I’ve always subscribed to Seneca’s philosophy: that “luck is what happens when preparation meets opportunity.” I’ve never thought of it in the precise context of how to plan a webinar, or how to execute one effectively, but it seems to work.

Let’s assume that you’ve got a great presentation – nothing but clean, impactful content – to start from. Let’s assume that you’ve got a solid marketing plan. Let’s assume you’ve got the right technology in place. Let’s assume you’re all set. Not so fast. There are plenty of other things to think about, but let’s call out two big ones here: challenge your content and engage your attendees.

Challenge your content. Not at the slide level this time, but at the core. There was a great post (roast?) on GigaOM last year that began…

“I spent the last week attending webinars. The topics were compelling enough that I carved out an hour at a time to attend. Each webinar used different technology solutions for delivery, and they were all “interactive” via emailed or IM’ed questions. And every single one of them was awful.”

7 Tips for Producing Winning Webinars makes a number of great points, but let’s focus on one that’s truly cringe-worthy and easily avoided with smart preparation: the sales pitch. Content marketing (so fundamentally right in principle, so often flawed in execution) can run amok, and live webcasts are the worst offenders. So before you alienate a prospect, challenge your content. The simplest question: if you charged for your webcast, would a prospect pay for it?

Now that you’ve got great content, how are you going to engage your attendees? What is your plan to make the webcast truly interactive? (Pet peeve alert: screening written questions and answering a few softballs at the end of the hour is not interactive!) Because no matter how great the subject matter, listening to someone talk at you for an hour is boring. It’s an invitation to check email or IM or text or…

So how can you keep them with you? If it’s practical, leave audio lines open for informal discussion or Q&A. If your group is very large, at least consider opening participant lines for verbal questions. Insert Q&A breaks throughout the presentation instead of holding questions until the end. Think about interactive features in the webcast software. Let attendees mark up the whiteboard. Conduct a real-time poll. Launch a survey.

If you’re lucky, your next great content idea might just come from your audience, because you were prepared for the opportunity.