“The best executive is the one who has sense enough to pick good people to do what he wants done, and self-restraint enough to keep from meddling with them while they do it.”
— Theodore Roosevelt
The Myth of a Single Leadership Style
In popular leadership discourse, the archetype of the heroic leader—charging up the hill, rallying the troops, leading from the front—has long dominated. But in real, complex organizations, that archetype breaks down. Great leaders understand that leadership is situational. Sometimes the job requires you to be out front, sometimes to steer from the back, and sometimes to disappear entirely and let the system lead itself. The hard part? Knowing which to use, when, and why.
Historical Context: Leadership Through the Ages
In military history, leaders like Alexander the Great literally led from the front, sword drawn. This visible courage galvanized armies. In contrast, Nelson Mandela wrote in Long Walk to Freedom about the tribal leadership practice of allowing others to speak first—leading from behind so others could shine. He applied this philosophy to help transform South Africa’s political landscape, demonstrating that transformational leadership can also be humble and facilitative.
In modern business, Steve Jobs often led from the front: setting vision, defining aesthetic standards, and challenging teams to “Think Different.” Conversely, Satya Nadella’s transformation of Microsoft is often cited as a case of empathetic, behind-the-scenes leadership that enabled autonomy and collaboration.
Defining the Styles
Leading from the Front
- What It Means: Visible, decisive action. Setting direction and demonstrating commitment by example.
- When It Works:
- In crisis situations.
- During cultural transformations.
- When initiating large-scale strategic shifts.
- In high-ambiguity environments where clarity is absent.
- Implications:
- Can inspire and energize.
- Risk of micromanagement or over-dependence.
- May overshadow team autonomy.
Leading from the Back
- What It Means: Empowering others to lead, guiding with questions instead of answers, enabling others to shine.
- When It Works:
- With mature, capable teams.
- During scaling or stabilizing phases.
- When developing successors or leaders.
- Implications:
- Builds ownership and long-term resilience.
- May be seen as passive if not intentional.
- Requires deep trust in team capability.
When It Goes Wrong (and What to Do About It)
Overleading:
- Symptoms: Bottlenecks at the top, innovation stifled, burnout.
- Fix: Step back. Delegate. Clarify decision rights. Empower.
Underleading:
- Symptoms: Drift, confusion, low morale.
- Fix: Step in. Set direction. Reestablish vision. Provide coaching or structure.
Other Leadership Styles to Consider
| Style | Description | Best For |
| Servant Leadership | Prioritizing the needs of the team. | People development, retention, and values-driven cultures. |
| Transformational | Inspiring change through vision and values. | Cultural shifts, innovation, high-growth environments. |
| Transactional | Focused on tasks, metrics, rewards, and punishments. | Operations, compliance-heavy industries, performance enforcement. |
| Situational Leadership | Adapting style based on maturity and capability of team members. | Diverse teams, early-stage teams, dynamic scaling. |
| Coaching Leadership | Asking more than telling, facilitating growth. | Developing high-potential individuals, succession planning. |
A Framework for Assessing and Adapting Your Leadership Style
1. Diagnose the Situation
- Is the team experienced or new?
- Is the organization in crisis, growth, or maintenance mode?
- Is clarity present or are people paralyzed by ambiguity?
2. Evaluate Your Impact
- Are decisions stuck at your desk?
- Are people acting with initiative?
- Are you being asked to do things your team should own?
3. Adjust Intentionally
- From Front to Back: Gradually hand off decisions, celebrate others’ leadership, shift from directives to open questions.
- From Back to Front: Establish or reassert vision, be visible, reset expectations, clarify boundaries and priorities.
4. Monitor Outcomes
- Track morale, delivery, engagement, decision velocity, and leadership distribution.
- Conduct skip-level feedback and retrospectives.
Thought Leaders to Follow
- Jim Collins – Level 5 Leadership emphasizes humility + will.
- Simon Sinek – Advocates for “Leaders Eat Last.”
- Marshall Goldsmith – Executive coaching on behavioral change.
- Liz Wiseman – Multipliers explores how great leaders amplify others.
- Bill Campbell – “The Trillion Dollar Coach” known for mentoring Silicon Valley CEOs with a coaching-first style.
Real-World Examples
- Done Well: Reed Hastings at Netflix initially set strong principles and then stepped back, creating a self-regulating high-performance culture.
- Done Poorly: WeWork’s Adam Neumann embodied aggressive front-leading but failed to know when to step back—resulting in chaos, loss of control, and eventual ousting.
Wrapping up…
The best leaders are not stuck in a style—they are students of context, team dynamics, and timing. Leadership isn’t a static identity; it’s an evolving practice of presence, influence, and humility. As your organization changes, so should your posture. Sometimes, it’s your job to carry the torch. Other times, it’s your job to pass it—and make sure others have the hands to carry it forward.
