Learning to Love Failure: A Startup Founder’s 8-Step Guide to Embracing Mistakes

Learning to Love Failure: A Startup Founder’s 8-Step Guide to Embracing Mistakes
Learning From Failure

8 min read
← Back to blog articles

Learning to Love Failure: A Startup Founder’s 8-Step Guide to Embracing Mistakes

“I've missed more than 9,000 shots in my career. I've lost almost 300 games. Twenty-six times I've been trusted to take the game winning shot and missed.”

Do these words make you think of failure? For those less familiar with his career, the speaker of this quote is basketball legend Michael Jordan. Clearly, failure did not prevent his ascent. In fact, Michael often credits failure with being instrumental to his growth.

As founders, we must adopt the same mindset that stumbling merely teaches us to walk taller. Rather than be sidelined by imperfections, we must meticulously mine our missteps for insights which inform future success. Through disciplined post-mortem analysis and systems enabling agile course correction, any startup can transform mistakes from the end of the road to signposts guiding the way ahead.

The Mindset Shift

In traditional companies, failure carries heavy stigma. It’s associated with bad performance warranting disciplinary action or termination. Those unlucky enough to have a major project or product flop see blame directed their way. Management consultant Kim Warren likens this dynamic to colonial witch trials determining who to burn at the stake.

Startups can’t afford such counterproductive thinking. In the unknown, errors are expected mile markers. Mistakes signal where faulty assumptions lurk and new learning is required. Without repeated trial and error, the step changes needed to advance industries wouldn’t emerge.

This fact demands startups adopt failure-positive cultures. Initiatives developing breakthrough innovation won’t always stick perfect landings. But breakdowns provide vital data. Startups thrive by building mechanisms to extract those learnings rapidly into future attempts. Failure equals learning; not proof of inadequacies.

The world’s most impactful founders embrace this. James Dyson made over 5,000 prototypes before producing a working vacuum. What others saw as repeated failure, he saw as eliminating dead-ends enroute to discovery. Through perseverance, imperfections transformed into a $5 billion empire.

Using Mistakes as Innovation Fuel

Thomas Edison once commented on his thousands of failed attempts to invent the lightbulb: "I have not failed once. I’ve just found 10,000 ways that do not work.” That’s the mindset startups need today. Experiments reveal truth; false positives expose the path forward. With each misstep, the odds improve of stumbling upon breakthroughs.

Pixar President Ed Catmull stresses this in outlining why failure is a prerequisite to originality:

“If you aren't experiencing failure, then you are making a far worse mistake: You are being driven by a desire to avoid it. And for leaders especially, this strategy -- trying to minimize mistakes -- is a terrible approach. The key is reducing fear. You want the people working for you to feel free to explore new ideas -- and free to fail...without fear.”

Google executives echo similar views. Former SVP of Products Jonathan Rosenberg argues that in a scaling-up company, avoiding errors actually increases errors. Conservatism is contraindicated because it treats every error as fatal...Yet with the right strategies in place, errors and failures are great assets.

Why? Mistakes redirect teams from less promising efforts before excessive resources are committed. Lost time and money tell startups where NOT to invest more. Negative signals magnify as positive indicators where to target attention.

Crumbled Paper into Successful Ideas

Turning Failure into Insight

To extract maximum learning, startups must institutionalize post-mortem habits. After any material mistake, misfire or failure, conduct an autopsy. Establish blameless, consistent reviews focused exclusively on gleaning strategic takeaways.

The emphasis should rest solely on extracting transferable nuggets to inform next moves; never finger pointing.

To standardize and scale this process across an organization, an 8-step post-mortem framework can be utilized. It ensures teams methodically evaluate what succeeded and why alongside what failed and how. Done in an evidence-based, non-emotional manner soon after a mistake, it accelerates turning losses into gains. The process involves:

  1. Setting Context – Outline initiative goals, team members, timeline, resources invested
  2. Describing Playback – Reconstruct key decisions made sequentially from start to finish
  3. Identifying Pivots – Flag key changes in strategy, obstacles or results that altered direction
  4. Scoring Outcomes – How did results measure against original hypotheses and metrics?
  5. Isolating Successful Factors – Which elements performed well and why? Can they be amplified?
  6. Pinpointing Failures – What underdelivered and why? Were faulty assumptions to blame?
  7. Extracting Insights – What are the 1-3 biggest lessons & takeaways for future efforts?
  8. Discussion Action Items – Based on above, what culture or process improvements make sense?

Codifying a post-mortem system trains employees to spotlight blindspots hiding promising pathways. It frames failure as healthy tension strengthening strategies and safeguarding from large fumbles. Gradually, setbacks no longer feel threatening but exciting signals that discovery is accelerating.

DNA

Baking Resilience into Team DNA

Beyond technical post-mortem mechanics, founders must nurture cultures normalizing mistakes to alleviate underlying emotions when things go wrong. Progress entails emotional resilience as ideas routinely disappoint in high variance domains.

Pixar calls teams to “amplify the signals of failure” as opposed to working to hide defects. This begins by leaders modeling humility and non-defensive openness discussing organizational shortcomings. When the CEO shrugs at botched initiatives, anxiety around failure dissipates.

Weave messaging reminding everyone mistakes mark progress. Demonstrate recalibrating based on imperfect outcomes is not scary course correction but exciting refinement. Celebrate learnings uncovered from less optimal results that strengthen strategy. Highlight examples of past failures that became stepping stones to breakthroughs.

And most importantly, resist knee jerk reactions. Early stage chaos breeds misjudgments. Stay calm and processes when interpreting apparent catastrophes. Some supposed disasters transform into catalysts given patience and wisdom. Remember setbacks sometimes produce breakthroughs in disguise.

Mastery emerges through the courage to fall, get back up as lessons elevate performance to new heights. Athletes, artists, entrepreneurs...all elite creators adopt mindsets recognizing stumbles as unavoidable companion on the ascent towards greatness.

Owning Errors with Accountability

While post-mortems shouldn’t focus on blame and punishment, accountability remains essential. Those responsible for decisive actions or oversights that critically impact outcomes must be identified, especially in severe cases. But accountability isn’t about fault-finding; it’s about responsibility.

Combining blameless cultures with personal responsibility honors how in innovation-driven environments all actions have tradeoffs with unknowable downstream effects. Discovery can’t happen without risk. Early decisions later prove right or wrong as new data emerges in unforeseeable ways.

This uncertain reality demands fairness in assessing impact. Outcomes can’t always be predicted. But individuals with agency over key contributions influencing downstream effects should be tracked, studied and refined for better alignment.

To enable this, leaders must separate contributor evaluation from action/outcome accountability. Judgements of performance, character or potential should never be entangled with responsibility for results. Evaluations address the person; accountability addresses actions tied to outcomes.

With this delineation between absolute accountability and context-based judgment, post-mortems avoid finger pointing while still tying results to choices at personal levels. This honors the agency all have over certain contributions while recognizing the many unknown variables that influence success in pioneering pursuits.

Turning Mistakes into Strength

In startups taming chaos into order, plans rarely survive contact with reality. But rather than collapse, founders respond by rapidly integrating hard-fought wisdom into newer, shinier, bolder plans. Mishaps shape resilient leaders.

Stanford researchers found that entrepreneurs don’t build tolerance by avoiding difficulties but through managing hardship: “They build resilience through choosing harsh over easy environments and by framing their exposure to challenges as an escalating ladder of difficulty.”

Like exercise straining muscle, every mistake tears fibers so that the lessons can rebuild us stronger. But this only works by first creating environments where people feel safe revealing flaws, exposing gaps, raising counter-positions without reprisal. Psychological safety unlocks collaborative strength compounding our collective efforts.

The catalyst for this dynamic lies in leadership mindsets that reframe trials as not liabilities but as learning opportunities for growth. Setbacks become rebranded as stepping stones when examined as treasure maps containing hard-won wisdom. The most impactful startups use these post-mortems to spotlight blindspots and uncover pathways hidden amidst the fog of war. This process gradually removes stigma from mistakes, allowing them to become waypoint markers that accelerate progress.

In this sense, errors are inverted. Rather than something to dread, they become valuable artifacts, welcomed for the clues they contain. Each misstep brings founders closer to the outcomes they seek, as long as they maintain systemic discipline in how they process and level up from temporary defeats. This is why high performers graciously accept failures, confident the feedback will compound into excellence.