Show the case against

If you don't present the downside, you are betting your career that your coworkers don't know the downside or aren't willing to present it in order to take you down. There is a great story about this in In The Plex book, about an exec who sabotaged another by encouraging him to propose a project and then embarrassing him in the meeting with the founders.

Within companies, this seems inherently challenging because most employees of companies aren't privy to enough information to enumerate the case against, and also it's (theoretically) a collectivist decision.

For example - in one's personal life, one can choose to learn woodworking. We'll ignore the case for for the sake of brevity.

The case against is primarily made of opportunity cost, both of time and money. What could I have done with that time instead of woodworking? What could I have bought?

It's all about your own choice. You know a lot about these things, and you're able to use that information to approach the best course of action.

But if you're an employee of a company that sort of thing is either impossible due to a lack of information, or might just run counter to the company's aims.

You might say "instead of doing this 6 month software project, we should just fire the developers and take a punt on the S&P500 with the savings".

Or "we should focus on other project A". But "other project A" might mean that you end up on a shrinking team and eventually get fired, so you're not going to suggest that.

Or maybe there's some internal project you don't even know exists that could do with some more dev time and would be more profitable. You probably don't even know that exists, though.

Money is not "literally worthless"; the state guarantees that you can use them to pay your debts, by cancelling all debts that you pay using dollars, whether your creditor agrees to it or not.

Just putting forward a case for something or case against something misses out a lot. Don't get me wrong, it can be used as a provocation to stimulate discussion. But that is only part of the benefit.

If one were to use an approach like Six Thinking Hats, one could use a hat sequence such as 1.Blue -> 2.White -> 3.Green -> 4.Yellow -> 5.Black -> 6.Green -> 7.Red -> 8.Blue. Each colored hat represents a specific thinking mode. We assign a predetermined time for each stage and use the thinking mode exclusively related to the hat color.

1.Blue: Establish a focus (for eg: building an app that does X)

2.White: What information do we have (for eg: addressable market size, MVP scope, any research/data available on prospective customers etc.,)

3.Green: The creative details (for eg: We will do Y1, Y2, Y3, ...)

4.Yellow: List the benefits

5.Black: List the drawbacks, pitfalls, challenges, risks etc.,

6.Green: Address the drawbacks, pitfalls and challenges creatively and try to mitigate risks

7.Red: Get a gut check from the team if the proposed idea/solution is trending in the right direction

8.Blue: Setup a follow-up action plan (for eg: Next steps on xx/xx/xxxx, task owner ABC).

The article's main point on putting forward the case against is only the #5.Black hat thinking. We are all natural black hat thinkers. But that is just one of the modes and focusing on that alone doesn't lead to a robust solution.

More on Six Thinking Hats in this book here: https://www.amazon.com/Six-Thinking-Hats-Edward-Bono/dp/0316...