Hire Help Now—No Need to “Make It” First! With Toby Myles episode artwork

EPISODE · Aug 11, 2026 · 27 MIN

Hire Help Now—No Need to “Make It” First! With Toby Myles

from Win The Hour, Win The Day · host Kris Ward

This week’s episode of Win The Hour, Win The Day Podcast interviews, Toby Myles. For years I blamed the assistant. Never to her face. I'm too nice for that (which, honestly, was half the problem). But in my head I'd decided she just didn't get it. The work came back not-quite-right and I'd think, well, I told her how I wanted this. Did I though? Here's what I actually said one time: "I wouldn't do it that way." That was it. My whole big direction. So she went and did it the way I said I wouldn't, and I sat there sure she'd dropped the ball. She hadn't. I never told her which way to go, or why it mattered. I handed her my opinion and called it leadership. I had Toby Myles back on the show this week, and she owned the exact same thing out loud. For years she figured her assistants were the problem. Wrong skills, oversold themselves, didn't get it. Then she landed in a setup that actually worked and the penny dropped. Oh. It was me. Now, when something comes back to me and my first thought is "they didn't understand," I already know how that sentence ends. I go hunt for the fuzzy thing I said. It's there about 99% of the time. I left a gap, and the person just walked into it. Nobody warns you about this part when you finally bring someone on. The instruction that lives crystal-clear in your head is almost never the one that came out of your mouth. So now I get clear before I hand anything over. Boring, specific, this-is-exactly-what-I-mean clear. Toby went from burning through assistants to building a full podcast in a month with one person she now calls her second brain. Same Toby. The setup was the only thing that changed. When something your team did comes back wrong, whose sentence do you go re-read first, theirs or yours?

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Hire Help Now—No Need to “Make It” First! With Toby Myles

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