Unpacking Failure: How Asking ‘Why?’ 5 Times Leads to Better Outcomes

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March 31, 2025
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3 min read
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Let’s be honest—stuff goes sideways sometimes.

You miss the mark. A project underdelivers. A campaign flops. It stings even more when it’s your team that put in the work and didn’t get the win. But when that happens, you’ve got a choice: either move on and hope it goes better next time… or dig in and figure out what really went wrong.

That’s where the 5 Whys technique can make a big difference.

I’ve used this simple but powerful root cause analysis method with teams to move past surface-level explanations and uncover what really needs to change. Whether it’s a process breakdown, a misfire in execution, or a misalignment in strategy—5 Whys helps us get better. And that’s the point, right?


What’s the 5 Whys Technique?

The 5 Whys method originated at Toyota as a way to investigate problems on the factory floor. The concept is beautifully simple: start with a problem and ask “why” five times in a row. Each answer should dig deeper into the cause until you arrive at the root of the issue—not just the symptoms.

Let’s say your fundraising campaign missed its goal. You don’t stop at “we didn’t get enough donations.” You ask:

  • Why didn’t we get enough donations?
  • Why didn’t people click on the ads?
  • Why wasn’t the message compelling?
  • Why didn’t the copy connect emotionally?
  • Why didn’t we test different angles early on?

Now you’re getting somewhere.


When Should You Use It?

Use the 5 Whys when the problem is:

Within your team’s control — If the root cause lies with an external partner or factors you can’t influence, this exercise won’t be as effective.

Moderately complex — Not too simple (like “we forgot the password”), not a massive organizational meltdown either.

Team-driven — This is best when your team owned the work and is close enough to the details to understand what might have gone wrong.


How to Run a 5 Whys Workshop

You don’t need much: a whiteboard, sticky notes, or a digital collaboration board like Trello or Miro. Here’s how I usually facilitate:

1. Start with the Problem

Pick one issue to dig into. Frame it as a question: “Why did [this] happen?” Example: Why did our campaign underperform?

2. Set Expectations

Let your team know this is a blame-free zone. The goal is not to point fingers—it’s to learn and level up.

3. Brainstorm the First Round of “Whys”

Have everyone pitch ideas for what caused the issue. Encourage volume over perfection. You’ll narrow it down next.

4. Pick the Most Insightful “Why”

Select one cause to go deeper on (you can vote if needed). That becomes your next question.

5. Repeat 3 More Times

Each answer should prompt the next “Why?”—until you’ve asked five times and reached what feels like the core issue.

6. Identify Actions

Once you’ve uncovered the root cause, brainstorm how to address it. Assign ownership. Set follow-ups. Keep it actionable.


Tips for Running a Great Session

  • Bring in a neutral facilitator if emotions are running high.
  • Run it backwards: Connect the dots from the final answer to the first using “therefore” to see if the logic flows.
  • Avoid blame-y language: “Human error” is rarely the real root cause—look upstream.
  • Go beyond five if you’re not quite there. It’s a guide, not a rule.
  • Try breakouts for big groups to explore multiple paths simultaneously.

Final Thoughts

It’s tough when things don’t go the way we planned. But failure can be a powerful teacher—if we’re willing to learn from it.

Tools like the 5 Whys aren’t just about fixing problems. They help create a culture of continuous improvement, psychological safety, and smarter decision-making. They remind your team that it’s not about being perfect—it’s about getting better, together.

Next time something doesn’t go your way, pause and ask: Why? You might be surprised by what you learn.

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