Planning is dead and we’ve killed it

“Planning is dead. No more business plans, design documents, and Gannt charts. Nore more waterfalls that end in bloodbaths.” That’s what I keep hearing everywhere. Every advice seems to lean toward leanness; agile is the new sheriff in town. What if that is a damaging narrative? Have we lost our appreciation for the age-old art of planing? Are plans useless?

“The measure of intelligence is the ability to change.”

― Albert Einstein

After 9/11 the FBI decided that it was time to overhaul their computer system, to help avoid another attack. It was to be called project Sentinel. The previous system was a slow non-digital disaster that needed to change. Stakes were high; this would be one of the most critical computer systems in American history.

The development process used was the same method that most projects had relied upon til that point: the dreaded waterfall method. Gantt charts tried to map out the entire project schedule and list every aspect and dependency. The Gantt chart is a relic from the WW1 era (by inventor Henry Gantt) that was somehow the go-to tool for software development. Requirements were collected and documented at the beginning of the project, so developers and managers knew what to make.

So how did this immensely important project fare? Well, not great. The software was delayed, over budget and pretty useless. Chaos ensued and something had to change; project Sentinel was looking like a fiasco. The dot.com bust, and failures like Sentinel, helped fuel the need for a new system. One that would prioritize differently within technological advances: enter Agile. A pivot finally saved sentinel to the now mainstream methods that we all recognize.

Agile is a collection name of development methods that break the process into shorter increments and iterations. It focuses on basing the requirements on the end user/customer. Agile teams are often smaller and cross-functional. The agile manifesto is as follows:

• Individuals and interactions over processes and tools
• Working software over comprehensive documentation
• Customer collaboration over contract negotiation
• Responding to change over following a plan

Business plans became lean canvases. Gantt charts became product backlogs. Planning became legend. Legend became myth…

Agile guides development to value and success through iterations.

Is planning dead?

“By failing to prepare, you are preparing to fail.”

― Benjamin Franklin

On June 6, 1944, Nazi Germany controlled most of western Europe. The USA has decided to intervene by invading Germany — Operation Overlord. 156 000 allied soldiers were set to land on Normandy beach in what would become the biggest naval invasion in history. As soon as the troops landed all bets were off; the meticulous plan created by Eisenhower and his staff became obsolete the second boots hit the French sand. However, this was to be expected. “In preparing for battle I have always found that plans are useless, but planning is indispensable” he famously said.

It should be evident to most, that “iterating” our way through Normandy would be a less than ideal way of launching an invasion and winning a world war. Conversely, Eisenhower is telling us that the plan is useless. So what makes planning indispensable?

Unfortunately, we can’t see into the future. However, there are good ways and bad ways of thinking about the future. A bad way is having a set idea of what the future will hold, and not considering the moving parts. A better way is seeing the future as a probability distribution. Plans themselves don’t tend to last long in terms of usefulness, but planning is great for analysis. It forces you to take into account every variable of whatever you’re trying to achieve. You see the moving parts, that can either make or break your future. Thorough examinations like that are laborious but equally rewarding. The agile method is excellent at dealing with futures; that’s what makes it agile. It can twist, bend and move around whatever happens. It deals with change like a Jeep deal with terrain.

Planning is delving into the entire spectrum of possibilities and trying to see the best path forward. Iteration is adapting to change and realizing the best path forward.

See the relevant variables — have a better understanding of the future. Image to the left tries to depict different futures. The image to the right is a simple probability distrubution. If you plan, and really think about what plays a role in the probability of a certain outcome, your more likely to be right.

Planning for Innovation

“If one does not know to which port one is sailing, no wind is favorable”

― Seneca

Peter Thiel, in response to the lean/agile movement, writes in Zero to One that the opposites of its tenants are “probably more correct”.

• 1. It is better to risk boldness than triviality.
• 2. A bad plan is better than no plan.
• 3. Competitive markets destroy profits.
• 4. Sales matters just as much as product.

He claims that the drama of the dot.com bust created the agile dogma, partly out of fear. And to an extent, I’m inclined to agree. Planning allows for grandeur and true innovation; it allows us to think big. Planning helps us solidify our focus. That focus becomes our vision; that vision becomes our future.

Planning forges a vision. Iteration realizes it. Yeah, that graphic kinda got out of hand…

There’s nothing mutually exclusive about agile development and planning. On the contrary, they go together like bread and butter. Most of the time planning isn’t so much about the actual plan, but the analysis of it’s constituents. Agile isn’t about replacing plans, but reacting to the randomness of creating value.