Give me someone’s calendar and checkbook, and I can tell you about their leadership. This sentiment captures a simple yet powerful truth: how leaders allocate their time and resources reflects their priorities, values, and ability to drive meaningful impact. In the modern business landscape, leadership is not merely about strategy or vision—it’s about intentional actions that build trust, foster growth, and sustain critical relationships.
Calendar: A Leader’s Investment in Time
A leader’s calendar is more than a scheduling tool; it’s a living document of their priorities. The time leaders dedicate to mentoring their teams, engaging with stakeholders, or refining strategies showcases their commitment to long-term success. Regular meetings, check-ins, and collaborative sessions signal intentionality in sustaining organizational momentum and fostering connection.
Time investment also reflects accessibility—a hallmark of outstanding leadership. Even during tight schedules, the willingness to engage demonstrates a leader’s value for the relationships they lead and support. Conversely, a lack of presence in critical areas of the business or team may highlight gaps in alignment.
Effective leaders consistently evaluate their time management by asking:
- Does my calendar reflect my strategic priorities?
- Am I dedicating enough time to mentor and develop my team?
- Are key stakeholders and partnerships getting the attention they deserve?
Checkbook: A Leader’s Financial Priorities
Just as time reveals a leader’s focus, financial decisions offer insight into their values and vision. Investments in employee development programs, team-building initiatives, or innovative tools speak volumes about a leader’s commitment to organizational growth and culture.
Financial resource allocation is a powerful reflection of a leader’s confidence in and commitment to long-term success. Decisions such as funding strategic initiatives, recruiting top sustainability talent, or championing impactful growth causes go beyond mere budgeting—they underscore a leadership philosophy rooted in purpose and vision. When leaders prioritize resources effectively, they signal clarity in their strategic direction and an unwavering belief in their organization’s future. Conversely, insufficient or misaligned investments often highlight a deeper issue—a lack of strategic clarity or hesitation to commit to transformative goals fully. Ultimately, how resources are allocated tells a story about what leaders value and where they believe success will come from.
Leaders should frequently ask themselves:
- Are my financial decisions aligned with my organizational mission and values?
- Am I investing in initiatives that empower my team and foster innovation?
- Do my spending patterns reflect a commitment to shared success
Relationships: The Core of Leadership
At its heart, leadership is relational. The connections leaders cultivate—both internally with their teams and externally with stakeholders—define their influence. In a post-pandemic world, where in-person interactions are often minimized, many leaders risk neglecting critical relationships. Yet, sustaining trust and rapport remains a cornerstone of effective leadership.
Current relationships—whether with employees, clients, or partners—require attention and care. Leaders should ask:
- Am I regularly engaging with key team members and stakeholders?
- How well do I understand my team’s motivations, challenges, and aspirations?
- Are my actions building trust and fostering collaboration?
At the same time, leadership demands forward-looking relationship-building. Identifying and nurturing “aspirational relationships” with potential collaborators, advisors, or industry leaders is essential for future growth. These relationships require intentional effort, alignment of values, and thoughtful engagement.
Leadership Reflected in Action
A leader’s calendar and checkbook are more than operational tools—they’re powerful indicators of leadership style, effectiveness, and legacy. They reveal how leaders prioritize their time and resources, demonstrating their ability to align actions with values and vision.
The best leaders use these tools to balance immediate demands with long-term goals, ensuring they build sustainable relationships and create meaningful impact. By intentionally allocating time and resources, leaders can inspire trust, drive innovation, and foster organizational resilience.
Every leader should ask the clear question: Do my calendar and checkbook reflect the leader I aspire to be?