Writing a Cover Letter

Someone wrote to tell me they really wanted to pay for Draft (I recently turned on paid subscriptions), but they were underemployed and short on cash. However, they were using Draft this very second to write a cover letter for a job application.

I wrote back to thank them for the nice things they had to say, and offered to look over their writing, if they wanted.

It was ok. It was like a lot of other cover letters. It probably looked identical to one I wrote 12-15 years ago. But I’ve learned a lot since then about writing, and finding jobs, and hiring people, and getting people’s attention. Here’s some advice I gave.


The first thing I noticed in this cover letter was how much language was boilerplate. I’m a team player. I work very hard. I know these software packages: X, Y, Z.

Great copy doesn’t remind people what they already know and expect about your product, it tells them why they should care.

Jason Zimdars, 37signals

I enjoy breakfast sandwiches. I’m amused by this bit of copywriting on their box:

Made with 11g of whole grains & real eggs

It’s a sausage, egg and cheese breakfast sandwich.

You’d never say this sandwich was made with fake eggs. Why waste the space telling me how real the eggs are, when you could spend time telling me something interesting?

This applies to anything you write, trying to grab someone’s attention. Like a cover letter.

Would you ever expect someone to say: “I am not a hard worker”, “I am not a team player”, “I am applying for an office job where I’d expect you use Microsoft Office, but I have never used Microsoft Office before.”

Use the space in your cover letter to write about what no one else is writing about. You.

As I was finishing their cover letter, something caught my attention at the bottom. They started to talk about how they’ve already been doing the job they were applying for in a very informal way. They already were in a position where they help a lot of people with this skill they have. But they don’t do it for a job.

Now that’s interesting.

I know the people I want to hire are already doing this job for fun. I want people that have a passion for what they do. So much so that they don’t need to be paid just to do this type of work. I’d still pay competitive rates for employees, but the greatest employees show an independence that they don’t need my money to enjoy doing their work.

That’s why open source projects are so useful for job applicants in the software industry. That’s the first place I look. “You like writing software, but you don’t have any projects online that you’ve written without someone telling you that you had to?”

I advised bringing this story up to the very top of the page. Flesh it out a little more. Spend a couple sentences on a detailed version. Who did you help? What were the circumstances?

There’s a reason why candidates for President on the campaign trail don’t just share the specifics of a tax or health care plan. They share stories of people they meet. “I met Joe, unemployed coal miner, and he can’t afford health care. Here’s how my plan will help him.” We remember stories.

Don’t waste this precious space telling me you’re just like everyone else. Tell a story with your cover letter of how you are already awesome at this job.

And the last bit of advice: put a testimonial or two in your cover letter. Not just the “references provided on request” boilerplate. But an actual quote. Someone, somewhere, is saying something nice about you. A former boss, a teacher, even a friend or fellow student. Keep a file of those so you can grab a couple and sprinkle them in places like your cover letter.

Having a testimonial makes a significant impact on getting people’s attention. Companies do this to get more people to click the Buy button. Presidential campaigns do this to get more donations. My wife did this and got a ton more interviews.


P.S. I’d love to meet you on Twitter: here.

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