When you ask him about what a 'good radio voice' is.. I think you should sound really keen an interested. Not at all sarcastic. If you can try and get him to give you examples, and then keep screwing it up. Plus keep calling him chief

"Ok Leo, sure. I just wanna make sure I'm doing things right for Paladin. How's this? [really enthusiastic voice] This is Charlie-Five over!"
"Uh.. no.. um.. less enthusiastic, you don't need to scream."
"Right Chief. How about this then? [completely monotone voice] This is Charlie-Five over."
"No.. you need more gusto than that -"
"Ok Chief. [normal voice] This is Charlie-Fi [COUGH! COUGH!] Sorry.. I got [COUGH!] Ugh.. [COUGH!] [COUGH!] Whoa.. sorry. Lemme try that again. [really dry raspy voice] This is Charlie-Five over. [clearing throat] Sorry.. Do you have some water or something? [clearing throat]"
"What?? Are you trying to make this difficult?"
"No way Chief. [clearing throat] There.. that's better. I just wanna win one for Paladin. Y'know.. make everyone happy. Maybe you could show me how to do it? I'm really sorry Leo. [getting sad] I'm honestly not trying to screw up.. I just want to know how to do it right."
"[feeling guilty] Um.. ok. No, it's ok. Uh... here. like this. [Pleasant, deep radio voice] This is Charlie-Five, over."
"[still kinda sad, but holding it in. In a slightly-too-deep radio voice] Charlie-Five, over."

"No.. no.. like.. [Pleasant, deep radio voice] This is Charlie-Five, over."
"[Pleasant, deep radio voice] This is Charlie-Five, over."
"There! [smiling] That's it [realizes he's forgotten Cliff's name] -- uh.. That's it! You got it."
"[Practicing. Pleasant, deep radio voice] This is Charlie Five. This is Charlie Five [normal voice] yah.. ok.. I think I got it. [Pleasant, deep radio voice] This is Charlie Five [insanely enthusiastic] Everything's A-OK here! Locked and Secured up *Right*!!"
"Whoa! What was that?!!"
"[pleasant, deep radio voice] This is Charlie Five [smiling]"
"No, no.. everything has to be in that voice?"
"It was. [confused look] Sorry Chief. What did I do wrong?"
"Like this [pleasant deep radio voice] This is Charlie Five, everything's secure."
"Sorry Chief. [Pleasant deep radio voice] This is Charlie Five, Everything's locked up and buttoned down."
"What? No you can't say that. It's not professional. Just say everything's secure."
"[pulling out handbook] I don't remember reading that. I remember the call-signs [flipping pages]"
"Just.. Listen, it's my company, just trust me."
"[putting down handbook] Sorry Chief. [insanely enthusiastic] Charlie-Five, Everything's *SECURE*"
"No, normal voice. Remember?"
"Right Chief. [insanely enthusiastic] Charlie Five!"
"No.. [pleasant] Charlie Five"
"[pleasant] Charlie Five"
"[pleasant] Charlie Five, Everything's Secure."
"[pleasant] Charlie Five, Everything's Secure."
"Perfect! Now you got it."
"[beaming] Right Chief. [pause] But what if everything's not secure?"
"What??"
"I mean, if I find some doors unlocked or someone sneaking around. Should I still use the voice? Or should I try and vary my pitch a bit more?"
"Uh.."
"Like, see should it be. [pleasant, calm radio voice] I've spotted an intruder. [normal] or should it be more like [semi-hysterical] Intruder! I've spotted an intruder!"
"Uh.. it doesn't matter, if you actually find an intruder it's okay to be frightened."
"[stiffening] Hey.. I didn't say I was scared. I'm just sayin.. maybe I'd be a little excitable."
"No, no.. I wasn't saying -"
"Listen Chief. You want to see what this cowboy's made of? Do you know what I've done with that MagLite?"
"What? [scared]"
"I'm just sayin' Chief. I'm out there. I'm *Rep-Re-Senting* Paladin. I'll take them down!"
"ooh... kaaay..."
"[in his own little world] But when the adrenaline's pumping it's like [picking up radio and screaming into it] MuthaFuckers! They's some intrudas! [pulling out maglite] I'm takin' these muthas *OWT* [letting radio fall to his side. Muttering] Fuck with my watch.. willya.."
"Listen [again trying to remember Cliff's name. Realizing it's on Cliff's name-tag] Rice-- Rish-- Uh.. [giving up on pronouncing Cliff's last name] Listen. I'm thinking maybe this isn't the right line of work for you."
"[all calm and appologetic] Oh, hey.. it's ok. It's just the adrenaline. No, no I'm ok [pleasant deep radio voice] Charlie Five [normal] See? I got it. I'm cool. I'm just sayin I'm there for Paladin, right? If something goes down. I just want you to know, is all. That I'm there for you Chief."
"uh..."
"[pleasant voice] Charlie Five. Charlie Five. Everything's secure. [normal] See.. it's cool. I got it."
"Ok. Ok then [reassured] I guess that about wraps everything up."
[[..later..]]
"[Pleasant, Deep radio voice] Hello everyone, this is Charlie-Five coming to you live from Surface Engineering. I'm pleased to report that everything is currently locked down and secure. I'll be making my rounds shortly and Mobile-One? I'm looking forward to seeing you in.. just a little bit. That wraps up my report - I'll be talking to all of you [smug voice] later."
[[..still later..]]
"[Insane] AHHH!! The door is *FUCKING* Open Man! Holy Shit! I can't believe it. Fucking on my watch too.... [...static...] -obile-One. Come-in Mobile-One. I NEED Backup. Repeat. Charlie-Five requesting immediate assistance. [...pause...] Uh.. wait... [Pleasant, Deep Radio Voice] This is Charlie-Five, Everything is secure. Seems I left the door unlocked the last time through. Over."