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.

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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?

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.

Launch week giveaway! Leave a written review, upload a screenshot here, and we’ll send you a free Leading Outward sweatshirt!

To claim your free Leading Outward sweatshirt, click here.

Have a burning question that you would like us to answer or a story you want to share? Click here to leave your suggestion!

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?

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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.

Launch week giveaway! Leave a written review, upload a screenshot here, and we’ll send you a free Leading Outward sweatshirt! To claim your free Leading Outward sweatshirt, click here.

Have a burning question that you would like us to answer or a story you want to share? Click here to leave your suggestion!

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?