Making a Mess In Order to Make Something Good

I gave a workshop on Stand-alone Discovery Projects at UX Hong Kong in March. About 30 minutes in, I was wrapping up my explanation of the first exercise the attendees would be working through.

I said, “Make sense? What questions do you have?” Sixty blank faces stared back at me. Confused silence was not the reaction I was going for.

I briefly explained it again. Sixty blank faces. Luckily, for me, I had an on-the-fly a-ha moment.

“This is the work, people. This is what it's like. You will very often find yourself walking into a room full of people who you don't know, who are stuck, you won't know what they are talking about, and they are looking to you to lead them to a great outcome. You have to be willing to get messy before getting to good.”

I got a low-mumbling agreement as they started the 20-minute exercise. The room didn't get loud until toward the end of the exercise. It was clear the attendees were struggling. My responsibility completely, but at the same time, the way I described what the work is like in practice is accurate.

Second exercise. I explained it. Sixty blank faces. What was I doing wrong?! I reiterated, “Messy. Get comfortable with the unknown.”1 It took only about 2 minutes for the room to get loud with attendees collaborating their way through the exercise.

The third exercise started with blank faces again, but they looked much less daunted by the challenge. Looking back, what they needed, in a way, was permission to make a mess. Permission to be an No Idea Cat.2 Permission to be wrong.3

I wrote recently:

Upcoming articles will address some of the ways we might get everyone's attention and interest. And, spoiler alert, it's going to be messy, difficult, and a lot of y'all won't want to do it.

So, let's get into trouble, baby.4

Learning Portfolio

In order to do the right work well, you need to be competent at some core capabilities.5 The good thing about being good at these things is they will help you in almost every aspect of a professional (and personal) life. In a lot of ways, we should be teaching this stuff to kids.

Speaking of Design Thinking (if you clicked the link above): Whatever your view of Design Thinking (DT), a lot of what this article is about is thinking like a designer. DT is super hot of late and that's one of the reasons why I'm likely to ignore it. DT is not new, it's not the only way to explore ideas, and it's not the solution to all life's problems. That said, if you get good at some of the core tenets of DT, you're most of the way to where you need to be skill-wise. The next step is getting to where you need to be to do the right work well.

My request of you is to actively, intentionally create a Learning Portfolio. Let it have blanks you need to fill. Capture what you learn (and what you know) and update it over time. These capabilities are living things that need to be practiced, questioned, tested, and refined. And, perhaps, you can use your Learning Portfolio to help others get better at their work.

The following capabilities are in a somewhat ordered list, in the sense that the ones toward the top are more important than the ones at the bottom. If you aren’t great at prototyping (yet!) you definitely need to be good at the things that precede it. But, to make an impact, you need to be good at all of it.

Each capability is a workshop (and continuous practical application) unto itself. Let's chat if you want to learn how to do this stuff. Also check out Make Meaningful Work for more about Learning Portfolios and related concepts.


Related to this section: Leadership comes in many forms.

As I said above:

You will very often find yourself walking into a room full of people who you don't know, who are stuck, you won't know what they are talking about, and they are looking to you to lead them to a great outcome. You have to be willing to get messy before getting to good.

As a leader or facilitator or consultant, however you feel like terming it, you have the opportunity and responsibility to be raising and razing people's hope and dreams.6 You have to lead people down the right path, even if it's not where they want to go, and make them feel good about getting to where they need to be.

You have to be confident even if you feel like a No Idea Cat.

Once you've established that mindset, your next task is to set it aside and remember that none of this is about you. It's about the people in the room with you, whether they are stakeholders, employees, or customers.

Asking Questions

You must learn how to ask questions properly. Many people tout The 5 Whys. And, conceptually, that’s fine. The idea behind that is to get to the root cause of something and it usually takes no more than 5 “whys” to get there.

The thing is, people can get super defensive if you ask them why. “Why did you do that?” Sounds like you are judging them. Which you shouldn’t be (see below). Better Why questions start like, “What led you to choose that?”

For bonus points, buy and read this text book: User and Task Analysis for Interface Design. It’s a classic and delves into a lot of the fundamentals of this work, which haven’t changed for a good long while, regardless of the new names people are using like Lean and Atomic.

Flexibility & Improv

You can and likely will have to Yes, And yourself through a meeting now and again.

Take an Improv class or two. Seriously. Like, for real seriously. I know many people will cringe at the idea of being on stage not knowing what you're going to say next, but, as I keep saying, it's the job. You’re often on stage, not knowing what you or anyone else is going to say next, but you have to convince people everything is fine and you are in charge.

Learning to roll with things while keeping an eye on time-spent and the need to get to an outcome is hard work.

Plus-side: it helps with non-work life, too.

Making Sense Out of Messiness

Basically, figure out what’s really going on. Reading between the lines, the silences, and the sighs. You need to be able to zoom in and out on the data or system you’re looking at and be able to make some sense of it.

You will have to iterate your way through it. Sometimes the answers present themselves, but more often than not you have to dig for them.

Straight up: this takes a lot of practice.


Everyone involved has to feel like they are part of things. You have to keep people in the loop. Whether that's updates during a standup, weekly newsletters, 1-on-1 meetings, you cannot work in the dark. No one likes The Big Reveal™. No one. Well, Ad Agencies seem to like it for some reason. Don’t be like them.

Creating Artifacts for Feedback

Low-fi vs High-fi. We can have this discussion up and down the wall, ad infinitum. I personally take the Least Amount of Work for Most Amount of Gain, or, as it’s better known: LAWMAG. Sure, better known, yeah… Sometimes all you need is a salt & pepper shaker, sometimes you need an incredibly realistic prototype. Or your competitors product. Or a group of people role-playing the system you’re designing/redesigning.

You can do this with anyone. Stakeholders, customers, would-be customers… But you don’t start with it. Prototyping is where you’re asking what things could be like. The bulk of the Discovery process is about defining with a high-level of confidence, what things are currently like. You can jump right in to creating artifacts for feedback after you understand the current state.

“You have to be able to find and measure the gap before you can figure out how to bridge it.” — Me, to anyone who will listen.

A prototype can even be giving a pen and paper to someone and having them write down/draw how they wished they could accomplish a task. You can use this process to cut through a lot of bullshit. Nothing tears apart someone’s view of a task, or service, or product as well as having them draw it for you. Or write down how it should work. Or does work. Or doesn’t!

Pro-tip: this works really well to undercut the ego-driven demands of C-level and upper-management types.

What’s the work itself like?

The work done by you and your colleagues/clients during Discovery Projects, or Design Studios, or any number of other titles, tend to have the following attributes in common; attributes that necessarily need to be learned and practiced.


This work is meant to be seen by all. When you use a shared document (on a computer or on a wall) that’s easy to find, see, learn from, and contribute to, you end up with better outcomes.

Get comfortable drawing and writing in front of a live, studio audience. Practice. Maybe everyone can’t draw, but they can certainly capture visually a conversation.


We work with humans and on behalf of humans. ‘Nuff said.

Multi-disciplined & Co-created

We don’t work alone and great ideas come from likely and unlikely sources. Also, we keep saying how much we hate silos, but then we don't work together. Does that seem right to you?
Everyone should contributes. Not to the same extent, but everyone should feel like they have the opportunity and should be able to explain where things are at and why.

That said, while everyone contributes, it's your responsibility to lead them. Everyone is a designer. Ev. Er. Y. One. But ultimately it’s your job to piece everything together.

Actively Iterated

You will (often) be creating something from scratch and you won’t be right about everything. You’ll do your best, find out something new, adjust. Repeat as necessary.

Sometimes you will have to discard or destroy your work because you started from a faulty premise (hello 98% of startups) and you need to feel comfortable crumpling up the work, tossing it on the floor, and starting over.

“[This work] is a living thing, and you can nurture it, or kill it.” — Matt Wallens, 1876-1954.

Holistic in Perspective

You must understand how the piece you are making fits into the entire system; certainly the system you have control over and, ideally, the system you can influence.7 You must understand all the inputs and outputs. And sometimes that means you need to map out the entire system. Hello, Service Design!


Or perhaps non-derisive, as we humans can’t help but make judgements about everything all the time.

Everyone comes to the moment you’re reacting to with a different history and set of experiences. If you find yourself judging others because they’re not where you are at, well, get out of this business.


You need to understand your own motivations as well as the motivations of others. And you need to be sure the choices you are making are well-thought-through and backed by external research/data.
Some people can get by in life making things up are they go, but if you want to do well you have to precede with purpose. It’s okay to not know where your work will take you, but it isn’t okay to make it up as you go. Might be too subtle a distinction, but it’s worth thinking about.

Start Your Learning Portfolio

This was a long article. Congrats for scanning all the way to the bottom! I thought about breaking it up, but it all belongs together. As I mentioned, each item listed could be its own article, but for now I feel this sums things up well enough. I’m sure there are more items that could be on the list, but I wanted to get more toward the core of this work; to define things that are true no matter your job title.

I hope you found all or part of it worthwhile and I hope you enjoy making a mess in order to make something good.

1 Something I stole from Jesse James Garrett via Cornelius Rachieru.


3 I'm purposefully not saying Permission to Fail. I get that's in for some people, but failure feels final. It's still too judge-y.

4 Tapeheads is a highly underrated movie and you should watch it. Also, Living in Oblivion. Maybe we should have a movie night...

5 Some of the terms above are “stolen” from a workshop I attended in January 2018 run by Territory. I had them written down as notes and only now as I am writing this do I realize I'm kind of stealing. Hence this footnote. I mean, it's not really stealing as it's core, well-trod stuff, but I didn't want it to seem plagiarize-y to three people who likely won't even read this. Transparency, y'all.

6 Homonyms For the Win!

7 One of the basic things you should figure out, regardless of your job title, is how to develop a good understanding of what you can control and what you can influence. Leave everything else alone (unless you are going to build skills/capabilities to expand the circles of control and influence). Applies to non-work life, too.