Failure gets a bad reputation. In reality, it’s rarely the end of the story. It’s often the turning point.

Leaders and entrepreneurs who thrive aren’t the ones who never stumble. They’re the ones who stumble often, ask the right questions, and use what they learn to move forward with a sharper vision and stronger conviction.

In a recent conversation, Bob Hoeffner and I explored how to “fail forward” — embracing missed targets and setbacks not as dead-ends, but as invitations to regroup and refine the strategy.

When “Non-Success” Becomes Your North Star

Sometimes a missed target isn’t failure at all — it’s helpful data. Learning to treat these “non-success” moments as raw material for growth helps you to develop an important muscle that eventually leads to success: resilience.

“When a goal falls short, the work isn’t in covering up — it’s in asking what went wrong.”

Take the restaurant industry. During COVID, Bloomin’ Brands (parent company of Outback and Carrabba’s) had to shut dining rooms overnight. Instead of freezing, executives met daily to ask “what if” questions to combat the sudden drop in restaurant visits. Outback rolled out car-side delivery, something they’d never done before, and it worked.

So while Bloomin’ entered 2020 with 88 percent of its business coming within the four walls, today 26% of Outback’s sales are off-premises, and Carrabba’s is at 35% — a permanent shift born from a crisis. (Source: FSR Magazine)

Asking the Right Questions Beats Blaming

When you fall short of your goals, it’s tempting to point fingers. But blame shuts down possibility. Curiosity opens it back up.

“The moment you stop asking why and start asking who’s fault, you’ve already killed the chance to innovate.”

Take the story of Toyota’s famous “Five Whys” practice. When a production error showed up on the line, leaders didn’t punish workers or scapegoat departments. Instead, they asked “why” five times until they uncovered the root cause — often a process flaw, not a person. That mindset built Toyota’s culture of continuous improvement and helped fuel decades of innovation. (Source: Interaction Design Foundation)

Leaders who trade blame for inquiry don’t just solve the immediate problem. They build systems that learn, adapt, and keep improving long after the crisis has passed.

Conviction Isn’t Arrogance — It’s Rooted in Evidence

Bob described a pivotal moment he had pitched an exciting new program to executives, only to be told, “Bob - this isn’t your job.” Instead of backing down, he insisted the executive take a closer look, armed with data. Sure enough, once the program was expanded into a second state, it proved its value and was quickly rolled out company-wide, becoming a major profit driver for the company.

“Getting kicked in the teeth is part of the deal. Use it to move forward.” 

History repeats this lesson. Blackberry clung to its keyboard obsession while Apple challenged its own assumptions by testing the limits in how streamlined its user interface could go. The result was a revolution in how the world communicates (keyboards not required).

Conviction without listening is arrogance. But conviction paired with data, humility, and persistence? That’s innovation.

The Power of Piloting & Iteration

Big, bold ideas don’t land overnight. Smart leaders think like experimenters: pilot, test, refine, repeat.

“Conviction is sticking behind an idea long enough to let it prove itself.”

When Kristiana worked at Target headquarters, early advocates were experimenting with drive-up ordering, but some leaders were skeptical, calling it a “luxury for lazy parents.” The team boldly pressed forward anyway, continuing to refine the experience with small pilots to grow adoption.

When COVID hit, Target’s investments in Drive-Up paid off, leaving others wondering how they had been so clairvoyant. They had the tech, the operations model, and a customer experience well defined to scale seamlessly while other retailers were behind the eight ball, scrambling to catch up. 

Today, Target's Drive Up service accounts for nearly half of its total digital sales (Source: DigitalCommerce360)

Those numbers didn’t come from one grand rollout. They came from iteration and relentless testing over time in service of a great customer experience.

Humility + Optimism: The Leader’s Balancing Act

At the heart of failing forward is a paradox. Leaders must be humble enough to learn from mistakes, yet optimistic enough to believe in a bigger future.

“Great leaders balance bold vision with grounded humility.”

Humility means asking deeper questions, listening to ideas from unexpected places, and owning the losses without blame. Optimism fuels the resilience to keep trying, even when you’re in the messy middle of learning and it doesn’t feel like winning.

Final Thought

Failure is inevitable, but stagnation is optional. The leaders who thrive are the ones who lean into the hard moments, extract the lessons, and keep thinking five steps ahead. My hope is that these stories will remind you that your next stumble might just be the seed of your next breakthrough.

▶️ Watch the full conversation here

Which of these lessons resonated the most with you? I'd love to hear your thoughts.

______

Kristiana Corona, PCC, is an ICF-certified leadership coach and founder of Worthy to Lead. She guides leaders to redesign their leadership with curiosity, courage, and commitment. WorthytoLead.co