In the dynamic, often chaotic, world of software product delivery, it’s important to ask the tough questions around worst-case scenarios, prepare for the unexpected, and anticipate challenges ahead.
By using skepticism (and Second-Order Thinking) in a strategic, sensible way, during critical moments throughout a project, is what I call Selective Cynicism.
When do you use Selective Cynicism?
This mindset comes in handy predominantly during planning cycles or when recalibrating a project plan or timeline.
If you don’t think about every scenario under the sun (think: holidays, a key developer leaves suddenly, an urgent C-level request, a time-consuming production issue that takes weeks to diagnose) your timeline will be blown before you even start. And the longer you've been in the game, the more relevant examples you accumulate and can be prepared for.
This mindset can also be used when making critical decisions and evaluating alternatives/possible outcomes.
What types of questions should you ask when applying Selective Cynicism?
- Why are we doing this? Why would we spend our time on that?
- Who is it for? Do they really need it or will they really use it?
- What risks have we not already considered?
- Did we account for the unexpected?
- Will we actually get the desired impact once this project is released?
- Does this scope realistically fit? What scope can we defer… b/c there is always scope that can be cut?
However, don’t overdo it.
This negative critical thinking is extremely important, though if applied too often or too much, it can be counter productive or misconstrued as a pessimistic attitude. It’s important to apply with tact, emotional intelligence, at the right frequency, and in limited quantities.
If you can strike the right strategic balance, Selective Cynicism will increase your project preparedness, ability to set accurate expectations & timelines, and ultimately, your chance of a successful project outcome.
The art of asking why in selective cynicism
In the world of product delivery, the power of asking "Why" cannot be overstated. Both for explaining the motives behind a request to fellow team members, but also to ensure you understand the “Why” yourself and believe it’s an appropriate, valuable next step.
Though don’t stop at a single “Why?”
Question all aspects of a given situation, task, or ask — poke holes in the purpose, audience, risks, complexities, anticipated effects, etc. This strategic exploration of Selective Cynicism helps you:
- Validate time will be well-spent (as time is never in excess)
- Uncover deeper motivations and potential pitfalls
- Assist in prioritizing the right solutions
- Discard the extraneous
- Anticipate the unexpected
- Prepare for worst-case scenarios
- …& more!
Ultimately, Selective Cynicism will help you hone in on the optimal, most efficient way to approach a project and keep delivery on track.
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