Leadership development is often treated as an investment with a beginning and an end. Leaders attend training programs, develop new skills, earn promotions, and assume those investments will continue paying dividends throughout their careers.
But some of the most important aspects of leadership operate less like a one-time purchase and more like a timeshare.
The initial investment may secure the benefit, but the maintenance fees never stop. Regardless of how much was paid upfront, there is an ongoing cost to keeping that investment valuable. Those fees continue year after year, whether the owner is prepared to pay them or not.
Leadership comes with similar obligations. Certain skills and behaviors require continuous investment, regardless of a leader’s experience, position, or past success. Neglecting them can gradually erode effectiveness, even among otherwise talented leaders.
Three areas in particular carry recurring maintenance costs: keeping pace with technology, managing increasing complexity, and building strong relationships.
1. Keeping Up With New Technology
Technological competence has become a baseline expectation for effective leadership. While exceptional digital skills may provide some advantage, a significant lack of those skills can substantially undermine a leader’s overall effectiveness.
Research conducted by Zenger Folkman examining leaders’ digital capabilities revealed a striking imbalance.
Leaders rated in the bottom 10% on digital skills received overall leadership effectiveness ratings at just the 22nd percentile. By contrast, leaders in the top 10% on digital skills were rated only 17 percentile points above average in overall effectiveness.
The implications are significant. Poor digital skills carry a substantial penalty, while strong digital skills are increasingly viewed as an expected part of the job rather than an exceptional advantage.
This challenge becomes even more pressing with the rapid integration of artificial intelligence into the workplace.
AI is changing how organizations analyze information, make decisions, communicate, and execute work. Leaders who fail to understand these changes risk losing credibility with employees who expect them to provide direction in an increasingly technology-driven environment.
Importantly, maintaining digital competence does not require every leader to become a technical expert. It does require enough understanding to evaluate opportunities, recognize limitations, ask informed questions, and make sound decisions about how technology should be used.
The leadership maintenance fee associated with technology is continuous learning. Skills that were sufficient five years ago may no longer meet today’s expectations, and today’s capabilities will require further development as technology evolves.
The leadership implication: Digital fluency is no longer an optional professional advantage. Leaders must regularly invest time in understanding emerging technologies and their implications for the people and organizations they lead.
2. Staying Organized as Complexity Increases
Organizational complexity rarely moves in reverse.
Businesses face expanding regulatory requirements, increasingly sophisticated technologies, more interconnected operations, and growing volumes of information. Decisions that once involved a handful of considerations may now require input from legal, financial, technical, and operational specialists.
Even relatively straightforward business transactions can generate extensive documentation, multiple layers of review, and complicated approval processes.
For leaders, this growing complexity creates a significant challenge: maintaining clarity and effectiveness without becoming overwhelmed by competing demands.
The solution is not simply to work harder or personally manage every detail. In fact, attempting to maintain direct control over increasingly complex operations can create bottlenecks and reduce organizational effectiveness.
Instead, effective leaders develop systems that help them prioritize information, delegate responsibilities, and draw on the expertise of others.
Strong organizational habits become especially valuable as responsibilities expand. Clear decision-making processes, reliable communication channels, effective delegation, and disciplined prioritization help prevent complexity from becoming chaos.
Equally important is recognizing when specialized expertise is necessary. Leaders who surround themselves with capable, trusted colleagues are better positioned to navigate challenges than those who attempt to solve every problem independently.
The maintenance fee in this area is the continuous refinement of how work gets organized and accomplished.
A system that functioned well when an organization was smaller may become inadequate as the business grows. Responsibilities change, information increases, and processes must evolve accordingly.
The leadership implication: Managing complexity requires ongoing attention to organizational systems, priorities, and delegation. Leaders should regularly evaluate whether their current ways of working still support effective decision-making and execution.
3. Building and Maintaining Relationships
Good relationships make a huge difference in our lives. Negative relationships can drag us down into discouragement, despair, anger, or retaliation. Many people reach a point where they feel they have “enough” relationships and no longer need to invest in new ones. But the problem is that people come and go — through changes in organizations, positions, and responsibilities.
Our research found that leaders in the bottom quartile on building relationships are rated at only the 19th percentile overall, while those in the top quartile are rated at the 82nd percentile. This one skill dramatically shapes how others experience you. The truth is, you can never have too many positive relationships — they influence how others rate you on communication, setting stretch goals, inspiring others, strategic perspective, technical expertise, and, in fact, all 19 leadership competencies we measure.
The Cost of Neglecting Leadership Maintenance
The challenge with recurring maintenance costs is that postponing payment can initially seem inconsequential.
A leader who stops learning about emerging technology may continue performing adequately for a time. An outdated organizational process may remain functional until responsibilities increase. A neglected relationship may appear stable until a difficult decision exposes the absence of trust.
In each case, the consequences of neglect tend to become more visible over time.
This helps explain why past leadership success does not guarantee future effectiveness.
Experience and established capabilities provide a valuable foundation, but they cannot eliminate the need for continued development. As organizational expectations evolve, leaders must evolve with them.
The research on digital competence and relationship-building illustrates this reality. Weaknesses in either area can significantly affect how others evaluate a leader’s overall effectiveness, regardless of strengths elsewhere.
The encouraging distinction between leadership and a timeshare is that leaders have considerable control over how they manage these recurring obligations.
They can deliberately develop their technological understanding, improve organizational practices, and strengthen relationships before deficiencies become serious problems.
The most effective approach is to treat these investments as part of the ongoing work of leadership rather than as occasional corrective measures.
Leadership Effectiveness Requires Continuous Investment
Leadership development is not a transaction completed when someone earns a management position or finishes a training program.
It is an ongoing responsibility that changes alongside the organization and the people being led.
Technology will continue advancing. Organizational complexity will continue creating new demands. Relationships will continue requiring attention as teams and responsibilities evolve.
These are not temporary challenges that can be permanently resolved. They are recurring costs of remaining an effective leader.
The leaders best positioned for long-term success are not necessarily those who made the largest initial investment in their development. They are those who recognize that maintaining effectiveness requires consistent attention, adaptation, and effort.
The maintenance fees of leadership never disappear. The choice is whether to invest in them consistently or face the accumulating cost of neglect.
