The trouble with leadership: Conundrums and challenges
The writer

The trouble with leadership: Conundrums and challenges

Leadership is the bedrock for societal and organisational progress. Organisations and societies struggle whenever they experience severe leadership imperfections. 


In some organisations and communities, leadership quality has moved from bad to worse, even though the general quality of leadership has improved over time.

The most egregious abuses perpetuated by leaders are no longer the norm in many parts of the world. 

The long history of leadership examples (both good and bad) and the insights uncovered from the study of leadership have boosted leadership practice globally. In spite of the above world moves from one leadership crisis to another. 

The world can’t get enough of the leadership it seeks. There are too many leaders whose approach to leadership is a source of concern for their stakeholders and the people who work with them. 

Many leaders who have started well with good intentions have not been able to end well. They have stumbled along the way or veered off the path they started and never made a course correction. 

The challenge of leadership does not get easier with time and more knowledge. Leaders still fall into the same traps as others did several centuries ago.

What trips leaders? 

It seems act of leading presents conundrums that the best leaders even have to confront. To lead is to experience the challenges inherent in leadership, no matter how well-intentioned one can be. And this is where most leaders fail. 

Many leaders have become ineffective due to their inability to appreciate the troubles associated with leading. I share below some of the challenges inherent in leadership and provide an idea to resolve them. 

Leadership is not about you:

Leaders have no vision except the vision of their stakeholders. Even though you start your leadership journey with your vision, the vision you carry must be the vision of your community. 

Leadership is constructed not on an individual vision but on the highest aspirations of every stakeholder. 

Every leader has to overcome the challenge of carrying a personal vision instead of leading the community with their fears, aspirations, doubts, and needs. 

Most leaders profess that they are leading in service of the people, while in practice, they fall for the trap of leading to have their needs met.

Leadership has dualities which must be embraced:

Embracing the dualities of leadership is one of the most difficult challenges for many leaders. Jim Rohn put it beautifully, “The challenge of leadership is to be strong, but not rude; be kind, but not weak; be bold, but not a bully; be thoughtful, but not lazy; be humble, but not timid; be proud, but not arrogant; have humour but without folly.” 

How can a leader be tender-hearted with people and tough-mined on performance? How can a leader be focused and flexible at the same time? 

Every leader has a favourite spot they operate from. However, staying stuck at one end of the spectrum leads to suboptimal results. 

Some leaders get stuck in a comfort zone that yields results, rendering them ineffective as the situation evolves. Leaders have to be nimble to oscillate with ease.

Leadership feedback becomes scarce when you are succeeding:

Effective feedback is one of the most critical development tools for every leader. 

Every leader begins their early journey surrounded by other leaders and elders who provide advice, feedback and encouragement. 

As the leader increases in stature, position and fame, their feedback circle becomes smaller, which leaves them with very few people in a position to offer the critical feedback every leader needs. Leadership success breeds confidence in leadership abilities. 


The few who surround the leader begin to withhold critical feedback the leader needs. 

Praise singing takes the place of effective feedback. With all the adulation around, some leaders consider those who offer feedback that does not align with their expectations as enemies of progress.

Leadership demands that you change first, not your team or the organisation:

Leadership requires change, but who has to change, the team or the leader? The leader has to demonstrate the change first. Unfortunately, many leaders see only the change their teams and organisations need to make. 


The trouble is that very few leaders realise the change they need to make in service of their leadership journey. 

So long as the leader has elected to lead the group, the leader must also embark on a personal change. As members of the team, leaders must make the necessary changes that make them the leaders their teams need. 

Every leader must be changing and flexing his skills and strengths constantly to align with the demands of the team. 

Leadership power must be used to protect, not to punish:

Increasing levels of success and influence lead to enormous leadership power. Not every team member will agree with your point of view. 


Some will vehemently oppose your ideas. A few others will actively take steps to undermine and derail your efforts. How do you respond when you succeed and the actions of the nay-sayers come to your attention? 

Leaders have the power to choose any response they wish but cannot be vindictive. Leaders should use their power to build the team, not to protect personal interests and secure even great power. 

The trouble with leadership is that some leaders use their power to corrupt the leadership endeavour. 

Resolving the trouble with leadership through reflection and journaling: 

One effective way to address the trouble with leadership is to engage in deep reflection and journaling. 

Leaders who successfully overcome the challenges associated with leadership regularly take the time to reflect on both their failures and successes on their leadership journey. 

By doing so, they can identify areas for improvement and protect themselves from the potential pitfalls of leadership. 

Reflection is a daily practice that enhances effective leadership. Leaders who become too preoccupied and fail to allocate time for self-reflection often find themselves entangled in the difficulties of leadership.

Be of good cheer!

The writer is a Leadership Development Facilitator, Executive Coach and Strategy Consultant, Founder of the CEO Accelerator Program ( and Chief Learning Strategist at TEMPLE Advisory ( 

The mission of The Leadership Project is to harvest highly effective leadership practices and share them in a manner that other leaders can easily incorporate into their leadership practice. 

If you have an idea or leadership practice to share, kindly write to [email protected]. Until you read from us again, keep leading.... from leader to leader, one practice at a time.

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