Welcome to a special Tuesday edition of In the Room, my biweekly private email on the intrigue and inside story behind what’s going on in the media industry.

In today’s column, what I’m hearing about NBC News chief Cesar Conde’s secret trip to Ukraine—and what the head-scratching inside 30 Rock reveals about the network’s deeper insecurities.

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Even after two years at the helm of NBC News, Conde remains something of an enigma to many of the company’s journalists. A polished, Harvard and Wharton-educated businessman, he’s an ostensibly brilliant guy who sits on the boards of Walmart and Pepsi. He is also a stark departure from news organization leaders of the past. Former NBC News presidents like Neal Shapiro, Steve Capus, and Andy Lack, and their contemporaries across broadcast and cable news, had largely come up as executive producers and considered themselves journalists. They were intimately involved in day-to-day editorial decisions and thrived off the competitive energy that comes with winning a news cycle. This rearingmade them natural talent whisperers, and often garnered them large measures of credibility in organizations where the talent is out front and the numbers people eat at the nerds table in the cafeteria.

Conde, for his part, comes from business and politics...