Are you one of our new listeners? Welcome! We’re giving away a free Leading Outward sweatshirt to any U.S. listener who hasn’t yet left a written review. Just upload a screenshot at leadingoutward.com and we’ll send one your way!

In season 2, we'll be taking you into the exact moments leaders realize they’re the problem.

You’ll hear raw, unscripted coaching sessions with leaders navigating high-stakes decisions and the impact of hard childhoods. While you can find leadership theory everyone, we show you real change that happens in the raw, sometimes clunky moments of professional and personal leadership.

New episodes drop every Tuesday starting September 16.

When was the last time you vented about someone? And why didn’t you just talk to them instead? 

In this season finale, we hear from three listeners whose lives shifted because of the show: a mom who saw her son differently, a leader who publicly owned his coaching experience, and a son who finally had an honest conversation with his parents. These are stories of ownership, agency, and the space where real change starts. 

Topics we address: 

01:05 — How we unintentionally take away people’s growth when we speak for them 

07:20 — How vulnerability can make people see you as a more credible leader 

10:30 — Why venting feels good but never solves the problem 

13:50 — How to remove the difficulty out of hard conversations 

18:00 — How old stories keep us from seeing who someone is now 

Have a leadership challenge or question you’d like us to explore on the show? Submit it here!  

Need help developing your leaders or organization? Schedule a complimentary strategy session.

What was it all for?

You've shared the vision, trained the team, and gave them everything they needed to succeed.

And they still aren't following through.

In part two of this raw coaching series, Daniel—a high school principal—continues to wrestle with this leadership challenge. What starts as a reflection on stalled execution becomes a deep reckoning with busyness, control, and the fear of leading in a way that might cost you your people.

If you’ve ever felt the weight of being ultimately responsible for the outcomes and still coming up short then this episode is for you.

Ideas we explore: 

01:20 — Why your team might be slow to act 

06:10 — What gets lost when you rush connection 

10:40 — How busyness is shaping the way you lead 

14:00 — The fear of being truly seen 

18:00 — What it actually takes to change a leadership habit 

Have a leadership challenge or question you’d like us to explore on the show? Submit it here!  

Need help developing your leaders or organization? Schedule a complimentary strategy session. 

Feel like you're just being thorough? Focused on quality? Clear about your expectations? You might call it leadership, but to your team, it might feel like control. So what happens when your high standards start getting in the way of growth?

In this raw coaching episode—part one of a two-part series—Daniel, a high school principal with deep experience across every level of school leadership, wrestles with that exact tension. With help from his Arbinger coach, Daniel uncovers how his desire for consistency and excellence is actually limiting his team’s growth and holding him back from the kind of leader he wants to be.  

Ideas we explore: 

01:35 — How to lead well when you’re stretched too thin 

10:55 — When your efforts to help actually cause delays 

14:30 — The difference between shielding your team and stealing their shot 

21:05 — How control quietly strains relationships at work and at home 

27:10 — What it means to delegate a task without delegating responsibility 

Have a leadership challenge or question you’d like us to explore on the show? Submit it here!

Need help developing your leaders or organization? Schedule a complimentary strategy session. 

Ever resented someone you were supposed to help? Or felt too exhausted to care, even when you knew you should?

Our guests have. Daren Forbes has dedicated his life to funeral service, and Dr. Steve Jackson serves people as a physician. They know what it’s like to feel called to meaningful, people-centered work—and still feel resentful, drained, or disconnected from the very people they’re trying to serve. They share their messy moments when their mindset became the deciding factor in their ability to show up effectively instead of shut down.

Ideas we explore: 

01:20 — How to keep showing up when you’re completely worn out 

05:45 — The shift that moves you from resentment back into service 

10:30 — Unlocking creativity and care even when exhausted 

13:50 — How an inward mindset clouds your judgment 

18:05 — Why caring for coworkers reduces burnout and turnover 

27:45 — How well-meaning policies can quietly set people up to fail 

Have a leadership challenge or question you’d like us to explore on the show? Submit it here!

Need help developing your leaders or organization? Schedule a complimentary strategy session. 

Can we let people—especially the ones we care about most—chart their own path? What about when we think they're making a mistake?

In this part 2 episode, Janette returns to examine how the same leadership patterns she’s untangling in her role at work are playing out at home—with her son, her daughter-in-law, and her husband. What starts as a family conflict becomes a raw reckoning with expectations, identity, and the cost of clinging to an ideal instead of truly seeing people.

Ideas we explore:  

01:15 — When stepping in to help actually gets in the way  

04:10 — How the ideal in your head is sabotaging your relationships  

07:00 — It isn't love when it's about you  

15:00 — Clinging to being right makes connection impossible  

21:50 — Your mindset shapes every relationship you touch  

28:00 — The courage it takes to truly see and acknowledge others

Have a leadership challenge or question you’d like us to explore on the show? Submit it here!

Need help developing your leaders or organization? Schedule a complimentary strategy session. 

Are your efforts to be helpful actually helpful? And when you step in, is it because your team needs your help or because you need to feel needed? If you’ve ever used the word helpful to describe yourself, this episode is for you.

Because in this raw coaching session, Janette—a former teacher turned HR director—works with her Arbinger coach, Mitch Warner, to confront how her well-intended desire to support her principals is preventing them from owning their work. What starts as a conversation about time management becomes a deeper reckoning with control, avoidance, and the leadership cost of doing for others what you should be developing them to do on their own.

Ideas we explore:

01:15 — It’s not a time problem...it’s a “doing too much” problem.

03:40 — The most “helpful” leaders often create the biggest bottlenecks.

08:50 — Not giving tough feedback protects comfort but prevents growth.

13:20 — Stepping in communicates a lack of trust in your team.

17:40 — Fixing everything turns you into the only one who can fix anything.

26:00 — The need to feel helpful is quietly undermining your leadership.

 Have a leadership challenge or question you’d like us to explore on the show? Submit it here!  

Need help developing your leaders or organization? Schedule a complimentary strategy session. 

How do you build a team that doesn’t sit around waiting for instructions? What if your people knew exactly what to do, even when the plan changed and you weren’t in the room to explain it?

This episode explores the tension between roles that demand split-second precision and those where ambiguity is the norm. McKinlay Otterson talks with Carey Jones, former Flying Training Wing Vice Commander at Laughlin Air Force Base and retired fighter pilot, and Brad Harker, a senior sales leader, about what it really takes to drive clarity, alignment, and high performance even when the feedback loop is slow and the outcomes aren’t obvious.

Questions we answer:

02:52 – How do you drive performance when your role has no clear feedback loop?

07:13 – How can leaders productively leverage subjectivity and interpretation?

08:30 – How do you know if your team is actually having the impact you intend?

14:37 – What does it take to create clarity without micromanaging?

19:32 – What happens when strategy lacks clear measures of success?

23:00 – What does it look like to execute on commander’s intent in business?

 Have a leadership challenge or question you’d like us to explore on the show? Submit it here!  

Need help developing your leaders or organization? Schedule a complimentary strategy session. 

We’ve all felt it: the tension between being real and being in charge. But as inner-city middle school teacher Carla and retired Air Force commander Naomi reveal, that’s a false choice. Connection isn’t a distraction from leadership—it’s the doorway into it.

This episode explores what happens when leaders stop hiding behind roles and start showing up as people. The result? Teams that listen, trust, and rise to meet the moment, not because they’re forced to, but because they want to.

Bottom line: The most credible leaders are the most human ones and trust is built at the intersection of expectation and empathy.

Questions we answer:

02:00 – How do you build real connection with people you also have to hold accountable?

06:10 – What is it like to lead in a culture that prizes command over connection?

08:55 – How do you decide between personal crisis and professional responsibility?

12:05 – How can vulnerability help strengthen trust and culture in a high-stakes organization?

15:45 – What happens when leaders avoid accountability conversations to preserve relationships?

17:55 – Why does accountability without connection lead to failure—and how can we avoid that?

19:55 – How can embracing our own humanity unlock deeper engagement from others?

 Have a leadership challenge or question you’d like us to explore on the show? Submit it here!  

Need help developing your leaders or organization? Schedule a complimentary strategy session. 

Have you ever started a new role only to feel like none of your past experience is recognized? Like no one sees the value you bring, no matter how much you’ve accomplished?

In this raw coaching episode, Jeremy—a senior leader in a construction and engineering company with 24 years of military experience—unpacks that exact challenge with his Arbinger coach, Chip Huth. Together, they dig into the mindset and behaviors that are keeping Jeremy stuck. And what begins as a story about being overlooked becomes something much deeper: a reckoning with self-doubt, avoidance, and the cost of trying to look competent instead of getting curious.

Questions we answer:

02:00 – How do you lead a team that dismisses your experience?

06:55 – What is causing your team to leave you out of key conversations?

18:45 – What is preventing you from getting as curious as you should be?

28:55 – How do you not let painful past experiences, continue to negatively impact you?

40:35 – How to use reg flags to stop unhelpful behaviors before they start?

43:50 – What’s the right way to recover when you've broken trust?

 Have a leadership challenge or question you’d like us to explore on the show? Submit it here!  

Need help developing your leaders or organization? Schedule a complimentary strategy session.