F2F #72: Ask questions to ask better questions

If you're like me, your brain fires on all cylinders 24/7. I even sometimes wake up in the middle of the night having an "a-ha" moment with the answer I needed for weeks.

AI has allowed me to go from an ideas guy to an action guy. Whereas before I'd have great ideas but didn't know how to start implementing them, how to design, scope them out or even define them altogether, now I have many armies of interns with infinite time in the guise of ChatGPT, Gemini, Lovable and the like.

One of the things my brain isn't very good at is laying out detailed descriptions of what I exactly need. I can see it in my brain but when I braindump onto paper, a project management tool or even another person, details slip through my fingers like beach sand. I then become more nervous because I fear I might forget something, succumb under pressure, and do an even worse job at describing what I wanted in the first place.

Luckily, AI has got a solution for people like me. I have come to solve this particular issue in two parts.

First, I talk to ChatGPT using the advanced voice mode. I already described what and how I do in this issue: F2F #29: Talk to me, bAIbe. Put simply, I open up voice mode when I'm walking and I braindump my idea there. I tell it to ask me questions to help me explain every little detail of what I want and within 10-20 minutes, I have explained everything.

This is very important: request to ask you more and more questions until you think you've explained every single detail you wanted to cover. LLMs tend to assume too much to favour completeness in otherwise lacking conversations but you can correct it by asking it explicitly to ask you more questions to the point of reaching absolute redundancy.

The second part of the equation is, now that you've given the AI all of the context, ask it to write the perfect prompt for you.

For instance, yesterday I discussed redefining the ICP (Ideal Customer Profile) for MarsBased in 2026. Voice mode was working like ass, so I decided to skip it and go straight to the prompt part.

My braindump was:

The result was:

Prompt for ICP-based Website Inspection

You will act as a decision maker evaluating MarsBased.com with the intent of researching whether MarsBased is a credible, relevant, and high-quality partner for software development and strategic technology services. Choose one of the following personas for this exercise:

• CTO of Stripe (large scale-up tech)

• CTO of Amazon (enterprise corporate technology lead)

• Project Manager at HP in California (corporate technology procurement)

• CTO of a small technical startup founded by engineers

• VP of Engineering at a mid-sized Spanish company

• VP of Engineering at a mid-sized tech company in another high-GDP European country (for example Germany, Netherlands, France)

For your assigned persona, open the MarsBased website and navigate it as if you are considering engaging MarsBased for a strategic technology engagement (outsourced engineering, product development, digital transformation). As you navigate, think out loud in a structured way:

Context Setting:

• Briefly describe your persona, what your company cares about when hiring external tech partners, and your expectations (scale, governance, quality, process, domain expertise).

• List your key questions you want the website to answer (e.g., clarity on services, evidence of delivery, trust signals, cultural fit, relevant case studies, senior talent).

Homepage First Impressions:

• What is your immediate reaction to the homepage?• Does the messaging clearly convey what MarsBased does?

• Is the value proposition easy to understand for someone in your role?• Do visuals and structure feel credible and professional?

• Does it match your expectations for a partner at your scale?

Navigation and Messaging:

• Walk through the main navigation items. For each key section (About, Services, Case Studies, Team, Contact), think out loud:
– What do you see?
– What message does it communicate?
– Does it answer your core questions?

• Identify any phrases, jargon, or concepts that are unclear or ambiguous.

Trust and Credibility Signals:

• Do you see clear evidence of expertise (case studies, client logos, testimonials, metrics, outcomes)?

• Are there signals of quality engineering practices (process, tools, standards)?

• For your persona, what credibility elements matter most and are they present or lacking?

Fit Assessment:

• Based on what you have seen so far, do you feel MarsBased could meet your needs?

• If yes, what specifically appeals to you (e.g., domain expertise, storytelling, quality of work, personality)?

• If not, what are the gaps (e.g., unclear services, lack of relevant examples, weak value messaging)?

Pain Points and Red Flags:

• Identify anything that would discourage you from engaging (messaging confusion, missing content, weak outcomes, uncertain expertise).

• What questions remain unanswered?

Recommended Next Steps:

• Would you request a call, download a whitepaper, engage a proposal, or drop the effort?

• What specific content or signals would change your view positively?

TL;DR Summary:

Provide a concise summary:

• Who you are (persona)

• Your high-level impression of MarsBased

• Main positives and negatives

• Whether you would consider engaging MarsBased today• What would convince you the most

Use clear, honest, and thinking-out-loud language. Reference specific sections, headings, and content you encounter. Include screenshots or excerpts if helpful. Provide your subjective reaction and reasoning in each step.

The goal of this process is to see a) whether the AI has fully grasped what you intended and b) whether the prompt is correct.

Now, I work on the prompt. I review it and tailor it down even further to meet 100% of my requirements by cutting out the fluff and giving it more examples and even the format of the expected output.

Once you have the refined prompt, you send it to your AI of choice and voilà!

Time to build!