10 Questions to Ask When You Fail

You can either plow forward and pretend that failure never happened, or you can treat it as an investment in your future success.


At some point in your career, you’re going to experience failure. Probably numerous times. And when you do, you have a choice. You can either plow forward and pretend it never happened, or you can treat it as an investment in your future success.

If you want to take the latter option, here are several questions to help you get the most insight out of the experience:

1. How did this happen?

Start with a simple, “How did this happen?” Unless the failure came out of left field and had nothing to do with you, there is typically chain of actions and events that led to the failure. Tracing that chain of events can help you find the weak links.

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2. Why did this happen?

Once you have a better understanding of how it happened, it can be helpful to understand why. Was something missing? Did you need more information than you had? Was your assessment of the opportunity off? Were you less prepared than you thought you were? Did your plan have holes in it? When you understand why something has gone sideways, you are in a better position to understand how to avoid similar troubles in the future.

3. What were the pieces in the puzzle?

The steps and events that led to the failure aren’t the whole picture. There are frequently influencing factors at work as well. Look at it as a multi-dimensional puzzle. What are the different pieces that had an impact on that failure? How did it all fit together? Knowing what all the pieces of the puzzle are gives you a better sense for what really happened and allows you to recognize similar patterns as they unfold in future efforts.

If you headed up a project that imploded, for example, some of the pieces of the puzzle could spring from your own handling of the project. But it could also have been influenced by a boss who hadn’t completely bought into the need for the project, or a lack of resources allocated to that project, or a shift in the market that made the project less desirable or important.

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4. Who played a role in this?

One of the pieces of the puzzle is the role other people played in that movement down the road to failure. Take stock of how other people had an effect. Don’t do this from a place of blame. You’re just trying to get the best objective understanding you can of what actually happened so you can both explore alternatives and recognize the red flags earlier in similar situations.

5. Who didn’t play a role in this that needed to?

You might also find that the failure was influenced by the absence of people. For example, you may realize that you thought you could do it all yourself, but you really needed others supporting you. Or that you really needed a mentor in the picture to guide you along the way. Or that you needed a detail person involved to complement your wild and woolly visionary ways (or vice versa).

6. What assumptions did I make? Were they right?

We all make assumptions. Sometimes we make them because of what we think we already know, and sometimes we make them because we don’t have enough solid information to go on and we have to make an educated guess. Check the assumptions you made along the way. Were they right? Were any of them off target? What can you learn from that?

7. What could I have done differently?

Tap into the power of 20/20 hindsight. Given what you know now, what would you do differently?

8. When could I have headed the failure off?

Go back to the steps and events you identified by asking, “How did this happen?” Is there any point where you could see things starting to drift off course? Are there any points where if you had taken a different action, gotten more resources, etc., you could have avoided the failure?

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9. Who could help me learn from this?

Mulling over what happened or sitting down and journaling is a good start, but it can also be helpful to bring someone else into the picture for an objective perspective. That could be a friend, a colleague, or even a career coach.

10. What are the key things I have learned from this? How can I apply that insight in the future?

Once you have gone through all the effort of exploring what happened and why, don’t just leave those insights in a pile on the floor. Make an inventory of the key insights that came out of it. It should be an at-a-glance summary, perhaps in bullet point form. You might even create a file to keep what you have learned from your mistakes and failures, and scan back through it regularly to keep those insights fresh.

Sometimes failures truly aren’t your fault, and occasionally your mistakes will be just boneheaded moves where the only thing to learn is “don’t do that.” But for a good chunk of them, there will be something to learn with a little extra effort. And since failure is bound to be part of your journey, doesn’t it make sense to make the most of it?

After years as a professional malcontent, Curt Rosengren discovered the power of passion. As speaker, author, and coach, Rosengren helps people create careers that energize and inspire them. His book, 101 Ways to Get Wild About Work, and his E-book, The Occupational Adventure Guide, offer people tools for turning dreams into reality. Rosengren's blog, The M.A.P. Maker, explores how to craft a life of meaning, abundance, and passion.


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