Hi Reader,

If you're a sports fan - or live in the San Francisco Bay area – you've probably heard by now about the uncomfortable situation involving Jed York, owner of the San Francisco 49ers.

York was arrested on August 24th in Ohio following an undercover prostitution sting. The prostitution charge was subsequently amended and, two days later, he pleaded no contest to misdemeanor charges of disorderly conduct and possessing criminal tools.

The legal case moved remarkably quickly.

The publicity problem did not.

And that’s the part that caught my attention.

What Are You Supposed To Say?

Within hours, the questions started flying.

York's conduct immediately became everybody else's communications problem.

• Coach Kyle Shanahan was asked about it.
• Players were asked about it.
• The 49ers organization had to respond.
• NFL Commissioner Roger Goodell had to respond.

Fans, sponsors and everyone else can now weigh in instantly — while social media makes sure nobody gets the luxury of pretending it never happened.

There was a time when an organization confronted with an embarrassing incident had at least a little time to gather the facts, decide what it believed and determine what it wanted to say.

Not anymore.

The police report is online. The body-camera footage is online. News organizations are publishing updates. Social media is doing what social media does.

Meanwhile, reporters are putting microphones in front of people who had absolutely nothing to do with the conduct in question and asking:

“What do you think?”

You’ve Got a Leadership Problem

This is where the story moves beyond public relations.

49ers linebacker Fred Warner may have captured the modern dilemma perfectly:

Exactly.

Your people may know about the controversy before you’ve decided what to say about it — and they may be asked publicly what they think.

That makes conduct at the top a leadership problem for everyone below it.

The 49ers issued a brief statement saying that the legal matter had been resolved and they would have no further comment.

The NFL can’t quite stop there.

The league has a Personal Conduct Policy that applies not only to players, but to coaches, employees and owners.

Commissioner Roger Goodell says the matter is being reviewed.

So now we have something much bigger than an embarrassing story about the owner of a football team.

Whose Rules Are They?

Every organization has standards of behavior, whether they’re formally written or simply understood.

But what happens when someone violates them?

Who is expected to say something?

Who should remain silent?

When does supporting a colleague become tolerating inappropriate behavior?

Does admitting wrongdoing make a difference?

Should a first offense be forgiven?

And here’s the uncomfortable one:

Do the same rules apply to the person at the top?

That last question becomes particularly interesting when the person at the top actually owns the organization.

It’s easy to write a Code of Conduct.

It’s much harder when you actually have to use it.

An Uncanny Coincidence

The timing is uncanny.

Before any of this happened, I'd already prepared Wednesday's upcoming newsletter about the West Point Cadet Honor Code, which extends our conversation about conduct and behavior in the workplace:

It's those last five words that create the dilemma.

When does loyalty become tolerance? When are you obligated to speak? Should someone get a second chance? And do the same rules apply to the person at the top?

Jed York just gave us a very public example of why those questions are so difficult.

We'll pick it up on Wednesday.