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Extreme brainstorming questions to trigger fresh ideas

10x Brainstorming

Extreme brainstorming
to trigger fresh ideas

Hello Product Leaders!

When I look back at my product career, asking powerful questions may be the most underrated skill during critical moments or meetings.

Do you recall being stuck in brainstorming sessions, trying to solve a problem or understand a user issue, and staring at a blank whiteboard?

I know it's frustrating.

As a product leader, you struggle to break free from routine and find fresh ideas.

But fear not!

I've got what you need for your next design or strategy sessions that'll spark your creativity, and demonstrate your leadership (and impress your team as a bonus)

I call it extreme questioning.

Let’s dive in.

Table of Contents

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The paradox in ‘think outside of the box’

The more you question the obvious, the deeper your insights into the complex.

So apply extreme questioning and you will start thinking outside of the box.

It is almost like the first principle framework made famous by Elon Musk.

This paradox highlights the idea that by questioning assumptions or commonly accepted truths.

While questioning the obvious may seem counterintuitive, that will force you and your team to reframe a given problem and lead them to innovative ideas!

1- No customers

  • Imagine, if we had to start from scratch with no customers, what would we build to grow our user base or product differently?

    I love this one

    I asked myself this question a lot and it forces you to make the right tradeoff especially if you have a large existing customer base.

    Without existing customers, would we streamline or remove certain features while adding new ones to enhance competitiveness?


    Rationale: Prioritizing future growth may require making bold moves, even if it temporarily upsets some customers. Remember, the potential customer base could be ten times larger in the future, but only if we adapt and innovate now.

2- No tech support

  • If tech support were off-limits entirely, what changes would be necessary?


    To enhance self-service, how could product onboarding be revamped? This is crucial since users are often least familiar and motivated during initial setup.


    Where should the product offer more user control without support assistance? What information needs clearer visibility without the option to ask for help?


    ✅ Rationale: Improving self-service not only reduces costs and enhances scalability but also boosts customer satisfaction and loyalty.
    Therefore, investing in significantly better self-service can yield both financial and customer satisfaction benefits.

3- Biggest rival clone

  • Imagine if our biggest rival cloned every single feature we have. How would we still come out on top?


    Could the answer lie in our product's features, ease of use, design, or innovation? Or is it in our higher purpose, brand promise, or customer trust?


    ✅ Rationale: good ideas will be copied eventually. So, instead of focusing solely on features, let's aim for bigger emotional connections.


    After all, winning is about capturing hearts and minds.

4- Rapid Fire

  • What if we had just two weeks to ship a brand-new feature that would surprise and delight our customers?


    Great things need a plan and a little time crunch. We must simplify and narrow the scope to maximize day one's learning.


    Can we stub out an API or implement a basic version of the feature manually? Maybe we could temporarily integrate a third-party system for efficiency gains. While we may skip documentation and in-depth training for now, let's focus on perfecting error handling to gauge initial reactions.


    ✅ Rationale: So, if you're feeling stuck in a waterfall approach with lengthy report-outs, perhaps it's time for a shake-up.

5- Innovating Without Direct User Contact

  • What if we were barred from ever speaking to our customers again? How would we determine what to build next?

    Could we analyze their behavior meticulously enough to swiftly gauge the impact of any change—A/B testing? What if we could speed up testing?


    Features could start as button placeholders to gauge interest before investing in development.


    ✅ Rationale: Improving signal interpretation helps us avoid missteps and find breakthrough ideas. Listening closely, even when not directly addressed, is key.

6- Unlimited Resources

  • Imagine if profitability was no longer a concern.


    How would you utilize unlimited funds to enhance value?


    Would you invest in infrastructure, software improvements, or prioritize personalized customer experiences? Could you replicate the essence of a dedicated concierge service with cost-effective software solutions?


    ✅ Rationale: Converting resources into valuable outcomes can be challenging, even without financial constraints. Yet, a practical approach could create new pricing options that blend philanthropy with sustainable business models.

7- Existential Risks

  • Consider the external factors that could potentially spell doom for the entire company.


    Could the release of a competitor's product, a significant security breach, or a drastic shift in the economy threaten your company's survival?


    Is there a proactive measure you could take to mitigate these risks?


    Perhaps a strategic pivot that transforms the company's trajectory and eliminates the threat altogether?


    ✅ Rationale: While it's impractical to worry about every possible threat, addressing the most pressing risks can lead to preemptive actions that fortify the company's resilience.

8- One Shot, One Impact

  • If you could only release one thing this year, what initiative would have the greatest impact?


    Pivotal decisions in business history come down to a few significant choices each year.


    These include critical product launches, strategic market entries or exits, key hires, and competitive insights. It's hard to predict transformative ideas, but prioritizing impactful possibilities is crucial.


    ✅ Rationale: This is super hard but that may just provide clarity on the one thing your product team needs to focus on for true innovation.

Key Takeaways

  • Brainstorming Paradox: 
    Want to think outside the box?

    Question the obvious leads to deeper insights, similar to Elon Musk's first principle framework

  • Why? 

    The questioning reframing encourages innovative solutions by challenging existing assumptions.

  • Pick 2-3 questions and run with them

In Case You Missed Them

👉️ Challenge your higher-ups (Link)
👉️ The Power of Summary (Link)
👉️ Career cheat codes for product leadership (part 2) (Link)

Get 1% Better Every Day. Execution Matters Most.

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