Why Leaders need people to challenge their decisions

One of the most vital qualities in effective leadership is the ability to make sound, informed decisions. However, when leaders surround themselves only with people who agree with them—those “pleasers”—they miss out on valuable perspectives and insights. The best leaders aren’t necessarily the ones who have all the answers, but those who seek out diverse viewpoints and are open to being challenged. By inviting alternative opinions and honest feedback, leaders strengthen their decision-making and create an environment that fosters innovation and resilience.

The Value of Constructive Challenge

Encouraging constructive challenge in a team is not about inviting unnecessary conflict; it’s about welcoming fresh ideas and diverse thinking. Having people around who can question, analyse, and critically assess decisions helps uncover blind spots, reduce risks, and encourage deeper thought. This approach helps avoid “groupthink,” where teams align too closely in their opinions to maintain harmony. Groupthink may feel comfortable in the short term, but it often leads to poor choices and missed opportunities in the long run.

Surrounding yourself with people who aren’t afraid to challenge decisions creates more robust solutions. Hearing different ideas and approaches strengthens leaders’ resilience, helping them face the unexpected and adapt to change with a broader perspective.

The Pitfalls of Pleasers

When leaders surround themselves with people who only agree, they can fall into the trap of “confirmation bias,” where they only seek and value information that supports their own views. Over time, this stifles creativity, as diverse thoughts and innovative problem-solving are sidelined in favour of a safe consensus.

Pleasers, however well-intentioned, can reinforce false confidence. Leaders might feel reassured that they’re on the right path when, in reality, they’re missing important details or heading towards obstacles. Leaders who work with teams willing to speak their minds benefit from a “reality check” that keeps projects and strategies grounded, rather than clouded by wishful thinking.

Why Great Leaders Value Disagreement

Long-term success in leadership often comes to those who cultivate an environment where honest feedback is encouraged, where it’s safe to say, “I see it differently” or “Have we considered this angle?” Rather than surrounding themselves with “yes” people, great leaders seek those who respect them enough to offer genuine, constructive challenge. Many influential leaders have embraced this approach:

• Steve Jobs valued the input of employees who weren’t afraid to push back. Jobs actively encouraged debate and discussion, seeing it as a route to the best possible outcome.

• Indra Nooyi, former CEO of PepsiCo, often asked her team to play “devil’s advocate.” By encouraging diverse viewpoints, Nooyi gained insights that were essential to PepsiCo’s growth and resilience.

• Elon Musk actively seeks out contrarian opinions, believing that disagreement is essential to the innovation and problem-solving efforts at SpaceX and Tesla.

These leaders understood that respect and honesty are the foundation of effective teams. By inviting different perspectives, they avoided the stagnation that comes with echo chambers and promoted a culture of open communication and mutual respect.

How myexec Can Help Leaders Embrace Challenge

At myexec, we understand that being surrounded by like-minded voices can sometimes limit a leader’s perspective. Our role is to act as an unbiased sounding board, providing the honest, constructive challenge that leaders need to make informed, well-rounded decisions. We bring a fresh perspective to the table, asking the tough questions and presenting alternative viewpoints that may otherwise go unconsidered.

Working with myexec isn’t about being told what to do; it’s about engaging in a collaborative, explorative process that encourages leaders to think deeply and make decisions that are both informed and resilient. Our approach ensures that leaders avoid the pitfalls of “confirmation bias” and groupthink, equipping them to lead with a clear, balanced view.

Building a Culture That Embraces Challenge

To avoid the pitfalls of surrounding oneself with pleasers, leaders can take several steps to cultivate a team that’s unafraid to challenge ideas:

1. Encourage Diverse Opinions: Actively invite team members to share their perspectives on key decisions, and recognise those who bring forward new ideas, even if they are unconventional.

2. Create a Safe Environment: Make it clear that all voices are valued and that constructive criticism is viewed as a strength rather than a threat.

3. Challenge Yourself to Listen: When team members offer opposing viewpoints, make a habit of truly listening and considering their perspectives before arriving at a final decision.

4. Seek Out a Trusted Network: Leaders benefit greatly from a trusted network of advisors or mentors who can provide honest, external feedback and bring fresh perspectives.

The Benefits of Welcoming Challenge

Building a team that feels empowered to challenge ideas has lasting benefits for an organisation. Leaders who value diverse perspectives make decisions that are well-rounded, carefully considered, and aligned with long-term goals. Such leaders earn a reputation for transparency, integrity, and adaptability, fostering respect and loyalty within their teams.

Ultimately, leaders who value differing perspectives—who understand that being challenged is an opportunity, not a threat—position themselves and their organisations for long-term success. Surrounding ourselves with people who respectfully encourage us to improve is one of the most powerful steps we can take towards effective leadership and growth.

By working with myexec, leaders are equipped to embrace this approach. We offer an objective, respectful space to explore different viewpoints and find clarity, helping leaders feel supported and prepared to navigate the complex landscape of today’s business world.