Leading Ain't Easy

Leading Ain't Easy

By Ryan Calkins and Erny EpleyBusinessCareersManagement
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Leading Ain't Easy episodes

  • The Meeting After the Meeting - Part I

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    John Moore was asked for honest feedback in front of a room full of people. He gave it, and he never came back. John and Ryan Calkins talk about the meeting after the meeting: why people nod along and then say what they really think in the hallway. It's for anyone who has stayed quiet in a meeting or led one where nobody spoke up.


    Everyone has been in this meeting. The plan gets presented, heads nod, nobody pushes back. Then the room empties and the real conversation starts.

    Ryan and John talk about the meeting after the meeting from both sides of the table. They've each been the person who kept quiet and the leader who wondered why nobody said anything.

    Ryan and John get into:

    • John's walked-out story. On a contract job, leadership asked a full room how training was going. John was the only one who raised his hand. He gave a fair, specific list of problems, and he was walked out and never returned. He talks about why that still shapes how he speaks up today.
    • Smiling and nodding. Ryan admits there were plenty of meetings where he didn't want to be the only dissenting voice, so he let things go.
    • Processing, venting, or undermining. Not every hallway conversation is a problem. Some people need time to think, some need to blow off steam, and some smile in the meeting and quietly fight the change afterward.
    • Getting it back into the room. Ryan describes what has worked for him when a side conversation turns up a real idea: getting the topic back in front of the people who make decisions.
    • "I thought I was approachable." Ryan talks about learning that his matter-of-fact style made decisions sound final even when he meant to invite discussion, and what he changed.
    • What a defensive reaction teaches. One bad response to feedback can shut down a whole team, and private conversations turn into workplace politics.

    This one has a lot of threads, and a Part II is coming is coming in two weeks!

    "Leading ain't easy, but you don't have to do it alone."

    Leading Ain't Easy was created by Ryan Calkins and Erny Epley, and is hosted by Ryan and John Moore.

    • Ryan is the founder of Reframe & Rise, where he works with veterans who transitioned successfully but still feel something's off; helping them find alignment, not just a better job title.
    • John is a certified life and career coach with 20+ years of experience helping people navigate transitions, find purpose, and lead with intention — drawing on backgrounds in corporate leadership, counseling, and entrepreneurship.
    • Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development, and joins the show as an occasional guest.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    42 min
  • When Good Employees Get Stuck

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    Some of the best employees on any team get great reviews, take on more, and still get passed over year after year. Ryan Calkins and John Moore talk through why that happens, including the times they were the reason it happened. This one is for managers wondering if they're holding someone back, and for high performers wondering why nobody's noticed.


    Most of us have seen it, and some of us have lived it. Someone does excellent work for years and earns praise and more responsibility. Then the promotion goes to someone else. Ryan and John take on the question at the center of it: when a good employee gets stuck, whose responsibility is that?

    Ryan and John get into:

    • Ryan's honest look back at keeping reliable people in place, sometimes by making career decisions for them without asking what they wanted
    • John's approach to cross-training and shared knowledge so no single employee can hold a team hostage, plus what it's like to inherit someone who was promised a role by a previous manager
    • The "keep your head down and the work will speak for itself" mindset, and why it didn't pay off for Ryan
    • Whether it's a manager's job to make a quiet high performer visible, or the employee's job to speak up without becoming that person in every meeting
    • A call center rep who got promoted straight into a data analyst role, and what it says about leadership that's willing to take a short-term hit
    • Small, no-budget ways to give people real leadership experience, and why it falls apart when leaders don't make the connections for them

    They close with a question for each side. Leaders: is there someone on your team whose growth you've limited because they're too valuable where they are? Employees: are you waiting for someone to notice an ambition you've never actually said out loud?

    "Leading ain't easy, but you don't have to do it alone."

    Leading Ain't Easy was created by Ryan Calkins and Erny Epley, and is hosted by Ryan and John Moore.

    • Ryan is the founder of Reframe & Rise, where he works with veterans who transitioned successfully but still feel something's off; helping them find alignment, not just a better job title.
    • John is a certified life and career coach with 20+ years of experience helping people navigate transitions, find purpose, and lead with intention — drawing on backgrounds in corporate leadership, counseling, and entrepreneurship.
    • Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development, and joins the show as an occasional guest.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    40 min
  • The Conversation You Keep Putting Off

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    Every leader has one: the conversation you know needs to happen, but keep finding reasons to delay. Ryan Calkins and John Moore talk honestly about why they've avoided hard conversations, what it cost their teams, and the difference between waiting thoughtfully and just waiting because it's easier. 


    You need more information. The timing's off. Maybe it'll work itself out. Ryan and John get into the reasons capable leaders put off difficult conversations, and why the person avoiding the conversation usually isn't the only one paying for it.

    Ryan and John get into:

    • The high performer you can't afford to lose. Ryan shares the story of an employee he relied on heavily, who was also condescending to the people around him. Ryan tried joking hints instead of a real conversation, and the team noticed.
    • What everyone else is watching. When one person's behavior goes unaddressed, some people get louder, some go quiet, and some start wondering why the rules don't apply evenly.
    • Empathy as a crutch. Ryan opens up about putting so much energy into how the other person will feel that the message never lands the way it needs to.
    • Documentation done right. Why keeping notes matters, why it means nothing without actual conversations, and how delays can leave you exposed with HR.
    • What "immediate" really means. The hot stove rule, why 24–48 hours is the target, and when waiting for a pattern or more context is the fair thing to do.
    • Being on the receiving end. Ryan tells the story of a manager who blindsided him with a list of issues and a book about his generation, and how it shaped the way he handles these conversations now.

    They close with two questions worth sitting with: What am I actually waiting for? And who else is paying the price while I wait?

    "Leading ain't easy, but you don't have to do it alone."

    Leading Ain't Easy was created by Ryan Calkins and Erny Epley, and is hosted by Ryan and John Moore.

    • Ryan is the founder of Reframe & Rise, where he works with veterans who transitioned successfully but still feel something's off; helping them find alignment, not just a better job title.
    • John is a certified life and career coach with 20+ years of experience helping people navigate transitions, find purpose, and lead with intention — drawing on backgrounds in corporate leadership, counseling, and entrepreneurship.
    • Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development, and joins the show as an occasional guest.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    48 min
  • When the Leadership Problem Is You

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    Ryan Calkins and John Moore talk through the moment every leader eventually hits. The moment when the thing they keep trying to fix in everyone else turns out to be them. It's for anyone who's ever managed people and hoped the feedback would just be good news.

    Most leadership training is built around changing other people: better coaching, better expectations, better feedback to others. What it rarely covers is the moment a leader has to turn that same lens on themselves. Ryan and John get into why that's so hard, and what it actually looks like in practice.

    • Ryan and John talk through the cultural roots of "the leader is never wrong," and why self-accountability still feels foreign to a lot of leaders today
    • They get into the feedback trap: leaders who say they want honesty but only want to hear good things, and what that does to trust
    • Ryan shares a real story about giving a boss blunt, unfiltered feedback, and the fallout that followed
    • They talk through how stress and burnout bring out the leadership habits you least want people to see
    • John and Ryan dig into why delayed feedback hurts more than it helps, using the "hot stove" idea as the throughline
    • They close with a personal reflection question for the audience about the leadership problem they keep blaming on everyone else

    "Leading ain't easy, but you don't have to do it alone."

    Leading Ain't Easy was created by Ryan Calkins and Erny Epley, and is hosted by Ryan and John Moore.

    • Ryan is the founder of Reframe & Rise, where he works with veterans who transitioned successfully but still feel something's off; helping them find alignment, not just a better job title.
    • John is a certified life and career coach with 20+ years of experience helping people navigate transitions, find purpose, and lead with intention — drawing on backgrounds in corporate leadership, counseling, and entrepreneurship.
    • Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development, and joins the show as an occasional guest.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    53 min
  • When Your Employee Knows More Than You Do

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    Ryan Calkins and John Moore talk through what it's like to lead someone who knows more than you do; the imposter syndrome, the ego, and the real tension of coming in as an outside hire over someone who wanted the job. It's for anyone who's ever walked into a new leadership role and wondered if they actually belong there.

    • Ryan and John open up about the moments they've each led people who were more technically skilled or more experienced than they were, and how that feels in the room.
    • John tells the story of inheriting a direct report who'd wanted his role, the power struggle that followed, and the surprising way it ended when the company laid him off and kept her.
    • Ryan shares how a colleague's constant "that's not gonna work" shut him down early on, and the conversation that changed the dynamic.
    • They talk about the tension between being an external hire and the internal candidates who feel passed over, and why leadership often fails to prepare those people for what comes next.
    • Both admit to the specific brand of imposter syndrome that comes with being new (the fear of sounding like you know things you don't) and what actually helped them get past it.
    • They close with a harder question: what do you do when the person you're leading would genuinely make a better leader than you?

    "Leading ain't easy, but you don't have to do it alone."

    Leading Ain't Easy was created by Ryan Calkins and Erny Epley, and is hosted by Ryan and John Moore.

    • Ryan is the founder of Reframe & Rise, where he works with veterans who transitioned successfully but still feel something's off; helping them find alignment, not just a better job title.
    • John is a certified life and career coach with 20+ years of experience helping people navigate transitions, find purpose, and lead with intention — drawing on backgrounds in corporate leadership, counseling, and entrepreneurship.
    • Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development, and joins the show as an occasional guest.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    47 min
  • The Promises You Never Made But Have to Keep (feat. Erny Epley)

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    Every new leader inherits more than a job — they inherit promises, contracts, and habits somebody else put in place. Ryan Calkins and John Moore welcome Erny Epley back for an honest conversation about what happens when someone else's decisions become your problem to fix.


    Stepping into a new role means inheriting more than a job description. Ryan and John welcome Erny back to the show to talk through everything a new leader gets handed without ever agreeing to it: promotions someone else promised, contracts nobody mentioned, habits that have just always been "how it's done."

    In this episode, they touch on:

    • Ryan and John get into the promotion that was promised before they ever took the role, and what it felt like to build trust with someone they didn't choose and couldn't fully vouch for yet
    • Erny brings in the layer most people forget; vendor agreements and union side-deals made off the books, and what it's like to be the one who has to say "I don't know what you were told, but here's where we are now"
    • They walk through Erny's own $2 million electric vehicle contract that surfaced out of nowhere with 30 days' notice, and John's experience walking into an operation running people ragged with six-week travel schedules nobody had ever questioned
    • The conversation turns to the double-edged sword of coming in and changing everything at once... when it works, when it backfires, and why "past practice isn't best practice" is a better starting point than assuming the last person got it all wrong
    • There's an honest stretch on taking ownership instead of blaming the leadership before you, on Erny's own hard lesson about learning who someone really is before promising them anything, and on how to hold a team accountable for behavior that's gone unchecked for years without making it personal

    "Leading ain't easy, but you don't have to do it alone."

    Leading Ain't Easy was created by Ryan Calkins and Erny Epley, and is hosted by Ryan and John Moore.

    • Ryan is the founder of Reframe & Rise, where he works with veterans who transitioned successfully but still feel something's off; helping them find alignment, not just a better job title.
    • John is a certified life and career coach with 20+ years of experience helping people navigate transitions, find purpose, and lead with intention — drawing on backgrounds in corporate leadership, counseling, and entrepreneurship.
    • Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development, and joins the show as an occasional guest.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    57 min
  • Some People Don't Want to Lead — And That's Okay

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    Not every talented employee wants to be a manager, and that's a harder thing for leaders to accept than it sounds. Ryan Calkins and John Moore discuss what it's like to see real potential in someone who isn't actively pursuing it, and why the instinct to push people toward a promotion can reveal more about the leader than the employee.


    There's a specific kind of frustration that comes with watching someone talented turn down every opportunity you put in front of them. This week, Ryan and John get into what that actually looks like from the leadership side, and what it might mean to finally let it go.

    • Ryan and John talk through why some of the best people on a team have zero interest in a title, more money, or more responsibility, and how hard that can be to accept when you can clearly see what they're capable of
    • They get into the real difference between leadership and management, and why someone can be a leader in every way that matters without ever wanting to manage anyone
    • Ryan shares a story from his time at a waste management company, where the pay structure actually made staying a driver the smarter move over becoming a supervisor
    • They talk through the employee who did the job of a department head for decades without ever taking the title, and what she got to keep in her life because of it
    • The conversation turns to how corporate culture has shifted, and why younger employees don't always see the leadership pipeline the same way previous generations did
    • They land on the harder question underneath all of it: are you offering someone an opportunity, or just projecting what you wanted onto them?

    "Leading ain't easy, but you don't have to do it alone."

    Leading Ain't Easy was created by Ryan Calkins and Erny Epley, and is hosted by Ryan and John Moore.

    • Ryan is the founder of Reframe & Rise, where he works with veterans who transitioned successfully but still feel something's off; helping them find alignment, not just a better job title.
    • John is a certified life and career coach with 20+ years of experience helping people navigate transitions, find purpose, and lead with intention — drawing on backgrounds in corporate leadership, counseling, and entrepreneurship.
    • Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development, and joins the show as an occasional guest.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    47 min
  • When Loyalty Becomes the Default

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    Ryan Calkins once turned down a job offer (and a $50,000 raise) because leaving felt disloyal. A year later, it turned out to be one of the biggest mistakes of his career. Ryan and John Moore talk through what loyalty at work really costs when it stops being a choice.


    Most leaders don't worry about being too loyal; they worry about being disloyal. But loyalty is one of those qualities that can turn into something else entirely: guilt, fear, or just habit wearing a nicer name. In this episode, Ryan and John sit with the uncomfortable side of a word that usually gets treated as an unqualified good.

    Ryan opens up about a real turning point in his career: a competitor offered him a substantial raise and a promotion, and he turned it down to stay where he felt invested and needed. He took a smaller raise instead, and thought he'd made the right call, until a year-end conversation with the CEO revealed how badly it had actually gone.

    John brings his own story from the other side: being told by leadership to clean house and fire an entire staff, and having to decide in real time whose side he was really on.

    Ryan and John get into:

    • What it actually feels like to stay somewhere out of obligation instead of choice
    • The moment loyalty stops being healthy and starts being self-sabotage
    • Why companies expect loyalty from employees without ever explaining their own decisions
    • The difference in how loyalty gets treated at the executive level versus everywhere below it
    • How to know when someone's history with you is clouding a decision you need to make now
    • Where boundaries fit into loyalty, and why loyalty without boundaries usually goes wrong

    This isn't a framework for how to be more loyal. It's two people who've been burned by their own loyalty, talking honestly about what they'd do differently.

    "Leading ain't easy, but you don't have to do it alone."

    Leading Ain't Easy was created by Ryan Calkins and Erny Epley, and is hosted by Ryan and John Moore.

    • Ryan is the founder of Reframe & Rise, where he works with veterans who transitioned successfully but still feel something's off; helping them find alignment, not just a better job title.
    • John is a certified life and career coach with 20+ years of experience helping people navigate transitions, find purpose, and lead with intention — drawing on backgrounds in corporate leadership, counseling, and entrepreneurship.
    • Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development, and joins the show as an occasional guest.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    48 min
  • When Being Needed Becomes the Problem

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    Being the go-to person on your team feels like leadership until you're the bottleneck holding everyone up. Ryan Calkins and John Moore discuss how managers unintentionally train their teams to stop thinking for themselves, and what it takes to build a team that doesn't fall apart when you leave the room. For anyone who's ever felt like they can't take a vacation because nobody else knows how to do the work.


    There's a version of leadership that feels great in the moment: being the person everyone counts on, the one with the answers, the one who gets it done. Ryan and John spend this episode being honest about what happens on the other side of that feeling: a team that can't function without you, and a manager who's now doing their own job and everyone else's too.

    • Ryan and John talk through how the "quick answer" habit builds a team that stops thinking for itself over time, and how good it can feel to be needed that much
    • They get into the difference between training someone to do it "your way" versus training the underlying process, and why that distinction matters when someone eventually replaces you
    • Ryan shares a personal story from his time as an operations consultant, becoming the only person in the department who could run site visits and write the reports, and what he'd change if he could go back
    • They talk through what actually happens when you try to take a vacation, and the person covering your work never does it
    • Ryan and John discuss when stepping in actually makes sense (safety issues, new employees, an upset client) versus when it's just become the default
    • They close with an honest question for anyone managing people right now: what keeps landing on your desk, and is it really because your team can't handle it, or because you've never let them try

    "Leading ain't easy, but you don't have to do it alone."

    Leading Ain't Easy was created by Ryan Calkins and Erny Epley, and is hosted by Ryan and John Moore.

    • Ryan is the founder of Reframe & Rise, where he works with veterans who transitioned successfully but still feel something's off; helping them find alignment, not just a better job title.
    • John is a certified life and career coach with 20+ years of experience helping people navigate transitions, find purpose, and lead with intention — drawing on backgrounds in corporate leadership, counseling, and entrepreneurship.
    • Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development, and joins the show as an occasional guest.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    48 min
  • The Leadership Nobody Notices Until It's Gone

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    Ryan Calkins and John Moore discuss the kind of leadership that often goes unnoticed: the quiet, preventive work that prevents disasters from happening in the first place. For anyone who's ever done the hard, invisible work and wondered if it mattered.


    There's a version of leadership that never gets celebrated: the person who saw the problem coming and simply took care of it before it became a story. Ryan and John spend this episode on why we tend to overlook that person, and why the "hero" who saves a burning project usually gets more credit than the person who made sure it never burned.

    • Ryan and John get into the difference between reactive firefighting and proactive, preventative leadership, and why the second one is so often invisible
    • Ryan opens up about a project report that got torn apart by a former consultant, and the weekend he spent rebuilding it from scratch
    • They talk through the "catch-22" of being proactive: the better you get at it, the less anyone realizes there was ever a fire to put out
    • John shares a story about going a year and a half without a single word of recognition, and then receiving a $14,000 bonus he never expected
    • Honest talk about arrogance, procrastination, and how self-inflicted fires compound once you're responsible for a team instead of just yourself
    • A close look at what actually gets rewarded at the end of the year: recognition, financial, or neither

    "Leading ain't easy, but you don't have to do it alone."

    Leading Ain't Easy was created by Ryan Calkins and Erny Epley, and is hosted by Ryan and John Moore.

    • Ryan is the founder of Reframe & Rise, where he works with veterans who transitioned successfully but still feel something's off; helping them find alignment, not just a better job title.
    • John is a certified life and career coach with 20+ years of experience helping people navigate transitions, find purpose, and lead with intention — drawing on backgrounds in corporate leadership, counseling, and entrepreneurship.
    • Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development, and joins the show as an occasional guest.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    47 min

About Leading Ain't Easy

From the publisher's feed

Leadership looks shiny on social media. But the reality is it’s messy, isolating, and full of self-doubt. Leading Ain’t Easy pulls back the curtain on the side of leadership nobody puts on…