Failure Shows You How

The most effective directors aren’t those who are always right, but those who never stop learning. This blog shows how thoughtful reflection on successes, setbacks, boardroom discussions, and difficult decisions can improve judgment and long-term contribution.

When I first heard Jamaican sprinting legend Shelly-Ann Fraser-Pryce say, “Failure shows you how," the words stayed with me.

They carry extra weight when you consider who is saying them.

Fraser-Pryce rose from modest beginnings in Kingston, Jamaica, to become one of the most accomplished sprinters in history. She won Olympic gold in the 100 metres in Beijing in 2008 and successfully defended her title in London in 2012. Along the way, she accumulated world championships, Olympic medals, and a reputation as one of the greatest female sprinters of all time.

After she became a mother in 2017, many assumed her best years were behind her. Instead, she returned to win another world championship in 2019, becoming the first mother in 24 years to capture a global 100-metre title. She did it again in 2022 at age 35, becoming the oldest woman ever to win a world sprint title. Along the way, she battled injuries and setbacks that would have ended many athletic careers.

Her story isn’t simply one of success. It’s a story of learning, resilience, adaptation, and growth.

That’s why her quote resonates.

Boardrooms look very different from Olympic tracks, but directors experience setbacks too. A recommendation gains no traction. A question fails to influence the discussion. A proposal is rejected. A vote goes the other way. A risk you've identified eventually materializes, but not before being dismissed.

These moments can be frustrating. But what if they are also some of the greatest opportunities for growth?

The most effective directors learn from both success and failure.

Success leaves clues. Failure shows us how.

Governance is a Learning Journey

LEARNING MINDSET
The growth lens
Board service is an opportunity to improve judgment, not prove expertise.

Many directors arrive in the boardroom with impressive accomplishments and considerable expertise. That's understandable. Boards are assembled precisely because directors bring valuable experience, insight, and judgment.

But board service isn’t a test of what we already know. It’s an opportunity to continue learning.

Every board operates in an environment of uncertainty. Directors make decisions with incomplete information, among diverse viewpoints, in an environment of competing priorities and a world of constantly changing conditions. No director can get every decision right, or have perfect foresight, or win every debate.

The most effective directors understand that their goal isn’t to be right every time. It’s to continuously improve the quality of their judgment.

The most effective directors aren’t those who are always right. They are those who never stop learning.

Setbacks Come in Many Forms

When directors hear the word failure, they often think about major corporate scandals, governance breakdowns, or strategic disasters.

But most boardroom failures are much smaller and much more personal.

A recommendation is rejected. An idea attracts little support. A committee initiative stalls. A concern is dismissed. A question seems to go nowhere.

Or maybe you discover later that a position you strongly advocated for was wrong.

None of these events will make headlines. Most won't even appear in the minutes.

Yet they can become some of the most valuable moments in your development because, along with  disappointment, comes information.

Failure is often feedback disguised as disappointment.

What Failure Can Teach You

LEARNING FROM FAILURE
The reflective lens
Setbacks provide information that can improve future decisions and contributions.

When things don't go the way we hoped, we have a choice. We can focus our energy on defending our position, or we can be curious.

The learning questions are often more valuable than the outcome itself:

• Did I have all the relevant information?
• Did I challenge my assumptions?
• Did I fully understand the perspectives of other directors?
• Did I communicate my concerns effectively?
• Was I asking the right question?
• Was I more focused on being persuasive than being understanding?

Reflecting on questions like these helps separate ego from learning.

Sometimes the issue wasn’t the quality of the question, but the timing, framing, or readiness of the board to hear it. Understanding that distinction can be just as valuable as evaluating the question itself.

It’s important to remember that failure doesn’t necessarily mean we were wrong. A well-reasoned recommendation may still be rejected. A prudent warning may still go unheeded. A thoughtful question may not gain immediate traction.

The real opportunity lies in understanding what happened and what can be learned from it.

Failure doesn't always tell us that we were wrong. Sometimes it tells us what we still need to learn.

Success Leaves Clues

LEARNING FROM SUCCESS
The importance of observation
Effective directors study the behaviors and practices that create impact.

The opposite perspective is equally important.

There’s an expression, “Success leaves clues,”  popularized by motivational speaker Tony Robbins.

Savvy Directors who want to get better at what they do pay attention to the clues left by success.

Every board includes directors whose contributions consistently add value. They ask insightful questions. They gain influence without dominating discussions. They challenge assumptions respectfully. They build trust over time. They know when to support and when to challenge.

Some directors speak often yet have little influence. Others speak sparingly but consistently move the discussion forward. Observing the difference can be one of the most valuable learning opportunities available for developing directors and seasoned board leaders alike.

What behaviors make these directors effective? What preparation practices support their performance? How do they frame difficult questions? How do they earn credibility?

Your goal isn’t to imitate these directors, it’s to observe and learn from them.

If failure teaches through reflection, success teaches through observation.

Learning from the Directors Around You

One of the underappreciated benefits of board service is the opportunity to learn from peers.

Every board includes directors whose example is worth studying.

Observe how accomplished directors prepare for difficult conversations, ask challenging questions without creating conflict, build support for ideas, encourage productive discussion, and influence outcomes through credibility rather than authority.

Similarly, observe effective board and committee chairs. Notice how they encourage participation, draw quieter directors into the discussion, and create a safe space for alternative views.

Success leaves clues everywhere. The challenge is noticing them.

• Rather than asking, "How did they convince everyone?"
• Ask, "What behaviors helped them earn influence and credibility?"

That latter question leads to deeper learning.

The Question That Changes Everything

THE LEARNING QUESTION
The reflective habit
What is this situation trying to teach me?

After an important board discussion, a difficult decision, or a disappointing outcome, consider asking yourself a simple question:

What is this situation trying to teach me?

It’s a surprisingly powerful question because it shifts the focus from frustration to learning.

Instead of asking:

• Why didn't they listen?
• Why didn't my idea succeed?
• Why didn't I get the outcome I wanted?

The focus becomes:

• What can I learn?
• What can I improve?
• How can I contribute more effectively next time?

With every board experience comes information. The question is whether we capture it.

Learning from Both Sides of the Coin

Shelly-Ann Fraser-Pryce reminds us that Failure shows you how.

Tony Robbins tells us that Success leaves clues.

Savvy Directors pay attention to both. They study what works, and they learn from what doesn't.

They don’t evaluate their own effectiveness by whether their proposal is accepted, the vote goes their way, or their prediction proves correct. Instead, they focus on becoming a little more effective after every board meeting, every discussion, every success, and every setback.

Because the goal of board service isn’t to be right all the time. The goal is to continuously improve the quality of your judgment, your influence, and your contribution.

And sometimes, the lessons that shape us most are found in the moments that didn’t go according to plan.

Board effectiveness isn’t built by always being right. It’s built by continuously improving judgment.

Key Takeaways

• Board service is a learning journey, not a performance test.
• Failure in the boardroom often appears as missed influence, rejected ideas, or unrealized outcomes rather than dramatic governance breakdowns.
• Setbacks provide valuable opportunities to strengthen judgment and effectiveness.
• Reflection turns disappointment into learning.
• Success leaves clues that directors can observe and learn from.
• Savvy Directors learn from their own experiences and the behaviors of effective colleagues.
• Asking, "What is this situation trying to teach me?" can transform both successes and setbacks into growth opportunities.

Resources

• Strategies for Learning from Failure. Amy C. Edmondson. Harvard Business Review. April 2011.
• Rebounding From Failure. Ashley C. Jordan, Ph.D. Psychology Today. August 2025.
• How Smart Teams Turn Failure Into Success. Christopher Wm. Linnane. LinkedIn. October 2024.
• Success Leaves Clues…Not a Blueprint. Danielle Miller. LinkedIn. October 2016.
• Learn from (and Celebrate) Failures. Padraig Coaching. Medium. April 13 2019.
• How to Create Psychological Safety in Your Boardroom. Samantha McGolrick
• Six Key Habits of the Savvy Director. © DirectorPrep 2023.

Thank you.

Scott

Scott Baldwin is a certified corporate director (ICD.D) and co-founder of DirectorPrep.com – an online membership with practical tools and valuable insights for directors at every stage – from first appointment to seasoned board leader.

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