Tips from a Recovered Planning Skeptic: Start Starting

Illustration of traffic intersection where none of the cars know where they're going
What happens when you don’t plan; no one knows what they’re doing or where they’re going

David J. Anderson, one of the brains behind the Kanban movement, famously said:

”Stop starting, start finishing.”

This is great for software teams on a tight deadline, and their managers who want status reports, or for GTA 6 to be shipped in time for Christmas 2022.

But for a lot of people, especially in creative fields, not enough time is spent on starting.

I get Anderson’s point. You don’t want to have a million tasks languishing in progress, the finish line always out of reach. He’s saying, “Just get on with it, stop fannying about.” And the cornerstone of Kanban is to limit work in progress and get products over the line.

But in many walks of life and work, people who constantly start new things without finishing them are the ones who didn’t start properly. And starting properly means you have to do that thing I used to hate: plan.

The beginning of a project should be exciting. Everything is new and fresh, and it’s the time for big, bold ideas flying in fast. But refining, organizing, and distilling those ideas into actual practical tasks through planning often gets a bad rap. Why? Because it sounds frickin’ boring.

My old self was like:

Brainstorming: :smiling_face_with_3_hearts: :partying_face:

Planning: :rolling_eyes: :sleeping:

The more spontaneous among us want to go on an adventure and leave the planning nerds to their meetings.

But spontaneity carries risk. Go hiking in the wilderness without a map and you could end up stumbling into a ravine or bear pit, much to the gleeful laughter of the map makers.

What I have learned is that there is a time and place for the impatient passions of creative improvisers, and a time and place for the foresight and wisdom of meticulous planners. A successful company needs both, and one without the other leads companies to tread water or be in constant damage control mode.

The need for planning in teams

As a creative, extroverted whirlwind of energy with a ridiculously good memory, I used to abhor planning. Until I started working on a team. And then I realized people were starting to abhor working with me.

Where’s the plan?

In Chris’ head.

OK, can we have a meeting to discuss that then?
No time for meetings, there’s too much work to be done!

What’s the goal?
We’ll draw targets around whatever shots we hit.

OK, but there must be some documentation somewhere.

Erm, sure. Chris has put every idea he’s had in the last four years on a Trello board.

And how is this Trello Board organized?

Who said anything about organized?

I now work with people who want their tasks written down, organized, and prioritized. People who want structure to their work day. People who want to know what they’re doing before they start it. These are all very reasonable desires, which is why I had to change.

As much as my ideal meeting is one where we all fling ideas around and get straight on with the ones that stick, I get that when you’re working in a team, everybody needs to know what they’re doing, how they’re doing it, and why they’re doing it. This isn’t just for the individuals predisposed to planning and structure. It’s important for team cohesion and making sure everyone’s pulling in the same direction.

Planning isn’t box-ticking

I’ve been in planning meetings that have felt like rushed box-ticking exercises, because the people in them are like me, hankering to leave. “There, we did the planning meeting, are the agile coaches happy? Can we get on with work yet?”

But if you treat a planning meeting like this, you’re only setting yourself up for a whole bunch of popup meetings along the way. “Er, what is it we’re doing again?” And that’s just one big unhealthy recipe for inefficiency.

Excellent planning meetings are the ones that set your whole team up for quicker and more efficient work with fewer popup meetings required later.

So the first thing the improvisers among us need to do is change our attitude. Planning isn’t just some bullshit ritual designed to satisfy the bureaucracy. It’s necessary to the smooth and efficient running of a team, and moreover to making sure the lessons learned from past failures aren’t repeated or become habits.

Let’s start at the very beginning

According to Malcolm X:

“The future belongs to those who prepare for it today.”

No one’s stopping us pursuing our dreams, but we do have to make decisions as to what those dreams are. Only by preparing for tomorrow can we make sure tomorrow happens like we want it to.

If you hadn’t guessed already, I’m a believer now. I’m a planner.

Sure, I may never be the best person to run the planning meeting. But since I starting working with a diverse group with different learning, working, and communication styles, I’ve become an enthusiastic attendee of them. And I’ve come to see the benefits of a well-organized planning session to the work that flows out of it.

So enough about finishing already. Start starting, and be like Julie Andrews.

Chris Cooke CEO Old Street Solutions

Chris founded three successful startups in Thailand: one was a Scuba Diving School/ Eco-Tourism company dedicated to saving turtles. Once he’d saved enough turtles, he moved back to the UK to pursue his dreams in software.

It was while working for the Atlassian Platinum Solution Partner Clearvision that Chris met Jacek. The two decided there was a gap in the market for easier-to-use Atlassian tools for Jira and Confluence users who don’t have a clue how to code (of which there are many).

“If we’re not making mistakes, we’re not trying hard enough.”