How to make big changes one step at a time

Hi there, Matt here.

Last June, I presented a case study at a product management conference called Front. I took the opportunity to share my work on the brand update and redesign of Bitly.com; it’s a project I led, one that I feel best demonstrates the challenges of big changes.

I’m jumping into another big change project now at Simple Health. I thought it’d be a good time to revisit my presentation, and translate it into a written essay.

Before we get into it, a song. Moon Duo are a group I love to rediscover. They’re always there, putting out solid psychedelic tunes; their seventh (!) full-length is no exception. This is Lost Heads, from Stars are the Light.

Now, on to the essay.

ps: the next chapter of Ethics for Designers (on deontology) comes out next Monday!

This essay is an adaptation of a talk I gave at Front, a UX and Product Management conference. If you prefer, you can watch the presentation here.

Great companies are defined by their ability to change. Apple changed when they re-hired Steve Jobs. Microsoft changed when they embraced open-source software. Amazon changed when they started selling groceries, and then cloud computing, and then original TV shows.

It is easy to imagine these changes as grand strategic moves, carefully planned and executed by a handful of luminaries. But lasting, meaningful change comes from many small, focused improvements over time. With patience, even a single person can make a substantial impact in even the largest organizations.

The ship of Theseus

One of the best illustrations of the power of small, incremental change is a parable called the ship of Theseus. It goes like this:

Centuries ago, a famous ship — sailed by a hero named Theseus in a great battle — was docked in harbor as a monument to naval victories. Over time, the ship’s wood deteriorated, worn away by salt and sea. One by one, each piece of the ship was carefully re-created and replaced as needed.

The ship still serves its purpose as a memorial, but nothing about it is original: Theseus didn’t stand on those exact boards, or steer that exact rudder. But at what point did it stop being original? Was it the first part that was replaced? The 10th? The 100th?

Change is hard to see in the present. Rarely does significant change happen all at once. But continuous change adds up; it tells a story of renewal that only appears in retrospect.

The first plank

If you’re thinking about setting out to make a big change — a rebrand, a reorg, or a product pivot — it’s tempting to start by planning the whole thing out. But the ship of Theseus didn’t get changed by plan; it happened plank by plank. Your first step in a journey of change is to simply replace a single plank.

The first plank is important because it creates momentum. It moves the needle. It’s never a triumphant moment, but it’s the only way to begin.

The best first plank is something on the edge. If you start by changing a major part of your organization, strategy, or brand, you’ll set off alarm bells in the institutional immune system you work within. You’ll get a lot of attention, and it won’t necessarily be the good kind. Instead of opening with a bang, pick your first plank to minimize the resources you need.

This is sometimes called a “quick win,” but it likely won’t feel like much of a victory. You won’t have time to reflect on it. Be ready to scale up, and get to work on the second plank.

The North Star

Just like a lonely plank, a single step has no direction. It’s just a point in space. But take a few steps together — connect two or more points — and you have a direction, a line, a path.

For as long as humans have been exploring, we’ve used the stars to guide us. In modern business parlance, a “North Star metric” is a goal that guides a team’s efforts. Volumes have been written about why North Star metrics are important and how to select them. I particularly like this post from Amplitude, as it addresses some of the pitfalls that accompany North Star metrics.

But if your North Star is a goal, you’re using it wrong.

Explorers didn’t treat the stars as their goal; they used them as a guide. That is, the stars told them if they were on the right course towards their goal, be it the West Indies or the farthest edges of Polynesia.

Your North Star should be a guide, too. In design projects, we use design principles to tell us if we’re going in the right direction. I’ve written lots about design principles in the past:

• The 1-hour design principles workshop
• What makes a good design principle?

Consistent principles let us know if we’re on the right track and help us course-correct if needed.

The roadmap

As you take more steps with confidence, you’ll hear a question from your team and your stakeholders: “So what does the roadmap look like?”

I wrote a response to this question in Responsive Roadmaps:

The essay goes on to suggest that instead of drawing out extensively detailed plans for the next quarter, half, year, or decade, you should tell a story. The story is about your goals, and how you’ll accomplish them.

That story, what I call a responsive roadmap, consists of four elements:

1. An ambitious objective that guides all the work your team is doing
2. Measurable key results that tell you if you’re on the right track
3. Concrete targets that will move the needle of your key result
4. Current projects that you have undertaken to reach your next target

The feedback loop

With repetition, the forward momentum of change eventually builds to a speedy pace. And that’s where another mistake of change-making is often made: teams restart their process from a blank slate every quarter, half, or year.

Annual planning kills the engine of change. The boulder rolls back down the hill.

Instead of big planning phases, projects of change require short feedback loops. Follow these three principles:

1. Keep course corrections small
2. Keep cycles short
3. Don’t assume your predictions are perfect

In the world of product design, we apply these principles by mirroring some of the practices of agile software development:

1. Invest in a design system — this keeps course corrections small
2. Ship in the smallest increment possible — this keeps cycles short
3. Get embedded in the team and don’t create a backlog of designs — this helps keep the team honest about the accuracy of their predictions

Scientists harness the power of short feedback loops, too. Kalman filtering, a simple feedback algorithm invented in the 1950s, enabled the feeble computer aboard the Apollo spacecraft to successfully traverse the 238,856 miles between the earth and the moon.

Kalman filters are so powerful that they’re still used today, on much more advanced hardware, to guide spacecraft to dock with the International Space Station.

Kalman filters are a deep, wooly subject. You can dive down the rabbit hole with excellent explanations like this blog post or this 55-part YouTube series. But there’s a lot on the surface here: apply the three basic principles, and you’ll be able to adapt to uncertainty without sapping the energy of change.

Putting it all together

Change is never done. Heraclitus said: “Everything changes and nothing stands still.”¹ David Foster Wallace put a modern spin on this in Brief Interviews with Hideous Men: “Everything takes time. Bees have to move very fast to stay still.”

Trying to corral change, to put reins on it, tame or domesticate it, is a losing prospect. By following a small set of principles, you can work with change, not against it:

1. Start small, and build momentum by showing results
2. Pick a North Star — not a destination, but a guideline
3. Plan the short term in detail but acknowledge the uncertainty of the future
4. Keep feedback loops lightweight and fast

By understanding and accepting the impermanence of things, looking for ways to borrow the energy of change, to go along for the ride — that’s how you can be intentional. That’s how you can use change as a tool for accomplishing ambitious goals.