How Sitting in 14 Legal Roles Created My DFIR Investigative Mindset

The DFIR investigative mindset no one teaches you but everyone judges you by. Most people in DFIR hear “investigative mindset” and think it means one of three things:

• Be curious.
• Think like a criminal.
• Ask better questions.

That’s beginner-level thinking and it’s what is told when we don’t have the time or depth to show them what this work actually requires. It’s also because we’ve not fully articulated a DFIR investigative mindset much beyond ‘critical thinking’ which is but only a part of the mindset.

Curiosity doesn’t help you if you’re blind to legal thresholds. “Thinking like an attacker” doesn’t prepare you for testimony. And asking better questions doesn’t matter if your audience is a judge and you don’t understand burden of proof.

The real DFIR Investigative Mindset is harder. It’s the difference between just documenting what happened and defending what happened when it’s challenged, whether that’s by an aggressive cross-examining attorney or a furious CISO.

When I talk about this mindset, I mean:

• You know what probable cause looks like in the totality of the data.
• You are looking for clues regardless if they are in data or outside the box.
• You recognize when your tools are lying to you.
• You write reports that hold up, not just to technical review, but to legal scrutiny.
• You can reconstruct human behavior, not just list artifacts on a timeline.
• You chase the story, not exports of data.
• You anticipate the questions others will ask, because you’ve sat in their chairs.

And that last one is the part almost no one teaches.

Perspective Is Power

I’ve sat in almost every role* a legal case touches. Each role rewired how I write. How I frame evidence. How I do DFIR. How I think.

When you’ve been the defense’s expert, you never again write a report with sloppy assumptions. When you’ve been a victim, you never again treat an attack like it’s “just data.” When you’ve had to testify, you never again pad a report with technical filler or false confidence.

Every chair I sat in made my work better.  Not perfect, but better.

And that’s what most of training and education in DFIR is missing: perspective.

It’s not about packets. It’s about people. It’s not about artifacts. It’s about actions. And it’s not about tools. It’s about truth; reconstructed, documented, and defended.

If this resonates with you, and if you want to build your mindset in a way that actually holds up in the real world, then join me for a free live webinar on August 7: “I Sat in Every Chair Except the Judge’s.”

In this webinar, I’ll show you what changed in my thinking, casework, and reports as I moved through each role in the justice process. It’s the kind of insight no tool training or certification teaches but every stakeholder expects.

If you’re looking at how to interpret logs or alerts or analytical theories, that’s not here. I’m about teaching how to work a case, whether it be a breach or crime that needs objective decision-making, accurate thinking, and actionable intelligence development.

And at the end of the webinar, I’ll give away 3 copies of my book, DFIR Investigative Mindset. Free shipping in the U.S. just as a thank you for showing up.  If you’re outside the U.S., you can still win but just cover shipping and I’ll send it your way.

Seats are capped (because my Zoom account has a limit).

Register for the webinar: https://www.suspectbehindthekeyboard.com/offers/UJ2LLPon

*Why is Brett the way he is….?

I’ve held nearly every role inside the courtroom, except the judge and court reporter. I’ve served or have been ordered as:

• Bailiff
• Fact witness
• Rebuttal witness
• Expert witness
• Defendant
• Pro se plaintiff
• Juror
• Court advisor
• Special master
• Victim
• Spectator

I’ve both deposed witnesses and been deposed. I’ve been cross-examined under oath and I’ve cross-examined others.

When it comes to legal filings, I’ve written and argued:

• Complaints, motions, replies, and responses
• Declarations and affidavits (for search warrants too)
• Expert and special master reports
• Trial briefs, pleadings, and discovery demands
• Answers, interrogatories, requests for admissions and production
• Privilege logs, meet-and-confer statements, and motions to compel
• Motions for summary judgment and judicial recusal
• Evidence hearing filings, objections to witnesses and exhibits
• Notices of appeal and petitions for rehearing
• Opening statements and closing arguments

This isn’t theory. It’s 30+ years of courtroom and legal experience, through one role, one filing, and one cross at a time. And it’s exactly why I teach DFIR the way I do. I’m not an attorney, and these experiences are through the eyes of a DFIR practitioner which has made my work and perspectives so much better.