Why messiness is a good thing for product teams

Main illustration: Aimee Bee Brooks

Here’s something I bet you experienced this week at work, probably most weeks at work: the feeling that things are kind of a mess.

You look at other companies, and they seem to have it all figured out. From the outside, maybe it looks like you do too. Your marketing site hopefully makes you look good. Your blog presents your people as sharp, witty and insightful. Maybe you even write books about how it’s done.

But when you pull the curtain back, how we create these things is almost always a mess. We frequently forget this. But actually, this mess is necessary, and it’s possible to adapt to messiness and use it to improve the products you build.

This post started life as a talk on the 2016 Inside Intercom World Tour. Interested in seeing us on stage this year? Tickets for the 2017 tour are on sale now.

Mess in the Messenger

At Intercom, we struggled with this when working on a major update to our Messenger. The Messenger is the part of our product that sits on our customers’ sites and apps. It’s how they communicate with their customers.

One of the things we were working on was the below animation. It’s a simple, scroll-to-reveal animation that works across web, iOS, Android.

Seems like no big deal, right?

This was the single most expensive interaction we’ve ever built at Intercom. It was incredibly hard to do. We went at it, we threw our hands up; we went at it again, we iterated; each platform struggled with making different parts of it work right. Finally, after lots of sweat, we got to a version we were happy to release.

But here’s where it gets more interesting. We ran a quick team retro a couple of weeks later. We were only midway through the entire project at this point, but we wanted to take a quick step back. We asked ourselves: Why was this so hard?

We discussed several ways we could have done it better. Maybe we should have prototyped more, spent more time going through requirements and not started engineering so soon.

But the more we explored what we could have done differently, the more it sounded like we were walking backwards into idealizing the waterfall process. Without realizing it, we were coming to the conclusion that if only we had used a waterfall-like process to build product all this pain would have magically gone away.

That’s what waterfall represents. It’s a mythical place of peace, calm, structure and clarity. And most of all, certainty. Because we all crave certainty.

Messiness at scale

If you’re a small startup, you expect things to be messy and chaotic. That’s almost the definition of life at a startup. All hands on deck; do whatever it takes.

But as you get bigger – from 50 people to 500 people – and when your company has been around for a few years, it’s hard not to think that you should know what you’re doing.

We all tend to think this, and I think we are all wrong.

When we were midway through this project I read an interview with Ed Catmull, President at Pixar, who talked about something very similar in his company.

“People coming in from the outside, as well as employees, look at the process and say, “You know, if you would just get the story right – just write the script and get it right the first time, before you make the film – it will be much easier and cheaper to make.”

His response? Yes, they could. But then they’d make B-grade movies. He explains: “What we’re doing is inherently messy. The goal isn’t to prevent the mess, the goal is to ensure it doesn’t get too messy.”

Managing the mess

The first thing we can do is adjust our expectations. Instead of expecting things to go smoothly, we have to expect they will be messy.

That’s easier said than done. No one wants to work on ground that’s perpetually shaky. When everything’s in a state of flux, what helps you get through this messiness is having a foundation, and that’s where your company mission and vision come in.

A strong mission

Above is a screenshot of the blog post our CEO Eoghan wrote for the launch of Intercom (appearing on the blog of his and the other co-founders’ previous company). It made the rounds in our all-company Slack channel last year, right as we hit our five-year anniversary. Pretty much all of what he wrote still holds true five years later. We still use his anecdote about the coffee shop today.

This stability of our mission gives us a rudder to steer amidst the chaos of all that’s changed since then.

Defining how you work

Another thing that helps you contain the mess is having principles for how you work. We have three that are at the core of how we do things:

  1. Think from first principles (new solutions to problems, not better versions of existing solutions)
  2. Ship to learn
  3. Think big, start small

The Messenger we were about to release had taken over a year to design and build. That broke 2 of our 3 foundational principles. It was as un-Intercom a project as we had ever done. We didn’t start with a small, well scoped project (we call them cupcakes), which would have proven the concept and helped us learn from real usage. Instead we built a wedding cake.

Sometimes, this is what needs to happen. In our case, the new Messenger was too far a leap from the old version. It’s messy, and it’s risky but, as the saying goes, you can’t cross a chasm in a series of small steps.

For the most part, we stick to our defining principles – and big projects like this help remind us why they are so important.

Are you going to get to done or are you going to get to great?

It’s important to try find a balance between the certainty that we all crave and the uncertainty that’s inherent if you’re trying to build something great.

You have to question everything, and constantly step back and reassess. There’s no right place to be. It depends on your team, your product, your company. That’s what makes this so hard.

What you need to be wary of is the gravitational pull towards the side of order. This will only get stronger as you get bigger. There’s a pull towards more processes, more meetings, more “Will you CC me on that?” type of conversations.

We all want to find a space of comfort in what we’re doing. But often, the result is mediocrity.

Expect it to be messy. If you’re trying to build something that’s really good, there’s going to be a lot of uncertainty and chaos.

If you’re shooting for something that’s really great, remember that creativity is inherently chaotic and uncertain. You have to expect it to be that way. You can contain this mess with your pillars – the foundation of your mission and vision, the principles of how you work – but fight the gravitational pull towards order. Because if it’s not messy, and you’re convinced you know exactly what you’re doing, you’re probably on the road to irrelevance.

My view has evolved on this topic since I gave this talk last year – look out for an updated take in an upcoming post ?

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