The problem-solver’s playbook: 17 questions to sharpen your thinking

Aviral Vaid

Hatched by Aviral Vaid

Jun 09, 2024

5 min read


The problem-solver’s playbook: 17 questions to sharpen your thinking

In the world of problem-solving, it's important to not fall in love with the problem or the solution. Instead, the focus should be on multiplying value rather than just solving problems. With this mindset, one can become a better problem solver. To achieve this, it's crucial to ask the right questions and consider various factors. Here are 17 questions that can help sharpen your thinking and improve your problem-solving skills.

  • 1. Is this problem merely a symptom of a bigger problem? Sometimes, what seems like a problem on the surface is just a symptom of a larger issue. By asking this question, you can dig deeper and uncover the root cause of the problem.
  • 2. How impactful is this problem for the customers? When assessing the impact of a problem, it's important to consider three dimensions: reach, intensity, and user segment. Understanding how many customers are affected, how deeply they are affected, and who they are can help prioritize the problem-solving process.
  • 3. Does it align with the company/product's long-term vision and strategy? Strategy is all about choosing what not to do. By aligning the problem with the long-term vision and strategy of the company or product, you can ensure that your efforts are focused on the right priorities.
  • 4. What do you need to deprioritize to work on this? Thinking about the cost of delay or the cost of doing nothing can be a powerful exercise. Some problems require immediate attention, while others can be addressed later. Knowing which problems to prioritize can save time and resources.
  • 5. What happens if you do nothing? Understanding the consequences of inaction can provide valuable insights. Some problems require immediate action, while others may worsen over time. By considering the potential outcomes of doing nothing, you can make more informed decisions.
  • 6. What is the customer's job-to-be-done? The jobs-to-be-done framework encourages thinking beyond mere product usability. Understanding what the customer is trying to achieve, rather than just how they interact with your product, can lead to more innovative solutions.
  • 7. How can I build a deeper moat for my product? Building a moat around your product is essential for long-term success. One effective way to do this is by creating network effects, where the value of your product increases as more people use it.
  • 8. If a new hotshot founder creates a pitch deck to disrupt my industry, what will they say about my company/product? Disruption is inevitable, so it's important to stay ahead of the game. By constantly challenging your own product and seeking ways to improve, you can avoid being disrupted by others.
  • 9. What future situation can make my product irrelevant? Anticipating future trends and changes is crucial in staying relevant. By proactively seeking potential threats to your product's relevance, you can take steps to ensure its longevity.
  • 10. Am I the best person to solve this? Recognizing your own strengths and limitations is important. If there are others who are better equipped to solve the problem, it may be more effective to involve them in the process.
  • 11. How much is our appetite to solve this problem? Assessing the level of commitment and resources available for problem-solving is crucial. It's important to gauge the willingness and capacity of the team to tackle the problem effectively.
  • 12. What is feasible to build? A good solution is one that is desirable for users, viable for the business, and feasible to build with the available resources and constraints. Considering these factors can help ensure that the solution is realistic and achievable.
  • 13. Where is the point of diminishing return? Understanding when the value gained from solving a problem starts to diminish is important. It's essential to assess the potential return on investment and determine if the effort is worth the outcome.
  • 14. What would the Red Team say about this solution? The Red Team exercise involves looking at your solution from a critical perspective. By identifying potential flaws and challenges, you can strengthen your solution and address any weaknesses.
  • 15. What is the riskiest assumption we have here? How can we de-risk it? Every solution is based on certain assumptions. Identifying the riskiest assumptions and finding ways to mitigate them can improve the chances of success.
  • 16. What is the smallest chunk of value we can deliver? Time is a crucial factor in problem-solving. By focusing on delivering the smallest chunk of value as quickly as possible, you can gather feedback and make iterative improvements.
  • 17. The more full-time employees a company has, the less likely product team members are to say they "have a strong understanding" of the product vision. Visibility into high-level objectives and goals is inconsistent. Granting autonomy to product teams not only motivates them but also has a positive impact on the business. Teams with high autonomy are more engaged at work.

In conclusion, sharpening your thinking as a problem solver requires asking the right questions and considering various factors. By focusing on multiplying value rather than merely solving problems, you can become a more effective problem solver. Here are three actionable pieces of advice to help you in your problem-solving journey:

  • 1. Dig deeper: Don't settle for surface-level problems. Ask questions to uncover the root cause and address the bigger issues.
  • 2. Prioritize strategically: Consider the long-term vision and strategy of your company or product. Focus on the problems that align with these goals.
  • 3. Anticipate and adapt: Stay ahead of the game by anticipating future trends and potential threats to your product's relevance. Continuously challenge your own solutions and seek ways to improve.

By incorporating these strategies into your problem-solving approach, you can enhance your skills and deliver impactful solutions.

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