Ask it Forward. 26 Questions for 26 Content Marketers

By Andy Crestodina

We were at Content Marketing World and the idea was simple. Answer a question, ask a question. Ask it forward. The #AskBucketChallenge. Here’s what happened…

It’s a video “chain letter” format. Each person answers the question of the person before them, and asks a question of the person who comes next. Simple right?

How could we spend four days in Cleveland for Content Marketing World 2014, the biggest and orange-est conference in the industry, without making a little content?

Here’s a run-down of the questions and answers.

00:36 Ian Cleary answers “Why content marketing?”


01:08 Kyle Akerman answers “There’s so much content, how do you stand out?”

01:47 Andrew Davis answers “What metric do you measure and how often?”

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02:35 Brian Clark answers “What makes a great story, a story that inspires an action?”

03:13 Hunter Boyle answers “What is the role of email in 2015?”

04:03 Bernie Borges answers “What are the most useless social media analytics?”

05:19 Marilyn Cox answers “What is stopping you from podcasting right now?”

05:46 Tom Martin answers “How do you adapt your content for specific industries?”

06:37 Mark Schaefer answers “Is it ethical to use social media data in sales prospecting?”

07:11 Brody Dorland answers “Is Google Glass going to be the big wearable technology? Or does it just make you look like a dork?”

08:19 Deana Goldasich answers “Are small businesses ever going to be able to do content marketing well?”

09:15 Grandma Mary answers “Are comments dead in blogging?”


10:26 Arnie Kuenn answers “How much should you automate Twitter?”

11:12 Phil Mershon answers “When will we reach the saturation point with content marketing?”

11:58 Gini Dietrich answers “How should you handle negative comments?”

12:49 Jeffrey Rohrs answers “Would you rather be trapped on a deserted island with Scott Stratten or Marcus Sheridan?”

13:18 Ann Handley answers “Underwater dogs or above ground cats?”


13:58 Doug Kessler answers “Is native advertising a total mistake? Or just a really bad idea?”

14:58 Ramon De Leon answers “What is the next medium for content marketing?”

16:03 Paul Roetzer answers “If you could go back five years, knowing what you know now, what would you do differently?”


17:06 Jason Miller answers “Are we going to continue to have many marketing technology tools? Or will they converge in the future?”

17:48 Lynette Young answers “What’s the best marketing analogy you’ve ever heard?”

18:16 Jon Wuebben answers “Who rocks orange the best at the conference this year?”

19:05 Heidi Cohen answers “Who will rock orange the best next year?”

19:24 Laura Mansfield answers “Which issues do most marketers miss?”

20:17 Andy Crestodina answers “How can we reconnect with each other and collaborate on content?”

You made it!

Yes, some of the questions degraded a bit toward the end, becoming more about fashion and less about marketing. Actually, the entire format was silly. As soon as we finished, Mike Stelzner gave us four ideas on how to do it better.

But it was really just an excuse to collaborate. To make friends. To have fun. I think the outtakes tell the real story of how goofy this mini-project really was…


Last year, we created the Content Marketing World Yearbook, and this year we did it again with the help of Amy Higgins and Erika Heald. We’ll share that once it’s live.

Ask it Forward

Until then, if you like the “Ask it Forward” format, turn on your own webcam and ask a question of your favorite marketer. Invite them to pass it on and ask a question themselves. You never know where it might lead to. Maybe Cleveland!


There is more where this came from…

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