Two Part Question for those in growth equity/late-stage venture

Started my first buy-side job out of banking at a tech-focused early-stage growth equity firm ~7 months ago and had my mid-year review a few weeks ago. Split of executions to sourcing is ~60/40. My mid-year review was extremely positive, but the two areas I was asked to focus on over the next 6-12 months are: (1) more fluid conversations with founders during intro calls (i.e., less asking questions in a checklist fashion) and (2) having a more holistic view of companies / opportunities after an initial intro call with a founder/CEO.

My mid-year feedback was basically: very strong technical skills and accurate/detailed models/analysis, but the next step for me is to improve on getting out of the weeds when I sync up with partners after an intro call with a founder. One of the partners mentioned using mental models to help assess opportunities at a high level. Does anyone have a rough checklist / mental model they use to help them assess and come to high-level conclusions? This is pre-data room access obviously. 

The other point of constructive feedback is to be less-structured during founder/CEO calls. They said at times I come across a bit “banking-esque” in my questions, like I’m just checking off a list. I put in a decent amount of prep before calls, so don’t think that effort is what needs to improve here.

TL;DR, looking for (1) a way to have more fluid/casual intro calls with founders (while still extracting the necessary information to decide if we want to allocate time to engage in the financing round) and (2) any advice on a framework to assess investment opportunities after intro calls with founders before data-room access.