Roger Goodell is the President of the NFL, and despite huge love for the NFL itself, Goodell is hated by many, even most, fans. At the NFL draft, which attacts arguably the biggest fans of the NFL, Goodell gets booed every time he walks on stage. One reason for this is the decision Goodell made a number of years ago to "police" player behavior. Tired of bad headlines about this or that player being involved in some sort of (alleged) criminal activity, Goodell decided to crack down. No longer was it enough that the criminal justice system had a process for punishing people who break the law, Goodell wanted the NFL to be seen to be layering on extra punishment.
I said from the very beginning that this policy was fraught with problems. If the NFL wanted a conduct policy, it should establish simple mechanical rules tied to outcomes in the justice system. For example, a rule that says that if convicted of a misdemeanor a player would get a standard X game suspension. Goodell's role should be limited to correcting the inevitable unfair situation where mechanical rules lead to poor outcomes.
But no, Goodell, like many smart people, fell into the trap of thinking he was smart enough to mete out punishments himself. This has led to a real mess. The public compares each punishment (and non-punishment) to all other such decisions and immediately get upset about perceived inconsistencies. Worse, having established the precedent of policing conduct, he is being pushed by various vocal constituencies to police even non-crimes, like unwelcome speech. On average day in sports talk radio, you are as likely to hear a discussion of Goodell's conduct rulings as you are about anything on the field.
In taking over Reddit, Ellen Pao is heading into the same technocratic trap. She has begun to ban certain forums and types of speech on the platform, but she has not established any consistent public rules for doing so other than her own judgement. She appears to be deleting things that offend her personally (and early mass deletions of content critical of herself personally seems a really bad way to start). And as with Goodell, two bad things are already happening (even beyond the more fundamental Reddit user issue that she is violating a core ethic of Reddit by censoring). First, she is being called out for lack of consistency with folks saying "how can you ban X and not Y." And second, she is apparently already getting pushed by various constituencies to be more and more aggressive at censoring certain classes of speech. Once she established herself as censor in chief, she became an immediate lobbying target for many, many groups, and that is going to just get worse. Just look at how much of Goodell's time is now sucked up into personal conduct issues.