I find it hard. I really try to check my assumptions and state my reasoning where I think it's relevant but if I am to draw a conclusion about anything then I have to make a lot of necessary assumptions first. Some I am more confident about, others less so, but they are almost always given the same status in a statement in the interest of brevity.

I make an unthinkable number of implicit assumptions every time I communicate any information to anyone, and considering the problem of infinite regress I don't even know where or if ever the assumptions end.

Some people are better at not coming across as assertive or arrogant (my partner, for one), and I admire that. I'm more the kind to throw a statement out there after thinking about it for a while and error correct if my assumptions are being challenged. The downsides to that method are many; unintentionally spreading misinformation being a major one, but also that people are frustratingly bad at criticising premises and instead often attack the conclusion itself and assume ill intent, or at best just disagree without further explanation.