Wherry’s how-to for founders took an unusual form — stories about typical scenarios in startup life and an audience-driven discussion of the mistakes within them. 
By Jessica Stillman (Editor, Women 2.0)

Of all the speakers that have so far graced the Women 2.0 conference stage, Meebo co-founder Elaine Wherry definitely presented the talk with the most unique format. Rather than tell her own personal story or offer a list of tips, Wherry decided to tell stories. If you talk about mistakes that way no one gets defensive, no one resists, she has discovered. What kind of stories exactly? Ones drawn from her own experience starting up and common missteps she’s seen other entrepreneurs make, illustrated with entertaining little drawings.

This visual, mistake-focused way of getting better at starting up is something Wherry is now developing into a graphic novel, which, she said, will hopefully will be out soon, but she gave the audience a taste of what dh’s working on by telling five of these vignettes and asking us all to call out the mistakes they see for discussion. Here’s one:

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Remember your first job? You were thrilled to join your company, but then shocked to find less than perfection there — software has bugs and reports have spelling errors. Your response? You send out an email to the whole company telling everyone how to fix these problems. No one responds but you get invited to an meeting. You are stoked!

There, one participant says his design project is a little behind, so you stick you hand up to offer to help out. Your manager warns you that you have a lot on your plate already, but you assure him you’ve got it all under control. But in reality you’re actually hugely far behind, so you pull an all-nighter — that’s always worked before. But unfortunately, the results aren’t as amazing as you’d like this time. So you get a two-week extension. Meanwhile, you feel like everything goes so slowly at the company and you see all your friends who are still in school posting pictures of themselves on the beach on Facebook. The result: you decide to make a change and move on to a new company.

Then she asked the audience the following question:

What mistakes do you see?

Jessica Stillman (@entrylevelrebel) is an editor at Women 2.0 and a freelance writer with interests in unconventional career paths, generational differences, and the future of work. She writes a daily column for Inc.com, contributes regularly to Forbes and has blogged for CBS MoneyWatch, GigaOM and Brazen Careerist, among others.