It depends a lot on the org and which channels you are focused on, but generally, I would start by scheduling any major launches, campaigns, promotions, and things that have a fixed date like content related to holidays. Think of this as your 'tent pole' content. From there, you can look at your calendar and see where there are holes in the schedule and fill those in with content that doesn't necessarily have a specific date or event to determine when it occurs. After that's done, the last step would be to schedule the distribution of all that content to make sure its being maximized across different channels. For instance, if you're launching a big YouTube video, schedule a newsletter email that uses that video as its lead. I would be remiss not to mention that the startup I'm currently working on and plan on launching soon is a solution for to this exact question. See more here: https:/callio.com :)