5 ways to attack ambiguity

Imagine you've just been asked to lead a new project 💭

You know... the kind that's full of complex, interconnected problems where it's super unclear how to get started 😅

How do you attack that ambiguity and get momentum quickly?

I asked Jenny Wen (the original designer of Figjam) this question and loved her answer.

So here's the breakdown (and a bit of my own process)👇

Attacking ambiguity in 5 phases

1) Write out all of the questions

When Jenny was conceptualizing Figjam, her first step was hopping into a design file and dumping every question she could think of.

Big questions like "what's the relationship between Figma and Figjam?" all the way down to more tactical questions like "how do you manipulate text on the canvas?"

Similar to Jenny, my process often starts out looking something like this 👇

Spatial writing is my favorite way to think which is why I always begin by opening up Figjam.

2) Identify tipping point questions

You goal is to figure out which questions, if answered, likely unlock answers to other questions as well.

Nerdier folk refer to these as "Eigenquestions" and they're a key way to frame problems more effectively.

"One of the critical disciplines of framing is to "find the right question." Too often debates start with "solutions," before we determine if we're asking the right questions, in the right order"
— Shishir Mehrotra (CEO of Coda)

So how do you get better at identifying and sequencing the right questions?

To start, check out this clip about time machines 👀

3) Create a spectrum of possibilities

Once you've identified the most important questions, the next step is to start exploring the possibilities on a spectrum.

The key is to paint the edges.

You're not trying to nail a production-ready design out of the gate. You're simply framing the problem and guiding stakeholders toward a winning middle ground.

"Pushing the extremes lets you see what the design direction looks like if you just optimize for one certain thing"
— Jenny Wen

For Figjam, Jenny talked about the spectrum of expressiveness which is what led them to move the toolbar from the left panel to the bottom of the screen 👇

Another great resource on this tactic is Brian Lovin's interview with Vivian Wang where she talks about "provocation work".

4) Organize these questions in a doc

Once I have my tipping point questions and my spectrum of concepts, I like to organize these into a Notion doc (the toggles are great for keeping things tidy).

I create two sections:

1. 📖 Open questions

2. 📕 Closed questions

Then within each question toggle I organize all of my concepts 👇

The key is to make a clear recommendation within each array of options.

If you simply provide a spread of concepts for each question you risk analysis paralysis and slowing momentum.

Sometimes I'll send this doc out async, but often times I'm using this as the outline for CRIT. I'll even give 5-10 min up front for people to read the doc so that we can dive right into the meat of the questions.

5 ) Move questions from open → closed

The more challenging the project, the more satisfying it is to drag questions into the "closed" section 🙌

Bonus points if you add a few sentences of context for why the decision was made.

That way, over time it becomes an artifact of alignment that you can point to as questions inevitably resurface ✅

I hope that sparks some ideas for your own process!

But the real reason I wanted to talk with Jenny was to understand her framework for delight 👇

🌅 The art of designing for delight

If you want to push past confetti animations then you're going to love this conversation with Jenny Wen.​

Her framework definitely shaped the way I think about delight in design.

"Delight is going above and beyond in moments where people don’t expect it"
— Jenny Wen

We also get into a bunch of other meaty topics:

• Ideas for facilitating live workshops

• Jenny’s vision for the future of Figjam

• What Jenny looks for in design candidates

• How to articulate why quality matters in software

• What we can learn from Figjam’s product strategy

• How she reverse-engineered delightful moments for Figjam

Listen on YouTube, Spotify, Apple, or wherever you get your podcasts 👇