Writing a letter of recommendation is a massive burden. Honestly, most people dread it. When someone asks you to vouch for them, they aren't just asking for a few nice words; they’re asking for your reputation on a silver platter. You’ve probably been on both sides of this. Maybe you’re the manager staring at a blank cursor, or the student trying to figure out how to nudge a professor without sounding entitled. It’s tricky. If you want to write letter of recommendation content that actually moves the needle, you have to stop being generic.
Generic is death. "He is a hard worker" means nothing in 2026. Everyone is a hard worker on paper.
The reality is that admissions officers and hiring managers at places like Google or Harvard see thousands of these. They can smell a template from a mile away. If you’re going to do this, do it with some teeth.
The Myth of the "Perfect" Template
People love templates. They want a fill-in-the-blank solution because it’s easy. But the truth is, the most effective letters are the ones that feel a little bit messy and deeply personal. I’m not saying you should be unprofessional. I’m saying you should be specific.
Think about a time the person you’re writing for actually failed. Yeah, failed.
If you can describe how they handled a botched product launch or a C- grade on a midterm, that carries ten times more weight than a list of their best traits. It shows resilience. When you write letter of recommendation drafts, look for the "inflection points." Those are the moments where the person changed the trajectory of a project or a team.
I remember a colleague who had to write for a junior analyst. Instead of saying the analyst was "analytical," she wrote about a specific Tuesday afternoon where the analyst found a $40,000 discrepancy in a spreadsheet that three senior partners had missed. That’s a story. That’s evidence.
Why the "Wall of Praise" Fails
If a letter is 100% sunshine and rainbows, it’s suspicious.
Reliable narrators acknowledge limitations. Maybe the candidate is brilliant but sometimes gets too bogged down in the details. Mentioning that—and then explaining how they’ve worked to improve it—makes the rest of your praise feel authentic. This is a concept often discussed by career experts like those at the Harvard Business Review; credibility is built through balance, not just relentless positivity.
Structure Is a Suggestion, Not a Law
You don’t need a five-paragraph essay. Sometimes a punchy three-paragraph letter is better.
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Start with the "How." How do you know them? How long? If it’s been six months, don’t pretend it’s been six years. Be honest about the scope of your relationship. If you only saw their work in one specific niche, stay in that lane.
The middle is where the meat is. Pick two—only two—core strengths. If you try to say they are a leader, a coder, a writer, and a visionary, you end up saying they are nothing. Focus. Did they lead the team? Or did they do the deep, quiet work that kept the team from falling apart? There is a difference.
The "Compare and Contrast" Technique
One of the most powerful moves you can make when you write letter of recommendation pieces is to compare the person to their peers.
"In my twelve years of teaching, Sarah is in the top 1% of students I’ve encountered regarding her ability to synthesize complex data."
That gives the reader a benchmark. It’s not just "Sarah is good." It’s "Sarah is better than almost everyone else I’ve seen in a decade." That’s a bold claim, so only use it if it’s true. Use it sparingly. If you say every intern is the "top 1%," you lose your power as a recommender.
The Logistics Most People Forget
Let’s talk about the boring stuff because the boring stuff gets people rejected.
Deadlines are real. If you’re the one asking for the letter, give your recommender at least three weeks. A month is better. If you’re the one writing it, don’t wait until the night before. You’ll end up using the "cliché" phrases we’re trying to avoid.
Also, the "Brag Sheet."
If you want someone to write letter of recommendation for you, give them a cheat sheet. Don’t make them hunt through their memory for that project you did in 2023. List the project, the result, and why it mattered. Give them the raw materials so they can build the house.
- Project name and date
- Your specific role (be honest)
- The quantifiable outcome (saved time, earned money, solved a bug)
- Why you’re applying for this specific new role
Dealing with the "Self-Write" Request
Sometimes a boss will say, "Just write it yourself and I’ll sign it."
This is a trap, sort of. It’s lazy, but it’s also an opportunity. If you find yourself in this position, don’t write it like a narcissist. Write it from their perspective. Use their voice. If they are short and direct, keep the letter short and direct. If they are academic and flowery, use more syllables.
Avoid These Career-Killing Phrases
Stop using "pleasure to work with." It’s filler. It’s like saying the weather is "nice."
Stop using "go-getter." It sounds like a 1980s motivational poster.
Instead, use "proactive." Or better yet, don't use a descriptor at all. Describe an action. Instead of "he is a go-getter," try "he independently initiated a revamp of our client onboarding process, which reduced churn by 15%."
The goal when you write letter of recommendation is to provide "transferable proof." You are telling the next person, "Here is what they did for me, and they will likely do it for you too."
The Final Polish
Before you hit send, read the letter out loud. If you stumble over a sentence, it’s too long. If you feel bored reading it, the recruiter definitely will be.
Check the formatting. Use a professional letterhead if you have one. It matters. It shows you take the request seriously. If you’re an alum of the school the person is applying to, mention it. That’s "legacy" weight that can sometimes help tip the scales.
What If You Can't Write a Good One?
This is the hardest part. If you don't believe in the person, don't write the letter.
"I don't think I'm the best person to speak to your strengths for this specific role."
It’s a hard conversation, but it’s better than writing a lukewarm, "meh" letter that actively hurts their chances. A bad letter is worse than no letter.
Steps to Take Right Now
If you're sitting down to write right now, follow these steps to get it done effectively:
- Request a Brag Sheet: If you don't have one, ask the candidate for a bulleted list of their three biggest accomplishments while working with you. This saves you 80% of the mental labor.
- Identify the "Power Trait": Pick the one thing this person does better than anyone else. Is it grit? Is it technical precision? Is it empathy? Center the letter around that.
- Draft the "Story": Write four sentences about a specific time they demonstrated that power trait. Forget grammar for a second; just get the facts down.
- The "Top %" Statement: Determine where they rank compared to others you've supervised. If they are truly exceptional, state it clearly.
- Check the Submission Link: Ensure you have the right portal or email address. Many systems like Common App or Interfolio have specific quirks that can cause a letter to get lost in the digital ether.
- Archive a Copy: Save the PDF. People often ask for updated letters a year later, and you'll thank your past self for not having to start from scratch.
Writing these doesn't have to be a chore if you treat it as a storytelling exercise rather than a bureaucratic requirement. Focus on the human, keep the anecdotes sharp, and avoid the fluff that everyone else uses. That's how you write a letter that actually gets someone hired.