31 Leadership Challenges- How To Comprehensively overcome them

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Leadership is a dynamic journey filled with trials, triumphs, and transformation. As leaders walk it, they daily encounter various leadership challenges that test their resolve, adaptability, and decision-making capabilities- to name a few. Such leadership challenges can be internal and external to their businesses or organizations.

This comprehensive guide explores 31 common leadership challenges and practical solutions to effectively overcoming them.

1. Perspective-Perception (Egoism)

One of the biggest leadership challenges facing both new and old leaders is that I consider the challenge of perspective and perception of a big ego.

Depending on a leader’s perspective and self-perception of Self, real or imagined, s/he can see leadership differently. For instance, if s/he pulled themself by the proverbial “bootstraps”. They are most likely to perceive their leadership ability as a given. However, if they have never led or were pole-vaulted to leadership, then they will see the position differently.

In both cases, this challenge of perspective and perception can be overcome by schooling and awakening them to what leadership is really about.

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Doing so requires them to accept that they are open to learning about leadership. Informally, this can be done by them either reading up on, watching, or being coached about leadership. This could be done either on the job or before assuming a leadership role. Better still, enrol in leadership courses.

Yes, formally, whether you are a natural-born leader or one who was groomed to lead, you need to change your attitude towards leadership and accept that you need more than just informal leadership lessons.

Many musicians have taken music lessons after going platinum. The same is sometimes required of leadership.

Never stop learning. Invest in your growth as a leader. Continually refine your leadership capabilities. Sometimes, it is only through leadership courses and objective self-assessment that you can identify the leadership skills you lack. Be prepared to learn them or recruit the requisite talent for your leadership journey.

However, recruiting much-needed talent is not a walk in the park and can be equally challenging.

2. Recruiting Talent

The pivotal search for the right team members with the right talent is perpetual and a common leadership challenge for many leaders. Finding the right people for your team and organisation can be daunting. That’s largely because securing a talented workforce, which everyone else is looking to recruit is not easy.

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To address this, investigate, establish and clearly understand the role requirements and culture that attracts high-calibre candidates. Define what your job requirements are. Then ensure you invest in branding and publicity that will attract top talent.

Use reputable and targeted recruitment channels to access quality candidates. Sometimes, it is best to get help with recruitment. Hire through a recruiting agency or by acquiring SaaS or AI hiring tools.

When found, invite your selected candidates for interviews and assess them thoroughly. Sift through them until only the most suitable remain. A word to wise though, keep in mind team dynamics.

Bringing together diverse personalities can lead to conflict. Gauge the personality and cultural fit of your recruits for a stable and harmonious work environment.

Once your team is in place, go about setting achievable goals. This too can be challenging.

3. Setting Achievable Goals

Though as a leader you should have some concrete ideas about what your goals are from the beginning, setting achievable goals is however what’s key. While having a pool of talent at your disposal helps, sometimes setting and balancing those goals realistically is still, and can be a leadership challenge for some.

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One way of setting achievable goals is by breaking them into smaller objectives and more manageable tasks. Similar to the abbreviation S.W.O.T. analysis, identifying your goal as guided by the acronym SMART (i.e. Specific, Measurable, Achievable, Relevant, Time-framed) can assist in setting clear goals.

As a leader, ensure that your short and long-term goals are specific, measurable, achievable, relevant and time-framed. By and large, define and communicate achievable objectives.

Align team efforts with organizational vision to foster a sense of purpose. Should you need help, don’t hesitate to engage it.

At Comecinc, assisted by artificial intelligence, we help leaders set, track, assess, manage and evaluate their business goals.

4. Delegation

When it comes to delegating, most leaders want to delegate “effectively”. Unfortunately, this “relinquishing of control” at times brings on its own set of challenges. That’s largely because, for leader-you, delegation implies either trusting a team member or the whole team with responsibilities that, ideally, as a leader, you would have wanted to do yourself.

Often, the urge is to micromanage the person or team you would have delegated to.

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To resist the urge to micromanage, do not delegate for the sake of delegating. Instead, delegate based on a team member’s strengths and empower your delegate with the necessary resources to succeed-not fail.

When delegating, always provide clear instructions to the delegate (s) and be on hand for clarifications etc. A leader who delegates maintains all available channels of communication open, without breaking his trust in the delegate.

5. Trust Issues

Trust is the foundation of any relationship. However, if you are a leader who bootstrapped or worked/clawed his/her way to the top, you might have trust issues. As with delegation, the fear of relinquishing control, “being vulnerable like that” can be challenging.

Worse still, if you are that leader who fears your more educated team members are after your business or position. Then you are less likely to “open yourself up” to being taken advantage of.

Such trust issues can deter you from trusting others.

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True leaders trust their own and their team’s capabilities. If you have trust issues concerning your employees, then it’s most likely they don’t trust you either. If this is the case for you, lead by example, be transparent, have an open-door policy.

As a leader, cultivate an environment of open communication. Actively listen, and above all, follow through on commitments. Trust is earned through actions that align with your words.

Be consistent, transparent and reliable to build and maintain trust within your team.

Whatever you do, keep top of mind that trust is essential for collaboration and productivity. Have an open-plan office space for your business if you must, but remember, it starts with you.

Look team members or employees in the eye and tell them, “I trust you.”

6. Leading by Example

It is said, “Actions speak louder than words.” As corporate and political corruption attests, some leaders find being exemplary challenging.

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As a leader, exhibit the behaviour you expect from your team. Don’t hold grudges towards subordinates. Resolve conflicts by finding common ground and aligning team members with the organization’s goals.

Doing so requires emotional intelligence, and that can be difficult for some.

7. Developing Emotional Intelligence

Emotional intelligence requires you to be empathetic. Your ability to put yourself in the place of another and feel as they would is challenging for some leaders. So important is emotional intelligence to interpersonal relations, it has become measurable.

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A high Emotional Quotient (EQ) is crucial for effective leadership. Being in a leadership position requires you to work on self-awareness, empathy, and interpersonal skills to better connect with your team.

You need to understand your emotions and those of others to build strong relationships. For some leaders, this is easier said than done.

8. Communicating Effectively

A leadership position often calls on you to give speeches or talks. At times, you might have to write articles or newspaper columns. Whether spoken or written, communication needs to be clear and effective.

Effective communication is the cornerstone of successful leadership.

Unfortunately, not all leaders can communicate effectively. Unfortunately, miscommunication can cause chaos.

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“Practice makes perfect”. Hone your communication skills to ensure clarity and understanding whether you are speaking or writing. Practice active listening and articulate your thoughts clearly.

It is not uncommon for leaders to hire writing and/or speech coaches to assist them with their writing and speaking.

Alternatively, when time and will do not permit, a leader will hire a writer to “ghostwrite” for them. Or get a more eloquent member of the team to give a speech.

Ideally, however, it is always best when the leader effectively gives the speech. It inspires confidence and motivates the team.

9. Inspiring Motivation

Motivation refers to the internal and external factors that stimulate employees to take actions that lead to achieving business goals. It is a crucial element for the success and growth of any organization.

Depending on your leadership style and your business or department’s performance, motivation and morale can decline.

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Take time to understand and implement effective motivational strategies. Investigate and understand what drives your team. Then tailor your incentives and recognitions to match your team members’ individual and collective aspirations.

Where morale has been lost, reignite and inspire motivation by revisiting and resetting goals. Realign your team’s skills with organizational objectives.

Through showing such leadership, you can inspire motivation and enhance productivity, and employee satisfaction, leading to overall success.

This calls upon you to manage your team’s performance.

p style and your business or department’s performance, motivation and morale can decline.

10. Managing Performance

Managing performance is something some leaders struggle with. This can either be due to a lack of knowledge or time. Either way, not effectively managing performance can derail the team and set goals.

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Ensure your business and team’s Key Performance Indicators (KPIs) or Key Performance Areas and consequences are in place beforehand. Establish performance metrics and provide regular feedback. Have set times by which certain milestones must have been achieved and stick to them.

Promptly identify, get reasons, and address any milestones or KPIs that would not have been met. A leader gives constructive feedback and the necessary support for improvement.

Recognise, reward and celebrate successes.

However, if performance is way below expectations, do not hesitate to mete out agreed consequences (e.g. a written warning). Managing performance speaks to accountability.

11. Accountability

Unknown to some leaders, accountability refers to the obligation of individuals or organizations to account for their activities, accept responsibility for them, and transparently disclose the results. It involves being answerable for actions and decisions, and it is a key component of effective governance and management.

Accountability is essential for achieving organizational goals and maintaining trust. It is key to performance. Akin to integrity, it begins with the leader.

Unfortunately, this is not always the case. Some leaders struggle with both.

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Lead by example. Set clear expectations and consequences for both you and your team. Hold both yourself and team members responsible for your actions.

Much as you provide regular feedback to your team members, be equally accountable to them. Fostering open communication and leading by such example can ensure accountability at all levels.

Doing so will ease the challenge of making tough decisions later.

12. Decision-making

Making life choices and decisions is hard enough. Add having to make business decisions to the mix, and some leaders procrastinate, overthink or simply crumble. That’s because not all decisions are popular.

So, what to do?

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Research the problem you need to make a call on and gather the necessary information and evidence.  Analyse it and then make an informed, ethical decision that considers the implications and how you will manage the fallout.

Next, and sometimes hardest of all, communicate your decision with clarity and conviction. Ultimately, ensure that your decision is one you can stand by, even if it’s unpopular.

Many a leader has fallen because of making populist decisions and landing themselves in crises.

13. Handling Crises

Crises, or a crisis, either self-inflicted or thrust upon a leader, test leadership. Guiding a business or an organization through challenging and uncertain times is never easy, but not impossible.

In such cases, effective crisis leadership is crucial if you are to minimize damage and ensure a swift recovery.

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Ideally, always have a generic crisis management plan at the ready to activate when a crisis hits. When it eventually does, respond calmly, communicate clearly, sagely research and chart your way out of the turbulent times.

Be proactive and take decisive calculated, strategic action. The same can be said of how you should handle conflict.

14. Handling Conflict

Conflict, be it internal (e.g. office politics) or external (compliance officers, SARS or IRS) can be distracting.

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Anticipate conflict and proactively cultivate a politics-free culture in your business or organisation. However, when conflicts do arise, leaders address internal disputes timely, swiftly and fairly.

Stay above the stain of disputes by focusing on merit and fairness. As a leader, avoid getting personally entangled in any drama.

Whether internal or external, use conflict resolution techniques such as mediation to guide conflicting parties towards a mutually beneficial resolution.

If not properly handled and left to fester, conflict can make team collaboration challenging.

15. Team Collaboration

A top leadership quality is the ability to foster team collaboration. A leader’s ability to do so fuels success.

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Recruit with the need for team collaboration in mind. Then encourage it by setting team goals. Facilitate teamwork by leveraging each member’s strengths against those of some members.

Failure to gel your team can cause and lead to stress, which some leaders find a challenge to deal with.

16. Coping with Stress

Due to the myriad challenges it presents to some leaders, leadership can be stressful. From its requirements to its impact on the mind, leadship needs you to develop stress coping mechanisms.

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Having to balance multiple responsibilities and deadlines can be overwhelming. Finances permitting, a leader should have a personal assistant or private secretary. S/he can be virtual or in-person.

Alternatively, manage your time by prioritizing tasks, setting realistic deadlines, and using time management tools to manage your time effectively.

17. Managing Change

Adapting to shifts in your professional life as a leader and the business environment around you can be challenging. So too is overseeing change, such as organizational restructuring or market shifts.

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Accept that your workload or the direction your organisation is taking has changed. On a professional level, delegate some of your less confidential tasks to reduce your workload and empower others. Trust your team.

In the case of organisational change, communication is key. Communicate the reasons behind the changes, and where possible, seek and involve employees in decision-making, addressing concerns, and highlighting the benefits.

As much as you have support from your team, also support them during transitions.

Otherwise, the failure to manage your time and the change to leader can lead to loss of motivation and momentum.

18. Momentum Loss

Keeping the energy high is challenging. Many self-starter leaders gradually lose motivation and momentum over time. Worse still, some suffer health complications like partial strokes, heart attacks or nervous breakdowns due to burnout.

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Maintain momentum by integrating artificial intelligence and Software-as-a-Service tools into your workflow. Take time out to relax and celebrate any wins with the team and with family.

Disconnect from the internet and have some alone or me-time. Relax and, if possible, meditate on your vision. Ideally, a vision integrated and assisted by the technological innovations happening around you.

Unfortunately, getting some leaders to adopt technological innovations can be challenging.

19. Innovation Adoption

Stagnation is the enemy of progress. That as it may be some leaders are still resistant to adopting the latest tech craze, AI and SaaS. Leaders of such organisations and businesses are doing themselves and their organisations a disservice.

If anything, as a leader, you should be at the forefront of encouraging a culture of innovation.

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That can be done by rewarding innovative creative thinking and risk-taking. Create an environment where new ideas are welcomed and rewarded. Adopt and adapt technological advances by staying abreast of technological trends.

Encourage continuous learning and integration of new tools to enhance productivity.

Your unwillingness as a leader to adopt innovation and technological integration into your workflow could lead to the challenge of managing teams remotely.

20. Remote Team Management

The virtual world presents new challenges. A technophobe leader soon finds him/herself challenged by responsibilities that call for him/her to be tech-savvy. Since the pandemic, one such tech requirement has been the utilization of technology to maintain connectivity with remote team members.  

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Post-Covid-19, it has become crucial for leaders to be conversant with virtual communication tools and platforms. More than ever, personal and professional development has become a prerequisite. Aside from your professional development and growth, provide opportunities for learning and development to keep your team engaged and evolving.

As a leader, at least learn and master as many of them as you can.  Or at least the popular ones like Butter, Zoom, Google Meet, Slack and Microsoft Teams. Know how to share your screen, mute and unmute, and switch on and off your camera.

When managing remote teams, set clear expectations and try as much as possible to create a sense of community among remote team members. Establish clear communication channels and regular check-ins.

Any bid to continue on the path of innovation resistance can easily lead such a leader down the rabbit hole of challenges in maintaining a work-life balance.

21. Maintaining Work-Life Balance

“All work and no play make Jack a dull boy”. The same goes with leadership.  Leaders who succumb to their workloads often have difficulty maintaining a work-life balance. Their scale usually tips more towards work than actual living-often with terrible consequences for some.

As a leader, you must lead by example and promote a healthy work-life balance to prevent burnout and maintain productivity.

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Maintaining a sound work-life balance can be done through practising mindfulness, meditation, or other relaxation techniques to manage stress. Self-care to ensure you take care of your physical and mental health through regular exercise, proper nutrition, and sufficient rest.

Failure to strike a healthy work-life balance could lead you to the challenge of feeling isolated.

22. Isolation

Covid-19 lockdowns revealed what can happen when some humans are isolated for a long time. Sadly, feelings of isolation are some leaders’ everyday existence. Such leaders may feel isolated as they cannot always share their burdens with others.

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Build or join a support network or club of like-minded people, and peers, or hire a coach to share your challenges with to get different perspectives.

23. Understanding Cultural Differences

Unlike ever before, globalization has made cultural sensitivity a must. Unfortunately, despite the diversity of their teams and workforce, some leaders are set in their ways or just do not have the time to learn the cultures of their multicultural teams.

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Research, learn and be mindful of cultural nuances in your leadership approach. Foster diversity and inclusion by objectively embracing diverse perspectives and opinions. Create policies and practices that promote inclusivity and equity. Doing so requires organizational ability.

24. Organizational

Business leaders play a pivotal role in shaping the vision, culture, and strategic direction of their companies. The organizational structure defines how tasks are divided, coordinated, and supervised within a company.

Effective leaders understand the importance of designing a structure that supports the organization’s goals and enhances communication and collaboration. Common organizational structures include hierarchical, flat and matrix.

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To overcome this challenge, design an organisational structure that supports your organization’s goals and enhances communication and collaboration. Integrate SaaS tools, live-in-person and chatbot assistants into your workflow to stay administratively organised.

Generally, no matter how challenging it might be, organise your enterprise in such a way that it builds a positive culture.

25. Building a Positive Culture

Aside from an unwillingness to research, learn and be mindful of cultural nuances in their leadership approach, some leaders find it challenging to foster and build a positive company culture. In such cases, the company climate is toxic, stressful and demoralising.

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Spearhead cultivating an environment of positivity, recognition and team spiritedness. Creating a positive culture is infectious and can only boost morale. So too, does a leader’s ability to manage resources.

26. Managing Resources

From financial mismanagement to general wasteful expenditure, some leaders are not good at handling resources, especially finances.

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For the sake of your company and leadership, you must learn the fundamentals of financial management. Insist on strategic financial planning, transparency, accountability, training, and reporting.

As a leader, you should either optimize the use of available resources to maximize efficiency and minimize waste or face the embarrassment of bankruptcy and business closure – on your watch. 

Leadership comes with more than its fair share of expectations of the leader.

27. Expectations

Leadership by its nature comes with many expectations.  Leaders often face high expectations from their team, stakeholders, and themselves. Those who are led have and demand certain expectations. Sometimes, these expectations can be too great, too diverse or simply beyond your leadership capabilities.

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Set realistic goals by breaking them down into manageable and achievable tasks. You can’t handle it alone, entrust your team with some of the load, delegate tasks to reduce your workload and have it carried by others. Continuous learning is key to great leadership.

Invest in leadership training and development to enhance your skills and confidence. Some such confidence can even be faith-based.

28. Faith Matters

In the modern world, the intersection of leadership and faith is a topic of growing interest. For instance, few successful business leaders openly attribute their achievements to their faith and spiritual beliefs. Most would rather glorify only their skills and strategies.

While in some cases this is true, in others it is a blend of business acumen and faith.

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Faith has been known to shape leadership styles, decision-making processes, and company cultures in various ways. However, while it can be a powerful guiding force, leaders need to balance their personal beliefs with the diverse perspectives of their employees and stakeholders.

Inclusivity and respect for different faiths and beliefs are essential to maintaining a harmonious and productive workplace. More so, if your organisation is to grow sustainably grow.

29. Sustainable Growth

For some leaders and their critics, the capability to sustain long-term growth is the ultimate hallmark of true leadership. Attaining and sustaining growth is however quite challenging. Some leaders find it a challenge and have failed at it.

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It begins with your business investing in people and processes that contribute to sustainable development. Put in place strategic plans for the core parts of the business. For instance, financial management, marketing and sales.  Your ability to organize so that the enterprise remains sustainably grows, will largely hinge on your succession plan.

30. Succession

Sometimes a leader can be so successful that s/he feels indispensable. As a result, when they eventually do realise it, it is already too late. They can no longer go on, and to worsen matters, there is no succession plan.

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A great leader plans and prepares for the future, when they will no longer be able or around.  Do not be threatened by the potential of your team members. Instead, identify and develop potential leaders within your team, organization or business.

31.  Cultivating Resilience

Lastly, the test of true leadership is about your ability to confront head-on some, or all the challenges outlined above and still survive. This is what makes leadership not just about guiding others; but also, about evolving yourself to meet the ever-changing demands and challenges of your leadership.

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The hallmark of great leadership is not the absence of problems but the ability to navigate them with grace and determination. So, embrace your leadership journey and stay strong.  Manage team dynamics, make tough decisions, and confront these challenges with strategic solutions.

There will be setbacks, don’t crumble. Instead, use them as opportunities for learning, growth and innovation.

Foster a resilient mindset, a culture of perseverance, a never-die attitude that bounces from failures, stronger.

Final Word

Leadership is an expedition filled with unexpected twists and turns. Overcoming leadership challenges is an intricate art that requires a delicate balance of skills, intuition, strategy, and resilience to steer through the myriad challenges that leaders face. Continuously learning, adapting and adopting helps address these challenges and grow you as a leader. Ultimately, it is your ability to organize resources, inspire teams, and drive innovation that will significantly impact your overall performance as a leader and the sustainability of your enterprise or organization.

Are there any other leadership challenges that you can think of, or which you have experienced that are not on this list? What are they?

A downloadable ebook of this article is available on our website.

Corwin L. Mhlahlo is, among others, the Principal Communications and Strategic Solutions Consultant at Comecinc C & SSS Inc., – a business consulting firm in Johannesburg, South Africa. His qualifications include certifications in Business Administration, Sales Marketing Management and Digital Marketing. Corwin is passionate and excited about the future of Artificial Intelligence and Software as a Service (SaaS) to business processes, operations and productivity.

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