Do Not Send a “Funny” Cover Letter Like This One
March 30, 2017

Do Not Send a “Funny” Cover Letter Like This One

by Brian de Haaff

“Comedy is not pretty!” That is the title of an old Steve Martin special and I have to agree with the sentiment. When you tell a joke you need to be ready for laughs and also prepare for the worst. Some nights, the audience might roll in the aisles with laughter. The next night? Tough crowd, tough crowd.


I am a fairly serious person but I enjoy a good laugh — there is a time and place for joking. You would not think a job application is a laughing matter, though. But it is surprising how often I have seen some ill-advised attempts at humor in cover letters.

One cover letter detailed a plan to create a wild movie parody that was certain to “go viral.” Another promised to make customers “seethe, sweat, and smile.” Or what about no cover letter at all? Instead, a list of the top 10 reasons to hire someone, including” “my mom loves me” and each one sillier than the last.

Candidates are looking for creative ways to make a positive impression. And it takes time to craft a cover letter and resume that a hiring manager wants to read.

I realize it can be tough to stand out from a crowd of applicants, all vying for attention. It is not easy to put yourself out there and risk rejection. I admire the effort — but the execution sometimes confuses me.

That is the reason I want to explain why I do not think it is wise to show your stand-up-comedian side in a cover letter. Because humor is:

Subjective What you think is patently hilarious, someone else might find juvenile, obnoxious, insulting, bizarre, or even offensive. There is no universal standard for what anyone considers funny. Once you consider all the possible ways your joke might go sideways, it probably will not seem quite so funny anymore.

Risky Using humor in your cover letter is a big gamble. After all, you probably do not know the person reading your email on the other end. The hiring manager may be a huge fan of comedy — or the most humorless person you will likely never meet (and could be annoyed that you are wasting time with silliness).

Distracting Even if you get the desired chuckle you want, your jokey asides can distract the hiring manager from the real reason you are writing — you want the job. You could earn some attention, but you come off looking like a goof-off rather than a viable candidate who is ready to get down to work.

Now, I am not suggesting that you should completely silence your personality. You certainly want to show vigorous signs of life.

But when you are looking for a job, you want potential employers to see you as a professional, not a workplace jester. So before you send out that next funny cover letter, consider it from the hiring manager’s perspective.

Ask yourself, “How will this joke or story be perceived by someone I do not know? Is the joke worth the risk that it might be a distraction?”

Better to consider a few of our suggestions for how to keep your cover letter simple and genuine. Describe your strengths and how your experience makes you a great fit for the role. Explain why you are excited about the opportunity and the company.

Just be your best self — save your dry sense of humor and crazy wit for later, when it will be better appreciated.

How have you seen humor backfire on the job?

Brian de Haaff

Brian de Haaff

Brian seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 product development software — and the author of the bestseller Lovability and The Startup Adventure newsletter. Brian writes and speaks about product and company growth and the journey of pursuing a meaningful life.

Follow Aha!

Follow Brian

Related articles

The Best Cover Letters That CEOs Love to Read
April 13, 2017
The Best Cover Letters That CEOs Love to Read

A well-crafted cover letter is a great way to get noticed. Find out what to include in your cover letter to catch the attention of a CEO.

New Marketing Managers — Do These 8 Things in the First 30 Days
January 28, 2019
New Marketing Managers — Do These 8 Things in the First 30 Days

Are you a new marketing manager? Check out these suggestions from eight marketing experts on how to show your true value in your first 30 days.

The tragedy of 'good enough'
June 4, 2024
The tragedy of 'good enough'

Leaders create an environment that fosters continual improvement when they: 1. Hire for achievement. 2. Invest in training. 3. Keep raising the standard.

6 Characteristics of the Best Bootstrapped Businesses
July 19, 2022
6 Characteristics of the Best Bootstrapped Businesses

Founding and running a startup takes courage and conviction. Bootstrapping is a mindset that can also serve as an operating model for sustainable growth. These are the…