Founder Red Flags in Hiring (That Top Candidates Pick Up On Immediately)

Over the last two years at Phoenix Court, I’ve had hundreds of conversations with early-stage founders—maybe even thousands. Spending time with founders is hands-down my favorite part of the job. I admire the intensity, the clarity, the commitment to building something that didn’t exist before.

Because most of our investments happen at Seed, getting to know the founder is often more important than anything else. It’s the person, not the product, that gets us to lean in.

But when it comes to hiring, even the sharpest founders sometimes fall into what I call “balcony syndrome.”

They view hiring from the top down—seeing only their side of the equation—and forget that great candidates are evaluating them just as much.

The economy might shift. The market might cool or heat up. But one thing never changes:

⇒ Top talent is recession-proof ⇐

There will always be a shortage of exceptional people—and the best ones can smell dysfunction from a mile away.

So if you’re not thinking about the candidate experience, you might already be starting from behind.

Here are some red flags I’ve seen great candidates pick up on immediately—often without founders even realizing it:

1.Treating Hiring Like a Side Project

This might be the biggest red flag of them all.

I’ve had the privilege of working directly with some incredible founders—Joshua Reeves (Gusto ), and Elon Musk (Neuralink) —and senior execs @ Meta . The one thing they all have in common? They never treated hiring as a side project. Quite the opposite—it was a top priority.

Reschedules, lack of prep, showing up late, scanning the CV mid-call—candidates pick up on all of it. And the best ones won’t stick around. It sends a loud message: “I don’t take this seriously.”

✅ Fix: Show candidates they’re a priority. A crisp, thoughtful hiring process is a proxy for how you build everything else.

As a founder, you need to drive the process—this isn’t a task for your chief of staff or founder associate. For the first 50–100 hires, you’re the face of the company. Own it.

🎯Example: When I first met James Smith, PhD and Jack Galilee @ Human Native, they immediately started to drive all hiring processes forward and still do to this day.

2. “We’re still figuring it out…” (but no clarity follows)

It’s fine to be early. What’s not fine is being vague and unprepared. Candidates expect some ambiguity—but if founders can’t articulate the mission, product direction, or how the role fits into it, top talent gets spooked.

✅ Fix: Be honest about the stage, but show clarity on your intent, direction, and how this person will make a dent.

3. The “Too Easy” Interview

When interviews are overly casual, vague, or unstructured, top candidates often walk away wondering: “Do they even know what good looks like?”

An interview that’s all vibes but no depth can feel flattering in the moment—but for top talent, it raises doubts about the bar, the leadership, and how important the role really is.

✅ Fix: Make your interviews thoughtful and well-calibrated. You don’t need to grill people, but instead show that you’ve done the work to define what good looks like and ask questions that reflect that. Ideally, candidates should leave the interview not knowing if they’ve done well. Top talent will be sold by a hard interview, not knowing if they have passed.

🎯 Example: While being humble and curious, James Dacombe @ CoMind will make sure candidates are challenged. This is constant feedback from candidates who meet with him and it's helped him to build an exceptional team.

4. Over-titling too soon

Offering someone a “CTO” or “head of” title when you haven’t even built v1 yet is a big flag for experienced operators. It signals either naivety or a lack of vision for scale.

✅ Fix: Focus on scope and ownership first. Titles evolve. Example: Call it engineering @ [insert your company name]. The candidate refuses to join? They aren’t the right fit.

🎯 Example: This is Amine Raji and Spore.Bio 's philosophy to attract the right talent. Amine has done an excellent job growing talent from within and focusing on impact rather than titles.

5. Selling too hard, listening too little

When the founder monologues for 25 minutes straight about how big the market is and how amazing the product will be—without learning anything about the candidate—it feels like a pitch deck, not a conversation.

✅ Fix: Ask good questions. Tailor the pitch based on what they care about.

Try to apply that rule for yourself when you meet a candidate: 30/70. You should only speak 30% of the time during that meeting. Focus on picking up clues rather than selling.

6. Dodging hard questions

If a candidate asks about runway, traction, or challenges—and the founder evades or spins—it kills trust. Great candidates want realism. The candidate will become a team member and eventually find out what the situation is like. What’s the point of avoiding what would help them make an educated decision?

✅ Fix: Be transparent. You don’t need to be perfect; you need to be credible.