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The Best Investigators Never Stop Asking Why

Curiosity as method, not temperament.

Anyone who has spent time around young children knows the relentless energy of a curious mind. “Why is the sky blue?” “Why can’t I have ice cream for breakfast?” It can be exhausting — but it is also, if you look closely, a masterclass in how to make sense of a complex world.

It turns out that same instinct is exactly what separates a good legal investigator from a great one.

In an article in Today’s General Counsel, iDS President Hunter McMahon and Managing Director Warren Kruse — together bringing decades of experience in consulting, law enforcement, cybersecurity, and digital forensics — make the case that curiosity is not a soft skill. It is a strategic one.

More Than a Task List

Too often, investigations get reduced to a checklist: pull the data, review the documents, summarize the findings. McMahon and Kruse argue that when consulting becomes a routine process, it loses its value. The shift that matters is from order taker to insight seeker.

The curious investigator doesn’t just accept the problem as given. They question the framing, clarify the goal, and ask what else might be going on beneath the surface. They understand that information is not the same as insight — and that sometimes the absence of data speaks louder than the data itself.

The authors share a pointed real-world example: a client once asked the iDS team to fly out same-day to image a custodian’s laptop, with no time for questions. As it turned out, the custodian didn’t even need the computer on-site, and the organization used a roaming profile — meaning no documents were stored locally at all. A few simple questions at the outset would have allowed the team to preserve the data remotely, saving significant time and money. The “just collect it” approach cost everyone.

Slow Is Smooth, and Smooth Is Fast

McMahon and Kruse are clear that curiosity must be purposeful, not directionless. Asking the right questions early isn’t inefficient — it protects against costly missteps and misdirected effort. As they put it, drawing on a principle familiar to the Navy SEALs: slow is smooth, and smooth is fast.

The most powerful move in an investigation is often not delivering an answer, but asking a better question — “What isn’t in this dataset that should be?” or simply, “Tell me more about that.” Those are the moments, the authors write, when you find the real story.

What a Curious Investigator Looks Like

For legal teams evaluating outside counsel or investigative partners, McMahon and Kruse offer a practical lens. The investigators worth working with are those who seek context before diving into tasks, let questions generate more questions, proactively offer ideas for related analysis, and develop protocols tailored to the specific matter — not a templated approach applied to every engagement.

At iDS, that mindset is embedded across our Investigations, Digital Forensics, and eDiscovery practices. We believe the best outcomes come from understanding what a client truly needs — not just what they asked for.

To connect with an iDS expert about your next investigation, visit idsinc.com.



iDS provides consultative data solutions to corporations and law firms around the world, giving them a decisive advantage – both in and out of the courtroom. iDS’s subject matter experts and data strategists specialize in finding solutions to complex evidence challenges, ensuring data can be leveraged as an asset, not a liability. To learn more, visit
idsinc.com.

Having trouble with a technical term used in this post? Check out our Data Investigators Glossary to crack the code. 

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