How to approach big tasks

In the heart of software development lies “the system”. The system is always complicated enough that you cannot fully grasp it and it is built by stacking parts on top of another that are just a tad too big to be called simple. The life of a software developer is an ongoing series of isolated projects that are at the threshold of his or her capabilities. We call these projects “epics”, “stories” or just “issues”. The sum of these projects is a system.

Don’t get me wrong – there a tons of issues that just require an hour, a cup of coffee and a few lines of code. This is the green zone of software development. You cannot possibly fail these issues. If you require twice the time, it’s still way before lunchtime. And even if you fail them, a colleague will have your back.
I’m talking about those issues that appear on your to-do list and behave like roadblocks. You dread them from far away and you know that this isn’t smooth sailing for an hour, this will be tough work for several days. This isn’t just an issue, it is an issue by itself for you. You are definitely unsure if you can make it.

Typical small project management

How do you approach such a project? It isn’t an issue anymore, as soon as you get emotionally involved, it becomes a project. Even if your emotion is just dread or fear, it is still involvement. Even if your management style is evasion, it is still project management. Sure, you can reassign a few of these icebergs, but they will always be there. You need to learn to navigate and to tackle them. Hitting an iceberg in the “frontal collision”-style isn’t a good idea.

On closer inspection, every project consists of numerous parts that you already know a solution for – typical one-hour issues – and just a few parts that you cannot estimate because you don’t know how to even start. Many developers in this situation take the route of least resistance and start with the known pieces. It’s obvious, it feels good (you are making good progress, after all!) and it defers failure into an uncertain future (aka next work week). Right now, the project is under control and on its way. We can report 80% finished because we’ve done all the known parts. How hard can the unknown parts be anyway? Until they strike hard and wreck your estimates with “unforeseen challenges” and “sudden hardships”. At least this is what you tell your manager.

Risk first!

My preferred way to approach those projects is to reveal the whole map, to estimate all parts before I delve into the details. I already know most of the easy parts, but what about the unknown and/or hard parts? I don’t know their solution so I cannot reliably estimate their size. So I sit down and try to extract the core problem that I don’t know how to solve yet. This is the thing that prohibits an estimate. This is the white area on my map. This is the “here be dragons” area. If I spend my resources doing all the work other than this, I will succeed until I stand on the border of this area and see the dragon. And I will not have sufficient resources left. My allies (like my manager and colleagues) will grow weary. I will have to fight my hardest battle in the most inconvenient setting.

My approach is to take the risk upfront. Tackle the core problem and fail. Get up and tackle it again. Fail once more. And again. If you succeed with your task, the war is won. Your project will still require work, but it’s the easy kind of work (“just work”). You can estimate the remaining tasks and even if you’ve overspent in your first battle, you reliably know how much more resources you will need.

Fail fast

And if you don’t succeed? Well, then you know it with the least damage done. Your project will enter crisis mode, but in a position when there is still time and resources left. This is the concept of “fail fast”. To be able to fail fast, you need choose the “risk first” approach of task selection. To tackle the risk first, you need to be able to quantify the “risk” of your upcoming work.

Assessing risk

There are whole books about risk assessment that are interesting and helpful, but as a starter, you only need to listen to your stomach. If your stomach tells you that you are unsure about a specific part of your project, put that part on the “risky” list. If you don’t have a reliable stomach, try to estimate the part’s size. Do the estimation game with your colleagues. Planning poker, for example, is a great tool to uncover uncertainty because the estimates will differ. Just remember: Risk isn’t correlated with size. Just because a part is big doesn’t mean it is risky, too. Your crucial part can maybe be developed in an hour or two, given an inspiration and a cup of coffee.

Failing late means you’re out of options. Failing fast means you’ve eliminated an option and moved on.