How to Get Unstuck: Draw Your Worst Ideas

It’s probably pretty easy for your team to look at your software and identify what doesn’t work. But getting beyond what doesn’t work and on to how to fix it can be the hard part. Usually you end up in circular, harry conversations, dancing around “if-then” scenarios and trying to imagine the best solution.

The gap between words and ideas

A lot of the time when teams are stuck, it’s because there’s a gap between what we can describe with words, and what the implications are in pixels and ones and zeros.

For example, everyone in the room can agree that “the graph should be the most prominent thing on the page. It should be all about the graph.” But what does that mean?


This is an ultra-simplistic example, but this kind of not-being-on-the-same-page comes up constantly on software teams. We humans are very visual creatures. Turns out that two people can totally agree on the description of a thing, but have two totally different mental pictures of the thing.

About 50% of what I do is draw stuff that doesn’t work. I draw out ugly, confusing, redundant ideas and deliver them to my clients — on purpose. And I recommend you start doing the same for yourself.

Why? First, drawing bad ideas gets everyone to understand more concretely what we’re even talking about. It’s no use having a conversation about an idea if we all have different mental pictures of the idea.

Second, low-stakes failures facilitate really great conversations.

You have nothing to lose by drawing out some really horrible ideas on a piece of paper. Drawing your bad ideas forces you to get into more detail than you could ever hold in your mind’s eye. Once the whole team can SEE an idea drawn out, and participate in a conversation about WHY it doesn’t work, hidden priorities will start to surface. You all get to see how one thing affects another. You’ll get to rule out some “maybe” ideas pretty fast so you can move on to the “YES” ideas.

Get over your fear of drawing

Free wireframing tools are really great for this. You need zero artistic ability — just drag and drop some pre-made boxes, fields, and drop-downs onto a browser-shaped canvas and you’re on your way. Paper works really great, too. Can you draw a box? A circle? An arrow? Do you have a pen in your possession? You’re good. I’ve seen people mock up ideas in powerpoint or excel, on whiteboards and napkins, in Balsamiq or Moqups (we do love those Qs don’t we?) or other basic wireframing tools.

If you go into it knowing you’re drawing a bad idea, then there’s even less pressure to have great drawing skills. This is also a great team exercise — just have everyone draw their bad ideas. Make them look really, really kindergarten-ish. It’ll be fun — and you’ll get unstuck faster.

What’s something your software team is struggling with right now? Have you tried drawing your ideas to keep the conversation moving forward? Do you have a favorite sketching tool or method?