Managing up is one of the most important leadership skills and one of the least taught.

In this episode of Leading Ain’t Easy, Ryan Calkins and Erny Epley talk about what it really looks like to lead when you don’t have authority over the people who influence your success: your boss, senior leaders, and cross-functional departments that control the data, budget, timelines, and decisions you’re expected to execute.

If you’ve ever been told “figure it out” without support… if you’ve been burned by a surprise that climbed the chain… or if you’ve struggled to communicate your vision clearly under pressure... then this episode is for you.

In this episode, we cover:

• Why leadership hates surprises (and how to avoid blindsiding your boss)
• How to tailor your communication to how your boss receives information
• How to challenge leadership without being seen as “difficult”
• Why documentation matters (and how to protect yourself with clarity)
• The mindset shift: clarity beats competence

Question for listeners:
Where do you struggle most with managing up; clarity, timing, politics, or trust?

Key takeaways

• Don’t let your boss get blindsided; give heads up early.
• Communicate to be understood, not just heard.
• Lead with the solution, then support with context.
• Use data to paint a clear picture fast.
• Document agreements and decisions (protects everyone).

Leading Ain’t Easy is hosted by Ryan Calkins and Erny Epley.

• Ryan is the founder of Reframe & Rise, a career and leadership coaching practice helping veterans and other professionals realign their work and lead with purpose.
• Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development.

Subscribe to the show 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.

Most leaders are coaching whether they realize it or not. The question is whether they’re doing it intentionally… or accidentally.

In this episode of Leading Ain’t Easy, Ryan and Erny are joined by Alicia Sanders, a Director of Supply Chain Management in hospital logistics, to break down coaching as a practical leadership skill; especially in high-pressure environments where deadlines don’t stop so “development” can happen.

We talk about the difference between managing vs coaching, why coaching creates real capability (not just compliance), and the hard reality leaders face when someone refuses accountability, including when coaching ends and performance management begins.

If you’re tired of doing the job for your team, this episode is your reminder: coaching is slower in the moment… but faster over time.

What we cover

• Managing vs coaching: directing tasks vs developing thinking
• Why coaching isn’t one-size-fits-all
• Coaching through strengths (and why EQ matters)
• Mentorship vs coaching, and when leaders must do both
• Daily huddles/check-ins as a simple, repeatable coaching practice
• The “cut your losses” question: accountability, engagement, and reality
• PDCA (Plan–Do–Check–Act) as a coaching framework
• The coaching pitfall: focusing only on the squeaky wheel and burning out high performers

Key takeaway

Coaching doesn't mean being “nice” or “helpful.” It’ means being effective and creating clarity, building capability, and holding standards without rescuing people.

Connect with us

YouTube: https://www.youtube.com/channel/UCCLoVJP2UfHuJzOyNx4fHpg
Instagram: https://www.instagram.com/reframerise/ or https://www.instagram.com/buspro_network/
LinkedIn: https://www.linkedin.com/company/leading-ain-t-easy-podcast/

Call to action

If this episode hit home, drop a comment or message us:
What’s the hardest part of coaching people in your environment?

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

Leading Ain’t Easy is hosted by Ryan Calkins and Erny Epley.

• Ryan is the founder of Reframe & Rise, a career and leadership coaching practice helping veterans and other professionals realign their work and lead with purpose.
• Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development.

Subscribe to the show 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.

If you’re stepping into leadership for the first time (or thinking about it) this episode is your warning label and your playbook.

Ryan and Erny break down what they wish they knew before they ever had direct reports: why leadership is more about people than technical skill, why your motivation matters more than your title, how to handle accountability for things you didn’t personally do, and what happens when you get promoted over your friends.

We also talk about the stuff nobody puts in the leadership books:

• The invisible mental load
• The emotional whiplash of “good days and bad days”
• Taking feedback when it comes in an ugly package
• The difference between “buy-in” and manipulation
• Why moving too fast as a new leader can backfire

If leadership has felt heavier than you expected, this one’s for you.

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

Leading Ain’t Easy is hosted by Ryan Calkins and Erny Epley.

• Ryan is the founder of Reframe & Rise, a career and leadership coaching practice helping veterans and other professionals realign their work and lead with purpose.
• Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development.

Subscribe to the show 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.

Middle management is a grind: high responsibility, limited authority, and pressure from every direction.

In this episode, we break down the invisible weight middle managers carry, like being the translator, mediator, protector, and problem-solver while taking heat for things you didn’t even control. We talk burnout, boundaries, empathy, and how to implement decisions you don’t fully agree with without abandoning your integrity.

If you’re in the middle and exhausted, this one will feel familiar; and it’ll give you language (and tools) for what you’ve been carrying.

Leading Ain’t Easy is hosted by Ryan Calkins and Erny Epley.

• Ryan is the founder of Reframe & Rise, a career and leadership coaching practice helping veterans and other professionals realign their work and lead with purpose.
• Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development.

Subscribe to the show 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.

Knowing your worth is easy to say but can be hard to live.

In this episode of Leading Ain’t Easy, Ryan and Erny unpack what it really means to understand your value as a leader; beyond titles, money, or years of service. From imposter syndrome and loyalty traps to quitting without a backup plan, they explore how self-worth quietly erodes when effort isn’t recognized and support disappears at the top.

This is an honest conversation about:

• When loyalty turns into self-sacrifice
• Why “prove yourself first” can cost you years of progress
• The difference between confidence, entitlement, and arrogance
• How leaders can objectively evaluate their worth using feedback, results, and integrity
• Why settling eventually leads to burnout (even when you don’t see it coming)

If you’ve ever stayed too long, taken less than you deserved, or waited for permission to be valued… this episode is for you.

Episode Chapters / Timestamps

00:50 — Intro: Know Your Worth (not titles or money)
01:33 — Erny’s story: stuck in a broken system + glass ceiling
02:10 — When effort isn’t valued at the top
04:54 — “They were chanting my name”
06:55 — The “donuts” moment: realizing support isn’t coming
08:51 — Walking away without another job lined up
10:22 — Worth vs perception: when others define your value
12:10 — Ryan: undervaluing yourself and the loyalty trap
14:59 — “You’re not the only idiot”: taking less pay to prove yourself
18:21 — Guilt, loyalty, and why companies won’t match it
19:54 — Negotiating up front vs earning your place
21:00 — A brutal interview failure and learning to sell yourself
24:18 — Turning failure into a long-term strength
25:29 — Advocating for yourself while staying team-oriented
28:13 — The hidden cost of settling
29:22 — Overvaluing yourself: arrogance vs entitlement
30:33 — Confidence vs arrogance (where it crosses the line)
32:23 — Slowing down and leading with data
34:30 — Measuring worth: metrics + intangibles
40:29 — How to actually gauge self-worth
41:00 — Ryan’s reflection framework
44:43 — Erny’s feedback-driven approach
49:21 — Key takeaway: Worth is earned through integrity
49:42 — Standing up for yourself without burning bridges
50:46 — Listener reflection question
51:16 — Closing

Leading Ain’t Easy is hosted by Ryan Calkins and Erny Epley.

• Ryan is the founder of Reframe & Rise, a career and leadership coaching practice helping veterans and other professionals realign their work and lead with purpose.
• Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development.

Subscribe to the show 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.

You don’t have to say a word for people to know exactly what you’re thinking.

Sometimes your face gets there first.

In Episode 6 of Leading Ain’t Easy, Ryan and Erny dig into the idea of “Fix Your Face” and how your nonverbal tells can completely change the way people experience your leadership.

In this episode, we cover:

• Why you can’t “not communicate”
  A workshop exercise makes it painfully obvious: even when you’re silent, your body and face are saying plenty.
• When your emotions live on your face
  Ryan talks about getting in trouble for “lack of bearing” in Marine Corps boot camp and how that same struggle followed him into his professional life.
• The coworker who kept whispering “fix your face”
  How one colleague’s honest feedback turned into a mantra Ryan still uses in every tough meeting.
• Erny’s public board meeting lesson
  A clerical error, a very public question, and the moment his panic face cost him trust and put his work under a microscope.
• Authentic vs. unfiltered
  Being real doesn’t mean letting every reaction show. You don’t have to give everyone your unedited response to be honest and trustworthy.
• Tools to keep your bearing when you disagree
  • Micro-resets: adjust your posture, take a sip of water, breathe
  • Re-centering questions: “Why are we here?” and “What’s the actual objective?”
  • Using silence to collect your thoughts instead of firing back defensively
• Choosing where (and with whom) to vent
  Why it’s healthy to have safe people and places to unload, and how venting in front of your team can quietly erode trust in you and your organization.
• Leading with intention, not impulse
  How to stay human and expressive while still being intentional about the message your face, body, and tone are sending.

If you’ve ever been told, “your face is saying a lot right now,” this one’s for you.

Leading Ain’t Easy is hosted by Ryan Calkins and Erny Epley.

• Ryan is the founder of Reframe & Rise, a career and leadership coaching practice helping veterans and other professionals realign their work and lead with purpose.
• Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development.

Subscribe to the show 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.

Being the “good guy” at work sounds great on paper.

You’re empathetic. You listen. You try to do right by people. You avoid unnecessary conflict. You take the high road, even when it stings a little.

But over time, that version of leadership can start to cost you.

In this episode, Erny and Ryan unpack what happens when being the good guy quietly slides into people-pleasing, conflict avoidance, and eventually burnout.

We get into:

• How empathy can quietly turn into people-pleasing
• Erny’s story of letting small behavior slide until it became a fairness and favoritism problem
• Why “being the hero” for your team can actually make everything harder
• Holding people accountable without becoming the office hard-ass
• The emotional weight of being everyone’s “go-to” person
• Why good-guy leaders burn out faster than we want to admit
• How to set boundaries before you hit the “I’m done” wall
• Being honest when you’re not at 100%, and how to lean on your team
• Doing the right thing even when it costs you time, energy, or popularity

We’re not telling you to stop being the good guy. The point is to stay compassionate without losing yourself; to care about your people and hold the line on what your role actually requires.

If you’ve ever found yourself thinking, “I’m trying to do right by everyone… so why am I the one who’s exhausted?” this one’s for you.

Leading Ain’t Easy is hosted by Ryan Calkins and Erny Epley.

• Ryan is the founder of Reframe & Rise, a career and leadership coaching practice helping veterans and other professionals realign their work and lead with purpose.
• Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development.

Subscribe to the show 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.

In this episode of Leading Ain’t Easy, we’re joined by special guest, John Moore (a longtime training leader turned coach) who has spent over 20 years leading teams in corporate environments that didn’t always make it easy to show up as himself.

We dig into what it means to “lead as yourself” in 2025, why so many workplaces feel colder and more transactional than they used to, and how you can still lead with empathy, love, and high standards without getting steamrolled.

John shares stories from the boardroom, layoffs, and leadership programs that tried to strip out personality, and how he’s intentionally done the opposite: building relationships, earning trust, and creating spaces where people actually want to work and learn.

Along the way, we also get into the messy parts: confidence vs. arrogance, being asked to “tone it down,” the cost of caring in environments that don’t, and how to stay human when you’re the one delivering hard news.

In this episode, we talk about:

• Why trying to copy someone else’s leadership style will burn you out
• The difference between confidence and arrogance (and how to tell which one you’re leading from)
• How corporate culture shifted from “we know your family” to “you’re a line item”
• What to do when you’re asked to cut people you actually know and care about
• Why new leaders should learn and do first before they start delegating
• How to build credibility and buy-in by being a doer instead of just a director
• Practical ways to stay grounded and authentic when the job demands hard decisions

If you’ve ever felt like you had to hide who you are to be taken seriously as a leader, this one’s for you.

"Leading Ain’t Easy, but you don’t have to do it alone."

Leading Ain’t Easy is hosted by Ryan Calkins and Erny Epley.

• Ryan is the founder of Reframe & Rise, a career and leadership coaching practice helping veterans and other professionals realign their work and lead with purpose.
• Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development.

Subscribe to the show 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.