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Leadership Issues: Common Challenges and How to Overcome Them

Discover common leadership issues and practical solutions. Learn to identify and overcome the challenges that prevent leaders from achieving their potential.

Written by Laura Bouttell • Mon 29th December 2025

Leadership Issues: Understanding and Addressing Common Challenges

Leadership issues are the recurring problems, challenges, and dysfunctions that prevent leaders from achieving their potential and delivering the results their organisations need. Research from the Center for Creative Leadership indicates that 50% of leaders fail to meet expectations within their first 18 months in new roles. Understanding the most common leadership issues—and developing strategies to address them—distinguishes leaders who succeed from those who struggle. Like physicians diagnosing illness before prescribing treatment, effective leaders must recognise their challenges before they can overcome them.

This guide examines the most prevalent leadership issues and provides practical approaches for addressing them.

Understanding Leadership Issues

What Are Leadership Issues?

Leadership issues are the patterns of behaviour, skill gaps, or situational challenges that impair leadership effectiveness. They range from individual limitations (poor communication, inadequate self-awareness) to systemic problems (organisational politics, resource constraints) to relational difficulties (conflict, trust deficits).

Categories of leadership issues:

Individual issues: Personal limitations in skills, awareness, or behaviour that reduce effectiveness.

Relational issues: Problems in relationships with direct reports, peers, supervisors, or stakeholders.

Team issues: Dysfunction within the leader's team affecting performance and culture.

Organisational issues: Systemic problems in the broader organisation that constrain leadership.

Contextual issues: External factors—market conditions, regulatory environment, societal changes—creating leadership challenges.

Why Do Leadership Issues Matter?

Unaddressed leadership issues create cascading consequences that affect individuals, teams, and organisations.

Consequences of unaddressed issues:

Level Consequences
Individual Career derailment, stress, diminished wellbeing
Team Poor performance, low morale, high turnover
Organisational Strategic failure, cultural dysfunction, financial loss
Stakeholder Customer dissatisfaction, shareholder concerns

The compounding effect:

Small leadership issues compound over time. A communication problem becomes a trust deficit. A trust deficit becomes disengagement. Disengagement becomes turnover. Early identification and intervention prevent issues from metastasising into crises.

Personal Leadership Issues

What Are the Most Common Individual Leadership Problems?

Individual leadership issues—the personal limitations that reduce effectiveness—appear consistently across leadership populations.

The five most common individual issues:

1. Poor self-awareness: Inability to accurately perceive one's own strengths, weaknesses, impact, and blind spots. Without self-awareness, improvement is impossible.

2. Inadequate communication: Failure to communicate clearly, listen effectively, or adapt messages to different audiences and situations.

3. Emotional dysregulation: Difficulty managing emotions under stress, leading to reactions that damage relationships and judgment.

4. Avoidance of difficult conversations: Reluctance to address performance problems, give honest feedback, or confront conflicts.

5. Micromanagement or under-management: Either excessive control that stifles autonomy or insufficient oversight that allows problems to develop.

Signs of individual leadership issues:

How Do Leaders Develop Self-Awareness?

Self-awareness—understanding one's patterns, impact, and blind spots—enables all other leadership development. Without it, improvement efforts are misdirected.

Self-awareness development approaches:

360-degree feedback: Structured input from supervisors, peers, and direct reports revealing how others perceive you.

Executive coaching: Professional support helping leaders see patterns and develop new perspectives.

Reflection practices: Regular examination of experiences, reactions, and outcomes to extract learning.

Personality assessments: Tools providing frameworks for understanding preferences and tendencies.

Trusted advisors: Relationships with people who provide honest feedback without political filtering.

Self-awareness barriers:

Barrier How It Blocks Awareness
Success Past success convinces leaders they don't need to change
Power Position reduces honest feedback from others
Defensiveness Ego rejects information that challenges self-image
Busyness Activity crowds out reflection time
Confirmation bias Leaders seek information confirming existing beliefs

How Do Leaders Improve Communication?

Communication issues underlie many leadership failures. Improving communication requires attention to multiple dimensions.

Communication dimensions:

Clarity: Making messages understandable—appropriate vocabulary, structure, and simplicity.

Listening: Genuinely hearing others, not just waiting to speak.

Adaptation: Adjusting approach for different audiences, situations, and purposes.

Feedback: Giving and receiving feedback effectively.

Presence: Communicating with impact through non-verbal elements.

Communication improvement strategies:

  1. Seek specific feedback on communication effectiveness
  2. Record and review important communications
  3. Practice active listening deliberately
  4. Study effective communicators
  5. Develop range across communication styles
  6. Request and act upon feedback immediately after key communications

Relational Leadership Issues

What Issues Arise in Leader-Team Relationships?

The relationship between leaders and their teams is the primary channel through which leadership happens. Issues in this relationship fundamentally impair effectiveness.

Common leader-team relationship issues:

Trust deficit: Team members don't believe leader has their interests at heart or will follow through on commitments.

Connection failure: Leader perceived as distant, disconnected, or uninterested in team members as people.

Accountability imbalance: Standards applied inconsistently, favouritism perceived, or consequences avoided.

Development neglect: Leader focused on task completion without attention to team member growth.

Communication breakdown: Information not flowing effectively, expectations unclear, or feedback absent.

Rebuilding team relationships:

Issue Recovery Approach
Trust deficit Consistent follow-through, vulnerability, transparency
Connection failure Deliberate relationship investment, genuine interest
Accountability imbalance Clear standards, consistent application, visible fairness
Development neglect Career conversations, stretch opportunities, coaching
Communication breakdown Regular forums, feedback solicitation, message checking

How Do Leaders Navigate Organisational Politics?

Organisational politics—the informal influence systems operating alongside formal structures—present inevitable leadership challenges.

Political challenges leaders face:

Coalition dynamics: Navigating competing factions and allegiances within organisations.

Information asymmetry: Managing what you know, what others know, and what remains hidden.

Influence networks: Understanding who influences whom and how to work through these networks.

Power imbalances: Operating effectively when others have more formal or informal power.

Reputation management: Building and protecting professional reputation in political environments.

Political navigation principles:

  1. Understand the political landscape before trying to influence it
  2. Build relationships broadly, not just with immediate allies
  3. Maintain integrity—short-term political gains rarely justify ethical compromise
  4. Choose battles strategically—not everything is worth fighting for
  5. Develop sponsors who advocate for you in rooms you're not in
  6. Stay focused on results—delivering creates political capital

What Causes Conflict Between Leaders?

Peer conflict—disagreements between leaders at similar levels—creates dysfunction that affects entire organisations.

Sources of peer conflict:

Resource competition: Competing for budgets, headcount, or other scarce resources.

Territorial disputes: Disagreements about responsibilities, boundaries, and authority.

Style differences: Clashing approaches to work, communication, or decision-making.

Historical grievances: Accumulated resentments from past interactions.

Misaligned incentives: Compensation or recognition systems that pit leaders against each other.

Conflict resolution approaches:

Direct conversation: Address conflict directly with the other party before involving others.

Interest exploration: Understand underlying interests, not just stated positions.

Common ground: Identify shared goals that create basis for collaboration.

Process agreement: Agree on how to make decisions about contested issues.

Escalation wisdom: Know when escalation serves resolution and when it entrenches conflict.

Team Performance Issues

What Issues Prevent Teams from Performing?

Teams led effectively can achieve what individuals cannot. Teams led poorly destroy value rather than create it.

Common team dysfunctions:

Absence of trust: Team members unwilling to be vulnerable, admit mistakes, or ask for help.

Fear of conflict: Artificial harmony preventing debate that would improve decisions.

Lack of commitment: Insufficient buy-in to decisions, leading to half-hearted implementation.

Avoidance of accountability: Reluctance to hold peers accountable for standards and commitments.

Inattention to results: Individual goals prioritised over collective outcomes.

Patrick Lencioni's framework describes these dysfunctions as hierarchical—each builds on those below. Trust enables conflict; conflict enables commitment; commitment enables accountability; accountability enables results.

Diagnosing team dysfunction:

Symptom Likely Dysfunction
Guarded behaviour, low vulnerability Trust absence
Meetings lack debate, decisions unchallenged Conflict fear
Delayed implementation, revisited decisions Commitment lack
Standards slip without consequence Accountability avoidance
Subgroup success despite team failure Results inattention

How Do Leaders Build Psychological Safety?

Psychological safety—the belief that one can speak up without punishment or embarrassment—enables team performance, learning, and innovation.

Psychological safety building blocks:

Leader vulnerability: Leaders modelling the vulnerability they want to see—admitting mistakes, asking questions, acknowledging uncertainty.

Response patterns: How leaders respond to mistakes, questions, and challenges either builds or destroys safety.

Inclusion signals: Explicit invitation for input, especially from quieter team members.

Learning framing: Positioning work as learning opportunities rather than just performance evaluation.

Failure treatment: Treating mistakes as learning opportunities rather than occasions for blame.

Building psychological safety:

  1. Model vulnerability by sharing your own mistakes and uncertainties
  2. Respond constructively to bad news and concerns
  3. Explicitly invite input and dissent
  4. Thank people for speaking up, especially when it's uncomfortable
  5. Separate learning discussions from performance evaluation
  6. Address undermining behaviours immediately

How Do Leaders Address Underperformance?

Addressing underperformance challenges many leaders, yet failure to address it harms the underperformer, colleagues, and organisation.

Why leaders avoid addressing underperformance:

Addressing underperformance effectively:

Early action: Address issues when they're small rather than waiting until they've become crises.

Clear expectations: Ensure the person understands expectations before assuming they're choosing not to meet them.

Specific feedback: Describe specific behaviours and their impact, not general judgments.

Exploration: Understand circumstances before concluding causes—performance issues often have explanations.

Support provision: Provide resources, training, or coaching that might enable improvement.

Consequence clarity: Be clear about what happens if performance doesn't improve.

Documentation: Maintain appropriate records of conversations and agreements.

Organisational Leadership Issues

What Systemic Issues Challenge Leaders?

Beyond individual and team issues, leaders face systemic organisational challenges that constrain effectiveness.

Common organisational issues:

Unclear strategy: Lack of clear direction from above makes alignment and prioritisation difficult.

Resource constraints: Insufficient budget, headcount, or time to accomplish objectives.

Bureaucratic barriers: Processes and policies that slow progress and frustrate initiative.

Cultural dysfunction: Organisational cultures that undermine rather than enable performance.

Change fatigue: Too many initiatives creating exhaustion and cynicism.

Navigating systemic issues:

Issue Leader Response
Unclear strategy Seek clarification, create local clarity, manage upward
Resource constraints Prioritise ruthlessly, make trade-offs visible, advocate
Bureaucratic barriers Work within systems whilst advocating for improvement
Cultural dysfunction Build positive subculture, model desired behaviour
Change fatigue Filter initiatives, protect team, maintain focus

How Do Leaders Influence Without Authority?

Many leadership challenges require influencing people, resources, and decisions outside the leader's formal authority.

Influence challenge dimensions:

Upward influence: Shaping decisions made by supervisors and senior leaders.

Lateral influence: Securing cooperation from peers and other functions.

Stakeholder influence: Managing expectations and gaining support from customers, regulators, or partners.

Influence without authority strategies:

Relationship investment: Build connections before you need them.

Expertise leverage: Establish credibility through demonstrated competence.

Reciprocity building: Create value for others that generates willingness to reciprocate.

Coalition formation: Identify allies with shared interests and coordinate influence efforts.

Framing skill: Present proposals in terms of others' interests and concerns.

Timing sense: Intervene when conditions favour the influence you're seeking.

What Issues Arise During Organisational Change?

Leading through change creates distinctive leadership issues as people resist, organisations strain, and uncertainty proliferates.

Change leadership challenges:

Resistance management: Addressing opposition ranging from passive non-compliance to active sabotage.

Transition navigation: Helping people through the difficult middle period between old and new.

Communication demands: The constant, repetitive communication change requires from leaders.

Energy maintenance: Sustaining personal and team energy through extended change processes.

Competing demands: Balancing change implementation with ongoing operational requirements.

Change leadership principles:

  1. Over-communicate the why—purpose and necessity
  2. Acknowledge what's being lost, not just what's being gained
  3. Involve people in how, even when what is fixed
  4. Provide support during transition periods
  5. Celebrate progress and quick wins
  6. Maintain patience—sustainable change takes time
  7. Model the change you're seeking

Developing Leadership Resilience

How Do Leaders Maintain Effectiveness Under Pressure?

Leadership issues often emerge or intensify under pressure. Building resilience enables leaders to maintain effectiveness when challenges multiply.

Resilience components:

Physical resilience: Health, energy, and recovery practices that sustain cognitive and emotional function.

Emotional resilience: Ability to maintain emotional balance through challenge and setback.

Cognitive resilience: Mental flexibility and clarity that enables effective thinking under pressure.

Relational resilience: Support networks that provide perspective, assistance, and encouragement.

Purpose resilience: Connection to meaning that sustains motivation through difficulty.

Building resilience:

Component Development Approaches
Physical Exercise, sleep, nutrition, recovery practices
Emotional Mindfulness, emotional regulation, perspective
Cognitive Mental models, learning orientation, flexibility
Relational Support network, mentoring, peer relationships
Purpose Values clarity, meaning connection, vision alignment

When Should Leaders Seek Help?

Recognising when issues exceed individual capacity to address—and seeking appropriate help—demonstrates leadership wisdom, not weakness.

Signs help is needed:

Sources of leadership help:

Executive coaching: Professional support for development and problem-solving.

Mentoring: Guidance from experienced leaders who've navigated similar challenges.

Peer support: Fellow leaders providing perspective and mutual assistance.

Therapy or counselling: Professional help when issues have psychological dimensions.

Medical consultation: When physical symptoms suggest health concerns.

Organisational resources: HR, leadership development, or employee assistance programmes.

Frequently Asked Questions

What are the most common leadership issues?

The most common leadership issues include: poor self-awareness (inability to perceive blind spots), inadequate communication (failure to convey messages effectively), avoidance of difficult conversations (reluctance to address problems), micromanagement or under-management (control imbalance), and trust deficits with teams. These individual issues often combine with relational and organisational challenges.

How do leaders develop self-awareness?

Leaders develop self-awareness through: 360-degree feedback revealing how others perceive them, executive coaching providing external perspective, reflection practices examining experiences and patterns, personality assessments offering frameworks for understanding tendencies, and trusted advisors providing honest feedback. Self-awareness requires ongoing effort since blind spots are, by definition, invisible to ourselves.

Why do leaders avoid difficult conversations?

Leaders avoid difficult conversations due to: discomfort with conflict, fear of damaging relationships, uncertainty about how to have the conversation effectively, hope that problems will resolve themselves, and concern about the other person's reaction. This avoidance typically worsens problems, making eventual conversations more difficult.

What causes team dysfunction?

Team dysfunction commonly stems from: absence of trust (members won't be vulnerable), fear of conflict (artificial harmony prevents debate), lack of commitment (insufficient buy-in to decisions), avoidance of accountability (reluctance to hold peers to standards), and inattention to results (individual goals over collective success). Leaders create dysfunction or address it through their behaviour and attention.

How do leaders build psychological safety?

Leaders build psychological safety by: modelling vulnerability themselves, responding constructively to mistakes and concerns, explicitly inviting input and dissent, thanking people for speaking up, framing work as learning opportunities, and addressing undermining behaviours immediately. Safety requires consistent reinforcement—one punitive response can destroy it.

How should leaders address underperformance?

Address underperformance by: acting early before issues grow, ensuring expectations are clear, providing specific feedback about behaviours and impact, exploring circumstances that might explain the issue, offering support and resources for improvement, being clear about consequences if performance doesn't improve, and documenting conversations appropriately.

When should leaders seek external help?

Leaders should seek help when: feedback themes persist despite self-improvement efforts, stress affects health or relationships, the same issues recur across contexts, trusted advisors express concern, or self-help efforts haven't produced change. Seeking coaching, mentoring, or professional support demonstrates wisdom rather than weakness.

Conclusion: Issues as Development Opportunities

Leadership issues, whilst challenging, are also opportunities. Each problem identified is a problem that can be addressed. Each pattern recognised is a pattern that can be changed. The leaders who succeed aren't those without issues—they're those who recognise and address their issues systematically.

The path from leadership issue to leadership strength requires honest acknowledgment, careful diagnosis, appropriate intervention, and sustained effort. Like the physician who cannot treat what hasn't been diagnosed, leaders cannot improve what they haven't recognised.

Issues will always exist—new challenges emerge as old ones are addressed. The difference lies in whether leaders engage with their issues proactively or let issues compound until they become crises. Prevention and early intervention produce better outcomes than remediation of advanced dysfunction.

Recognise your issues honestly. Address them systematically. Seek help when needed. Transform challenges into capabilities.

Face your issues. Develop deliberately. Lead more effectively. Grow through challenge.