After being a project manager in the digital marketing industry for 10 years, I am pretty sure I know a thing or two about launching stuff. So here are a few thoughts on taming the timeline monster and the tasks dragon...
When it comes to launching a product or program, there is usually a deadline, date that you start work, and how much time you need to achieve all the steps. The best way to go about planning your timeline is to reverse engineer, starting from your launch date. Of course, this launch date has to be reasonable, not two weeks from today, but know that you can compress and/or overlap some tasks in your timeline so that you don't have to have absolutely the "ideal" amount of time to bring everything to perfection (which is overrated).
Your launch date can be affected by many factors - your target market's schedule and lifestyle (is middle of summer a good time if you want to attract busy moms whose schedule may be filled with shuttling kids around?), you own marketing calendar, seasonality of your offerings and of course, you own schedule such as travel, vacation, and family obligations.
If you are starting today, your reasonable launch date should be around at least 8 weeks away for a product that is relatively small in scope, and at least 10 - 12 weeks away if you are more ambitious. Then work backwards from you launch date to plan out the tasks and the milestone. If everything fits nicely with time to spare, great. If it turns out that, after putting down your ideal schedule, you should be starting 2 weeks ago... don't panic! You can usually find some tasks that you can work on simultaneously or in parallel, or compress the timeline for a couple of deliverables. If you do this, you just need to make sure that your schedule, your workload and your sanity allows a more aggressive work schedule. If not, you may just need to go back to your launch date and see if you can bump it down by a few days to make some room.
Keep in mind that your project plan or timeline should be a living document and you should be able to adapt as your project evolves so that your timeline meets the objective of your project. Use it as a reality check, and if you are not meeting the milestones, it may be an indication that you have to re-evaluate your expectation, change the way that you work, or see if there is something that is blocking you from buckling down and taking the necessary action.
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