Outside attorneys for Uber might soon have a chance to do something few trial attorneys ever get to do: depose a chief legal officer. What makes the situation even more unusual is that the CLO is one of the country’s most high-profile in-house legal leaders—Alphabet Inc. chief legal officer David Drummond, who was the first outside lawyer for Google and eventually became general counsel for the internet search giant.

The process, said several lawyers, is tricky. The problem of privilege—what a GC can and can’t divulge—seeps into nearly every part of a deposition, from defense counsel pushing back on any question they believe encroaches on attorney-client protected information to attorneys having a GC’s statements reviewed for privilege issues too late in a trial process, only to be considered inadmissible.