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

dogs in sunglasses and jester hats

“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?

About Brian and Aha!

Brian seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 product roadmap software — and the author of Lovability. His two previous startups were acquired by well-known public companies. Brian writes and speaks about product and company growth and the adventure of living a meaningful life.

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