How to plan to do something you’ve never done before

There are things that someone can show us how to do, like how to tie our shoelaces or how to fry an egg. Then there are the things you can really only learn by doing: riding a bicycle, managing people. However, it’s always helpful to have some frameworks for how to approach the new thing as you’re learning while you’re doing it.

Every time I have to do something new that is big enough in scale to warrant a plan (or feels overwhelming enough that I want to make a plan), I start with what I call the “What’s Needed Exercise.”

This exercise is very simple: I ask myself what is needed to make this thing happen and don’t stop writing (or typing) until I run out of ideas of things that might be needed. Then I organize them.

Regardless of what the new thing is – a volunteer training, version 2 of a custom grants management system, moving to a new country – there are typically a few categories of things that are needed.

Here are some prompts for thinking through what’s needed:

• What are the steps or tasks to do the big new thing?
• What decisions need to be made? By whom?
• What information* is needed? How do we get this information (ask someone, conduct design research, analyze the website data)?
• Which people are needed and for what? (This could be people on a MOCHA or DARCI chart, or this could be people to do X thing, or it could be that you need an expert in alligator wrestling.)
• What supplies, tools, equipment, systems, or venues are needed?
• What time or budget or commitments are needed?

*If you can’t articulate what success looks like and how you’ll be able to tell that you’ve made it to your destination, then you’ll want to add to the list of information that is needed (or decisions to be made).

I don’t try to answer those questions in order, though you can if it’s helpful. Typically, I’ll make my massive list (in a document or a spreadsheet or as sticky notes on a board) and then organize them.

Here are some groups I find useful:

• To do
• To decide
• To find out
• To get

Once they’re organized a little bit, it will be easier to see the dependencies. Then you can begin to sequence them.

And there’s your game plan! Well, okay, you probably have a specific timeframe for getting this thing done, or you might be working on this with other people, and so you’ll need to work on the timeline and how you and the others will work together. But this can get you started on estimating the level of effort, how much time you’ll need to allocate, and when it can fit on the calendar, how many people (and which ones) you need to get to help you, and so on. Here’s a way you can start when you’re not sure where to start!

What approaches or tactics have worked well for you when planning to do something new? I’d be interested to hear what works well for you or how it goes if you try this out. Of course, it’s common, when you do something for the first time, that things don’t always go according to plan and you find yourself having to make some course adjustments along the way. Stay tuned for a post on how to plan to change the plan…