36 Questions to Turn Your Litigation Wins Into Powerful “How We Did It” Articles

Wayne Pollock • May 29, 2026

“How We Did It” articles are quintessential thought leadership pieces. Here’s how to decide what to cover in your next one.


Any favorable result you secure for a client in litigation can be the basis for a thought leadership article.

Whether you’re discussing a favorable verdict, settlement, or summary judgment decision, you’re taking readers behind the scenes and showing them how you overcame certain obstacles to secure that result for your client.

These “How We Did It” articles are quintessential thought leadership pieces. It doesn’t matter if you’re a plaintiffs’ attorney or a defense attorney. Explaining how you overcame obstacles in litigation to secure a favorable result for a client demonstrates your knowledge and wisdom in action, positioning you as the attorney that past, current, or potential clients or referral sources would be foolish not to reach out to if they or someone they know has a similar legal or business issue.


The Simple Structure of a “How We Did It” Article

“How We Did It” articles follow a straightforward format:


First: the introduction. You’ll set the scene and provide context regarding the case and posture.


Next: the meat of the article. You’ll describe three to five obstacles you faced over the course of the litigation, including during discovery, mediation, settlement, and/or trial, and explain how you overcame them.


In a moment, I’ll walk through 36 questions that will help you and your colleagues identify the obstacles you might want to discuss in the article.


Finally: the conclusion. You’ll wrap up the outcome and provide additional insights if needed.


A Few Caveats Regarding “How We Did It” Articles

“How We Did It” articles focus on the advice you gave your clients. That could be an issue for some attorneys who aren’t comfortable or familiar with writing articles for public consumption regarding the counsel they gave clients. Those attorneys—and everyone else—should keep the following caveats/reminders in mind when writing “How We Did It” articles.


First, you can discuss how you overcame obstacles without divulging privileged or confidential information. That said, be careful you’re not inadvertently disclosing information that falls into either bucket.


Second, there’s no need to reveal truly proprietary processes that you employ, even if they technically fall outside of privileged or confidential protections. You can mention that you have a proprietary process for evaluating experts, running focus groups, etc., but you needn’t go into the details of those processes that you would like to keep confidential.


Third, you’ll likely be talking a fair amount about actions you took that have been captured, discussed, or reflected in public court filings; non-confidential litigation materials, such as correspondence and deposition transcripts; and court hearings that are open to the public.


There should be plenty of things for you to discuss that won’t be affected by concerns about privilege, confidentiality, or your proprietary processes, since they’ve already been made public.


With these caveats in mind, let’s explore the questions that will help identify the obstacles worth discussing in any “How We Did It” article.


The 36 Questions That Fuel “How We Did It” Thought Leadership Articles

Your answers to 3 to 5 of the following 36 questions, which are grouped by litigation phases, will give you and your colleagues food for thought for obstacles to write about in your “How We Did It” article.


The Big Picture (6 questions)

1.Where was the case most vulnerable?

2. Which issues required the most creativity to resolve?

3. Where did experience—and not just hard work—make a difference?

4. Was there an obstacle that most attorneys may have underestimated?

5. Was there a misconception about litigating against certain entities that you had to overcome?

6. Did you face challenges regarding co-counsel, conflicts, or opposing counsel?


Pre-suit Investigation and Case Intake (4 questions)

These tend to lean more toward the plaintiff’s side, except for #10:

7. Did you face challenges in unearthing certain facts or documents?

8. Did you face challenges corroborating older allegations?

9. Was there statute of limitations concerns?

10. Was there any resistance from the client that made building or defending the case complex?


Drafting and Filing a Complaint (3 questions)

Again, these tend to lean more toward the plaintiff’s side.

11. Did you face challenges pleading with certain facts?

12. Did you face challenges deciding which causes of action to include?

13. Did you face challenges avoiding causes of action that would be easily knocked out by certain defenses?


Early Motion Practice (1 question)

14. Did you face challenges regarding early motions, dispositive or otherwise?


Discovery (3 questions)

15. Did you face challenges with document discovery?

16. Did you face challenges with depositions?

17. Did you face challenges maintaining confidentiality or getting around confidentiality concerns?


Experts (2 questions)

18. Did you face challenges with your own experts?

19. Did you face challenges or obstacles when dealing with opposing experts?


Summary Judgment (1 question)

20. Did you face challenges with summary judgment motions—whether with yours or opposing the other sides?


Mediation (1 question)

21. Did you face challenges with the mediation process?


Settlement (1 question)

22. Did you face challenges regarding the settlement process, such as negotiating terms, or drafting the settlement agreement and releases?


Trial Preparation (5 questions)

23. Did you face challenges with pretrial motion practice, including pretrial evidentiary rulings?

24. Did you face challenges preparing your client to testify?

25. Did you face challenges preparing other witnesses to testify?

26. Did you face challenges planning your trial presentation?


Trial (10 questions)

27. Did you face challenges choosing a jury?

28. Did you face challenges with how the trial began, such as with rulings from the court or your or the opposing side’s opening arguments?

29. Did you face challenges with any of your direct examinations?

30. Did you face challenges with your cross-examinations?

31. Did you face challenges caused by the other side’s direct examinations or cross-examinations?

32. Did you face challenges with trial exhibits?

33. Did you face challenges with your or the opposing side’s closing arguments?

34. Did you face challenges with the jury’s deliberations?

35. Did you face challenges with any post-verdict motions?

36. Did you face challenges with trial publicity?


Putting It All Together

These 36 questions should get your and your colleagues’ gears turning regarding the obstacles you faced on the way to securing a favorable litigation result for your client. Not every question will apply to a particular litigation, and that’s fine. Your goal is to identify the 3–5 most compelling obstacles that will form the core of your article.


By the way, if you’re curious about what makes a particular obstacle and how you overcame it compelling, here’s what I would look for:

  • The obstacle required a creative or innovative approach, which included an element of boldness or counter-intuitiveness
  • Experience played a key role in overcoming the obstacle
  • The obstacle is one likely to be faced by other clients/litigants


As you write “How We Did It” articles, you might discover more questions you can add to this list to help get your creative juices flowing in the future. But as is, this list of 36 questions should give you plenty of inspiration for your next “How We Did It” article.

Wayne Pollock is the founder of the Law Firm Editorial Service. The Law Firm Editorial Service sets free the knowledge and wisdom trapped inside Big Law and boutique law firm partners by collaborating with them to strategize and ethically ghostwrite book-of-business-building marketing and business development content. Learn more at: www.lawfirmeditorialservice.com.

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