124 Questions to ask BEFORE You start your Next Challenge
John Klick
July 17 2024
John
We live in an era where immediate action and rapid ideation are highly celebrated. However, as experience has shown, the path to effective problem-solving is rarely a straight line from challenge to solution. More often than not, the initial problem we perceive is not the right problem that needs to be solved.
To get at the right problem we need to be curious and dig into the “facts” of the problem you or your stakeholders think you are facing.
To do that we start with Fact Finding. And I gather you might have the following question…..
What is Fact Finding?
The Fact-Finding approach has been around for generations. It has its roots in Creative Problem Solving. The purpose of fact finding is to create alignment AND build insight into your challenge. We do this by asking and answering a series of questions within four categories.
Purpose & Goals:We use this to define the outcome you’re looking for, both in the short term as well as in the long term.
Context: The context is everything around the challenge that gives shape to the problem and helps you understand the missing pieces.
Constraints & Resources: Here is where we uncover the things that are getting in the way of solving the challenge.
People & Perspectives: You should understand who can be an enabler as well as who might be a derailer of your success.
Now with that background, on to the questions you came here for 🙂
#1 Purpose & Goals
Our Top “go-to” questions for Purpose & Goals
Start here if you have limited time for yourself or with your stakeholder.
What does success look like in 3 years?
In one year from now what have we accomplished?
How will we know we are successful? (how might we measure success?)
If this is solved, what will we have that we don’t now?
How do you want this work to be talked about in our company?
Questions to go Deeper into Purpose & Goals
What specific outcomes are expected in the next 12 months to consider this project successful?
Looking ahead 24 months, how will the organization be different if these goals are achieved?
How do you envision quantifying success for this project?
If we conquer this challenge, what new opportunities will be available that don’t exist now?
How would you like this project to be described when discussed within the company?
How will achieving these goals contribute to the organization’s mission and vision?
What role does innovation play in the success of this project?
How do these goals align with the needs and expectations of customers or clients?
What’s the broader impact of this project on the industry or market?
How will achieving these goals affect the company’s competitive edge?
What aspects of the organization’s culture will be influenced by this project’s success?
How does this project connect to the organization’s long-term growth strategy?
Can you describe a scenario where we’ve faced similar goals and achieved them?
What’s the desired timeframe for reaping the benefits of this project’s success?
How will success in the short term contribute to the realization of long-term objectives?
How do these goals align with the company’s values and ethos?
What potential risks or challenges should be anticipated as we work toward these goals?
Can you identify any potential conflict between the project’s goals and other ongoing initiatives?
What’s the core essence of these goals that makes them crucial for the organization?
How might these goals positively impact employee engagement and satisfaction?
What will be the primary indicators that demonstrate progress toward these goals?
How do these goals reflect changing customer preferences and market demands?
How will achieving these goals affect the company’s overall financial health?
Can you provide specific examples of how these goals align with the needs of stakeholders?
Are there specific performance metrics that need to be met to consider the project successful?
#2 Context
Our Top “go-to” questions for Context
Start here if you have limited time for yourself or with your stakeholder.
What have you tried before that has worked?
What have you tried before that has not worked?
What do you think you know about this situation?
Why is this important to address now?
Why can’t you make this go away?
What do we know right now?
Questions to go Deeper into Context
What have been the most successful strategies employed in the past for similar challenges?
Are there instances where similar challenges were addressed but unsuccessful?
What prior experiences inform your understanding of the current situation?
Why has the urgency to address this challenge risen at this particular moment?
What factors contribute to the persistence of this challenge despite previous efforts?
What information do we currently possess that aids in understanding the context of the challenge?
How have external factors, such as technological advancements, impacted the challenge?
What internal dynamics or relationships have influenced the framing of this challenge?
How do you perceive the perception of this challenge among different teams or departments?
Why is it crucial to tackle this challenge rather than postpone or ignore it?
Can you elaborate on what we already know about the challenge and its components?
How have changes in customer behavior or preferences affected the relevance of this challenge?
What insights have been gained from customer feedback or market research?
How has the competitive landscape evolved and influenced the urgency of this challenge?
What assumptions might we be making about the challenge that need to be examined?
What implications might arise if the challenge remains unresolved in the long term?
How has the internal organizational structure affected previous approaches to similar challenges?
What past strategies were effective at shifting perceptions or resolving challenges?
How have regulatory changes or legal considerations impacted the challenge’s context?
What knowledge or insights have we gained from partnering with external experts or consultants?
How might current global trends impact the urgency and significance of this challenge?
What cross-functional collaborations could potentially yield fresh perspectives on the challenge?
How does the historical context of the company inform your approach to solving this challenge?
What are the key unknowns or uncertainties that complicate the understanding of this challenge?
Are there any industry benchmarks or best practices relevant to this challenge?
#3 Constraints & Resources
Our Top “go-to” questions for Constraints & Resources
Start here if you have limited time for yourself or with your stakeholder.
What can we do?
What can’t we do?
What’s stopping you from solving this challenge?
What resources do you wish you had to be successful with this project?
What are the time restrictions?
What are the budget restrictions?
Questions to go Deeper into Constraints & Resources
What limitations or constraints should we consider when formulating potential solutions?
Are there specific strategies or approaches that are off the table due to resource limitations?
What factors have historically prevented a full resolution of this challenge?
If resources were not a concern, what additional support would be most beneficial?
What’s the maximum timeframe available for implementing a solution to this challenge?
What financial constraints might influence the feasibility of different solution paths?
Are there any specific technological constraints that need to be accounted for?
What trade-offs might be necessary due to resource limitations?
How do staffing limitations influence the development and execution of potential solutions?
What internal expertise or knowledge gaps might affect our ability to address this challenge?
How can we optimize the allocation of resources to achieve the best outcome?
Are there any legal or regulatory restrictions that need to be navigated?
What existing tools, technologies, or assets can be leveraged to address this challenge?
How can partnerships with external entities potentially alleviate resource constraints?
What’s the acceptable level of risk when considering potential solutions?
How might resource constraints impact the timeline for implementing a solution?
What alternative resources could potentially be acquired to bolster our capabilities?
What insights can we gain from benchmarking against industry peers with similar challenges?
How can we creatively work within the existing resource constraints to achieve success?
How can efficiency and cost-effectiveness be balanced while addressing this challenge?
How might resource limitations impact the project’s ability to scale up in the future?
What are the implications of prioritizing this challenge over other ongoing initiatives?
How do resource constraints influence the level of innovation possible in solutions?
What aspects of the challenge might become more complex due to resource limitations?
How do budget constraints impact the scope of potential solutions?
#4 People & Perspectives
Our Top “go-to” questions for People & Perspectives
Start here if you have limited time for yourself or with your stakeholder.
Who is the business sponsor?
Who is our primary audience?
Who might hinder this?
Who might champion this?
Who ultimately makes decisions?
Who else might influence the outcome?
Questions to go Deeper into People & Perspectives
Who within the organization is actively sponsoring and championing this project?
Who constitutes the primary target audience or beneficiaries of the solution?
Are there individuals or teams that have historically posed challenges to similar initiatives?
Who, aside from the core team, will be affected by the outcome of this project?
Who holds the ultimate decision-making authority for approving project solutions?
Who are the key stakeholders whose input is crucial for shaping the project’s direction?
What roles do cross-functional teams play in influencing the outcome of this challenge?
Who could potentially resist the changes proposed by the project, and why?
Who within the organization can help build consensus and overcome resistance?
Who within the organization has the power to allocate necessary resources to the project?
Who will be directly responsible for executing and implementing the chosen solutions?
Who within the organization has a vested interest in the successful resolution of this challenge?
Who could provide insights from a customer perspective to guide solution development?
Who can act as a bridge between different departments to foster collaboration?
Who can provide historical context and lessons learned from similar challenges?
Who might have valuable perspectives from previous attempts to address this challenge?
Who can help convey the importance of the project to stakeholders and decision-makers?
Who possesses the necessary technical expertise to evaluate and guide potential solutions?
Who might have concerns about the project’s impact on their roles or responsibilities?
Who can help ensure that the proposed solutions align with the company’s values?
Who can serve as a voice of reason, providing an unbiased perspective on potential solutions?
Who could be potential champions to advocate for the project’s success throughout the organization?
Who will be responsible for communicating progress and results to relevant stakeholders?
Who within the organization could provide unique insights due to their unconventional viewpoints?
Who can provide valuable insights or expertise to inform potential solutions?
What potential ripple effects or consequences might the proposed solutions have on other departments or functions within the organization?
Conclusion
This is the conclusion of this guide but just the start for your journey in solving one of your big problems!
Armed with these 124 questions, you’re equipped to not only jumpstart your next big challenge, but to redefine how challenges are met and conquered. Remember that the questions you ask are not just tools—they are pathways to clarity, alignment, and transformation.
To be successful, you absolutely do not need answers to all of these questions for every challenge you face. Use them as a guide as you work though your next challenge or guide a stakeholder thorough one of their big problems.
If you ever find yourself in need of a thought partner to bounce ideas off of or help you get unstuck. Reach out! We are always eager to help.
Check out the Fact Finding Tool!
Learn more about how to apply these principles to your challenge!
John is a trainer, corporate speaker, tech-geek, and expert facilitator. He has led hundreds of executive teams through applied creativity, design thinking, and lean startup techniques to solve their most strategic business challenges. Across his 20-year career he has experience in non-profits, start-ups, management consulting spanning from Pharma to Finance.