I’m betting that Drew Houston, his investors, and the rest of the board of directors of Dropbox are wondering how far the company’s reputation can fall based on one incredibly bad board appointment. Of course, I am talking about the decision to ask Condoleezza Rice, the former US Secretary of State who was a key member of the G. W. Bush team  that led us to the disastrous war in Iraq, but more important to Dropbox, was allegedly instrumental in tapping UN Security Council members.

Leaving aside the politics — Republican or Democrat isn’t the issue, per se — just zoom in on the fact that Dropbox has to be viewed as completely trustworthy and a standout with regard to security, up to and including resisting efforts of US and other governments to gain access to personal and corporate information.

Yes, Dr. Rice is no longer working for the government, and, yes, she’s served on other technology boards. However, the optics are bad. There are too many unresolved issues regarding her role and character.

I recommend that for the company’s good, Dr. Rice should step down. This is going to be Brendan Eich all over again, otherwise.

Of course, others take a different tack, like David Holmes at Pando Daily, who argues that companies like Dropbox will need unique skills at the board level to interact with governments. But even he suggests that of all the people to bring in, Dr. Rice may have not been the best choice:

Of course, it’s perfectly valid to argue that of all the government insiders to add to your board, Rice’s history as a proponent of warrantless wiretapping doesn’t make her an ideal candidate.

But I disagree with his view that they won’t drop her because it will make them look ‘weak and incompetent’. If the shouting gets loud enough and enough people start to drop the service, they will change plans.

This is particularly bad since Dropbox was shown to be one of the companies about to become part of PRISM when the first word of it leaked out, and Mike Mansfield points out:

As for Dropbox, there have certainly been quite a few concerns about how private your data is on the site. When the first slides about PRISM came out, it was noted that Dropbox was about to become a part of the program. And while the fears about PRISM are greatly overstated, Dropbox has been fighting against public perception over this for some time. Dropbox’s CEO, Drew Houston, spoke out against the NSA’s efforts at the State of the Net conference back in January, and the company recently changed its privacy policies to address concerns about NSA spying. The company has also taken a strong stand saying that it will protect users’ data against blanket government requests and backdoors.

Those were all good moves, that should have calmed many people’s fears — but to then appoint Rice to the board, and have her handling “privacy” issues basically blasts a major hole in that. I’m less inclined than some to simply assume this means bad things for Dropbox’s privacy efforts in general. But from a public perception standpoint, this move does come across as exceptionally tone deaf by Dropbox.

[…]

At a time when people around the globe are increasingly worried about American tech firms having too close a connection to the intelligence community, a move like this seems like a huge public relations disaster. While Rice may be perfectly qualified to hold the role and to help Dropbox with the issues it needs help with, it’s hard not to believe that there would be others with less baggage who could handle the job just as well.

As I said, it’s all moot if Dr. Rice steps down.