It was around 9 p.m. on Tuesday night, and Stengel was weaving his way through the throng at the CNN Grill, an election-night party thrown by Time Warner, which was attended by... everyone in town, or so it seemed.
"There has to be a new era of transparency," Stengel told me, raising his voice to be heard over the din.
I asked Stengel what the next president's priority should be.
"Communicator-in-Chief," Stengel said animatedly. "That's his main job."
Speaking for the media, who have been frustrated by outgoing President George W. Bush's infrequent public pronouncements over his eight years, Stengel urged Obama to be a constant presence in our lives.
"The more press conferences, the better," Stengel said, suggesting one a week. "The new president should also post his daily schedule online." Stengel said he looked forward to the day when there was so much transparency that Americans even knew with whom the president had lunch each day.
Obama, up close
I met Obama in October 2006 in Phoenix at a magazine conference. This was before he formally declared himself a candidate for the White House.
He had just finished playing tennis and was still wearing his tennis whites as he entered a private dining room to greet reporters in an informal manner. Magazine publisher Jason Binn had organized one of his patented well-attended dinners for the media and somehow managed to lure Obama there for a meet-and-greet.
Obama clearly enjoyed meeting people and making small talk. But I thought I got a glimpse of a slightly churlish Obama, too, when I asked him, rather bluntly, if he was worried about peaking in popularity with the media any time soon.
He cocked his head and took in my question, looking displeased at being buttonholed in such a friendly setting.
"No," he declared, throwing cold water on my theory. He then explained that he was confident he could continue to do well.
At the time, Obama had failed to thrill the gathering in Arizona. Maybe he was jet-lagged after taking a long flight from Washington. Maybe he was preoccupied with a looming doubles match on the tennis court. Who knows?
Obama showed himself to be a guarded, private man on the campaign trail. Befitting his Harvard Law School pedigree, he chooses his words very carefully. He seemed to agonize when he had to speak off the cuff during his debates with his opponent on the campaign trail, Sen. John McCain, and wasn't at his best when he had to wing it.
I'd advise our new president to loosen up a bit when he deals with the media from this point on. The easiest way to get potential antagonists on your side is to smile and make light jokes. But Obama sometimes acts uneasily, as if he's about to sit down and take the LSAT.
Everyone in the media will be watching Obama, waiting for him to trip up and look bad.
It's nothing personal against him. But as I have written in this space before, the media love nothing more than to build you up, and then knock you down. This phenomenon takes place in every strata of life, from politics and business to sports and entertainment.
The worst thing Obama can do right off the bat is gain a reputation for complaining about his coverage in the media.
He should accept it, much as he did during the campaign against Sen. Hillary Clinton, then versus McCain. Obama took the high road, time and again, and it paid off.
The Washington media will appreciate it when he grants interviews and holds press conferences. But Obama will thrive in the spotlight when he shows that he's in charge -- not the pesky reporters.
Obama would be smart to take advantage of his popularity now and create more goodwill.
He would be wise to go to the New York Stock Exchange and ring the opening bell one morning. Not only would he show Wall Street he is on its side, but the gesture would be an undeniable publicity bonanza as well.
As Bush knows from his own experience, Obama won't always have the media in the palm of his hand. He should take advantage of every opportunity.
By Jon Friedman