The Blind Spot of Strong Leaders
By Dr. Andrea Lensing-Kramer, WiseForce Advisor
During my more than thirty years as a partner at Freshfields, I’ve had the privilege of working with many highly talented and successful individuals, including CEOs, general counsels, executives of all kinds, and partners at global law firms and consulting firms. They have all managed major transactions and crises of every kind with remarkable composure and poise.
Looking back, what surprises me—and has been on my mind a lot lately—is that many of these exceptionally competent people, who were always perfectly prepared for everything, become insecure and lose their confidence when their traditional professional careers come to an end—even when it’s their own decision.
We were prepared for earlier stages of life—but not for this one
When you think about it, it’s actually not that surprising. Our families, schools, universities, companies, and so on systematically prepare us for major life transitions early on. Choosing a school or college, deciding on a career, and perhaps even choosing a partner—these are all processes that are guided, discussed, and sometimes prepared for over the course of years.
No one prepares us for the end of our careers and the time that follows—especially when it comes to a transition that, particularly for successful people who have dedicated their professional lives with such passion and commitment, marks a profound turning point, one that we hope will be followed by many more years.
I enjoyed the work—that’s the key point
People pursue a career because they love it, with all its ups and downs. Anyone who spends half their life working at the highest level doesn’t do so out of a sense of duty alone. The intellectual complexity, the responsibility, the creative freedom, the collegial relationships, mentoring younger colleagues, a title that immediately signals status in any room, colleagues who understand your context without needing an explanation, a calendar that fills every day with meaning, and working at the limits of your own abilities. All of this has an effect on you: it gives you purpose, structure, and identity—and a place where you’re needed.
All of this is what makes the process of moving on and transitioning so challenging. It’s not about being glad to finally be done. On the contrary, you’re now looking for something that’s just as fulfilling, that brings just as much joy, and that meets your own standards—just in a different way, perhaps with less external pressure and more freedom.
Questions That Deserve Attention
When one’s so-called career comes to an end, a silence settles in—a time that no one warns you about and that was never part of your goals. During this phase, the questions that had been pushed aside by decades of progress resurface:
- What do I stand for outside of my professional life?
- How do I introduce myself at an event to someone who doesn’t know my title or the organization I work for?
- What does a fulfilling day look like now that I’m no longer completely booked?
- What relationships in my life exist independently of my professional role?
- What did I truly enjoy about my work, and how could that continue?
- What have I always wanted to explore, but kept putting off?
- What will my contribution look like in the coming years? Not out of obligation, not out of habit—but because it truly fulfills me?
These are leadership questions that are relevant both to oneself and to the people around you. These questions deserve the same care that we have naturally given to other strategic decisions.
When is the right time to ask these questions?
Some people start seriously thinking about what comes next two or three years before they retire. Others don’t begin this process until after their last day of work. Still others treat themselves to a deliberate break at first—a pause that creates space before the next chapter begins.
There is no right time. There is only the right process—an honest examination of oneself, of what truly matters to you, what drives you, what brings you joy—beyond job titles and roles.
What has consistently impressed me in my conversations with experienced leaders is this: Those who navigate this transition particularly successfully are the ones who approach it with the same seriousness with which they have prepared strategic decisions throughout their entire professional lives.
A smooth transition—for the company as well
Those who consciously plan this transition early on are not only investing in their own future, but also in the company they are leaving.
A leader who knows what lies ahead hands over the reins with confidence and dignity. She does not cling to her position—often out of an unconscious fear of what comes next. She remains present until the very end, calm and generous in sharing her knowledge, experience, and networks. This is a measurable advantage—not only for the leader herself, but also for her successors, for teams, and for the company.
“Transition Readiness” is beneficial for everyone involved, both professionally and personally.
You don’t have to walk this path alone
One of the great ironies is that the people who are best trained to guide others through complexity and change often hesitate to seek support themselves. Self-reliance is a professional virtue that can become a personal limitation.
Having a trusted sparring partner—someone who asks the right questions without an agenda of their own, who knows and understands what makes a long, successful career special, and who can help you shape the next chapter with clarity and intention—is not a luxury. It is a wise investment in one of life’s most important “transitions.”
Dr. Andrea Lensing-Kramer is a former partner at Freshfields, one of the leading international law firms, and a WiseForce Advisor. As a sparring partner, mentor, and coach, she supports young lawyers in building their careers, but now also, in particular, helps leaders who are nearing the end of a long career and want to shape the next phase of their lives with clarity and purpose. She can be reached via WiseForce Advisors. If this resonates with you, please feel free to contact us.
