Perform an effort/impact analysis for all tasks / features
Items in that upper-left area – high impact, low effort – and obvious wins; items in the bottom right – low impact, high effort – are obvious “no’s”.
Hard-to-estmate work
It can be nearly impossible to know upfront exactly what tasks will be required. In cases like this, my go-to technique is timeboxing: picking an arbitrary length of time – a week or two, usually – and just seeing how far we get. At the end of a timebox, we’ll have more knowledge about the work.
When Timxing is useful
Timeboxing is also very useful for projects that clearly can’t be completed in a reasonable about of time. For example, think about a team with a massive backlog of bug reports. It might be untenable to spend the time required to drive the queue to zero, but spending one day a week driving the queue down might be fine. Timeboxes are a great way of making progress despite mountains of work or significant unknowns.
Write playbooks before automation - don’t automate first!
A playbook is nothing more than a set of instructions for performing the task – a “recipe” if you will. The key is to be as specific as possible.