The Job Hunt

How to Write an Extraordinary Cover Letter (Without Paper)

Isaac Morehouse
December 2019

Dear Sir or Madam,

You feel like a generic unit of humanity now, don’t you? I opened this article–this attempt to get your attention and win your respect–addressing you like one member of the faceless mass. Like I don’t care who you are at all. Like one reader is no different than the next, and I don’t expect you to have any personality.

That is what hiring managers feel like just about every time they read a cover letter.

And not just the ones that actually use “Dear Sir or Madam”. Even those that put the hiring manager or company name upfront usually go on to be just as impersonal, canned, copied, and generic.

As weird as it may seem, hiring managers are humans.

Humans feel bad when you treat them like robots. Heck, I bet even some robots feel bad being treated impersonally.

What’s the point of a cover letter?

A cover letter is the personal part. The specific part. The idea is a resume or pitch provides the background and shows who you are and what you have accomplished (and by extension, what you can accomplish). The cover letter is the chance to connect you and your skills to that specific company and show how you fit like a glove.

If you blast the same, “I am passionate about helping people and always strive to do my best” stuff to every company, you defeat any value the cover letter can bring. Better not to send it at all.

What if we got creative?

If the point is to map you and your skills onto a specific company and role, why limit yourself to a piece of paper with a bunch of words? How compelling is it to just tell someone you will be a good fit? Don’t get me wrong, a good cover letter or email is nice, but what if you could do better?

Show–Don’t Just Tell

Instead of, “I would be a valuable member of your team”, maybe there are some ways to show them something that makes it obvious.

Here are four paperless approaches to the cover letter I have seen work like magic on the job hunt for hundreds of seekers:

1. Outline your first 90 days on the job.

It’s so much easier for a hiring manager to know what it’d be like to work with you if you go ahead and show them directly! This exercise has the benefit of making you think hard and clearly about the role and figure out if you actually want it. It might push you to do some research or ask people who work there for more detail. All of these increase the odds you’ll get hired. This is a wonderful exercise for you and a great way to stand out to them.

2. A project.

Few things pack more punch than actually doing the job before you have the job. An email that says, “Hey Jane, I’m so excited by your sales development role that I went ahead and created a list of 100 leads I think could be great for your company. It’s attached. I would love to be able to do more of this as your newest SDR!” is really hard to ignore. Creating something for a company and leading with it in your application makes them feel obligated to at least give you an interview. Who spends all that time and attention if they’re not serious?

I’ve seen people win interviews with something a simple as creating a higher quality image for a website and sending it to the site owner, or making a fun promo video for a popular podcast and sending it to the host, or creating an FAQ for a product.

Show ’em what you can do!

3. A pitch deck (or video!)

Pitch decks are an easy, more narrative-based twist on a cover letter/resume. A simple deck that walks through who you are, the experiences you’ve had, outcomes you’ve generated, and how all of that leads to you being a perfect fit for this role at this company is way more captivating than a piece of paper. It creates a story that pulls people in. Instead of a static list of bullets and generic prose, you can connect the dots for people and show why your story was destined to lead you to this next opportunity.

A video pitch is awesome, too! People get to see and hear you and feel your energy. Creating a Loom video to walk through your deck can be a great way to combine the two and take some pressure off you just being alone on camera.

I’ve seen video+deck pitches get interviews better than anything else.

4. Trial period proposal.

Hiring is a big commitment. There’s a high cost to being wrong about a candidate. You can lower that cost to employers right up front and make it really hard to say no.

I’ve hired many and seen many more get hired using a trial period. Sometimes a single project, or a week, or a month. Sometimes paid, sometimes free. It’s an incredibly powerful way to stand out and earn a shot. It shows confidence and starts things on the right foot. You are creating value right away, and the hiring manager feels the need to reciprocate. It also allows you to discover if you actually like working with them.

“I want to join your team as the newest marketing associate” is not that hard to say no to. “I want to provide SEO, content creation, and social media marketing for a 30-day trial to prove what I can do” is pretty hard to turn down and warrants at least a call to discuss.

This approach to the cover letter takes some time, but that’s good!

The time and effort alone are enough to impress and win you an interview, even if the content isn’t amazing. It’s rare and makes you stand out.

It also forces you to focus on companies you actually like enough to put in the energy. You are much more likely to win a job from a company you’re genuinely excited about. And ten of these have better results than 100 generic paper cover letters blasted out of a cannon. Oh, and even if a project or pitch doesn’t get you hired with that company, you will learn a ton doing it and become more valuable and employable. Bonus: it’s something you can show off online, and other companies will be impressed by it, too.

Try it out. Instead of a few paragraphs about your personality, try creating something unique for them and sending it.

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