17 Questions to Ask When Reviewing a Plan
A list of questions to challenge a plan and make it better.
Organisations and teams often need to make plans. Plans that span days, weeks, months or even years. Most plans I have seen have two things in common: they are flawed and they derail.
Some more than others.
But if you are going to take the time and energy to make a plan, it makes sense to put some critical thought and work into it. Make it worthwhile. That way you can make the plan more robust and be better prepared when things go wrong.
Sometimes this is all we can do.
This is a structured list of questions I have asked when working on plans. It is an attempt to make the best of the limited knowledge we have at the moment we are planning.
🔗 Dependencies
Dependencies affect the order in which work can be done, and delays can have a long-term impact on planned releases.
Have dependencies between features and tasks been identified and documented?
Have dependencies between teams been identified and documented?
Do we have a rough timeline for the features and tasks that have dependencies?
Do we have too many high-risk and impactful changes in the same timeframe that could break feature flows, blocking or slowing progress?
Do we have too many changes in the same timeframe that require knowledge from a specific person, which could block or slow progress?
🌊 Flow
Staying focused helps us to be more efficient.
Do we have many different topics that require us to switch context, which can slow us down?
Can we bring future changes for the areas we are working on now into this iteration and leave others for later?
Do we have tasks that affect the same areas and are planned in the same timeframe, which could complicate things and slow us down, for example due to merge conflicts?
↬ Responding to Change
Thinking about what might happen if a plan goes wrong will help you get an overview and make good decisions when it happens.
Is the priority clear so we know which features to focus on?
Is it clear which features are planned for which release?
Are there any features with hard release dates, due to legal reasons or dependencies?
Do we already know the risks that could affect our plan, and are there ways to resolve or mitigate them? (ROAM)
🧪 Testability
The better the testability, the earlier testing can start and provide feedback.
Is there a (better) way to break down the tasks of a feature to allow earlier testing and feedback?
When such a breakdown causes extra effort: Is it worth the earlier feedback?
When a feature is broken down into several tasks: What tasks allow us to start testing as early as possible?
Do we need explicit testing tasks that are not part of the regular test scope, e.g. for performance, load, security or resilience testing?
Do we need to prepare test data or a test environment that can be started in parallel with development?
Feel free to choose the questions that best suit your context. I hope this list inspires you to ask even more questions.
This is one of many tools I have written about and work with.
Happy planning,
Florian

