Nov 19, 2025

The 20 Questions That Will Launch Your Diligence Research To A New Level

ResearchTools

How do you efficiently perform diligence research and also allow yourself the space to be curious and open to finding those vital unexpected bit of information? The answer is…

You set up a Framework.

Research in the digital age is a gift and a curse. There is so much material available literally at your fingertips and at the sound of your voice that it is hard to find nothing and easy to find way too much. Both of these are unhelpful outcomes.

To efficiently conduct useful diligence research you need a simple, flexible approach that allows you to research different projects but keeps you from “reinventing the wheel”. The answer is to create a framework that guides through key research concepts so that perform the research in a systematic and methodical way without locking you into a rigid set of definitions and steps.

To help you create your own diligence research framework, I have put together these 20 questions. These are not in a ranked order, each is equally important and can be used in the way you think best for your issues and concerns. This is a way to focus your attention and organize your thoughts so that you can find what you need in an efficient manner.

Some Suggestions on How to Use The Questions

Breakdown the diligence project – Consider breaking down large diligence projects into manageable segments and then apply the questions to each segment. You might organize the segments by topic, time period, geography, subject matter, or other ways that fit your project.

Adapt as needed – Not every question will apply — and that’s fine. Add or refine as your project evolves.

Write it down – Turning questions into a list and documenting your answers helps you create a working research plan. This record becomes part of your own diligence research file.

Define what’s acceptable – Different projects allow for different degrees of completeness or confidence. Decide in advance what’s “good enough” for your purposes with the understanding that this may change.

Stay flexible – As you find sources and materials, your questions and parameters may change. Treat this as a living guide, not a static list.

Build your own framework – Over time, refine these 20 questions into a research checklist (or series of checklists/guides) that fits your diligence style and projects. But remember: checklists or guides support diligence — they don’t replace it.

20 Questions

The Why

&

Preliminaries

1. Why are you doing research? what is the goal?

2. Are there:

  • legal,
  • regulatory,
  • compliance
  • industry
  • traditional

requirements that define parameters of the research?

3. Are there internal policies or guides to follow?

4. Do you need a budget? For example, for:

  • Consulting experts
  • Travel
  • Paying for sources/technology
  • Hiring people to review or compile results

5. Can you estimate how much you will need?

6. Do you need to ask for funds/approvals to go forward with the research?

7. What is your research timeline, as in when do you need to finish the research?

The Targets

8. Who, what and where are your research targets?

9. For each target, what do you need your research to do? For example:

  • Teach you something or expand existing knowledge
  • Answer a question
  • Verify existing information
  • Supplement what you have
  • Fill a gap
  • Prove or disprove a claim
  • Provide expert corroboration

10. What are the connections between your targets?

The Sources

&

Materials

11. What type of information will you need to accomplish your research?

  • Facts
  • Data/statistics
  • Interpretation
  • Opinions
  • Ideas

12. What type of sources do you trust to generate the information?

  • Official
  • Expert (people, company, or topical)
  • Industry
  • Amateur

13. Can you define or list types of sources/platforms allowed/preferred/ for example:

  • Government or quasi government sources
  • Academic peer reviewed publications
  • Industry resources
  • News related materials
  • Social media platforms, if so which
  • Open sources and if so does it matter how it was obtained.

14. Is there any type of source/platform/material that is not suitable? For example information on or generated by:

  • dark web
  • AI
  • leaks/spying
  • hacking
  • particular countries, political units, organizations

15. Do you need offline resources such as interviews with individuals?

16. What time periods are relevant?

17. What formats are acceptable/required?

  • Written
  • Visual – images, films, video
  • Audio

The Process

18. What order is most efficient, for example will the outcome of one segment of the research eliminate another segment, are there dependencies between the segments?

19. How will you capture and document your research?

The Future

20. How can you leverage your research findings for the future? For example:

  • Adding to or generating a source library
  • Cataloging lists of experts
  • Using the diligence research project or a portion of the research for teaching
  • Composing checklists
  • Recording techniques, hints or “how to” tips

Some Final Thoughts

  • Always evaluate your sources
  • When in doubt verify
  • Think and plan before you start

Some Additional Posts

It’s Content Judgement Time – Are you up to the task?

Wondering How to Simplify Your Diligence Research

4 Important Reasons to Pay for Content on the Web

10 Powerful Reasons To Use The Web for Diligence

Some Inspiring Words of Wisdom

Research is formalized curiosity. It is poking and prying with a purpose.

Zora Neale Hurston – Writer, Anthropologist, Filmmaker

Research is creating new knowledge.

Neil Armstrong – First Person on the Moon