to draw upon more pure forms for schools of thought than what is necessarily adhered to by an individual person. So for example, one might see the association of someone with positions of liberalism or Marxism, and then project all sorts of conjecture based on their concept of the two which might not properly reflect the nuances of the person's own beliefs as they are treated as synonymous with the system of thought.
One can of course expand ones concept if they're actually opening to engaging with you, as opposed to yammering on about their already established presuppositions without any stated and clear connection to your position.
In drilling in on details one finds a gulf of differences in thought which hide superficially those who think they're on the same side but not, as well as those who superficially disagree but are closer in agreement on a subject.

But I would say a difficulty is that we simply aren't experts in all areas and have uneven and very different educations and areas of study. The well lived and read person might be more adaptable to varied circumstances than some.