We’ve all had that “one that got away” moment in dating. You meet someone amazing but you hesitate. And next thing you know, they get swept away by someone else.

Hiring isn’t all that different.

One of our clients recently interviewed a development director who was a total catch. She’d led a multimillion-dollar campaign, understood donor cultivation inside and out, and clearly shared their passion for free-market principles. The hiring team was smitten.

Their response after the interview?

“She’s great… but let’s see a few more people. Just for comparison.”

Comparison to what, exactly? A unicorn who can raise $2M annually and quote Bastiat?

Three weeks later, the candidate accepted an offer elsewhere. The position sat vacant for four more months, and the organization missed an entire giving season.

Unfortunately, we see this all the time: organizations freezing at the finish line, holding out for perfection while strong, mission-aligned candidates move on.

Why does this happen, and how can you avoid letting your perfect match get away?

Let’s take a few lessons from the world of dating.

1. Define What “The One” Looks Like

Ever gone on a date with someone who “isn’t really sure what they’re looking for”? Spoiler alert: it rarely ends well.

The same goes for hiring. If your team isn’t aligned on what success looks like, no number of interviews will clarify it.

We saw this when an organization interviewed five stellar candidates for a senior policy role. After each conversation, the goalpost shifted: “I wish they had more Hill experience.” “But do they have enough research chops?” “What about media skills?” By round five, it was clear the job description was trying to be three different positions.

The fix: Hit pause before swiping right on another resume. Gather your hiring team and define success. What gap will this hire fill? What does success look like at six months? What’s a must-have versus a nice-to-have? Getting crystal clear up front helps you recognize “the one” when they’re sitting across from you.

2. Ask the Questions That Matter

Bad first dates often boil down to bad questions. “So… why are you still single?” Cue polite laughter and internal screaming.

Likewise, unstructured interviews can lead to confusion and indecision. One organization we know had interviewers asking completely different questions to each candidate. Sometimes the questions were focused on management philosophy, sometimes it was on technical skills, and sometimes it was cultural fit. The result was a jumble of impressions but no complete picture.

The fix: Structure your interviews to assess what truly matters. Ask every candidate the same core questions so you’re comparing apples to apples. And make those questions meaningful: ask the kind that reveal how candidates actually think and problem-solve, not just how well they’ve rehearsed a short list of talking points.

A clear, consistent process makes it easier to spot real chemistry and prevents you from endlessly searching for something that doesn’t exist.

3. Don’t Let the Connection Cool Off

If you’ve ever waited days for someone to respond after a great date, you know how fast excitement fades.

The same goes for candidates. After interviews, debrief quickly — ideally within 24 hours, while impressions are still fresh.

Dragging out decisions doesn’t make you more thorough; it just increases the odds your top choice will accept another offer. In today’s market, mission-aligned talent doesn’t linger.

The fix: Treat follow-up like good dating etiquette — prompt, clear, and genuine. If you liked them, tell them. And if you’re ready to move forward, don’t play hard to get.

4. Stop Waiting for “The Perfect Match”

At some point in dating, you stop analyzing profiles and start planning the future. Hiring shouldn’t be any different.

One client spent half a year chasing a communications unicorn — six years of experience, world-class writing, media savvy, video skills — all for $55K. Eventually, they hired someone with half that experience, most of the skills, and plenty of drive. She’s thriving.

They could have saved half a year (and countless cups of coffee) if they’d recognized a great fit when they first saw it.

The fix: If your structured interview revealed someone who has the skills, shares your values, and energizes your team, that’s your answer. Not a reason to keep searching for their mythical better-looking twin.

Hiring, like dating, is about finding alignment — skills, values, chemistry, and a shared vision for the future. When you find that person, don’t let them get away while you wait for perfection.

Because in hiring (and dating), hesitation rarely ends in happily ever after.

And when you finally hire that mission-aligned superstar, it’ll feel a lot like finding the one — just with fewer awkward first dates and a stronger commitment to limited government