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The Value of Uncomfortable Questions

“When virtue founds a town, the town thrives and abides.” – Ghanaian Proverb

Great and effective leadership is not merely about making decisions or giving orders. It is about creating an environment of openness, growth and continuous improvement. It has to do with fostering a culture of truth-seeking for efficiency and effectiveness. And it should ensure the needs of everyone can literally be tuned in. Put simply, it is about the leader attuning him or herself with the team and the community at large. And one of the most impactful ways leaders can achieve this is by asking difficult questions that elicit honest answers, even when those answers might be uncomfortable.

It is no secret that leaders often grapple with the complexities of decision-making. And it is well known that leaders are often advised and encouraged to seek answers that challenge their perspectives. This attitude is both an art and a necessity. The reason being that leadership is not immune to self-deception or a distorted perception of reality. The essence of asking uncomfortable questions is forcing leaders to confront their biases, assumptions and blind-spots, paving the way for creative and effective leadership and meaningful organisational progress.

As human beings, we have a natural leaning for our comfort zone. It grants us a state of familiarity and security. Sadly, this zone inhibits our growth. And in the case of leaders, it limits their ability to make a difference in their sphere of influence. Interestingly, embracing discomfort ignites a process of self-discovery that challenges our boundaries and expands our horizons. That is why we have been told time and time again that it is within the uncomfortable zone that the seeds of personal development are sown.

Stepping into the uncomfortable zone starts with asking uncomfortable questions.  Not only does that attitude serve as a reality check, but it also prevents leaders from operating in a bubble. Every leader should have knowledge about the motivations of their team members. Questions like “why teams members joined the organisation” should be frequently tackled to shed light on the alignment between individual aspirations and organisational goals. Where there are misalignments, leaders can then work toward strengthening the organisation’s engagement and culture.

Asking uncomfortable questions requires courage and a willingness to face potential discomfort. As a leader, you must overcome the fear of receiving answers that challenge their preconceived notions. The key lies in recognising that growth often emerges from discomfort. Thus, welcoming constructive criticism and acknowledging that not all answers will be positive with an open mind is essential to the success of your leadership. It helps you to recognise areas of dissatisfaction and empowers you to address concerns promptly, fostering a workplace and community wherein employees and the general populace respectively feel valued and motivated.

One of the fundamental reasons leaders should cultivate the art of asking uncomfortable questions is related to the factor of self-awareness in leadership. Asking questions like “How am I doing as a leader? What could I improve?” demonstrates vulnerability and humility. Leaders who seek feedback acknowledge their imperfections and express a willingness to grow. By identifying areas of improvement, leaders model a culture of continuous learning; thus inspiring their teams to embrace self-improvement.

We all cringe at hearing uncomfortable truths, but it is better to cringe early and cringe fast than to fail and firefight. The call, then, is to confront realities head-on without delaying or avoiding the truth, to become a better leader. It involves treating uncomfortable insights as opportunities for positive change rather than threats to one’s ego. This mindset shift is transformative, enabling leaders to embrace discomfort as a catalyst for growth.

And to effectively incorporate the practice of asking difficult questions, leaders must foster a culture that values transparency, trust and open communication. That leaders everywhere must create safe spaces where people can express their thoughts without fear of retribution is fundamental. When individuals feel secure in voicing their concerns, leaders gain access to valuable insights which might otherwise remain hidden.

The impact of asking uncomfortable questions goes beyond individual growth. It extends to the transformation of businesses, communities and nations. By addressing issues proactively, leaders create an environment where challenges are tackled head-on. This approach prevents minor concerns from snowballing into significant problems that impede progress. At the very least, regular feedback loops are essential. Leaders can set up mechanisms for anonymous feedback or one-on-one conversations to encourage honest dialogue. This demonstrates a commitment to improvement and sends a message that diverse perspectives are valued.

Embracing the potential discomfort of seeking truth fosters an environment of authenticity, continuous learning and collaboration. Effective leadership is not about preserving a comfortable status quo; it’s about propelling individuals and organisations toward their fullest potential. By embracing uncomfortable questioning, leaders not only invite transformation but also demonstrate the courage to face challenges head-on. As we navigate the complex terrain of leadership, let us remember that growth often arises from embracing discomfort and seeking answers that inspire positive change.

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Kodwo Brumpon is a partner at Brumpon & Kobla Ltd., a forward-thinking Pan African management consultancy and social impact firm driven by data analytics; and with a focus on understanding the extraordinary potential and needs of organisations and businesses to help them cultivate synergies that catapult them into their strategic growth and certify their sustainability.

Comments, suggestions and requests for talks and training should be sent to him at kodwo@brumponand kobla.com

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