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Planning to Plan

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7 min read

How does anything ever get done? Have you ever thought about it, I mean — it’s amazing that tunnels or bridges are built, elevators are renovated, inventions are made and progress happens. Sometimes I take a step back and marvel at the fact that emails are sent, plans are drawn, and things get done.

Other times — emails are sent, plans are drawn, and things don’t get done.

XKCD

A parable: Asana

In 2004, Justin Rosenstein dropped out of Standford to go work at Google. According to Wikipedia, he began there as a project manager. At Google, he helped create and launch various products, from Gchat, to Google Sites. Almost immediately, he noticed that most of the time at work — wasn’t real work. It was mostly planning and status meetings and ensuring project timelines were met.

While at Google, he put together a project management tool to internally keep track of projects and deadlines. When Rosenstein left Google to oversee product design at Facebook. He had to leave the software he made behind. Almost immediately, he saw that Facebook was struggling with status meetings, and wasted productivity as well. So he built a new and improved project management software again.

Only this time, Dustin Moskovitz (co-founder of Facebook) immediately took note of just how important project management software is in the workplace. Rosenstein and Moskovitz ultimately left Facebook in 2008 to create Asana. A key player in the project management toolspace. In the beginning, it was really the only true competitor to Basecamp.

Nowadays, you have so many to choose from it’s not even funny. More on that later.

What’s fascinating about this Silicon Valley tale, is when Justin and Dustin were initially planning Asana, they figured they could launch in a year’s time. However, Asana wouldn’t launch for another 3 years. The fact that a prestige ex-Googler and one of the co-founders of Facebook couldn’t iron out a solid release date for their product should serve as a warning to anyone. Wether you’re a product manager, or a designer scheduling production estimates — no one can say, with certainty, just how long anything takes to do.

It’s so evident that making plans aren’t really making plans. They’re really just guesses. So why don’t we treat them as such?

Let’s call perfection what it is: low-priority.

To make matters worse, when deadlines are fast approaching and it’s all hands on deck — the last thing you want to worry about is perfection. There’s a fantastic French adage that supposedly Voltaire once said:

Le mieux est l’ennemi du bien (The perfect is the enemy of the good).

— Voltaire

He’s so fucking right. If you waste your precious time perfecting every last detail on a painting, it will never be done. If you laboriously edit and re-work your writing you’ll never publish. The same goes for literally every work category, from producing films, to getting your business up and running. The time is now. Focus on what’s at hand, and focus on meeting your deadline.

I’m not saying “just get it done and worry about quality later.” There’s a stark difference between a rush job and a completed one. Completing a task or hitting a deadline should feel good, and it should feel right. It should make your world feel lighter. If you complete a task in a rush, you’ll regret it. Chances are you’re going to have to do the work twice over. And that my friend, nobody plans for.

So, what’s the solution here?

The stark reality is we all live and die by the deadline in the end. If projects are piling up, and quality control is becoming an issue — it’s time to level up.

So, first we need to breakdown projects into sub-tasks. This is called chunking, more on that here.

If we breakdown a project into sub-tasks, we can plan our project (err I mean guesses). Furthermore, we all strive for good work, but if we can get ahead on the smaller sub-tasks we can focus on delivering before a deadline. Even better we may even have time to spare to perfect a project, and exceed expectations.

Tackling each individual sub-task (an I mean everything) inches us one step closer to crossing the finish line. This is really important here. Track. Everything. From concepting to production to hand-off. Everything. needs a checkbox. Seriously.

Now, arm yourself with a project management tool and get to tasking! There’s plenty to chose from:

Once you begin adding your various projects, it will feel less like a to-do list, and a lot more like note-taking. Offloading meeting notes, small details or dates you need to remember should feel refreshing.

The #1 reason why this is so important is because due-dates are at best, guesses. Since, we’re armed with a project management software, we can assign tasks, and the entire project is public to your organization. So, everyone is on the same page. Everyone is 100% aware of what’s on their plate, aware of what’s holding a project back, or what’s up next.

With any luck, there shouldn’t be anymore frantic searches for the latest email chain, or referencing a private Slack message in an email. All of your project communication belongs in the project management interface. All in one place. Make sure to inform your team that any discussion, changes or notes for a project should live in a project or task. If anyone is feeling lost on a project status — they can just go to the project and see the living document from inception to its current state.

Death to status meetings.

The beauty of all of this? No more status meetings. Simply put, there’s no reason to have them. If everyone can see each-other’s tasks, projects and dates, why even bother with a status meeting? The modus operandi of the modern-office worker should no longer be decoding cryptic emails.

But if you’re weary to let go of email, I would recommend Basecamp. It’s simply-put — the best, and almost every kind of notification you can imagine is recorded and batched into emails. Imagine a status update every morning of what your team is up to the day before.

Even better, Basecamp has a feature called Check-in Questions, pre-formatted questions you and your team can answer at the end of the day. All of the replies are rolled up into a thread, and the whole team can read them. So if you’re really into daily or weekly statuses, that can still be a part of your business — but it doesn’t have to be a disruptive all-hands on deck meeting that derails productivity for an hour.

Further Reading (and Listening):