I love a good plan. I love planning almost as much as I love doing. And man, do I love doing.
But not without a plan.
Let me explain the perfect plan in a simple way. When I’m going on a trip, I plan what I’m going to pack at least a few days in advance. Then I spend a couple minutes each day reviewing that pack list, visualizing the trip, and making sure I’m prepared for any contingency.
I know what you’re thinking. I’m Clark Griswold. You would never go on vacation with me.
But it’s actually the opposite. You would kill to go on vacation with me. I crush vacations. Because I don’t have to think about them. I’ve been the wing-it adventure guy my whole life, and it wasn’t until a couple vacations got absolutely train-wrecked by one unplanned contingency or another that I learned to be a planning guy before the trip so I could be the wing-it adventure guy during the trip.
It’s a method that works great in life. So why doesn’t it work in tech? Why do we do so much planning before the build that results in so much chaos during the build?
Today’s Business Environment Is No Vacation, But…
I’ve been the wing-it adventure guy my whole career as well. So as you might imagine, I have a love/hate relationship with project and product management. It’s necessary, but sometimes it can be evil. And it almost always turns evil when that planning is done by a central committee.
Let me explain that this way. I have a wife and three kids. When we started taking family vacations, I used to do all the planning for the whole family. You can guess how that turned out.
Disaster. Every time.
The same planning magic that used to give me the freedom to find myself backstage at Green Day concerts or enjoying cocktails on a secret rooftop bar in Vegas turned into hours waiting in line at an Orlando Walgreens because someone forgot that their prescription would need to be refilled halfway through the week.
So you know what I did? I stopped planning for the family and started teaching them my planning methods instead. Decentralizing. At first, they hated me every minute of every day before the trip.
We’ve been crushing family vacations since 2015.
Let’s crush project and product management.
Why Am I Planning Your Work?
This has never made sense to me. So I’m going to ask a version of the “five whys” about central committee product development. It’s my favorite way to understand why things happen the way they do.
Hey. Tim. You’re a great software developer. Seriously. One of the best I’ve ever worked with. So let me ask you something. Why am I planning your work?
“Because I need to be focused on writing elegant and efficient code.”
Timmy, how are you supposed to write elegant code if you don’t know how that code fits into the big picture?
“Because the big picture is too big for me to worry about. That’s your job. You tell me what I need to know about the big picture and I’ll make accommodations for that in my code.”
Timothy, why are we doing Agile, Scrum, and two-week sprints if what we’re really doing under the hood is waterfall?
“Because it’s more productive. I don’t need to understand the big picture, just my piece of it.”
Timbo, why are you here if you don’t have a handle on and a passion for what we’re building?
“Because paycheck?”
Ah, Timathan, I love your honesty. But seriously, where am I going to get the technical specs and time estimates that neatly fit your piece into the big puzzle?
“Oh, that comes from me. Or maybe my manager. Someone will give you a T-shirt size. Then you can set up meetings with every single team for every single process my code touches. We just have to coordinate everyone’s schedule and leave plenty of room for focus time. It’ll only add a few weeks to the schedule. And by the way, when we have those meetings, I’ll just be sitting there and writing code, because I’ll already be way behind and catching up.”
The Solution is Decentralization
In my last post, I talked about why technical project management no longer works, and I laid the blame squarely at the feet of tech teams giving up ownership to productivity tech. The logical end to this “tech boss” trend, seriously, is for AI to tell tech companies not only what to build, but how and when.
Eventually AI will just tell us to get the hell out of the way so it can do it itself.
I’m only half-kidding,
But like every thorny issue in the tech industry, this one comes with multiple layers of nuance. I’m not the first “expert” to call for decentralization or distribution of planning, because it’s an easy call to make. In fact, most tech startups use a decentralized approach out of necessity — they don’t have enough resources to form a central committee. And it works because of proximity — I can just turn to my CTO or hit her up on the video to discuss a change in plans.
But what do you do in high-growth mode?
Well, when fast-growing companies say “hire a project manager,” they’re already screwed.
The Tools Are There
But those high-growth companies can get unscrewed. The thing is, a lot of productivity tech is already catching up to the fact that waterfall-disguised-as-Agile hasn’t been working for a while now. New productivity tech players have started life as workflow tech, catering to a customized development process. The problem is that the waterfall-as-Agile approach became so popular that productivity tech still needs to accommodate it.
And because of that, productivity tech has turned into being all things to all kinds of product developers.
“Wait, you want our productivity tech to run the entire technical arm of your company? Well, we’re not going to say no to that.”
I’m looking at you, Jira.
But the tide is indeed turning for those companies who want to decentralize their planning, and more recent entries in the productivity tech field allow a more custom-first approach to getting shit done. As long as the organization sees the light and chooses to run their technology arm that way.
Did you know that modern technical project management is a science and software born out of the construction industry? It’s one of the first things I learned about it. And back in the 1970s and 1980s, software was indeed built a lot like buildings — it took years to stand up, was stable and unchanging for decades, and never really had to worry about serving more customers than the capacity of its physical footprint allowed.
Software doesn’t work like that now. It’s time for project and product management to disband the central committee and give everyone involved control over the process.
I’ve got one more of these productivity-in-tech pieces in mind, one around using a no-code approach to product development. Please join my email list and get a heads up as soon as it’s live.
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