Oh man, I remember the first time someone asked me to write a character reference letter. It was for my neighbor’s kid who’d applied to be a summer camp counselor — and I froze. My brain went totally blank, like when you forget your Starbucks order mid-sentence. I ended up writing something stiff and generic that sounded like a robot quoting Webster’s Dictionary: ”To whom it may concern… [insert name] is punctual and responsible.” Cringe.
Here’s what I’ve learned since then (the hard way):
A few years back, my cousin needed a character reference for a teaching job. This time, I sat down with her over Dunkin’ coffee and just asked, “Tell me about a time you messed up at work and how you fixed it.” Turns out, she’d once calmed a parent meltdown during a PTA fundraiser by staying two hours late to reorganize donation spreadsheets. THAT story became the heart of the letter. She got the job — and her principal later said the fundraiser anecdote “made her real, not just resume bullets.”
The rookie mistake most of us make:
We treat character references like Yelp reviews (”5 stars, would recommend!”). But hiring committees and judges (I’ve written letters for both) aren’t looking for cheerleaders. They want proof wrapped in a story.
My tested formula:
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Start with a hook they’ll remember
Instead of “I’ve known Sarah for 5 years,” try “Sarah’s the kind of person who’ll drive through a snowstorm to return your Crockpot — and apologize for being 10 minutes late.” -
Pick 1-2 SPECIFIC examples
Last year, I wrote a letter for our Little League coach who was applying to mentor foster teens. I didn’t just say he’s “patient.” I described how he handled the season when 8-year-old Tyler kept missing catches: ”Every Tuesday, Coach stayed 30 minutes after practice throwing pop flies until Tyler’s mitt finally went thwack — and the whole team erupted like we’d won the World Series.” -
Show growth, not perfection
My friend’s parole letter for his brother included this line: ”When Jamie relapsed in 2020, he called me at 2 AM instead of lying. That raw honesty — even when it’s hard — is how I know he’s ready.” Brutal? Maybe. But the judge said it was the most convincing part.
The awkward thing nobody warns you about:
Sometimes you HAVE to say no. Like when my college roommate asked me to vouch for his “leadership skills”… but he’d ghosted our group project senior year (Ricky, if you’re reading this — still salty about that B-). I told him, “I’ll write the truth, but let’s find someone who’s seen you crush it at work.” It stung in the moment, but he thanked me later.
Template? Sure — but make it yours:
[First line that sounds like YOU]
[2-3 vivid examples — think “camera moments”]
[Why this person’s flaws don’t scare you]
[Contact info + “Call me anytime” if you mean it]
I keep a Google Doc of bullet points for people I’d recommend in a heartbeat — stuff like ”Natalie coordinated the neighborhood BBQ after the 2023 flood” or ”Jose fixed my iPad without making me feel tech-dumb.” Life’s too short to start from scratch every time.
Final tip: If you’re stuck, imagine you’re telling a friend about this person at a backyard cookout. Would you say “They demonstrate exceptional integrity” or “Remember when they tracked down Mrs. Wilson’s stolen Costco gnome? That’s them.”
You’ve got this. And hey — if your first draft feels awkward, that’s normal. Mine looked like a Hallmark card written by an IRS agent until I figured out the secret: Write like a human, not a thesaurus.
(Coffee emoji)
— Jen, mom of two, DIY disaster survivor, and reluctant reference letter pro after helping 17+ people nail job apps, custody cases, and even a firefighter exam
P.S. Need a gut check? Read it aloud in your best “formal voice.” If you cringe, add a sentence about that time they did something totally them.