30: The Art of Delegation

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 (https://www.amazon.com/Monday-Morning-Leadership-Mentoring-Sessions/dp/0971942439/ref=tmm_pap_swatch_0?_encoding=UTF8&qid=1647907753&sr=1-1&tag=leaderfables-20) by Juli Baldwin - Free to Focus: A Total Productivity System to Achieve More by Doing Less (https://www.amazon.com/gp/product/0801075262/ref=ppx_yo_dt_b_asin_title_o09_s00?ie=UTF8&psc=1&tag=leaderfables-20) by Michael Hyatt - The Power of Moments: Why Certain Experiences Have Extraordinary Impact (https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/0593079264/ref=monarch_sidesheet&tag=leaderfables-20) 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: 1. 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 (https://www.loom.com) - Free to Focus (https://a.co/d/cJkMh4i) by Michael Hyatt - Michael Hyatt's "Freedom Compass (https://www.reesehopper.com/blog/2020/11/17/the-freedom-compass-michael-hyatts-free-to-focus)"

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.

In this episode, Casey and Jacob discuss their favorite productivity apps and tools. They also share their experiences with analog tools like the Full Focus Planner and their preferred pens. They emphasize the importance of having a consistent strategy for organizing notes and emails, and discuss the benefits of having a good work bag. They caution against constantly switching between new apps. Mentioned in this episode: Flexibits | Fantastical | The calendar and tasks app you won't be able to live without. (https://flexibits.com/fantastical) Task Management Software Built For Pros - OmniFocus - The Omni Group (https://www.omnigroup.com/omnifocus) Nozbe - best project management and collaboration tool (https://nozbe.com/) Obsidian - Sharpen your thinking (https://obsidian.md/) Best Note Taking App - Organize Your Notes with Evernote (https://evernote.com/) TextExpander: #1 Text Replacement & Keyboard Shortcut App (https://textexpander.com/) LaunchBar 6 (https://obdev.at/products/launchbar/index.html) Irradiated Software - SizeUp - The Missing Window Manager (https://www.irradiatedsoftware.com/sizeup/) Keyboard Maestro: Work Faster with Macros for macOS (https://www.keyboardmaestro.com/main/) Readwise (https://readwise.io/) Amazon.com : Full Focus Leather Coil Planner by Michael Hyatt (https://www.amazon.com/dp/1737211955?_encoding=UTF8&ref_=cm_sw_r_cp_ud_dp_PQQ0M0MMAYM703HN4QR0&th=1) Amazon.com: Pilot, FriXion Clicker Erasable Gel Pens, Fine Point 0.7 mm (https://www.amazon.com/dp/B009ZMFI88?ref_=cm_sw_r_cp_ud_dp_MSDXJ0JYMGG2BK2TC1XD&th=1) Amazon.com: uniball Vision Elite Rollerball Pens with 0.5mm Fine Point Micro Tip (https://www.amazon.com/dp/B00006IE9I?_encoding=UTF8&psc=1&ref_=cm_sw_r_cp_ud_dp_02DN2A8V9CDEM9KPD27P) Amazon.com: Care Touch Lens Cleaning Wipes for Eyeglasses (https://www.amazon.com/dp/B01NCOUY05?_encoding=UTF8&psc=1&ref_=cm_sw_r_cp_ud_dp_PM7E96JNKRJ9QDR5R56J) TOM BIHN - Travel Bags - Laptop Bags - Backpacks - Totes (https://www.tombihn.com/) Drafts | Where Text Starts (https://getdrafts.com/)

In this episode, Jacob and Casey discuss the importance of hobbies in preventing burnout, maintaining motivation, and promoting a healthy work-life balance. They share their personal hobbies, ranging from stargazing and 3D printing to traveling and building Lego sets. They also discuss the therapeutic benefits of hobbies, such as relaxation, stress relief, and intellectual stimulation. Finally, they highlight the importance of hobbies being enjoyable, non-monetized, and not tied to a set timeline. Casey and Jacob encourage leaders to avoid hobbies that involve screens, especially for those who spend significant time working on computers. They are also encourage folks to be comfortable with changing hobbies if they no longer bring enjoyment, and to start small when picking a new hobby. Mentioned in this episode: Play: How it Shapes the Brain, Opens the Imagination, and Invigorates the Soul (https://a.co/d/2U4Z1VN) by Stewart Brown

In this second part of a two part topic on making ideas happen, Casey and Jacob discuss the art of project execution. But before they do they briefly recap the importance of capitalizing on inspiration and strategies for effective persuasion. They then share many tips for effective project execution, including what to do when it all goes to hell. Mentions in this episode: Discipline Is Destiny: The Power of Self-Control (https://www.amazon.com/Discipline-Destiny-Power-Self-Control-Virtues/dp/0593191692?_encoding=UTF8&qid=1693273841&sr=8-1) by Ryan Holiday Leader Fables: Altitudes of Planning Overview (https://www.leaderfables.com/12)

In this next installment of Leader Fables, Jacob & Casey share their process for making ideas happen. They discuss the importance of capitalizing on fleeting inspiration, explore the art of persuasion, highlighting the use of leading questions and inclusive brainstorming to gain support for ideas. They conclude by sharing some tips for effective project execution strategies. Mentions in this episode: Drafts | Where Text Starts (https://getdrafts.com/) Mind Map & Brainstorm Ideas - MindNode (https://www.mindnode.com/) Traction: Get a Grip on Your Business (https://www.amazon.com/Traction-Get-Grip-Your-Business/dp/1936661837?crid=1BKGRLX8XVBZG&qid=1691928871) Scaling Up: How a Few Companies Make It...and Why the Rest Don't (https://www.amazon.com/Scaling-Up-Mastering-Rockefeller-Habits/dp/0986019593?crid=1WXBQLO5X0AOL&qid=1691928964&s=books&sprefix=scaling+up%2Cstripbooks%2C136&sr=1-1) The Agile Samurai: How Agile Masters Deliver Great Software (https://www.amazon.com/Agile-Samurai-Software-Pragmatic-Programmers-ebook/dp/B00AYQNR5K?qid=1691929115&s=books&sprefix=agile+sam%2Cstripbooks%2C164&sr=1-1) David Tannen - The Inception Deck (http://davidtannen.com/project-managment/the-agile-samurai/102-the-inception-deck)