A Pack of Lenses for Entrepreneurs

There are obvious reason why entrepreneurs fail, like having too many competitors and too little funding. But if entrepreneurs know about these obstacles they can adapt and make more efficient decisions to success.

The far trickier problems happen when entrepreneurs do not know about an obstacle and waste valuable time doing the wrong thing. Because of this, one of the best things an entrepreneur can do is to look at their company from as many angles as possible. The more lenses an entrepreneur has at their disposal, the fewer unknown obstacles.

Jesse Schell, the author of the Art of Game Design, created lenses for the game design world to help game designers look at their projects from many angles. Inspired by his work, I have adapted many of these lenses for entrepreneurs. This is an evolving list, so if you know of more questions that should be added, please feel free to reach out to me at rachel@adjacent.us.


  • What emotions do I want people to feel towards my company?
  • What is essential to my company to help people obtain this experience? Customer service? Visual design?
  • How can I reinforce this emotion towards my company along every stage of people’s interactions, from sign-up, to weekly emails, to memories of my company?


  • What is the best venue to reach my customers at?
  • What venue best expresses the experience I want my customers to have towards my company?
  • What properties about the venue imbue the experience I want people to have?


  • What way can I surprise my first customer to not simply give them a product or service, but delight them?
  • What elements of that experience with my first customer can I scale up to many customers?
  • Are there elements that are hidden, unique, or different?


  • It takes energy for people to interact with a product or service. How can I design my company to lower the energy people need to exert to interact with my company?
  • How can I use elements of gamification to increase the energy people want to exert on my product or service and keep them coming back?


  • What motivates people to interact with my company?
  • Is there a gap between the motivations that people say and what they do?
  • How does this motivation tap into larger human goals (the search for food, shelter, or larger meaning) ? How can I tap into ever deeper goals?
  • Are the motivations of the people who use my product or service external or internal?
  • Are there conflicting motivations of different groups who interact with my company?


  • What problems is my company solving?
  • Is this a problem that people are currently paying to have solved?
  • How are people currently solving this problem?
  • Are there hidden problems underneath this one problem that need to be solved first?
  • Why hasn’t this problem been solved already?
  • How can I tie my solution to something that is already evaluated, and costs people money? The clearer I can say, “I am saving you X amount” the more successful I will be.


  • Who came to my platform or service once but either did not finish, or did not come back?
  • Are there themes in terms of the kinds of people who are not coming back? Are there similarities in the point in the process at which they don’t come back?


  • What component of my company gets people excited? Is it something about the sign-up process? Holding the object in their hands? Lasting impact to the field? Find the most exciting kernel and reinforce it!


  • If there were no constraints on time and money, what would my company look like? Are there people who not just like the current product, but are excited about the different kind of future that I propose?
  • How do I feel about the world and what it should be? How can I express this vision through my product?
  • What will the company look like in two years? Four? Twenty?
  • Will the world be a better place if my company exists?


  • What basic assumptions do I have about: the market, my customer base, marketing to these customers, creating the product.
  • How can you most cheaply test whether each of these assumptions are true?


  • Do I have enough time and money to create a working prototype?
  • Is what I’m doing new?
  • Is this problem big enough that I will be able to sell my solution?
  • What kind of revenue can I expect? Will this be able to support myself? Will this be able to scale to be a larger company?
  • Is it technically possible to create the solution I want? Are there limits with current technology that would impede the development of my company?


  • What are the biggest risks to my company’s success? Customer interest? Money? Competitors? Make a list of all the potential known risks.
  • What can I do to mitigate these risks?


  • Who is my customer? What are their likes and dislikes?
  • Who are my most passionate customers? Who are the late-comers who would use my product or service when all of their friends are?
  • Is it clear from my product or service who my company is targeting?


  • Is the goal of using my product or service clear? What do people get out of it?
  • Write out the goal I intend people to get from my company.
  • Are there people who are using my company with different goals? What are these goals? How do these different goals interact with each other?
  • Are these goals concrete and rewarding? How do I evaluate whether they have accomplished their goals?


  • How much time do people interact with my product or service? Do they want to be spending more time or less time with this interaction?


  • Who has access to certain sets of information has incredible power. Who knows what on my platform? How would altering who knows what change the experience people have? Would it change power between different people? Would this shift in who holds information create a change in a larger field or market?


  • Are the rules for interacting with my platform or service clear?
  • Are there punishments for those who do not abide by the company’s rules?


  • How many times can a person use my product or service?
  • Is my company easily understood by newcomers?
  • Is there a way the use of my product or service deepens after longer use? How can I develop levels (newcomer, expert, etc.) to want people to keep coming back and growing their commitment?

Virtual vs. Physical

  • What would an all-physical version of my product or service look like? What would a fully automated version of my company look like?
  • What balance will I strike? What are the pros and cons of which parts I’m making physical and which I am making digital?
  • What mental model do people have of how my company works?


  • What feedback can I give to people signing up for my product or service that they have successfully done so?
  • What feedback can I continue to give them to help them further advance their goals through my company?


  • What data is the most fundamental on my platform?
  • What data is exchanged between different parties in my company?
  • On what channels am I transmitting this data? (face-to-face, phone, text, web)


  • Are people immediately interested in my company?
  • After they gain the product or service, does their interest decline or increase?
  • How can I get their interest to increase after using my product or service once?


  • What part of my product or service tells a story to customers?
  • How does the product or service fit into the story customers want to say about themselves?
  • How can customers personalize their story?
  • What meaningful choices can people make when using my product or service?


  • When is there a clear pathway of how a user should interact with my product or service?
  • Is there an open-ended route through my system?
  • The constraints vs. openness is likely to be related to how many different potential parties there are that use your company, and how many different goals they have.


  • Do I have a way to make money? What is this way?
  • Is the way I make money contrary to some of the interests and goals of the people who use my product or system?


  • What skills are needed to create my product or community?
  • What can my company offer to those people for them to join the creation of this product or service?
  • Do I have the right team to build this company?
  • Is there shared communication between the team? How can I develop a common communication foundation and style between people?
  • How do I get people to share new opinions but also all coalesce and agree around larger decisions?
  • Is there a shared identity, trust, and respect amongst team members?


  • How are decisions communicated amongst people in the team?
  • Where are communications stored?
  • How is information evaluated for importance, put into a calendar of tasks, and then tracked?
  • How is information communicated to customers? How is information communicated to investors or other stakeholders?


  • What is the smallest test possible to see whether people like this product or service?
  • Who will you do this test with?
  • Where will this test occur?
  • What questions will I ask?
  • What will a successful test look like? What does an unsuccessful test look like?


  • What can I convey to people about my company within 30 seconds on an elevator?
  • What next action do I want people to take when they leave that elevator?
  • What basic knowledge of my space does my pitch assume these people know?


  • Does my product or service make people better? Can it make people worse?
  • What is the purpose of building this company? The purpose for me? The purpose for my customers?

The questions should not end here. As an entrepreneur a part of your job is to take every meeting as a moment to not simply pitch your start-up, but accumulate new lenses to help you look at your company differently. Are you starting a fashion company and meet an environmental activist? They might raise questions about water usage or sustainable materials sourcing that you did not think about. Are you building a software company? A home decor expert might offer questions about how you create a cohesive feeling on your website. If you stay inside the boxes of the business model canvas, you miss many important angles. You get out of these boxes when you surround yourself with people that ask diverse questions and can help you identify potential obstacles early enough to adapt to them.

To learn more about how to think about entrepreneurship and develop companies from the perspective of information theory, continue to my class on Information Architecture for Entrepreneurs.



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