Why Technical Project Management Doesn’t Work Anymore
A central planning committee bugging people was never a solution
When I’m in full-on growth mode, whether it’s one of my own companies or a company I’m working for, I’m doing at least a dozen full-time jobs at once.
Some of those jobs involve keeping employees moving in the same direction towards the same goals. Then there’s the multitude of tasks around building a great product, but not getting bogged down in trying to build a perfect product. And I’m also doing a lot of little things to sell that product to customers so, you know, we get more money.
It’s a lot. Building and growing a business would be much easier without the employees and the product and the customers. I know this because I see those kinds of businesses all over social media. They seem to be having much more fun. They have expensive watches.
But back to the real world. Chances are, when you’ve got 12 jobs to do, you’ll wind up doing exactly zero of them well. You’ve probably mucked around with project management tools, maybe you’ve adopted various forms of technology to automate and optimize output, and you might have tested every productivity tool on the market, all of which worked well until they didn’t, at which point they became just another checkbox on your daily task list.
The irony.
But here’s the thing about adopting technology tools to enable more employees to get more products out the door to more customers for more money.
We’ve been doing it wrong the whole time.
Productivity Tech is a Solution for the Wrong Problem
As a technology lifer, I’ve been railing against the slippery slope of Agile, Jira, and Scrum for a while now. But each time I’ve opened my big fat mouth, I’ve made it clear that it’s not the tools that are the problem, it’s the way they’re being used.
Productivity tech — whether it’s personal or platforms or even AI — is often adopted into an organization as a solution looking for a problem. This is even true — especially true — for tech companies and startups.
We think we know the problem — usually too-fast growth — and we think we know the solution — usually productivity tech.
As companies have globalized and teams now stretch across multiple locations with responsibilities for disparate pieces of the puzzle that need to be glued together at the same time, we keep turning to tech to make the management of those tasks more centralized, more efficient, and more predictable. But those tech tools rarely perform as promised, often becoming a bigger burden to manage than the tasks they purport to manage.
It’s a Catch-22. But something I’ve learned over three decades of getting companies started or unstuck or accelerating, is that the tech is often not the problem. The concept of central planning is the problem.
And almost every single project management or product development or productivity tool is built around central planning — from MS Project to Jira to Click-Up.
So what is one to do to get out from under the Soviet-style Gosplan?
Stop Letting Tech Be The Boss
Even with my multitasking powers operating at full machine-mode, I know I can only knock out so many tasks in a day, let alone make sure those tasks are still targeting the goals that birthed them.
And let’s face it, if I’m not being creative about how I’m executing said tasks, well then productivity starts to look more and more like a mirage. Anyone who has ever spent an entire day or more working on a task that ended up only looking like progress will agree.
Technology was supposed to be the lifesaver here, the little ring thrown off the boat that we could grab ahold of when we get thrown off, then just paddle for a bit while we figured out what we needed to do next. But that premise has changed. Productivity tech is the new boss. And the more influence the tech boss has on our lives, including and especially AI, the more learning curves and hard stops and outliers sneak into our day.
Now we’re trying to solve the tech boss problem by throwing more AI at it, because AI is sitting there as a solution looking for just that kind of problem.
But I don’t need AI in order to be successful at goal-driven execution, I need the opposite.
I Don’t Want To Know When a Task Gets Done
I love clicking off checkboxes too. That’s not management.
I want to know when a task isn’t going to get done. And I want to know what changed that threw off our plan, and I want that change absorbed and accommodated for. Then I want the person who’s task isn’t going to get done on time to change the plan for me.
That sounds bossy, right? It’s actually the opposite. It’s me not having to sit over someone’s shoulder. It’s decentralization.
Think about it. Usually, with traditional project management, when a task doesn’t get done, one or more links in the chain of central planning needs to first identify the gap in the critical path, and then one or more of those central planners starts yelling at someone in the chain of command of the person who didn’t get the task done on time.
All of the software engineers who just read that are now thinking, “You could have just said the project manager yells at the development manager who yells at the developer.”
It’s inefficient, it’s not goal-oriented, and it doesn’t do anything to change the plan except to delay the finish date.
Ooh. Maybe we could use AI to ChatGPT the excuse the project manager gives to the stakeholders.
Let’s Change the Plan Instead
As much as I’ve tried to take a nuanced approach to calling for the end of the central planning tech boss, I got called out a lot for misunderstanding what Agile, Scrum, Jira — and all the rest of productivity tech — was supposed to be.
I get that. Because as a lifelong product inventor and developer, I’ve learned that one of the hardest concepts to understand is to stop complaining about how the product is supposed to be used and instead figure out why the product is being used that way.
I called for the end of those productivity tech tools. And maybe I called for the end of traditional project and product management too. In my mind, it might be too late to save either the tools or how they’re implemented.
But if those tools and roles can be saved, then we have to let go of the myth of central planning as the foundation for project and product management, especially in technology and startups. Once we do that, managers become champions, creativity gets unleashed, and we can lean on productivity tech to paddle back to the boat with a creative new plan.
I’ll talk more about how to decentralize productivity in future posts, along with other tech industry problems and solutions. Now would be a good time to join my email list and get short emails when I’m published.
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