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The Right-Hand Roadmap

The Right-Hand Roadmap

Written by: Megan Long
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About this listen

 The Right-Hand Roadmap is the only podcast for Seconds-In-Command of founder-led companies. I’m your host Megan Long, an award-winning executive & entrepreneur, pro athlete, and owner of Second First. Together we explore the unique world of being a #2 Leader in entrepreneurial companies. This is the place where we dive into the challenges, opportunities, and strategies that can help you excel in your role. Our mission is clear: to transform the relationships between entrepreneurs and, you, their Second-In-Command. We’ll cover a wide range of topics, from navigating your relationship with the founder to mastering the role through best practice knowledge, tools, and insights you need to thrive in your position. But this podcast isn’t just about learning; it’s also about being part of a community. This role is lonely and often misunderstood - together we’re stronger and supported in ways we can’t find within our companies or at home. If you’re ready to embark on a journey of growth, l...© 2023 Economics Management Management & Leadership
Episodes
  • #57: Two Delegation Secrets That Will Transform How You Lead Your Team

    #57: Two Delegation Secrets That Will Transform How You Lead Your Team
    Jan 29 2026
    Free Up Your Time While Developing Your Team In this solo episode, Megan Long breaks down why so many Seconds-in-Command and Integrators struggle with delegation, usually because it was modeled poorly for them or they've fallen into the trap of thinking "it's faster if I just do it myself." The game-changer comes from understanding two critical frameworks: first, before giving any feedback, ask yourself "is this preference or is this policy?" Most leaders waste time correcting work that's different from how they'd do it, not work that's actually wrong. Second, there are five levels of delegation—from "carry out instructions" for new employees to "act independently" for trusted team members—and the biggest mistake is not being clear about which level you're using before handing off work. For Seconds-in-Command specifically, you need to factor in what your CEO will ask you about and remember that your entrepreneur's preferences become policy, even when they seem trivial. When you get delegation right, you're not just getting work off your plate, you're building the skill sets of your team. You'll hear all about: 01:32 - Breaking the mental stigma around delegation: it's not about dumping tasks, it's about developing people and giving opportunities for growth 02:53 - Common false narrative: "It's faster if I just do it myself" because you don't like how they do it 03:16 - Delegation Secret #1: Preference vs. Policy - Before giving feedback, ask yourself if the work needs to change to be correct, or if it's just different than how you'd do it 03:48 - Real-world example: The agenda with mixed fonts and no icebreaker - is this worth feedback? 04:46 - The flip side: Ruinous empathy from Kim Scott's "Radical Candor" - when you avoid giving necessary policy feedback to protect feelings 05:17 - Delegation Secret #2: The Five Levels of Delegation - delegation isn't all-or-nothing; clarity on the level is key to success 05:57 - Level 1: Carry Out Instructions - for new employees or when you've already made the decision 06:42 - Level 2: Research and Report - gathering information while you reserve decision-making 06:56 - Level 3: Research and Recommend - they provide pros, cons, and their opinion; you give final authorization 07:24 - Level 4: Decide and Inform - they make the decision and tell you after; high trust, just avoiding surprises 08:06 - Level 5: Act Independently - highest level; full autonomy with no required reporting back 08:57 - How to choose the right delegation level: consider who's doing the work, your trust level, criticality of work, and what your CEO will ask you 10:12 - Creating a success checklist before delegating so you can define what "nailing it" looks like regardless of preference 10:40 - The exception to preference vs. policy: When it's the entrepreneur's preference, treat it like policy Rate, review & follow on Apple Podcasts Click Here to Listen! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Second First MembershipSecond First One-on-One CoachingSecond First on InstagramSecond First on LinkedInMegan Long on LinkedIn
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    12 mins
  • #56: From Doer to Leader: Training Managers at Every Level of Your Organization with Ryan Castle

    #56: From Doer to Leader: Training Managers at Every Level of Your Organization with Ryan Castle
    Jan 20 2026
    Stop Promoting Your Best Employees Without Training Them to Lead

    Growing companies hit a predictable wall when their star employees get promoted to management positions without proper training. Ryan Castle, co-founder of Level 10 Leaders, joined The Right-Hand Roadmap to tackle this common entrepreneurial business challenge head-on.

    After working with over 250 organizations, Castle has identified the gap that stops companies from scaling: while visionary founders and Integrators may excel at leadership, they often struggle to develop the next layer of managers. Most businesses take their best doers, slap a manager title on them, and hope for the best, creating bottlenecks and overwhelmed Seconds-in-Command who end up co-managing departments instead of leading strategically.

    You'll hear all about:

    • 02:07 - What Level Ten Leaders does and how they help entrepreneurial companies scale leadership across the organization

    • 03:18 - The difference between leadership (doing the right things) and management (doing things right), and why entrepreneurial founders often excel at one but not both

    • 06:18 - The biggest mistake companies make: promoting top performers without teaching them how to lead, creating a capability gap between executives and managers

    • 10:19 - The Peter Principle problem and why being great at a job doesn't automatically mean someone will be a great manager

    • 13:54 - Navigating the transition from peer to manager while maintaining relationships

    • 16:06 - Why second-in-commands and managers have the toughest jobs in organizations

    • 19:00 - The player-coach dilemma: balancing individual contributor work with management responsibilities

    • 20:42 - Transformation story: how Level Ten's program changed a "blame guy" into a valued team member

    • 22:26 - Advice for second-in-commands: stop being a bottleneck and delegate to create leverage

    • 26:16 - How to connect with Level Ten Leaders and get a free copy of "The Active Manager" book

    Rate, review & follow on Apple Podcasts

    Click Here to Listen! OR WATCH ON YOUTUBE

    If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode.

    Links mentioned in the episode:

      • Free Book from Level 10 Leaders!
      • Ryan Castle LinkedIn
      • Level 10 Leaders
      • Second First Membership
      • Second First One-on-One Coaching
      • Second First on Instagram
      • Second First on LinkedIn
      • Megan Long on LinkedIn
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    28 mins
  • #55: I'm Running the Company, So Why Don't I Feel "Seen"?

    #55: I'm Running the Company, So Why Don't I Feel "Seen"?
    Aug 26 2025
    Always visible, but feeling unseen.

    At Second First, we hear this all the time from seconds-in-command: “I’m running the company. I’m making the decisions. I’m keeping the team on track… but I don’t feel seen.” It’s a hard feeling to name, but it’s real. You’re essential to the business, yet your impact is often invisible.

    This invisibility shows up in two ways. First, your contributions don’t always get recognized, because smooth operations and prevented crises rarely make headlines. And second, you may feel like no one at work truly knows you as a person. It’s a strange loneliness: surrounded by people all day, yet carrying the sense that the “real you” isn’t visible.

    You'll hear all about:

    • 00:28 — The paradox of being a second-in-command: running operations yet feeling unseen.

    • 01:16 — Two dimensions of invisibility: lack of recognition for contributions and not being known personally.

    • 01:43 — Why your best work often feels invisible: preventing crises, aligning teams, and acting as the "glue."

    • 02:40 — How wins get attributed to others—and why that’s by design for team development.

    • 03:15 — Why founders struggle to articulate your value (and the absence of formal reviews).

    • 04:04 — The emotional toll: loneliness, wearing a mask, and feeling like no one knows the “real you.”

    • 05:07 — Why this matters: the cycle of over-communicating, second-guessing, or retreating into tactical work.

    • 06:28 — Three strategies to feel more seen:

      1. Work Out Loud — Track and share decisions and their impact.

      2. Think Out Loud — Make your strategic thinking audible in meetings.

      3. Personal Value Statement — Create a one-sentence mission for your role.

    • 10:41 — A mindset shift: some of your best work will always be invisible—and that’s part of your power.

    • 11:19 — Combatting loneliness: finding peers who understand your role through community.

    Rate, review & follow on Apple Podcasts

    Click Here to Listen! OR WATCH ON YOUTUBE

    If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode.

    Links mentioned in the episode:

    • Second First Retreat September 16-17
    • Second First Membership
    • Second First One-on-One Coaching
    • Second First on Instagram
    • Second First on LinkedIn
    • Megan Long on LinkedIn
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    12 mins
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