Anticipating the Questions

I had a great lunch meeting with Glenn Kelman of Red Fin yesterday. Forty out of the forty five minutes of our went off just as I would have hoped. He asked great questions and I hit them out of the park. I could definitely sense there was some "clicking" taking place. Then the "but" happened. As in (paraphrased), "you've got some great ideas, but you don't really have any experience in our space. Give me an idea of how you might steer our marketing plan."

Do you know the feeling you got in college when you sat down to take an exam and realized that you had been studying the wrong chapter? That's how I felt at that moment. Though I spent plenty of time building my knowledge of the Red Fin story, I failed to anticipate that question. Which is crazy, because in hindsight, it's an obvious question for a hi-tech CEO to ask a candidate with no hi-tech experience.

My answer to the question wasn't great and I knew I was capable of much more. Unfortunately, I gave him every reason to believe that his suspicions were true. I left the meeting with that sinking feeling that I had blown a great opportunity. Playing the question back in my mind as I ran some errands afterwards, I came up with some great ideas (I thought, anyway) that I shared with Glen in my Thank You note afterwards. He replied positively and promised to re-engage once they have hired a CMO, so I think I saved the day. But I sure wish I got it right the first time. Next time I will for sure.

Is blogging essential for a CEO?

I attended a great panel discussion last night featuring journalists from 5 different media outlets to discuss the dos and don'ts of media relations for startup entrepreneurs. (A big thanks to Glenn Kelman and the folks at Red Fin for putting it all together - and buying the beer and barbecue!)

One comment that our group found provocative came from Michael Arrington of Techcrunch who said that it was absolutely essential for CEO's to be blogging. Those who pushed back on that statement seemed to feel that sometimes there are just more important things for a CEO to be doing than blogging and also that some just aren't suited to blogging at all.

I couldn't disagree more. The startup CEO's blog is the mortar that fills in the cracks for his audience. When a company is struggling to cement its mission (last masonry analogy, I promise) in the minds of its investors, customers and employees, a blog can work very well to provide the necessary tidbits of background stories and personal philosophies with an editorial thread to complete the story for the reader. Yes, there are many times when a CEO has more important things to do, but that should never be a reason to abandon the blog. Shorten the posts, solicit contributions from other team members, take a week off, but by all means keep telling the story.

My approach to communicating with my audience is similar to the way I communicate with my kids: Don't leave any holes in the story, because if they need to fill in the blanks themselves, you're not going to like the results.