We have some road construction near our house right now. As I drove by recently, I noticed 3-4 guys standing around while one person actually did some work. It was just a quick snapshot, but it always brings up in my mind the meme of the construction workers standing around while one guy shovels out a hole.

Guy digging hole himself Blank Template - Imgflip

It’s been a long time since I worked construction (my college days), but I was always the guy with the shovel in the hole (I worked excavation and it was terrible). There generally weren’t enough of us to have an entire group watching, but I was never just standing around, so I’m not sure what that would feel like.

Fast forward to today. Industries change, but people don’t. Too often we get managers and executives watching work without understanding it. And then getting upset or worried when the process of getting work done is messy.

I’ve changed the classic meme to reflect some of my experience, especially recently. As product dev teams create the work that drives a company forward, how many managers and executives are simply watching and critiquing without understanding?

The middle is messy, but it’s also where the magic happens - Brene Brown

An Example

I was recently leading several product development teams. Many of the managers wanted to get involved in every aspect of the work. Meaning they wanted to come to meetings and watch the work, just like the meme above.

I was inherently opposed to this because good meeting hygiene means having the right people at the right time. Too many people (or the wrong people) leads to poor meetings. And having a host of managers watching the work was a recipe for poor meetings. But they came anyway as we dug our holes and went through the messy process of creation.

Unfortunately, several of the managers were shocked at the messiness of digging holes (metaphorically speaking). They seemed to think that everything about product development should be clean and precise. They thought that questions should have been resolved before we met and that everything should have been documented and ready.

Of course, all of those things were the reason for the meetings. We were there to resolve questions, document ideas, and go through the messiness of the product development process. But watching the hole get dug (like the meme above) was something they weren’t prepared for. They didn’t expect to find mud when we started to dig, but a pristine hole ready for work to begin.

But we never begin with pristine holes that have been dug already. We have to do the work, get our hands dirty, and go through the messiness of the work (to continue to belabor the metaphor).

The Messy Middle

The beginning of a product, a project, or a company is usually shiny and exciting. As we reach the end—a product launch, a successful buy-out—we also put a shine on the entire job or process.

But the middle is always messy. Doing the work to get from beginning to end is messy. Digging the hole is messy.

In his book, The Messy Middle, Scott Belsky illustrates this well with stories from his journey creating a company that eventually became part of Adobe:

In reality, the middle is extraordinarily volatile—a continual sequence of ups and downs, expansions and contractions. Once the honeymoon period of starting a new journey dissipates, reality hits you. Hard. You feel lost and then you find a new direction; you make progress then you stumble.
Every advance reveals a new shortcoming. Major upsets give rise to new realizations that lead to breakthroughs in progress. At best, you move two steps forward, one step back—at worst, you realize you’ve been walking the wrong path entirely for months. This is what that journey actually looks like…
The volatility of this tug-of-war is hard to stomach. You must pay less attention to the day-to-day incremental advances and more on achieving an overall positive slope. And that’s entirely determined by how you navigate the messy middle.

The middle is where we dig our holes. It is where we get dirty and messy finding solutions and creating new things. But it can be difficult, especially to see from the outside.

The middle isn’t pretty, but it is illuminating and full of essential realizations to finish whatever it is you set out to start.

Good vs Bad

Not all managers and leaders sit and watch, critiquing those actually doing the work. The bad ones do, like my example above. But good ones take a different approach. Good managers and leaders understand the messiness of the product development process.

Product Thinking

The Messiness of Doing The Work

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