The One Question Every Founder Needs to Ask Their First 10 Hires

Photo by Per Lööv on Unsplash

Founders like to romanticize the early days. Two laptops, one idea, and a steady IV drip of cold brew. You’re moving fast, breaking things, and thinking the next hire is going to be your Wozniak, your Sheryl, your everything.

But here’s the dirty truth: hiring your first 10 employees isn’t about charisma, pitch decks, or beer fridges. It’s about surgical clarity. Because at this stage, every hire is a tectonic shift—every person adds mass and friction. Get it wrong, and you’re not building a startup—you’re assembling a slow-motion disaster.

So what’s the most important question a founder should ask when interviewing an early hire?

"How will you move the business forward in the next 90 days?"

That's it. That’s the test.

Why? Because this question slices through the BS. It forces clarity, ownership, and alignment. And if they can’t answer it with specificity, you’ve got a tourist—not a teammate.

Founders, Meet Reality

Let’s be clear. You are not running a Fortune 500 company. You don’t have middle managers or a people ops department to mop up bad hires. You are hiring functional arteries—core extensions of your vision, grit, and strategy.

Every early hire must tie directly to a core business function. So ask yourself: What are we actually selling? How does money move through this business? Who builds the product? Who sells it? Who supports it?

It’s tempting to go after the shiny stuff—growth hackers, innovation ninjas, a Head of Vibes. But unless you’re manufacturing social media clout or renting co-working desks to college students, you need builders, closers, and problem solvers. You need doers.

Here’s the litmus test: If you disappeared for a week, would this person keep the machine running, or would they be sending Slack messages asking where the coffee filters are?

Skills That Matter More Than a Resume

Early hires should be “utility infielders with teeth.” Yes, they need functional skills—but just as importantly, they need a founder’s mindset: resourceful, adaptive, and allergic to excuses.

Look for:

• Problem-solving: Can they make decisions without asking permission every six minutes?

• Communication: Can they articulate their thinking clearly and concisely?

• Adaptability: Can they thrive in chaos, or do they need a Kanban board and four team syncs just to breathe?

Your startup is a moving target. Today’s roadmap is tomorrow’s kindling. You don’t need experts in one thing—you need people who can learn fast and give a damn.

Write the Damn Job Description

Too many founders hire on vibe. “He seemed sharp,” or “she crushed it at [insert shiny brand].” That’s fine if you’re casting for a reality show. But you’re building a company. Clarity matters.

Write a clear job description. Not a 47-point HR wishlist. Just answer three things:

1. What will they do?

2. What skills are required to do it?

3. How will this role move the business forward?

If you can’t articulate the role, you’re not ready to hire. Full stop.

Build for Now—and Next

Yes, you need someone who can ship product or close deals today. But don’t forget that your first 10 hires will shape culture, process, and velocity for years. These people are not just employees. They’re your future VPs, your culture bearers, your therapists during down rounds.

So don’t just think about the immediate fire. Ask:

• Can this person grow with the company?

• Will they still be valuable at 50 people? 100?

• Are they someone others will want to follow?

The best early hires aren’t just executors—they’re multipliers. They raise the bar for everyone around them.

The 90-Day Litmus Test

Back to our original question: “How will you move the business forward in the next 90 days?”

If a candidate says:

• “I’ll need some time to ramp…” — Pass.

• “I’ll start by understanding the culture…” — Pass.

• “I’ll talk to customers, fix the onboarding funnel, and reduce churn by 15%.” — Now we’re talking.

You want someone who’s already in motion. Who sees the business like a founder. Who’s thought beyond salary and benefits and understands that velocity wins.

Final Thought

Early hires aren’t about filling seats—they’re about accelerating impact. If you’re not clear on what that impact looks like, your startup will become a nonprofit... and not the good kind.

So ask the damn question. Not “Where do you see yourself in 5 years?” Not “What’s your biggest weakness?” But how will you make us better—fast?

Because in the early days, there are only two types of hires: those who create momentum, and those who create meetings.

Choose wisely.