Tag Archives: Ben Montgomery

The art of asking questions, part I


This week marks the first of two episodes in which five writers and I discuss the art of asking questions. Today, it’s Tampa Bay Times enterprise writer Ben Montgomery and CBSSports.com national columnist Gregg Doyel, and next week, we’ll entertain author Jeff Pearlman, Cincinnati Enquirer beat writer Bill Koch and Columbus Dispatch beat writer Bill Rabinowitz.

Montgomery tells a fantastic tale of how one journalist slowly adds details to a story about a hero by the way he approaches the question-asking, while Doyel talks about why it’s important not to be scared to ask the challenging questions (“Fear is weakness,” he says). Also, Doyel and I chat about this:

Plus, a sneak peek at what next week’s trio says.

Ben Montgomery/Tampa Bay Times, enterprise writer


Montgomery is an interesting character, and we had a fascinating in-depth conversation about his craft and about how we can improve the newspaper industry. In our chat, we discussed his approach to covering the George Zimmerman/Trayvon Martin trial, why he live-tweeted his father’s wake and funeral, and how he originally wanted to run his grandfather’s farm.

A quick homework assignment. We discussed two of his stories in depth, so before you press play, if you’re so inclined, read these pieces: 1) How most of the witnesses to the Martin shooting were actually watching TV during the struggle with Zimmerman, and 2) Montgomery’s return to his home state of Oklahoma after the mammoth tornado in May 2013.

Seriously, if you want an enlightening discussion about how to write the hell out of some stories, let Montgomery’s soothing tone educate you.

In case you were wondering about the song Montgomery talks about, here’s Steve Earl’s “Someday.”

And here’s the rundown of what did (and didn’t) talk about.