While we acknowledge that “It’s lonely at the top”
how much attention do we give to supporting leaders?
Do They Have Someone?
Leaders face the relentless demands of day-to-day operations while trying to stay focused on strategic responsibilities. Add in the professional and personal challenges discussed in The Pinball Theory of Business & Life—even if beneficial—and it’s a lot to manage alone.
Mentoring typically flows from senior colleagues to junior colleagues—a top-down arrangement. That’s as it should be, but not enough.
A Fortune 50 CEO told me that after reaching a certain plateau, he realized he needed a personal advisor—a senior mentor—to help him take the company to the next level. He hired Peter Drucker, one of the most influential management thinkers of all time. The CEO gushed about the impact and sheer pleasure of working with Drucker, appreciating his outsider’s insights and deep wisdom. He was invaluable. Having someone at that level—completely outside the company—helped me see things I would have otherwise missed.
Not every leader has access to a Peter Drucker. That’s okay. The question is, do they have someone?
Who?
Maybe it’s a trusted family friend, a retired or non-competitive executive, a CEO Roundtable, or a seasoned outside professional. It could even be someone on the board (though that can get tricky with potential conflicts of interest). The point is, leaders need someone—a confident or a mentor like Drucker they can speak to freely, vent frustrations, and receive honest, confidential feedback or guidance.
Resistance
If there’s a well-functioning executive committee or a board of directors, they could encourage the leader to find such support. But they may be met with resistance:
I’ve got it under control. I don’t need more meetings on my over-crowded calendar. If I ever need that kind of support, I’ll let you Know. (Translation: Stay out of my business.)
At the end of the day, it’s up to the leader to accept support—genuinely or grudgingly. But if they reject it while clearly struggling, the board might have to ask, Does this leader need someone to challenge their way of doing business? and act accordingly.
I consulted with the founder of a company that had scaled to thousands of employees—but was still operating like a scrappy startup. The company’s CPA recommended creating a badly needed advisory board of outside, experienced professionals to provide guidance. I assembled a team of talented advisors. The problem? The founder didn’t want to engage with them. The needed changes never materialized. Unfortunate for the founder – and – for the company.
Executive Team
The benefits of mentorship don’t stop with CEOs—executive committees also stand to gain. When mentors help bring awareness to the internal dynamics of the executive team and its relationship with the CEO, the results can be transformative.
We can’t assume that an executive team is fully formed, experienced, or well-integrated. In young or fast-growing companies, executive roles often need to be created or rapidly filled. In startups, even senior officers may have limited leadership experience. A lack of a full or well-functioning executive team can be the starting point for mentorship. Beyond the obvious benefits of nurturing talent, mentoring executive teams provides critical advantages, such as:
Pressure Release Valve – Mentors can point out that even those who work closely with the CEO should consider the possibility that their chief may be struggling behind a polished facade of confidence.
The Onslaught – The daily barrage of expectations—deadlines, reports, performance reviews, quarterly targets—can overwhelm even the strongest executives. A mentor, reinforcing the lessons taught by Stephen Covey, can help leaders step out of their silos (and chaos) to focus on what truly matters:
The Important vs. The Urgent
The key is not to prioritize what’s on your schedule, but to schedule your priorities.
Purpose-Driven Focus – Executives receive plenty of role-specific training and corporate ladder guidance, but mentorship should go deeper. A strong mentor helps leaders explore:
- Why does this organization exist – beyond making money?
- How can I align my leadership with the company’s mission?
- What kind of leader do I want to be?
Regardless of how leadership reacts to “mentoring,” one truth remains:
Everybody Needs Someone
