The Right-Hand Roadmap

Megan Long
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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...

  1. 20H AGO

    #59: What It's Really Like Doing Business with You

    Walk Your Buyer's Journey: Finding the Friction Points Killing Your Customer Experience When was the last time you actually experienced what it's like to be a customer of your own company? Most operators and Seconds-In-Command are so deep in the weeds of delivery that they've never walked the buyer's journey from first contact to final goodbye, which means customer experience issues go unnoticed until they become complaints. The exercise is simple but revealing: map out every single step from that first phone call or website visit all the way through fulfillment, including timelines between steps and who the customer interacts with at each point. Together you'll cover a case studio of a company that discovered two major friction points through this process. The businesses winning right now aren't always the ones with the best product or pricing - they're the ones making it easy and pleasant to work with.  You'll hear all about: 00:29 - Introduction: Walking the buyer's journey - what does it actually look like to do business with you 01:02 - The reality check: It's rare that you have firsthand experience being a customer of your own company 01:14 - Why minor problems go unnoticed until they become customer complaints 01:26 - The exercise: Start mapping from the very first phone call, email, or website visit 01:47 - How to map it: Take a blank piece of paper and document every single step, no matter how small 02:15 - Include timelines between steps and who in your company interacts with the buyer at each point 02:37 - Map all the way to the last touch: fulfillment, project close-out, or the final goodbye 02:45 - Two key things to analyze: How many people are they interacting with? Where are the significant time gaps? 03:16 - Critical insight: Buyer's remorse sets in as soon as payment is processed 03:37 - Real example: Landscaping company case study reveals two major issues 03:50 - Issue #1: Admin takes initial info, then client waits a week or more for the design team to contact them 04:14 - Issue #2: Multiple waiting periods create a roller coaster of excitement and frustration 04:57 - The harsh truth: Silence and time kill deals 05:17 - How gaps create anxiety even for clients who stick around 05:23 - The coffee shop analogy: Two long lines might look like success, but customers are actually frustrated 06:03 - Important caveat: Not every gap is bad - custom work takes time, but are you managing expectations? 06:19 - Your homework: Walk the buyer's journey yourself or have a team member act as an internal secret shopper 07:00 - Level up move: Ask a recent customer to walk you through their experience (15 minutes of insight) 07:17 - Fall retreat preview and the four CSat questions discussed at the last event 08:05 - Question #1: Who owns customer satisfaction? (If everyone owns it, no one owns it) 08:33 - Question #2: What decisions in the past year impacted CSat most (positive or negative)? 08:43 - Question #3: What complaints led to the most significant operations changes? 08:53 - Question #4: What opportunities exist in your buyer's journey to improve customer experience?   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 Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    10 min

  2. FEB 5

    #58: Stop Wasting Money on AI Tools: Why Operators Need Skepticism in Their Tech Stack

    The Operator's Guide to AI Tool Selection (Before Your CEO Buys Another One) Your entrepreneur is excited about another AI tool, but before you add it to your tech stack, you need to know this: MIT research shows that 95% of AI investments have produced zero returns at the company level.  The Salesforce disaster is the perfect case study: they laid off 4,000 employees to pivot to AI (after promising it wouldn't impact jobs), then had to pivot back when the large language models proved unreliable and experienced drift.  As operators and Seconds-In-Command, you're fielding these AI tool requests constantly, but most SMBs aren't ready for agentic AI or even vibe-coded applications that pose serious security risks (60% of businesses shut down after a cyber attack). In this episode, host Megan Long covers some basic frameworks and points of skepticism to be aware of before adopting any AI tool - agentic or vide-coded.  Beyond ROI concerns, there are real ethical considerations. Being intentional about AI tool selection isn't just about avoiding wasted budget; it's about building efficiencies responsibly without compromising security or causing harm. You'll hear all about: 00:29 - Introduction: The plethora of AI tools promising the world and how operators are fielding these from excited CEOs 00:59 - Origin story: Second First Mastermind quarterly cohort meetings and how vendor selection became a hot topic 01:49 - The 6 critical questions to ask before purchasing any software or tool (pull up your notes app!) 02:57 - The overwhelming answer: Yes, we've all wasted significant time and money on failed software purchases 03:14 - The AI reality check: MIT research shows 95% of AI investments have produced zero returns 03:36 - The nuance: Individuals find personal efficiencies, but company-level P&L shows no benefits 03:45 - Surprising finding: Most AI investments go to Sales & Marketing instead of Operations 03:59 - Salesforce case study: Laid off 4,000 employees for AI, then had to pivot back when it failed 04:40 - Vibe coding concerns: Security and compliance risks when beginners code their own apps 05:18 - The scary stat: 60% of businesses shut down following a cyber attack 05:43 - What is agentic AI and why it sounds so promising (systems that act autonomously on your behalf) 06:14 - Why most SMBs aren't ready: Clean your house before inviting the AI guest over 06:52 - Four guidelines for selecting AI tools: Start low-cost, tie to value creation, plan to scale, use KYA framework 08:11 - The Know Your Agent (KYA) framework: Capability, behaviors, decision tracing, abuse prevention, sandboxes, and human overrides 09:15 - Soapbox moment: Using AI ethically and understanding why people are anti-AI 09:50 - The creative industry impact: Animation directors, musicians, and the elimination of royalties 10:27 - Other ethical concerns: Deepfakes, surveillance, misinformation, environmental harm in rural communities   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 Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    11 min

  3. JAN 29

    #57: Two Delegation Secrets That Will Transform How You Lead Your Team

    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 Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    12 min

  4. JAN 20

    #56: From Doer to Leader: Training Managers at Every Level of Your Organization with Ryan Castle

    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

    28 min

  5. 08/26/2025

    #55: I'm Running the Company, So Why Don't I Feel "Seen"?

    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: Work Out Loud — Track and share decisions and their impact. Think Out Loud — Make your strategic thinking audible in meetings. 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

    12 min

  6. 08/07/2025

    #54: The "I'm Too Busy" Trap

    If you’re always too busy to invest in yourself, your career might be stuck. In this short but powerful solo episode, Megan Long addresses the all-too-familiar excuse: “I’m too busy.” Whether you're putting off professional development, skipping strategic planning, or just stuck in back-to-back meetings, it’s time to ask what that busyness is really costing you. This is a pep talk for every second-in-command who’s running on fumes—and a reminder that making time for yourself is a leadership skill, not a luxury. You'll hear all about: 01:30 – The mastermind retreat in Nashville and what people are saying about why they “can’t go” 02:09 – The real cost of saying “I’m too busy” Common trap: saying no to opportunities that would help you grow EOS implementer insight: teams are skipping Rocks because of day-to-day chaos 03:14 – The pandemic slowdown vs. the current pace of business Remembering daily 2pm walks—and why they feel impossible now Just being busy doesn’t mean you’re making an impact 04:15 – 3 reflection questions to reclaim your time and direction: When was the last time you invested in your own growth? When was the last time you asked for something you want at work? When was the last time you created space to think about your future? 05:00 – Selflessness is admirable—but it shouldn't mean self-neglect Entrepreneurs don’t want their right-hand leaders burning out Make the second half of the year count for you   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

    6 min

  7. 06/19/2025

    #53: 5 Problems to Solve Before You Grow

    Before you chase growth, fix these foundational cracks that could break your business.  Before you chase aggressive growth targets, you have to ask yourself a hard question: Is your business actually ready to scale? We work with leaders every day who are stuck in the messy middle: growing revenue while cash gets tighter, roles get blurrier, and the founder still has a hand in every decision. In this week’s episode of The Right-Hand Roadmap, Megan Long walks through five common problems that must be fixed before you scale. From cash flow visibility to repeatable sales processes and reducing founder dependency, this episode is your growth-prep checklist. Growth can’t be powered by vision alone. It takes clarity, systems, and some financial truth-telling to make growth possible. If your 2025 plan is off track, or if you're leading through a pivot, this episode will help you assess what to fix now (and what you can build mid-flight).   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: Episode #49: The Lead-Gen Blueprint for SMBs & Perfecting an Outsourcing Partnership with Cindy Dodd Second First Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    12 min

  8. 06/03/2025

    #52: No Bullsh*t Strategy: How to Clear Competition and Craft a Profit-Driven Strategy with Alex M H Smith

    Most companies don't have a real strategy.  What’s the difference between being the “best” in your industry and being the only one of your kind? In this episode, bestselling author and street strategist Alex M H Smith joins Megan Long to break down the myths of business strategy. If you’re a COO or second-in-command trying to steer your company toward a clear, scalable, and profitable future, this conversation is your shortcut. Learn how to avoid the trap of generic positioning, unlock strategic leverage, and bring a real strategy to the table.   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: Alex's LinkedIn Basic Arts Website "No Bullsh*t Strategy" Book Second First Membership Second First One-on-One Coaching Second First on Instagram Second First on LinkedIn Megan Long on LinkedIn

    54 min
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Ratings & Reviews

5
out of 5
5 Ratings

About

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...

Information

  • Creator
    Megan Long
  • Years Active
    2024 - 2026
  • Episodes
    59
  • Rating
    Clean
  • Copyright
    © 2023
  • Show Website
    The Right-Hand Roadmap

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