Transitioning onto portfolio companies - what to know?

This is a good question, and something most junior PE professionals will experience at least once. In my experience, there's probably a few things to ask:

1. Ask to see the historical materials that have been prepared for the company (initial investment committee underwriting, materials for follow-on financings and acquisitions, etc.). This will be instructive both as general background information and to see how things have changed over time. Do the materials use the same language, or are new perspectives added over time? Have additional strengths or weaknesses been uncovered? What has been the trajectory of the financial projections, and what does that say about how the investment expectations may have changed?

2. Ask about workload and typical interactions between the Associate and the company. Is this a company where you need to handhold the CFO every month to complete the compliance certificate? Will you be spending days at a time on-site for strategic planning or putting together the budget? Or will your role be more limited to helping with add-on acquisitions / financings and sitting in on board meetings?

3. I think this is probably under-emphasized by many but ask about the personalities involved. What do you need to know about the executive team? Does the CEO have a big ego, where he wouldn't take well to a young Associate providing critical (but well-meaning and thoughtful) feedback? Is there subtle tension between the older CEO and the younger COO who wants his job? But also, it's important to understand the INTERNAL dynamics. Has the investment received a lot of scrutiny from the CIO/Managing Partner where the Partner leading the investment feels a lot of pressure and will be much more anal about everything you do?

There's probably more and I'll let others contribute those thoughts, but those are the things I would point out from my experience.