Generalist Investor - Seeking Guidance

Hi all - hope this note finds you well. I recently joined a multi family office on the west coast. We operate a generalist investment model (funds and directs across all sectors). We have a really small investment team and are really active from a deployment perspective. 

I am only three months into the role, but I am facing a challenge with the generalist investment approach. Every single industry is different and it feels like every transaction has some weird nuance that I've never seen before. It feels like I spend so much time just trying to understand the business model / industry before even evaluating the deal. How do you know what questions you should be asking? Does this just come with reps? 

Has anyone been in a situation like this before? If so, what did you do to get more comfortable? This is the first job I've ever had where I don't feel like I'm doing a good job. I don't come from direct PE or VC. Any tips or advice would be great. 

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