Fail more to learn faster

Context shapes every aspect of software testing, yet its dynamic nature often requires testers to operate with humility, curiosity, and a willingness to challenge established norms. “It depends” is not a deflection but an honest reflection of the uncertainties teams face, especially as technology and organizational priorities rapidly evolve. By asking better questions, focusing on collaboration, and remaining open to failure as a source of learning, software testers can influence both quality strategies and team culture. The constant demand for adaptability reveals that questioning processes and embracing the unknown are powerful drivers for lasting improvements in software quality.

Podcast Episode: Fail more to learn faster

In this episode, I talk with Chris Armstrong about context in testing. We talked about why "it depends" is an honest answer in complex work. Chris shows how decisive humility helps. Say what you do not know. Find the people and data to learn fast. We talk about fear, optimism, and why winners collect more failures. I ask how testers grow influence. We land on trust, social skills, and asking better questions. Challenge tools and processes with respect. Start small with clear hypotheses and visible outcomes. Remove unnecessary friction. AI comes up as a fresh field for testing. Join early, shape it. Stay curious. Context moves, and so should we.

"We don't really exist in a world where everything is known before we start our work. And so the value of context is incredibly important." - Chris Armstrong

Chris Armstrong is tester always looking to improve. His testing journey began in 2004 and has crossed several different industries. He identifies as a pragmatic agilist and quality practices geek.

He advocates for inclusion, collaboration and continuous improvement.He loves learning and storytelling, and aims for his blog to be a platform for him to process his thoughts and observations. It is not intended to be instructional, but more an insight into how he sees the world and to be an outlet.

He also podcasts as part of a group of test leadership peers, the Testing Peers

Highlights der Episode

• "It depends" is an honest answer in complex work
• Admit unknowns and seek data to learn fast
• Grow influence through trust, social skills, and better questions
• Start small with clear hypotheses and visible outcomes
• Join AI testing early and help shape practices

Embracing Context, Uncertainty, and Growth in Software Testing”

Context - The Cornerstone of Honest Testing

In a recent episode of Software Testing Unleashed, host Richie sat down with software testing veteran Chris Armstrong to untangle one of the craft’s most habitual, but misunderstood, answers: “It depends.” But as Chris explained, this isn’t a cop-out. In fact, it’s the most honest answer a tester can give, because every project, team, and even every day brings a slightly different web of people, software, expectations, and uncertainties.

Chris made it clear: “I can give you an answer of what I think from history and from experience and from reading what something might be. But until I understand full context, I don’t know what will happen.” In modern projects—where tech, tools, and requirements constantly shift—being flexible and pragmatic has become more important than rigid expertise.

This understanding of context shapes better strategies, smarter collaboration, and more sustainable improvements.

Decisive Humility: The Tester’s Superpower

It’s not just about what you know, but knowing what you don’t know. Chris coined the idea of “decisive humility”—being upfront and even confident about your uncertainties, while knowing how to channel them into finding answers. This isn’t just a philosophical stance. It’s a practical skill that lets testers tread the line between caution and optimism, especially in disruptive times like the current boom in AI tools and methodologies.

The most future-ready testers aren’t those with the most certificates, but those who can admit gaps in their knowledge, ask for help, and stay in learning mode. As Chris put it, “Comfort in the unknown is kind of something that we have to become masters of.” When testers see uncertainty not as a threat but as a chance to experiment and grow, they position themselves at the heart of innovation—rather than being swept aside by it.

Collaboration, Social Skills, and Asking Better Questions

Testing is a social activity. That’s not just a slogan—it's a survival tactic. Success rarely happens in isolation, and testers who ask smart questions, show empathy, and tailor their messages to the values and needs of their teammates build trust and leverage. Chris touched on his experience adapting the “Five Love Languages” for tech teams, arguing that understanding what makes your colleagues tick (whether developers, business analysts, or support staff) is as essential as knowing a testing tool or framework.

Listening, empathy, and respectful questioning turn testers from naysayers to quality advocates who unite teams around improvement. “We can’t succeed as an island,” Chris stressed. “We need other people to succeed.”

Challenging Tools, Processes, and Status Quo

Chris and Richie also explored the role of testers as critical thinkers—not just about software, but about the tools, processes, and decisions that underpin teams. Testers are often uniquely placed to sense friction: “If we don’t question why something exists, what its purpose is, what the story behind it is, then we might be using the wrong technology.”

This willingness to challenge, gently and respectfully, isn’t about scoring points—it’s about making sure the team isn’t stuck with decisions that no longer serve them. Even if it takes courage to ask why a tool was bought or a process is followed, most people appreciate the opportunity to share their reasoning—especially when approached with humility, not aggression.

Focusing Questions and Efforts for Real Impact

With so many possible avenues for inquiry, prioritization is crucial. Chris recommends beginning with hypotheses—perhaps focusing on frequent pain points around releases or support. “You need tangible outcomes for your work,” he advised. Pursue the questions and initiatives that show visible benefits and reduce friction, then build trust by sharing these small wins.

And when uncertainty leads to the occasional failure? That’s part of the process. As Chris reminded listeners, “Winners have more failures than losers.” Each learning experience, especially when shared, adds richness to the team’s collective wisdom—and ultimately moves quality forward.

Today’s testers face ever-shifting challenges, but Chris and Richie’s conversation is a reminder that context awareness, decisive humility, and strong collaborative skills aren’t just nice-to-haves. They’re the very qualities that turn testers into influential change-makers—people who not only adapt but drive continuous improvement in this complex, unpredictable software world.