My partner and I got called to a local business where a bank deposit had gone missing.

When we arrived, the manager of the store told us that he had given the deposit to one of the delivery drivers to take to the bank. We spoke with the driver, who was fully cooperative. He said he took the deposit to the bank, put it in the after-hours dropbox, and came back to the store.

We spoke with the bank and they said the deposit never got there.



Great detectives ask great questions. 

But questions alone aren’t enough. But the secret sauce for detectives is structure. I.e. asking directed and specific questions. Detectives just don’t question aimlessly; they question to understand. To do this, detectives use a framework to guide their questioning. 

The basic framework that guides a detectives question is simple—who, what, when, where, why, and how. 

The interesting thing is that you can use this framework to understand your customers and markets also.

The question of who.

When a detective is asking who, they are asking who are the victims, who are the witnesses, and who are the suspects. In short; who are the players?

A good detective doesn’t take things at face value. Knowing the backgrounds of the people you are investigating matters. This applies to both victims and suspects. People can be motivated by strange things. Because of this, you quickly learn that not all victims are actually victims. You also learn that not all suspects are actually suspects.

Want evidence of this?

Look no further than Amy Parker, the white woman who called the police on Christian Cooper, a black man in Central Park. Cooper had asked Parker to put her dog on a leash. She got pissed off and called the police to report a crime.

His crime? WBWB (watching birds while black).

This is what she actually said (caught on video):


As we all know, this was bullshit.

The reality is that people sometimes lie about crimes. What detectives are looking for when asking "who" is simply an identification of who the players are. Their roles begin to take form as they continue to ask questions.

How this applies in business: It always pays to know who you are working with. Here are a few key who questions:

  • Who are your customers? 

  • Who are your competitors? 

  • Who are potential business partners? 

  • Who are key stakeholders?

The question of what.

One of the primary things a detective seeks to find out is the chain-of-events, i.e. they need to know what happened. After we have identified who the key players are, we need to understand the role each of them played. We want to get their stories. We want to understand what happened from their perspective. 

Do the stories from the people we identified align? Where are they similar? Where are the different? 

This is the point where we can start building a fact pattern. These are the things that we can (hopefully) all agree on. This will be the framework or narrative. 

As Joe Friday has famously (actually not said), “Just the facts.”

How this applies in business: You must be aware of what is happening. Here are a few key what questions:

  • What happened?

  • What happened to our sales?

  • What is the customer journey?

  • What are people doing when they visit our website?

The question of when.

Detectives want to know when something happened. The timing of an event starts to build out the context. 

This enables detectives to begin to make connections to other events. These connections are crucial in identifying causal relationships or correlations. Causal relationships occur when A causes B. Correlations occur when A and B happen around the same time, but aren’t related. 

How this applies in business: You must be aware of the timing of things.Here are a few key when questions:

  • When did most customers purchase?

  • When did our sales decrease?

  • When did customers leave our website?

  • When did customers decide to repurchase?

The question of where.

Location matters. It helps build out the story. Detectives need to prove that suspects were actually at the scene of the crime. The location also helps identify witnesses and victims. Where things matter helps you further build the story. 

How this applies in business: You must be aware of where things happen. Here are a few key when questions:

  • Where was the customer when they first realized they had a problem?

  • Where did customers bounce from our website?

  • Where (in our store) did customers decide to purchase?

  • Where are customers spending most of their time?

The question of why.

If you’ve ever watched a crime show, you have heard of motive, i.e. “what is his (or her) motive for killing Mrs. Peacock with the candlestick?” Motive is often elusive. What seems like the motive at face-value is often only a small piece of the puzzle.

To get to motive, sometimes you have to dig deep. People don’t need money. They need what money can get them. People don’t generally commit the crime for crime’s sake. They commit it for some other reason. That is the motive.

How this applies in business: You must be aware of why things happen. 

  • Why do customers choose us over the competition?

  • Why did the customer leave our website?

  • Why did our customer churn?

  • Why are customers spending less this month than last?

The question of how.

How questions identify the catalyst for something happening. These questions give you background. They tell you how something works, or how something doesn’t work.

How this applies in business: You must be aware of how things go down.

  • How are customers landing on our website?

  • How do customers become aware that we exist?

  • How do customers choose our product or service?

  • How do customers make purchasing decisions?

Detectives ask focused and targeted questions to understand things. 

They use a framework because it works.

Do you?

P.S. If you are interested in learning more about how conducting interviews can help your business, check out