How Forward Deployed Engineers can ask Better Questions

Asking Questions as a Journalist

In Journalism, we follow this process:

• Who? What? When? Where? Why? How?
• Past? Present? Future?

The quick brown fox jumped.

 Why did he jump? How?

Some questions are more important than others. In journalism, we identify more important questions to ask through:

• The number of people it impacts
• The intensity of the effect
• High proximity to the audience
• High subject matter relevance to the audience
• How much of an anomaly it is
• If there is a problem/conflict, it implies an equilibrium that has not been reached

On each of these, there is likely information online that can answer the question.

You can look up:

> The fox is known for being quick. He even won an award in 2016. There’s a report that he jumped for a Christmas celebration

At that point, the obvious questions are exhausted. The more interesting ones start to look like:

• Why did you, specifically, feel compelled to jump?
• How did it feel before and after?

We can apply the above a surprising number of times to get to better questions.

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Patterns

Over time, some patterns in the best questions to ask emerge.

• Run the experiment 1000 times
  • Can this joint survive 1000 strains?
  • Can this team structure combat 1000 threats?
  • Where will this project be after 1000 iterations?
• Look for soft spots.
  • If a mentor asks us about this, can we explain it?
  • If many people use this set of equations, is it convenient?
• Pay attention to many repeated human interactions.
  • When many people share the same knee-jerk reaction, it reveals something interesting and important about human nature.

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In Practice

I ran into this directly while doing user research for my archeology startup.

Reality isn't perfect -- you don't live in your users' skins. If you visit a factory for an hour, you don’t know what happens after you leave. If you visit for a day, you don’t know what happens the rest of the week.

Let's say you are working with 3 initial customers: 2 factories in Phill and one in New York. On one trip to the Philly factories, you may arrive at 8:00 am, just as it opens. Best-case scenario: the factory head is there and willing to meet with you, and all personnel and machines are functioning as normal (it's very rare that this is the case).

Even in this case, if you visit for an hour, you won't know what happens after 9. If you visit for a day, you won't know what happens on a particular day of the week. You would have to ask an infinite number of perfect questions in your user interviews to know everything that happens, and even if you did, it would only be from 1 person's perspective.

We dealt with many unknowns and unknown-unknowns. Is X Factory part of a <5 or >5 location conglomerate? And "what is the factory's interface w/ the world?" -> "How are locations transporting parts?")

The "solvedness" of your GTM then scales with the time and effort you spend on the user and the strength of your relationship with them. If your point of contact within the factory is the factory manager, a variety of factors can create inhibitions about being there for a full day or about talking to other people in the supply chain.

You never get a complete view. You’re always working with partial information, filtered through people, time, and context. Better questions don’t fix that, but they help you move through it more deliberately — noticing what’s missing, and what might actually matter.

Thank you to Lela Sengupta, N. D. for edits.