56 Questions I Ask Myself Every Time I Fail

Like all Atlanta Falcons fans experiencing dashed championship dreams, I’m asking, “What happened?” The sun didn’t come out that day. It was chilly, rainy and dreary. We blew a 25 point lead with 20 minutes left.

Asking the Tough Questions

I’ve been in technology startups for 40 years as an entrepreneur, investor and advisor. A few times, very few, I’ve been on championship-caliber teams. More often, it is just an okay team. And then there were some losing teams. Without a doubt, I have learned more from the losses than the wins.

After each loss, I have consistently taken the time to dig deep and ask myself tough questions. I need to know what happened. Here are the areas I explore and the questions I force myself to answer.

My performance

  1. Did I believe?
  2. Did I lead?
  3. Did I do all I could have done?
  4. Did I listen?
  5. Did I learn what I should have learned as we were building the company?
  6. Was I as prepared as possible for this investment?
  7. Should I have partnered with others on this deal?

Team performance

  1. Did we love each other?
  2. Were our conversations real?
  3. Did we say what needed to be said, or did we fall victim to platitudes and artificial relationships?
  4. Did we address the right personnel issues?
  5. Did we trust each other?
  6. Did each of us do our job to the best of our ability?
  7. Did we have the wrong people in leadership positions?
  8. What functional areas failed and which succeeded?


  1. Why did I think the strategy would work in the first place?
  2. Did I believe in the strategy, or did I just go along?
  3. When did we know it wasn’t working?
  4. When should we have known it wasn’t working?
  5. Was there a clear alternate strategy?
  6. Did I stick with a losing strategy just because it worked once before for me?
  7. Was our product right?
  8. Was our market right?
  9. Was our offer right?
  10. Was the market buying from anyone?
  11. Was the strategy too broad or too focused?
  12. Did we have a fallback?
  13. Did we have a hard quit point identified?


  1. Did we make the calls we should have made when we were supposed to make them?
  2. Were we talking to the right people?
  3. Did we have intensity?
  4. Did we have persistence?
  5. Was everyone doing what they were supposed to be doing?
  6. Did we measure results?
  7. Were we coordinated?


  1. Was the founder the right person at the right time?
  2. Was there humility?
  3. Was there openness to coaching?
  4. Was there confidence?
  5. Was there communication?
  6. Was there commitment?
  7. Was there engagement on the ground?
  8. Did the team believe in the leadership?
  9. Did the leader manage well up and down?
  10. Did the leader unite or divide?


  1. Were they better than we were? Why?
  2. What was their weakness?
  3. What was their strength?
  4. Why did they beat us?
  5. Were we our greatest competition? Why or why not?
  6. Were we too focused on ourselves?
  7. How did we match up in product?
  8. How did we match up in sales?
  9. How did we match up in ease of doing business?
  10. Were they more persistent or committed to the market than we were?
  11. Did they want it more than we did?

When you win, you learn one thing. Whatever you did worked. And the result is, you won. Losing is the opportunity to figure out what happened so you can improve and ultimately succeed.

Please note: I reserve the right to delete comments that are offensive or off-topic.

4 thoughts on “56 Questions I Ask Myself Every Time I Fail

  1. What a great list. We need more debriefs in life. Great questions are the starting place for any good debrief.

    • I had a close which was taken out in editing which I still think is worth while. We are always interested in what happened when we fail or lost but the people who win more than lose also ask these questions after a big win. I’m sure Brady and Bellichick did after the SuperBowl.

    • Interesting you found them so helpful. I had a VC friend of mine call it “self flagellation.”

      I am always stuck by how much people like lists.

      Thanks for reading the articles and commenting publicly. You are an encouragement to me and others.

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