Aug 10, 2026 · 58 min · 15 segments
A-10 squadron commander Derek "Woody" Oaks on the three things almost every leader gets wrong. Retired A-10 fighter squadron commander Derek "Woody" Oaks joins host David Befort to break down the…
Derek OaksGuest
David BefortHost
Do you do you does that translate to like having kids like we both have kids treating, you know, giving them that kind of autonomy? Like, how is that different in, you know, a fighter squadron versus a boardroom versus at home? You know, how do you how do you translate that?

You know, I felt like I had a successful fighter squadron command and I have a lot of guys in the squadron, yourself included, who have gone on to do great things.

They're doing amazing things in a lot of different areas that I probably wouldn't have picked for them.

And so at the time, I look back and I think, I don't know if I trust as well as I should have.

I don't know if I tried to set too many rules or not, but they're doing okay now.

And I partly just attribute that I married well, but I'm not sure when it comes to family.

I mean, I think my most self-conscious area probably is, am I a good dad? Am I a good husband?

I think the jury's, I mean, when is the jury out when you have kids? Like my kids, you know, my oldest is 19.

I hate to break it to you, but Preo and I have found, my wife and I have found that raising 20-somethings is a whole lot harder than raising teenagers.

And it's not because, I think the challenge as a parent is they're out of your house for the most part.

think they don't need your advice, you see some of the challenges you're going through and you want to help them, but you really need to, you know, the better part of Bower and that is just shutting up.

And really when they ask you for advice, you give it, but you don't give it any other time.

And so you see them struggling and that's hard as a parent to watch your kids struggle and you have zero control over it and helping them when they don't think they need any help, but they do need help if that makes sense.

Do you do you does that translate to like having kids like we both have kids treating, you know, giving them that kind of autonomy? Like, how is that different in, you know, a fighter squadron versus a boardroom versus at home? You know, how do you how do you translate that?

You know, I felt like I had a successful fighter squadron command and I have a lot of guys in the squadron, yourself included, who have gone on to do great things.

They're doing amazing things in a lot of different areas that I probably wouldn't have picked for them.

And so at the time, I look back and I think, I don't know if I trust as well as I should have.

I don't know if I tried to set too many rules or not, but they're doing okay now.

And I partly just attribute that I married well, but I'm not sure when it comes to family.

I mean, I think my most self-conscious area probably is, am I a good dad? Am I a good husband?

I think the jury's, I mean, when is the jury out when you have kids? Like my kids, you know, my oldest is 19.

I hate to break it to you, but Preo and I have found, my wife and I have found that raising 20-somethings is a whole lot harder than raising teenagers.

And it's not because, I think the challenge as a parent is they're out of your house for the most part.

think they don't need your advice, you see some of the challenges you're going through and you want to help them, but you really need to, you know, the better part of Bower and that is just shutting up.

And really when they ask you for advice, you give it, but you don't give it any other time.

And so you see them struggling and that's hard as a parent to watch your kids struggle and you have zero control over it and helping them when they don't think they need any help, but they do need help if that makes sense.
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