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Leadership of the Leadership: Guiding Those Who Guide Others

Explore leadership of the leadership—the unique challenges and strategies for executives who lead other leaders. Learn how to build effective leadership teams.

Written by Laura Bouttell • Fri 8th January 2027

Leadership of the leadership represents the most complex form of organisational influence—guiding accomplished leaders who themselves command teams, budgets, and strategic responsibilities. Research from McKinsey indicates that senior leadership team effectiveness accounts for nearly 40% of variance in organisational performance, yet fewer than 25% of executive teams operate at high-functioning levels. This gap reveals both the difficulty and importance of leading leaders well.

The challenge differs fundamentally from leading individual contributors. When your direct reports are themselves leaders—each with their own vision, experience, and authority—traditional management approaches fail. You cannot simply direct; you must orchestrate. You cannot merely instruct; you must align. The skills that created successful functional leaders often prove insufficient for the meta-leadership required at executive levels.

Field Marshal Bernard Montgomery understood this distinction acutely. Commanding the Eighth Army, he led not soldiers directly but generals and senior officers—each a proven leader with strong views and established reputations. His effectiveness came not from tactical brilliance alone but from his ability to create unified purpose among accomplished subordinate commanders who could have operated independently.

This comprehensive examination explores the unique challenges of leading leaders, the competencies required for this meta-leadership, and the practices that distinguish effective executive teams from dysfunctional ones.

Understanding Leadership of the Leadership

Before developing strategies, understanding what makes leading leaders fundamentally different clarifies the approach required.

What Is Leadership of the Leadership?

Leadership of the leadership describes the specific practice of guiding, aligning, and developing individuals who themselves hold leadership positions. This creates a unique dynamic:

  1. Multiplied impact - Decisions and directions cascade through multiple leadership layers
  2. Distributed authority - Direct reports hold significant independent power
  3. Complex stakeholders - Each leader represents their own team's interests
  4. Experienced followers - Those being led understand leadership deeply themselves
  5. High visibility - Executive team dynamics are observed and interpreted throughout the organisation
  6. Strategic focus - Concerns are enterprise-wide rather than functional

This context demands different approaches than leading individual contributors, however talented those contributors might be.

How Does Leading Leaders Differ from Leading Teams?

Dimension Leading Teams Leading Leaders
Authority relationship Clear hierarchy; leader directs Shared authority; leader orchestrates
Information flow Leader has more context Direct reports have unique domain expertise
Decision-making Leader often decides Must balance autonomy with alignment
Development focus Building skills and experience Enhancing strategic perspective and collaboration
Conflict nature Task or interpersonal disputes Resource competition, strategic disagreements
Communication Clear direction Creating shared understanding across domains
Motivation Individual engagement Maintaining commitment whilst managing frustration

Understanding these differences prevents applying inappropriate approaches that work with individual contributors but fail with senior leadership teams.

Why Is Leading Leaders Particularly Challenging?

Several factors compound the difficulty:

Ego and identity - Leaders at senior levels have succeeded through their individual capabilities. Being led can feel threatening to identities built on leadership.

Competing priorities - Each leader advocates for their function or division, creating inherent tension in resource allocation and strategic priority.

Information asymmetry - Each leader knows their domain more deeply than you can; you must lead without informational advantage.

Political dynamics - Senior leadership positions involve complex political relationships, alliances, and rivalries.

Performance pressure - At executive levels, scrutiny from boards, investors, and markets intensifies pressure on everyone.

Limited development time - Senior leaders have packed schedules and may resist activities framed as "development."

"Leadership is not about being in charge. It is about taking care of those in your charge." — Simon Sinek

The Competencies Required for Leading Leaders

Effective leadership of leaders demands specific competencies beyond those sufficient for earlier leadership roles.

What Skills Are Essential for Leading Leaders?

Strategic synthesis - The ability to integrate diverse functional perspectives into coherent enterprise strategy:

Executive presence - Projecting authority and credibility sufficient to lead accomplished leaders:

Political navigation - Managing complex dynamics among senior leaders:

Developmental orientation - Continuing to grow leaders even at senior levels:

How Does Emotional Intelligence Manifest at Executive Levels?

EI Component Executive Application
Self-awareness Understanding how your behaviour affects leadership team dynamics
Self-regulation Managing frustration when brilliant leaders make poor decisions
Motivation Maintaining drive despite isolation and pressure of top roles
Empathy Understanding pressures each leader faces from their teams
Social skill Building cohesion among leaders with competing interests

Daniel Goleman's research demonstrates that emotional intelligence differentiates outstanding executives from adequate ones by a factor of 2-to-1. At levels where technical capability reaches parity, emotional skill determines effectiveness.

What Mindsets Support Leading Leaders?

Servant leader orientation - Paradoxically, leading leaders effectively often requires subordinating your ego to their success:

Systems thinking - Seeing the leadership team as a system with dynamics beyond individual components:

Intellectual humility - Accepting the limits of your knowledge whilst maintaining confidence:

Building an Effective Senior Leadership Team

Leadership of leaders occurs primarily through the senior leadership team—the group of leaders who collectively guide the organisation.

How Do You Construct an Effective Leadership Team?

Composition considerations:

  1. Complementary capabilities - Assemble diverse strengths rather than similar profiles
  2. Collaborative potential - Assess ability to work together, not just individual excellence
  3. Culture fit - Ensure alignment with desired team norms and values
  4. Strategic diversity - Include voices that challenge as well as support
  5. Succession integration - Build the team with future transitions in mind

Team design elements:

Common composition errors:

What Structures Support Leadership Team Effectiveness?

Structure Element Purpose Implementation
Regular meetings Creating consistent collaboration rhythm Weekly or fortnightly standing meetings with clear agendas
Strategic offsites Enabling deep thinking beyond operations Quarterly or semi-annual dedicated sessions
One-to-ones Maintaining individual relationships Regular, protected time with each leader
Subcommittees Managing cross-functional initiatives Defined membership, charter, and reporting
Communication channels Enabling asynchronous connection Shared platforms with clear norms
Decision frameworks Clarifying authority and input requirements Documented matrix specifying who decides what

Structure alone doesn't create effectiveness—it enables effectiveness when combined with healthy dynamics and clear purpose.

How Do You Develop Team Cohesion Among Senior Leaders?

Building genuine cohesion among accomplished leaders requires deliberate effort:

Shared experiences:

Mutual understanding:

Aligned incentives:

"Coming together is a beginning, staying together is progress, and working together is success." — Henry Ford

Managing Dynamics Within Leadership Teams

Leadership teams develop dynamics that either enable or undermine effectiveness. Leading leaders requires actively managing these dynamics.

What Common Dysfunctions Affect Leadership Teams?

Patrick Lencioni's model identifies five dysfunctions forming a hierarchy:

  1. Absence of trust - Unwillingness to be vulnerable, admit mistakes, ask for help
  2. Fear of conflict - Avoiding productive debate, preserving artificial harmony
  3. Lack of commitment - Ambiguity, hedging, failure to support decisions
  4. Avoidance of accountability - Tolerating poor performance, avoiding difficult conversations
  5. Inattention to results - Prioritising personal or departmental interests over collective outcomes

Each dysfunction builds on those below—addressing trust unlocks ability to engage in healthy conflict, enabling genuine commitment, supporting mutual accountability, and ultimately producing focus on collective results.

How Do You Address Political Behaviour in Leadership Teams?

Politics at senior levels is inevitable—managing it requires:

Distinguishing productive from destructive politics:

Interventions for destructive patterns:

Structural approaches:

How Do You Handle Conflict Among Senior Leaders?

Conflict among leaders requires sophisticated handling:

Conflict Type Appropriate Response
Task disagreement Facilitate productive debate; ensure all perspectives heard
Resource competition Establish clear criteria; make trade-offs explicit
Strategic differences Explore assumptions; find integrative solutions or decide
Personal friction Address privately; coach individuals on collaboration
Value conflicts Surface and discuss; determine if differences are tolerable
Power struggles Set clear boundaries; address attempts to circumvent

Principles for executive conflict management:

Aligning Leadership Around Strategy

A primary function of leading leaders is creating strategic alignment that enables coherent enterprise action.

How Do You Create Strategic Alignment Among Leaders?

Alignment doesn't happen naturally—it requires deliberate creation:

Co-creation processes:

Communication approaches:

Accountability structures:

What Prevents Strategic Alignment?

Barrier Description Response
Incomplete understanding Leaders don't fully grasp strategic intent Invest in explanation; check comprehension
Disagreement Leaders believe strategy is wrong Surface concerns; address or explain trade-offs
Functional loyalty Leaders prioritise own function over enterprise Restructure incentives; address persistent behaviour
Capability gaps Leaders can't execute required changes Develop capability; provide support; adjust timeline
Competing priorities Daily pressures overwhelm strategic focus Protect strategic time; address immediate issues
Poor translation Strategy unclear for functional application Work with leaders to translate; provide examples

How Do You Balance Alignment with Autonomy?

Effective leadership of leaders requires finding appropriate tension between alignment and autonomy:

Where alignment is essential:

Where autonomy should prevail:

Managing the boundary:

"The task of the leader is to get his people from where they are to where they have not been." — Henry Kissinger

Developing Leaders Who Lead Leaders

As leaders rise to lead other leaders, their development needs change—traditional leadership development often proves insufficient.

What Development Do Senior Leaders Need?

Perspective expansion:

Relationship evolution:

Personal evolution:

How Do You Provide Development at Senior Levels?

Development Approach Application for Senior Leaders
Challenging assignments Cross-functional initiatives, enterprise projects, crisis leadership
Coaching Executive coaches for confidential support and challenge
Peer learning Action learning sets with leaders facing similar challenges
External exposure Board service, industry associations, advisory roles
Feedback 360-degree assessments, board input, stakeholder feedback
Reflection Protected time for strategic thinking and learning

Challenges in senior leader development:

How Do You Prepare Leaders to Lead Leaders?

Succession planning for roles that lead other leaders requires specific preparation:

Early identification:

Stretch experiences:

Deliberate mentoring:

Common Challenges in Leading Leaders

Certain challenges recur across contexts when leading leaders.

How Do You Lead Former Peers?

Promotion to lead former peers creates particular dynamics:

Immediate challenges:

Effective approaches:

What to avoid:

How Do You Lead Leaders Who Were Previously Your Seniors?

Acquisitions, reorganisations, and lateral moves sometimes place you above former superiors:

Specific dynamics:

Effective approaches:

How Do You Manage Leaders with Larger Teams or Budgets?

When your direct reports command more resources than you ever have:

Inherent challenges:

Positioning your value:

Measuring Leadership Team Effectiveness

Leading leaders effectively requires understanding whether the leadership team is functioning well.

How Do You Assess Leadership Team Effectiveness?

Outcome indicators:

Process indicators:

Health indicators:

What Assessment Methods Work for Leadership Teams?

Method What It Reveals Implementation
Team surveys Aggregated perspectives on team dynamics Periodic, anonymous surveys on team effectiveness
360 feedback How individual leaders affect team Individual assessments with team dynamic questions
Meeting observation Real-time dynamics and patterns External facilitator observation with feedback
Decision audits Quality and process of key decisions Retrospective analysis of major decisions
Stakeholder feedback External perceptions of team Input from board, investors, key customers
Performance data Outcomes team produces Enterprise metrics tracking

Using assessment data:

Frequently Asked Questions

What does leadership of the leadership mean?

Leadership of the leadership refers to the practice of guiding and aligning individuals who themselves hold leadership positions. This meta-leadership occurs at senior executive levels where direct reports are functional leaders, division heads, or other executives with their own teams and authority. It differs from leading individual contributors because those being led understand leadership deeply, hold significant independent authority, and bring domain expertise that may exceed the leader's own knowledge in those areas.

How do you effectively lead other leaders?

Leading other leaders effectively requires focusing on strategic alignment rather than tactical direction, respecting their domain expertise whilst providing enterprise perspective, building genuine trust that enables productive conflict, creating structures for collaboration without micromanagement, and developing their capabilities even at senior levels. Success comes from orchestrating rather than directing—enabling accomplished leaders to contribute their best whilst maintaining coherent enterprise action.

What are the biggest challenges in leading a senior leadership team?

The biggest challenges include managing ego and politics among accomplished individuals who are accustomed to leading rather than following, creating alignment when each leader advocates for their function's interests, navigating information asymmetry where each leader knows their domain more deeply than you, balancing autonomy with coherence, addressing conflict constructively, and maintaining trust when stakes are high and scrutiny intense.

How do you build an effective senior leadership team?

Build an effective senior leadership team through thoughtful composition emphasising complementary capabilities and collaborative potential, clear operating structures including regular rhythms and decision frameworks, investment in relationship development and shared experiences, explicit norms for behaviour and conflict management, collective accountability for enterprise outcomes alongside individual responsibilities, and ongoing attention to team dynamics and health.

How do you handle conflict among senior leaders?

Handle conflict among senior leaders by distinguishing productive disagreement from destructive fighting, creating psychological safety for expressing different views, facilitating rather than suppressing debate, addressing personal friction privately whilst keeping task disagreements in open forums, establishing clear criteria for resource allocation decisions, holding leaders accountable for resolving their own conflicts, and intervening when conflicts begin damaging organisational effectiveness.

What skills are needed to lead other leaders?

Skills needed to lead other leaders include strategic synthesis (integrating diverse functional perspectives), executive presence (projecting authority among accomplished peers), political navigation (managing complex dynamics without appearing partisan), emotional intelligence (especially empathy for each leader's context and self-regulation under pressure), systems thinking (understanding leadership team dynamics), and intellectual humility (acknowledging limits whilst maintaining confidence).

How do you develop leaders for executive roles?

Develop leaders for executive roles through challenging assignments that build enterprise perspective, cross-functional rotations expanding beyond functional expertise, exposure to leadership team dynamics through observation and participation, executive coaching providing confidential support, peer learning with others facing similar transitions, and deliberate mentoring from current executives who can share the realities of meta-leadership.

Conclusion: The Art of Leading Leaders

Leadership of the leadership represents the culmination of a leadership career—the point where your impact depends entirely on your ability to guide, align, and develop other accomplished leaders. This meta-leadership is both the most challenging and most leveraged form of organisational influence.

Success at this level requires:

The Royal Navy developed a tradition of "primus inter pares"—first among equals—describing the relationship between an admiral and the captains under their command. Each captain was a proven leader commanding their own ship; the admiral's role was to create fleet effectiveness from individual excellence. This remains the essential challenge.

Begin by honestly assessing your current approach. Are you leading leaders the way you led individual contributors—only with higher-level people? That approach fails. Or are you developing the distinct competencies, mindsets, and practices that meta-leadership demands?

Then focus on your leadership team as a team, not just a collection of talented individuals reporting to you. Team effectiveness at senior levels doesn't happen naturally—it requires deliberate construction, ongoing attention, and continuous development.

The organisations that outperform their competitors often do so because their senior leadership teams function extraordinarily well. That team effectiveness reflects the quality of leadership provided by whoever leads those leaders. Your effectiveness in this meta-leadership role may be the single most important factor in your organisation's success.

Leadership of the leadership is not simply leadership at a higher level. It is a fundamentally different practice requiring distinct approaches. Master those approaches, and you unlock the full potential of leaders who themselves unlock the potential of everyone they lead.