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.

“Privilege is going to be the biggest hurdle that you’re going to meet over and over again,” said Steve Kardell, a Dallas-based corporate investigations attorney who recently represented former GC-turned-whistleblower Ashley Yablon in Yablon’s fight against his company. Kardell said most in-house counsel will be able to “hide” under privilege “as long as there is a quasi legal overlay” to the internal communications reviewed as part of the deposition.

Drummond might get called in for a deposition because of his involvement in an ongoing, messy legal battle between his company’s self-driving unit, Waymo and Uber Technologies Inc. In February, Waymo accused the San Francisco-based ride-hailing giant of using trade secrets stolen from Waymo in the development of its own self-driving technology. Legal teams have amassed at a rapid pace, with Morrison & Foerster and Boies Schiller Flexner attorneys representing Uber and Quinn Emanuel Urquhart & Sullivan attorneys representing Waymo. Lead attorneys at MoFo and Quinn Emanuel did not return calls seeking comment.

Rudy, Exelrod, Zieff & Lowe partner David Lowe, who spoke from personal experience and not specifically about the current battle between Waymo and Uber, said all deposition strategies are the same: Get as much information as possible that can be used at trial. Doing that with a GC means proving any sought-after information exists within a GC’s responsibility as a business adviser, not a legal adviser. But there’s a danger in being too eager to prove a GC’s communications are all business-related, Lowe said.

“All attorneys need to be careful of being too aggressive in pushing that perspective, and, as a result, you obtain information that an arbitrator or a judge later concludes was privileged,” Lowe said. “It could cause problems down the line that could tank the proceeding.”

For instance, according to Lowe, a deposed GC could answer a question that does include privileged information, but the GC’s representative counsel may not catch it at the time. Later, as the two sides prepare for trial, the GC’s lawyers could ask a judge to remove certain statements, explaining that, upon further review, the GC’s statements are privileged. If a judge removes those statements, and those statements were crucial to the other team’s legal arguments, that could blow a hole in the trial strategy, Lowe said.

In a July 6 filing in the Northern District of California, Uber’s lawyers argued Drummond needs to be deposed because, during his three-year position on Uber’s board of directors, Drummond “had access to Uber’s business plans and strategy for its self-driving car program.” Uber’s lawyers also argued that Drummond has information about Uber’s 2016 purchase of Otto—a self-driving truck startup founded by former Google engineer Anthony Levandowski, the employee who allegedly stole trade secrets from Google. A magistrate judge granted Uber’s request in part, but determined that Waymo can prevent that deposition if it promises that Drummond won’t testify on summary judgment at trial.

According to Wilkinson Walsh + Eskovitz partner Sean Eskovitz, who has personally defended GCs and has litigated the issue of privileged information, attorneys also shouldn’t be discouraged by predictable challenges to any questions directed at a GC that might produce privileged information.

“Aggressive defense counsel will vociferously object to questions that might get into privileged information,” said Eskovitz. “Questioning counsel should not be deterred from pursuing lines of inquiries just based on aggressive defense tactics.”

Eskovitz added that lawyers who depose a GC should be certain to ask foundational questions as a way to safeguard any information learned in a deposition as admissible in court. He said if a GC veers into hearsay, that information is useless.

“Make sure to establish the witness’ personal knowledge of the information,” Eskovitz said.

And one easily forgotten hurdle, said Lowe: Attorneys make bad witnesses.

“While it’s always dangerous to generalize, and I wouldn’t say this is universally true, I would say in my experience, lawyers make terrible witnesses,” Lowe said. He said lawyers either say too much or too little, avoiding direct answers when questioned.

“I think we all tend to think we’re clever,” Lowe said, “and we have a hard time following our own advice to just answer the question,”

Contact David Ruiz druiz@alm.com.