Ricardo, great questions! I think we ought distinguish between culture fit and personal work-style fit, and both are important to get right. When we look at cultural fit, we are normally referring to values and practices, the overall organizational context — looking at what sort of behaviors are rewarded and discouraged, how an organization measures against variables like autonomy vs. independence and novelty vs. routine. Recent research has revealed ways to measure this objectively by baselining a particular organization, and some tests claim to measure this in hiring contexts. At Shortlist, we are experimenting with some new ideas around this as well. This is different, at least to me, about whether two people will personally gel when working together, and agree that it’s challenging to assess that personal fit without simply giving it a try. That said, there are also more processes you could experiment with before or at the start of a working relationship to get ahead of this. At Shortlist, with our team, each new joinee fills out a “work styles” document to help people understand if you’re the type of person that prefers getting emails or having conversations; starting early or working late; powering through or taking a break; getting immediate feedback vs. structured reviews at intervals; etc. Those preferences are saved on our shared folder so folks can refer as useful. No easy answers, but it is something I hope we can all get better at!