What Are You Trying to Learn?

“If I had an hour to solve a problem, I’d spend 55 minutes thinking about the problem and 5 minutes thinking about solutions.”

—Albert Einstein

In school, we’re constantly taking tests to gauge how well we learned last week’s material. We cram geographic boundaries, the dates of battles, and multiplication tables into our heads, and then we spit out the results.

Sadly, those rote memorization skills used to answer preformulated questions don’t help us as entrepreneurs. When building a new business model, there is no test or quiz that we can cram for. It’s a wildly unstructured dive into the unknown.

As an entrepreneur (or intrapreneur), we can’t build a product or solution before we figure out what the customers actually need. If we take a guess and build a fully functioning product, it’s likely that the market will judge us wrong and punish us with a silent cash register.

Our job as entrepreneurs is to first ask the right questions, and only then can we find the right answers.

What Are Good Questions?

The questions we must answer are fundamental gaps in our business model. Questions like:

• Who is our customer?
• What job do they want done?
• What channels can we use to reach them?
• Which features should we build for our first product?
• Is our solution good enough?

If we can identify the right question, there is a corresponding method (or methods) in this book to help answer it.

If we apply a method without first identifying the right question, the results of that experiment are typically very difficult — if not impossible — to correctly interpret.

For example, if we’re selling a new type of shoe that cures plantar fasciitis we could put up a landing page and a “Buy Now” button before we even product the product. The test will check if anyone wants our value proposition enough to click the buy now button.

We can put $1000 into Google AdWords for “shoes” to drive traffic and wait for the money to start rolling in.

However, the data shows that our conversion rate is 0 percent. No one wants it.

Should we give up? The landing page test says that there is insufficient demand for this product.

But what is “plantar fasciitis?”

If the people coming to our website aren’t familiar with that medical term, then the test isn’t failing because no one has platar fasciitis. It’s failing because no one understands what we’re talking about.

In this case, we were asking, “Does anyone want my product?” when we should have been asking, “Does our customer understand what plantar fasciitis is?”, “What’s the right keyword to advertise on?” or even, “Who is our customer?”

When the question doesn’t match the method, the data is often misleading and can lead to missed opportunities.

How Do We Ask the Right Questions?

Asking the right questions is important, but actually identifying those questions can be a challenge. How do we know we’re not missing anything? How do we know we are asking the most important questions?

It’s impossible to see our own blind spots. (That’s the definition of a blind spot.)

Unfortunately, it’s often those gaps in our vision that hold the deadliest questions and business risks.

Ideate

One way to generate these questions is brainstorming around problems, challenges, opportunities, assumptions, and risks. Then, we can reframe them as questions. For example, we might identify risks such as:

• Unclear cost structure
• Cost of customer acquisition
• Google Adwords as a channel

We can then take those potential risks and transform them into one or more questions such as:

• What is the cost of manufacuring at scale?
• What is the cost of customer acquisition?
• What are the right keywords to target?
• Is there sufficient keyword traffic to be a channel?

You may find that for each risk there is more than one question. The more the better.

Starting a company is risky. There are a lot of unknowns and a lot of open questions. If we can only see five or six questions, it does not mean our business is less risky than someone with twenty questions. It actually means our idea is more risky because we are probably not acknowledging and dealing with all the unknowns.

There are many ways to brainstorm questions and identify gaps in our business model, such as using the Business Model Canvas. We don’t list them all here, but we are including an AI prompt to help ideate, however this should not be used in place of human judgement. Use the AI prompts to augment existing ideas, not come up with potential risks from scratch.

//: # (Need to update this section with an AI prompt to help people brainstorm / ideation risks. The prompt should, by default facilitate the user through 1) the human ideating themselves 2) coming up with additional ideas to help the human 3) converting those ideas into questions. Step 1 can suggest multiple facilitation techniques until the human has at least 10 ideas. Step 2 should come up with at least 5 normal ideas, 5 wildly creative ideas, and then maybe another round of 5 ideas spinning off the previous examples. Step 3 should come up with addition questions for each risk. Overall. I’m open to suggestions on the prompt. Do some web research on best brainstorming prompts. The prompt should spawn subagents with different contexts for ideation if available.)

Peer Review

Every ideation approach will still leave blind spots where our own assumptions hide. Fortunately, it’s easy for other people who have a little emotional distance from our business to see where we are making risky assumptions.

A peer review is a time-honored method of eliminating oversights. It can be used to proofread a document or make sure we’re not about to walk out of the house with mismatched socks.

To peer review our business model, we don’t need to ask a seasoned entrepreneur or industry expert. Almost anyone is able to provide the input we need. We can present our business idea and business model to someone else and ask them to ask us questions. Encourage them to ask any question they want, and remind them that there are no dumb questions.

We simply need to write down those questions that we forgot to ask ourselves. If we go through five peer reviews and everyone asks us, “Who is your target customer?” or says “Gee … your target customer seems broad,” we probably haven’t defined our target customer very well.

We should not defend our idea or try to explain in excruciating detail why their question is not a risk for us. Our job is only to note the questions that are being asked and include them when we prioritize.

It’s possible to use AI agents to help brainstorm, challenge business ideas, and surface hidden assumptions. However, more perspectives are always going to be better. To that end, we’d recommend using multiple models and/or prompt in addition to humans. It’s not advisable to only rely on AI for peer review as it usually lacks the context of an emotional human response.

Priority Does Not Have a Plural

Once we’ve finished brainstorming and conducting peer reviews, we should have at least ten questions, and hopefully much more. If you have fewer than ten, you are probably missing questions in your blind spots.

However, we can only address one question at a time effectively. So we have to prioritize.

Again, there are many methods for prioritizing, and we won’t list them all here. We should just pick one question where the answer could potentially destroy our entire business model.

We may choose the wrong question to start with. That’s ok.

It’s better to pick the wrong question and answer it quickly than to spend days, weeks, or months agonizing over multiple priorities to develop a perfect plan of action for the next year. Just pick one and get going.

The following chapters will show you how to take that one priority question and figure out how to answer it with research or an experiment.

Locate the Question

Once we have the right questions, we need to find the right method. To do this, we need to understand the difference between market vs. product questions and generative vs. evaluative questions.

1. Do we need to learn about the problem (ie, market) or the solution (ie, product)?
2. Do we have a falsifiable hypothesis to evaluate, or do we need to generate a clear idea?

Market questions are those relating to levels of customer demand, user problems, segmentation, or market size. Product questions relate to what solution would solve the market need.

Generative questions are open-ended where there is not necessarily one clear answer. Evaluative question are specific, closed-ended questions where there is one specific true answer or a yes/no answer.

Mapping the intersection of these two distinctions gives us a 2x2 matrix with four possible quadrants:

Each of these quadrants directly relates to a set of questions to answer and methods than will generate the exact right data to answer those questions.

If we have a clear hypothesis of who our customer is and what we think they will pay for, then we can conduct an Evaluative Market Experiment such as a smoke test.

If we don’t have a clear idea of who our customer is and it’s open-ended, we can do Generative Market Research, such as data mining.

Similarly, if we have a clear hypothesis of which features will solve the customer’s problems, we can do an Evaluative Product Experiment such as Wizard of Oz testing. If we do not know which features will lead to an acceptable solution, we can do Generative Product Research such as a Concierge Product to try to come up with new ideas.

Any framework is an oversimplification of reality, but this index is a quick way to navigate to the correct method.

The Index of Questions and the Index of Methods show a list of example questions and their corresponding methods. But the next few chapters will go into more detail on how to distinguish the different types and help you navigate the four quadrants.