Your First Hire: A Step-by-Step Strategy for Founders

Claire Monroe

Hey everyone, welcome back to The Science of Leading. I’m Claire Monroe, and—yep, you guessed it—I’m here with the one and only Edwin Carrington. Edwin, how’s it going?

Edwin Carrington

Doing well, Claire. Always glad to be here—especially when we’re diving into something as make-or-break as… that very first hire. I mean, that decision? It can totally shape the future of a company—for better… or not-so-great.

Claire Monroe

Right? And I don’t think people always get how big of a deal it is. Like—I remember this one founder I worked with—she hit that burnout wall, and just, like, hired the first person who seemed okay. Not great. Just… “good enough.” And yeah… that did not go well. The person quit a few months in and honestly? It kind of tanked her momentum. Is that... normal?

Edwin Carrington

It’s more common than you’d think. When you're buried in tasks, running on caffeine and panic—it’s easy to just grab the first lifeline. But hiring out of desperation? That almost always backfires. You might get someone competent, sure—but if they’re not aligned with your mission, or they don’t click with your way of working… it won’t last. OAD’s research actually shows that these kinds of “panic hires” are one of the top reasons new businesses stall out. It’s not just about capability—it’s about alignment. Fit. Shared vision.

Claire Monroe

So it’s not just like, “Can they do the job,” but more like, “Are they the right person for where we’re headed.” That totally tracks. I mean… the founder I mentioned? She didn’t really stop to think what kind of person would help her grow—she just needed someone to take stuff off her plate. But there was zero thought about values, or long-term culture. Is that where people usually mess up?

Edwin Carrington

Exactly. Your first hire… they’re not just an extra set of hands. They’re the foundation of your culture. Of your future team. And if you rush that? You risk building on, well… quicksand. But if you slow down, define what you need, and hire with intention—suddenly you’ve got something stable. Scalable. It’s still a leap of faith… but now it’s a calculated one.

Claire Monroe

Yeah… a calculated leap. I like that. So okay—how do you actually make that leap without faceplanting? Let’s talk about what a strategic hiring process actually looks like.

Edwin Carrington

First step? Hit pause. Before you post anything, get crystal clear on what your business actually needs. What’s missing? What’s keeping you stuck? And—this part gets skipped a lot—what kind of person complements you, instead of just being another you?

Claire Monroe

Sooo… it’s not just like, “Here’s a list of tasks,” right? It’s more like, “What does success in this role look like?” ‘Cause yeah—I’ve seen job descriptions that are just, like, laundry lists of stuff to do. But the good ones? They talk about the mission. The impact. The why. Is that the difference?

Edwin Carrington

Spot on. The best job descriptions don’t just tell—they inspire. They show candidates how they’ll actually move the needle. They talk about values. About what success looks like in those first few months. And they draw a clear line between must-haves and nice-to-haves. That clarity? It pulls in people who are excited about your vision—not just folks job-hopping.

Claire Monroe

Okay, so let’s say you’ve got a solid job post. Now what? How do you not fall into the trap of hiring the first person who looks decent on paper?

Edwin Carrington

That’s where structure comes in. You start with a quick phone screen—see how they communicate, how they vibe. Then maybe a small paid project or skill test, especially for specialized roles. Finally? Dig deeper with interviews that use behavioral questions. Ask how they’ve handled real challenges. And of course, tools like OAD’s behavioral assessments can help you see what’s underneath the résumé—things like decision-making style or natural motivators. All the stuff that makes or breaks a fit.

Claire Monroe

Yesss—behavioral interviews. We went deep on that in Episode 1, remember? I love those. But okay… here’s something I always wonder: how do you really know if someone’s gonna fit your culture? Is there a way to predict that—or is it just, like, vibes?

Edwin Carrington

Great question. And yeah—gut instinct can help… but it only gets you so far. I worked with this tiny tech startup—just the founder and one dev. Super lean. They kept hiring for technical skills, and the turnover was brutal. Finally, they stopped and said, “Okay—what kind of mindset do we need?” They looked for someone adaptable, mission-driven… not just skilled. That person? They clicked instantly. Grew with the team. Took initiative. Total game-changer. That’s what happens when you prioritize alignment over credentials.

Claire Monroe

I love that. It’s such a good reminder that your first hire isn’t just about plugging a hole—it’s about choosing the kind of company you’re trying to build. Okay—so you find that person. You make the offer. Now what? ‘Cause I know that’s when the legal stuff starts sneaking in…

Edwin Carrington

That’s where the fun begins. So—once you’ve got your yes, it’s time to get official. First, grab your EIN from the IRS. Make sure you’re classifying the role right—are they an employee or a contractor? Register with your state’s tax agency. Set up payroll. And in most states, you’ll also need workers’ comp insurance… even if it’s just one person. Miss one of these? You could get hit with fines or delays. So yeah—it’s worth slowing down and doing it right.

Claire Monroe

Okay, wow. I had no idea it was that involved. I always thought onboarding was, like, “Here’s your laptop, coffee’s over there, good luck!” But… there’s way more to it, huh?

Edwin Carrington

Oh, definitely. Onboarding is where you build momentum—or lose it. It’s your chance to set expectations, explain the culture, and show someone how their role fits into the big picture. Clarity matters. So does mentorship. Frequent check-ins. Early feedback. All those little touchpoints add up. And when onboarding’s rushed? Even the best hire can flounder. But when it’s thoughtful—it builds trust. And retention.

Claire Monroe

That really surprised me when I started reading about all this. Like—I always thought people left jobs because of money, or workload. But turns out… if you don’t feel supported? Or you’re just confused all the time? You’re way more likely to peace out. So what about after that initial onboarding? How do you keep people moving forward?

Edwin Carrington

It’s all about structured feedback and growth. Set goals early. Check in often. Ask where they need support. Offer challenges—new projects, learning tools. And keep checking your hiring playbook. Your needs evolve as you scale. That first hire? Just the beginning. But if you keep investing in their growth, and your process stays intentional… you’re setting the foundation for a team that actually sticks.

Claire Monroe

That’s such a great note to wrap up on. So yeah—if you’re out there and you’re about to make your first hire, remember—it’s not just about getting some help. It’s about, like… building your future. Edwin, thank you—as always—for being our hiring Yoda.

Edwin Carrington

Thank you, Claire. And thanks to everyone listening. If you want to dive deeper—or see how tools like behavioral assessments can actually simplify all this—check out o-a-d-dot-a-i. That’s OAD.ai. You can book a free demo and see how it all works.

Claire Monroe

Do it! It’s seriously cool. Alright—we’ll see you next time. Take care!

Edwin Carrington

Goodbye, Claire. Goodbye, all.