30: The Art of Delegation

In this episode, Jacob and Casey discuss their feelings and experiences on how so much of the work and impact that leaders make is unseen or goes without credit. They reflect on specific instances in their careers in which they needed to be patient, defer recognition, and suppress their egos or emotions in order to best serve their teams as leaders. The two also discuss how leadership is commonly misunderstood in terms of visibility and the various ways in which it has both downsides and tremendous value that often leads to some of the most meaningful work.

Casey and Jacob work through all the pros and cons of scheduling true vacations from work throughout the year. The two discuss why leaders need to be open to taking off more time from work, how a vacation can actually improve your ability to maintain present and future work output, and signs that you seriously need to get a vacation (or three) scheduled. Additionally, they lay out smart ways to make the most of a vacation and to feel confident that your team has everything in place for things to run smoothly while you’re away.

In this episode, Jacob and Casey discuss the importance of working on your own work by developing principles and practices that can help you get ahead of potential work obstacles and improve your own output individually and as a team leader. Jacob shares key takeaways and reflections from one of his favorite recent reads – Ray Dalio’s book “Principles”. Jacob discusses how the book has become a great reference and motivated him to formulate many of his own principles based on truths he has discovered over his career and experience. The two spend time discussing and brainstorming on some of Jacob’s most important principles with themes like: No surprises Being calm in crisis The Peak-End Rule Speaking candidly and in-person Gaining trust by being transparent Simple and complex systems Empowering small teams Mentions in this episode: Ray Dalio's Book "Principles"

Jacob and Casey discuss crafting an ideal week—-a proactive approach to planning time for what matters most, protecting margin, and sustaining energy both at work and home. They share how regularly reviewing and updating an ideal week template helps leaders hedge against chaos and interruptions, while staying focused on key priorities. Their discussion covers essential steps such as starting with a blank calendar, blocking out recurring meetings and personal routines, auditing current time use, and ensuring built-in flexibility and white space. Casey and Jacob stress the importance of critical reflection: questioning the necessity of each meeting, reserving "deep work" periods, and blocking time for daily startup and shutdown routines. Other practical advice includes color-coding calendars, sharing ideal week philosophies with teams for alignment, and tracking "hit rates" against the plan to drive accountability and continuous improvement. Key Points Discussed: The value of designing an ideal week as a "budget for your time" The importance of regular audits and revisiting the plan to account for shifting priorities Strategic scheduling of deep work, meetings, and buffer times Differentiating between unmovable meetings and those worth challenging Using color-coding and recurring calendar events to maintain visibility of the ideal week Encouraging teamwide alignment and transparency around availability and expectations Actionable Takeaways: Begin with a blank calendar and define what your perfect week would look like, free from outside constraints Audit your current calendar for time sinks and low-value meetings, then start from zero when building your template Block your most critical routines and "deep work" sessions before adding less essential commitments Incorporate ample buffer time for transitions, breaks, and the unexpected Share your availability philosophy with your team and review progress against your ideal regularly, adjusting as needed Take charge of your time by designing your ideal week now and commit to revisiting it routinely, empowering yourself and your team to focus on what matters most.

Listen as Casey and Jacob explore why consistent one-on-ones are the highest-leverage activity for leaders, addressing the common dread around them and sharing strategies to transform them into relationship-building and coaching sessions. Key Points Discussed: The value of consistenat one-on-ones as a high-leverage leadership activity and why they should not be canceled or rescheduled. The three core functions of one-on-ones: building relationships, providing coaching and feedback, and clearing the decks. Strategies for agenda-setting, including having the direct report set the agenda first, using a three-question framework (“How are you?”, “How is the business?”, “How can I help?”), and feeding topics through shared channels or documents. Techniques for structuring meetings: frequency (monthly to weekly), duration (avoid back-to-back or front-loading), and context (changing location, shared meals or coffee, disabling distractions). Coaching tips: letting the direct report speak most of the time (aim for 70/30 listening to talking ratio), using individual development plans, and exploring collaborative book readings. Actionable Takeaways: Schedule recurring one-on-ones at least monthly, aim for weekly when possible, and avoid rescheduling. Create a shared agenda space (Slack channel or document) for continuous topic capture. Use a clear agenda framework: direct report first, fallback prompts from the manager. Reserve the last minutes for administrative updates and handle most updates asynchronously. Enter each session distraction-free: enable Do Not Disturb and choose a setting that fosters open conversation. Ready to elevate your leadership? Commit to consistent, purposeful one-on-ones and start building stronger, more engaged teams.

Jacob and Casey discuss how the isolation inherent in leadership roles can affect decision-making and performance, drawing on research that highlights the prevalence of loneliness among senior leaders. They explore the challenges of maintaining a confident persona while shouldering heavy responsibilities and the importance of having a trusted inner circle to share concerns and gain objective feedback. Key Points Discussed: The impact of loneliness on leadership performance and decision-making. The difficulty of finding peers and trusted advisors within an organization. The benefits of developing a supportive network or mastermind group for honest conversations. The role of strategic vulnerability in building trust and enhancing team dynamics. The practical use of journaling and self-reflection as tools for managing stress. Actionable Takeaways: Invest in building and maintaining peer relationships both within and outside your organization. Incorporate regular self-care practices, such as brief journaling sessions, to externalize thoughts and reduce stress. Consider engaging with a coach or therapist to gain unbiased perspectives and navigate complex decisions. Proactively establish check-ins or mastermind sessions with trusted peers to discuss challenges and solutions. Plan difficult conversations in advance to ensure they lead to constructive outcomes. Take control of your leadership journey by implementing these strategies to reduce isolation and enhance your effectiveness.

In this episode, Casey & Jacob share personal stories and professional experiences from 2024, shedding light on what it takes to lead effectively. They discuss their key accomplishments and the challenges they faced. They also outline their aspirations for the future, Casey and Jacob provide a thoughtful and engaging analysis of their leadership journey. Beyond recounting their own experiences, they offer practical advice for listeners on how to plan for personal and professional growth. With a focus on setting realistic goals, learning from setbacks, and staying adaptable, this episode is packed with valuable takeaways for anyone looking to enhance their leadership skills. Whether you’re a seasoned leader or just starting out, you’ll find inspiration and actionable tips to help you navigate the year ahead with confidence.

In this episode of Leader Fables, Jacob & Casey discuss the art of team development. While lots of conversations regarding leadership often focuses on individual growth through 1:1s, this conversation explores ways leaders can nurture team cohesion and collaboration. Jacob & Casey share practical, actionable tips, including how to: Build camaraderie and learning by reading books together. Plan meaningful team retreats that inspire connection and creativity. Maximize conferences to foster team growth. Create shared experiences through fun, low-cost activities like pasta-making nights or axe throwing. Honorable mentions in this episode include: Monday Morning Leadership: 8 Mentoring Sessions You Can't Afford to Miss by Juli Baldwin Free to Focus: A Total Productivity System to Achieve More by Doing Less by Michael Hyatt The Power of Moments: Why Certain Experiences Have Extraordinary Impact by Chip Heath With relatable examples and their signature humor, Jacob & Casey make the case for why investing in team development isn’t just worth it—it’s essential. Listen in for strategies that are easy to implement and guaranteed to make your team stronger.

In this episode of Leader Fables, hosts Casey and Jacob discuss the challenges and benefits of delegating work as leaders. Through personal anecdotes of triumphs and failures, they explore why delegation can be so difficult and why it’s essential for effective leadership. Key Discussion Points: Why Leaders Struggle to Delegate Many leaders hesitate to delegate due to perfectionism, control tendencies, fear of failure, or insecurity. High-visibility tasks often amplify these concerns, making delegation even more daunting. The Case for Delegation Delegating is crucial for scaling leadership, empowering teams, and fostering growth. It provides opportunities for team members to develop their skills and for leaders to focus on higher-level responsibilities, advancing careers on both sides. How to Delegate Successfully Build trust with regular check-ins Assign significant projects and celebrate team success Involve team members in decision-making processes to foster ownership Clearly define success criteria for tasks and projects Honorable mentions from this episode include: Loom Free to Focus by Michael Hyatt Michael Hyatt's "Freedom Compass"

In this episode, Jacob and Casey dive deep into the topic of goals, exploring the common perceptions and challenges leaders face when setting and achieving them. They discuss goals in a leadership context, and highlight the often negative connotations associated with goals, such as doom, gloom, and the pressurethat comes from high expectations. The episode is divided into two main sections: what to do when you realize you might miss a goal and what to do after you have officially missed it. They stress the importance of acknowledging potential issues early and communicating transparently with stakeholders. Whether you're a seasoned leader or just starting out, Jacob and Casey's discussion provides a thoughtful and encouraging perspective on the journey towards achieving your goals.