Steve Jobs’s decision to streamline Apple’s product line in 1997 was a pivotal moment in the company’s history. Confronted with a cluttered array of over a dozen Macintosh models, Jobs recognised the need for a radical overhaul. According to Walter Isaacson’s 2011 biography, ‘Jobs interrupted a product strategy session, grabbed a marker, and drew a horizontal and vertical line to make a four-squared chart. Atop the two columns, he wrote “Consumer” and “Pro”; he labeled the two rows “Desktop” and “Portable.” Their job, he said, was to make four great products, one for each quadrant.’ This move epitomised Jobs’s commitment to challenge groupthink and focus on quality over quantity—a strategy that would define Apple’s resurgence in the years to come.

As we all know, effective leaders not only ask good questions but, like Steve Jobs, they also challenge assumptions and groupthink. They particularly have their antenna up when they encounter the dreaded refrain of “that’s the way we’ve always done it.” In a world where complacency is the enemy of progress, leaders must disrupt the status quo and embrace contrarian viewpoints. Innovation thrives in environments where dissent is welcomed, and conventional wisdom is subject to rigorous scrutiny. By encouraging a culture of intellectual curiosity and constructive dissent, leaders can empower their teams to think differently, drive meaningful change, and achieve extraordinary results. But how do you best do that?

One effective way of addressing the challenge is adopting the concept of red teaming—a practice borrowed from military strategy — which has gained prominence as a means to mitigate cognitive biases and foster critical thinking. Bryce G. Hoffman’s seminal work on the topic, ‘Red Teaming: Transform Your Business by Thinking Like the Enemy,’ serves as a testament to the value of seeking contrarian advice to challenge entrenched assumptions and overcome organisational blind spots.

Drawing parallels between military operations and corporate decision-making, Hoffman offers a powerful framework for challenging assumptions and combating groupthink. He advocates appointing dedicated teams tasked with scrutinising strategic plans and assumptions from an adversarial perspective. By adopting the mindset of a competitor or adversary, red teams are empowered to identify vulnerabilities, anticipate challenges, and propose alternative courses of action.

🙋 Where could you challenge groupthink and embrace contrarian views? 🙋‍♀️

Best regards, Brian