You'll Figure It Out

I'm sure we're taller in another dimension

You say we're smaller and not worth the mention

  • Frank Ocean

When I worked at AOL, we typically worked from 8am until 9 or 10pm. At the end of every day, we'd congregate in the office of our boss, to sit around and bullshit and catch up on email and talk about deals we were working on and issues in those we were facing.

One evening we were doing this, and the conversation turned to the renewal of a content distribution deal with The New York Times, one of AOL's largest and most important partners. The difficult issue here, as with most of these, was whether AOL could demand exclusivity in exchange for distribution. For example, we knew AOL members loved the Times' crossword puzzles. We wanted them for ourselves, or at least before they went up on the Times' website. The Times wanted to limit exclusivity, or at least get paid. We believed our distribution was so massive that it alone was a fair exchange for some exclusivity. Thus, the deadlock.

I remember this conversation, sitting around the conference-like table in that corner office, 4th floor of a 5-floor building. Winter was outside and the view from the windows of the Dulles, Virginia office reflected the black and cold early evening.

Bob Pittman, the President of AOL, walked around the corner and stood in the doorway. This was relatively early in his tenure at AOL, yet he was known to us already as a media and business legend.

"What's going on?" he asked, smiling. Our boss replied by explaining in detail the exclusivity issue, the various choices and options we had, questions about where we might push and where we might give.

Bob listened. He paused for a moment and replied:

"You'll figure it out. Have a good evening."

He lightly tapped the office door with his open hand twice, as if he was slapping it five. And then walked off.

There was a moment of silence before we got right back into it. We figured it out - or at least we tried. Ultimately, we didn't appreciate the move to the more "open" web would have on the proprietary AOL platform; nor would the Times appreciate the traffic AOL brought and our ability to allow them to experiment on a new generation of Internet users. We met somewhere in the middle, maybe even paid them, and it turned into a relatively good relationship over the years.

The thing is, maybe we got it right. Or maybe we didn't. I assume Bob knew that. I'd also like to believe he didn't really care. Or rather, he cared about the outcome but equally cared about making sure his team - us junior members - thought for ourselves. To empower us. To demonstrate his trust in us by specifically letting us make the decision. And figure it out.

A formative idea for a younger me: give the people who work for you a chance to resolve complex issues on their own.

Mark Randolph, the co-founder and initial CEO of Netflix, writes about this in his book, That Will Never Work. He describes what he came to understand about managing people:

What they really want is freedom and responsibility. They want to be loosely coupled but tightly aligned.

There is no way Bob, or anyone else in that room, remembers that evening. Yet I do, in detail, years later.

And still find myself saying to people "you'll figure it out."