Dr. Leahcim Semaj
Psychologist | Author | Social Philosopher | Spiritual Guide | Management Consultant
Every so often, a truly transformative book appears — one that goes beyond media hype and strikes a raw nerve, offering insights that immediately resonate. Michael Useem’s Leading Up: How to Lead Your Boss So You Both Win (Crown Business, 2001) was one such book. Drawing on powerful stories from business, natural disasters, military operations, politics, religion, and humanitarian crises, Useem presents a compelling case: leadership is not just a top-down process. In today’s complex, fast-moving world, it is often necessary to lead upward — to guide and influence your boss or superior for the success of the entire organization.
If subordinates are too afraid or too passive to help their leaders lead, those leaders — and by extension, their organizations — are destined to fail.
In this blog, we explore how you can develop the rare and valuable ability to lead up.
The New Reality: Frontline Perspective Matters
As the pace of change accelerates and hierarchies flatten, frontline employees often have a clearer, more up-to-date view of emerging realities than their distant leaders.
You see what they might miss.
You have a clearer view of “the emperor’s wardrobe.”
It becomes your responsibility to inform, challenge, and guide from below — not through rebellion, but through intelligent, courageous engagement.
1. Take Intelligent Risks
Leading up requires you to be a calculated risk-taker.
You must develop the skill to make decisions quickly and accurately, even when the pressure is high — rather than defaulting to kicking difficult decisions upstairs.
Useem highlights the story of David Pottruck at Charles Schwab, who helped revolutionize the U.S. brokerage industry. Pottruck knew that launching an online platform was a massive risk; failure would have cost him his career. But he seized the opportunity, led upward, and ultimately changed the future of investing.
Key Lesson: If you want to lead up, you must sometimes bet your future on a vision your superiors cannot yet see.
2. Speak Up: Courageous Communication
Even in strict hierarchical structures, such as the U.S. Marine Corps, junior officers are expected to challenge flawed orders before they are executed.
General Peter Pace, when serving as Commander-in-Chief at the U.S. Southern Command, institutionalized this practice. He never closed a meeting without actively soliciting critical feedback from his team, reinforcing a culture of courageous dialogue.
Key Lesson: Leadership is not about blind obedience. It’s about creating an environment where truth rises to the top, even when it’s uncomfortable.
3. Master the Art of Reverse Mentoring
One of the most revolutionary examples of leading up comes from General Electric under Jack Welch. Recognizing that technological change was outpacing senior leaders’ expertise, Welch launched a reverse mentoring program.
He instructed 600 senior executives to pair up with younger, tech-savvy employees to learn about the Internet and emerging technologies.
Welch himself led by example, choosing the young leader responsible for GE’s main website to coach him on e-business.
The results?
- Middle managers became more comfortable pressing ideas upwards.
- Senior executives became more adept at listening and learning from those below them.
- The overall organizational agility and innovation increased dramatically.
Key Lesson: Leaders who stay learners — especially from those younger or less senior — become more effective. Reverse mentoring makes upward leadership a normal, expected part of organizational life.
(Reference: Useem, M. (2001). Leading Up: How to Lead Your Boss So You Both Win. New York: Crown Business.)
The Jamaican Context: A Call for Upward Leadership
In Jamaica, as in many parts of the world, there is a cultural tendency to defer unquestioningly to authority — in politics, in business, and even in civil society.
However, as we seek to build a more resilient, innovative, and globally competitive Jamaica, we desperately need more people who are willing to lead up.
Minister Phillip Paulwell years ago set a promising example by selecting the young Makonen as a key consultant, recognizing the need for fresh perspectives and upward mentorship.
We must cultivate more environments where:
- Subordinates respectfully challenge decisions.
- Young professionals coach senior leaders on new trends and technologies.
- Employees at all levels feel empowered to contribute to leadership decisions.
Final Thought: Leadership is a Two-Way Street
Leadership is no longer a one-way street flowing from the top down.
It is a dynamic, two-way exchange of insight, courage, and responsibility.
When you learn to lead up, you help your boss win — and you create more room for your own growth, your team’s success, and your organization’s future.
As the old saying goes:
“The boss may be the head of the organization, but it is often the feet and eyes that see where it needs to go.”
Are you willing to lead from where you stand?
A Note to My Readers
If this message speaks to where you are in life, let’s talk. Book a 1-on-1 MindSpa consultation and begin your transformation journey today. You’re also invited to subscribe to my newsletter and share it with those who may benefit.
I’m available to bring this message to your organization or audience through keynotes, workshops, or customized seminars.
I don’t write to convince or convert — only to share insights gained from years of observation, study, and experience. These are simply perspectives, offered to inspire thought, not debate.
If my words resonate with you, I welcome that. If not, I invite you to take what serves you and leave the rest.
My MindSpa consultation sessions are different. They are sacred spaces where I partner with individuals who are seeking clarity, transformation, and growth. If that’s what you desire, I would be honored to support your journey.
Until then, may you continue forward with curiosity and grace
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