Failing to Plan is Planning to Fail

This is one of those aphorisms that most of us would claim to agree with, but we’ve all experienced times where something wasn’t planned well. Planning is not only a learnable skill, but also habit that must be cultivated. It doesn’t matter what field you’re in or what your role is, a failure to plan and account for all the minutiae that needs to occur between Point A and Point B means you’re going to have a bad time.

Point of fact, learning to plan requires repetition/practice just like anything else. I think this is true for just about every job in the world, but in marketing my planning process follows these steps:

1. Define the objective. You’ve gotta know where you want to end up before you can pick a direction to go. Example: I want to write a productive blog post with helpful advice and humorous anecdotes to help people learn how to write better workback schedules.
2. List the key milestones. What are the key points of interest in the journey to your destination? Put another way, these are the “big rock” tasks that contribute to the overall goal. Example: I need to write an outline.
3. List the dependencies. These are generally smaller “in-between” tasks for the above milestones. These typically become subtasks. Example: I need to understand my point of view on planning.
4. Forecast the Timeline. If you don’t know what a SWAG is, it’s a Scientific Wild Ass Guess. That’s literally all this is. Something that’s worked well for me is to consider what I think is a realistic timeframe to accomplish a given task, and then add ~25%. That’s useful for accounting for the unexpected. There’s a fine line between padding and sandbagging and you need to be careful not to cross that threshold because otherwise you erode trust in your stakeholders. Example: Writing an outline should take me about 10 minutes. So I’m going to set a due date for ~12.5 minutes from now.
5. Assign Owners. Very few plans are a solo effort, but if you’re an individual contributor that doesn’t have the luxury of delegation, there’s another step here to align on the request with your colleagues. That doesn’t mean you can’t straight up assign things, but… be human and have a conversation. That also can pay in dividends by fostering a team atmosphere, like “we’re all rowing in the same direction.” Example: Well shit, I guess this one is me if we’re sticking to this very on-the-nose example.
6. Sync Regularly. This is the part of the follow-through swing people often forget. I like to schedule recurring standup meetings, which might be daily, weekly, or more sparse depending on the project. When I say “standup meetings,” I literally mean “this meeting should be short enough that no one gets uncomfortable while standing around talking about it, and if anyone talks more than 30 seconds at a time you’re doing it wrong.” The main objective of this recurring sync is to true up the forecasting. Maybe you nailed it and things are perfectly on track, but that’s usually not the case. Example: Yeah, I talk to myself. Probably too much.

Mind-shattering stuff, right? The most frequent planning error I see is deciding on a deliverable date without first listing out all the tasks/subtasks along with a realistic estimate for completing them. The planning error best described as “I think you might be too stupid to live” is when you see people defining a goal as anything other than the first step of planning. Even reading that statement back, I wouldn’t have thought that scenario was even possible if I hadn’t lived it at least a couple times. Which brings me to my next point…

Unless you’re an intern, you’re not an order-taker. Which means you need to be planning with some sort of framework, whether you use the above or something different. If you have a lot of projects, I also recommend prioritizing them based on the impactfulness of the final objective. That really helps you avoid spending a disproportional amount of time on pebbles when you could be hurling boulders into the sea. For example, not having a 47-comment Slack thread about where to place the customer quote you don’t actually have.

Not that that happened or anything. /s

Also, thanks to DALL·E 2 for the heckin’ sweet cyberpunk decision tree image