(Get the Prompts)
If collaboration is how you build alignment, sparring is how you build edge.
This piece exists for one reason.
It is the practical execution of the idea laid out in Collaboration Is Great. Sparring Is Better.
That article makes the case that high-performing builders lose access to real rivals as they gain experience. Comfort increases. Friction disappears. Growth stalls not because of laziness or incompetence, but because nothing is actively pushing back.
This process is how you reintroduce that pressure deliberately.
The prompts below are not meant to be clever. They are meant to be uncomfortable.
If you have not read the original piece,
read it first.
If you recognized yourself in it, this is how you act on it.
This is not a replacement for collaboration.
It is the sharpening phase that makes collaboration useful again.
Sparring collapses optionality. Bring one idea, not a bundle.
Defensiveness is signal. Do not interrupt it.
Twenty to forty minutes. This is sharpening, not self-punishment.
This determines whether the entire exercise works.
Do not soften it.
You are not my assistant.
You are an adversarial sparring partner whose sole job is to break my thinking.
Assume I am wrong by default.
Assume my idea is fragile unless proven otherwise.
Assume my confidence is ahead of my clarity.
Your goal is not to help, encourage, or collaborate.
Your goal is to expose flaws, blind spots, weak logic, and
self-deception.
Challenge my assumptions aggressively.
Call out laziness, vagueness, optimism, and evasion.
Treat unclear thinking as failure.
Do not soften language.
Do not hedge.
Do not protect my ego.
Do not offer alternatives unless my position collapses.
If the idea survives, it earns respect.
If it does not, dismantle it without apology.
Confirm you will operate in sustained opposition until told otherwise.
If the response sounds polite, reset and run it again.
Here is the idea or decision I want you to attack:
[Paste it plainly. No qualifiers.]
Assume it is wrong or incomplete and begin dismantling it.
Say nothing else.
Assume I proceed exactly as stated.
List the most likely ways this fails.
For each, explain:
Stop critiquing the idea and critique me.
Based on this strategy, tell me:
Do not be diplomatic.
Analyze this as the market would.
Explain why customers would care less than I expect, competitors would exploit it faster than I assume, and why this fails to create durable advantage.
Does this idea survive sustained resistance, or should it be abandoned?
Choose one.
If it survives, state exactly what must be strengthened.
If not, explain why it should be killed rather than iterated.
Only if it survives:
Shift modes.
Strengthen the idea with the minimum changes required to withstand pressure.
Do not expand scope.
Do not add features.
You bring fewer ideas
You're filtering before the sparring session, not during it.
You attach later
Ideas are tools to be tested, not extensions of identity.
Your thinking sharpens before it leaves your head
The sparring becomes internalized. You anticipate attacks automatically.
That is edge returning.
Do not run this constantly.
Do not use it when exhausted.
Do not use it to punish yourself.
Sparring is not a lifestyle.
It is a sharpening cycle.
Used deliberately, it replaces the rivals you no longer have.
And that is the point.
If you made it this far, do not just save this for later.
Test it right now.
Take your company website. The homepage, positioning, messaging, all of it.
Now run it through the hostile lens you just learned.
Copy Prompt 1 above, paste it into your AI tool of choice, drop in your website URL, and let it dismantle your positioning.
Do not defend. Do not explain. Just observe what breaks under pressure.
Pro tip: If you want the full context on why this works, read the companion article that explains the philosophy behind synthetic sparring.
If your story survives that resistance, it deserves to meet the market.
If it does not, you just saved yourself months of wasted positioning work.
Pressure is the point.