We are biologically wired to seek validation. When we build a new product, write a pitch deck, or redesign our portfolio, we instinctively show it to people who like us: our friends, our colleagues, our supportive peers.
And they usually say the same thing: “Wow, this looks great! Good job.”
This feels good. It is also completely useless.
Your friends are biased by their relationship with you. They want to preserve the social bond, so they subconsciously smooth over the rough edges. They give you Social Feedback (meant to maintain harmony) when what you desperately need is Market Feedback (meant to test reality).
This is the most underutilized power of 1:1 expert bookings: The Paid Takedown.
Instead of paying an expert to tell you how to succeed, you should occasionally pay them to tell you exactly why you are going to fail.
The Value of “Red Teaming”
In the military and cybersecurity worlds, “Red Teaming” involves hiring a group of professionals to aggressively attack your own defenses to find the cracks before the real enemy does.
You can apply this same logic to your career or business by booking an expert for a “Roast Session.”
Because the transaction is financial, not social, the emotional baggage is removed. You aren’t asking a favor; you are buying an audit. This gives the expert permission to be radically candid in a way your mentor or co-founder might hesitate to be.
How to Handle the Heat
Booking a session like this requires a specific mindset. It is not for the fragile.
- Disarm them early: Start the call by saying, “Please don’t sugarcoat it. I am paying for the hard truth. You won’t hurt my feelings.” Most experts are polite by nature; you have to explicitly give them permission to be critical.
- Don’t defend; just listen: When they say, “This part is confusing,” do not interrupt to explain why it actually makes sense. If it’s confusing to them, it’s confusing. Period. Write it down.
- Ask “Why?” three times: If they say your pricing is off, ask why. Then ask why that matters. Dig until you find the root cause of their objection.
The ROI of Friction
Validation is free; you can get it from your mom. Friction is expensive, but it is where the growth happens.
Spending $200 to have an expert dismantle your idea might feel painful in the moment. But it is infinitely cheaper than spending two years building a company based on a flaw that a 30-minute conversation could have exposed.
Stop paying for compliments. Start paying for the truth.
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