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A practical guide on what to do and not do in your cover letter and resume.

Applying for a job is thankless work. Literally, most of your applications will be ignored. Even great companies often won’t acknowledge job applications.

In large part, this occurs because the modern internet has made it very easy to apply to jobs. Just fire off an email to the [email protected] address and you’re done.

Of course, this only heightens the problem, more job applicants, less time for the hiring manager (or HR) to look at each one.

When you don’t hear back, it reinforces the hopelessness of getting noticed in the first place and makes it more likely you’ll put even less effort into the next job you apply for.

Small Companies

It’s not impossible to get hired by simply firing off a resume into the HR black hole. It does happen. It’s more effective at large companies where the first scan may be a simple keyword filter and so finding the right combination of terms for your resume will get you to an actual human.

I’m not here to talk about getting hired by big companies though. These days, many of you are seeing the benefits of working for smaller companies and startups. More responsibility, more flexibility, competitive salary and benefits, a chance to have a direct impact on the company vs being a cog in The Man’s wheel.

That’s great, I love this. Having run our little software company for 10 years it’s lovely to see so many people excited about small companies. That’s very different from when I graduated college or was starting UserScape.

Alas, so many of you are applying to small companies the same way you apply to large ones. This really hurts your chances of getting interviewed and hence hired.

The Founder

If you’re serious about getting hired at a small company it’s critical you understand founders. In pretty much all small business/startup hiring scenarios the founder will be either the sole hiring authority or have a significant say in the matter.

The founders #1 priority is trust. They’d hire only people they personally know if they could, but they can’t, so they’re begrudgingly forced to look outside their circle of trust.

To a founder, their business IS them. Customers are their children.

Let that sink in, because that is how you have to approach this. If you were hiring a babysitter and they showed up at your door half dressed, dirty, and smelled like a bar would you let them watch your kids? They might be the best person in the whole world and have a great explanation as to why they look this way, but that first impression is everything.

The first impression is critical to trust, and this is where everyone drops the ball. Applying to BigCo’s has taught you to be lazy, and that is why you fail when applying to small ones. Laziness will kill your job application INSTANTLY.

What sorts of lazy things are you doing that are making founders not trust you with their children?

Cover Letters

Far and away the most important aspect of your application is the cover letter. The resume is practically irrelevant in comparison. Unlike Bigco filtering systems, a founder is going to read that cover letter. The cover letter is our first filter.

Obviously generic cover letters

Trash. Instantly. No second chances for this, you’re too lazy to take a minute and at least customize a cover letter for my company? How can I trust you with my customers?

Addressing the cover letter

To whom it may concern — Perhaps not instant trash, but we’re not looking good. This is a small business you’re applying to (You don’t know it’s small? You didn’t research it first? I don’t want your application then you lazy bastard). Address the owner by name.

Not 100% sure the owner is who’s going to be hiring? Use a more comfortable and welcoming opening. A simple Hello works nicely. Alternatively, you could do something like: Ian and the UserScape Team,

It lets the founder know you’ve done a little homework and that we should read further to learn more about you.

What to cover in your cover letter

The hiring process is a series of steps. Much like a marketing funnel the point of step A is simply to get you to step B, who’s goal is to get you to step C, etc.

If your cover letter is bad I’m not looking at your resume. So the cover letter has a few things to accomplish.

A) Help me trust you
B) Make me interested in you

If I trust you and you sound interesting (in the context of the job to be done, not interesting as a person though that helps also) I’m likely to read your resume.

So how do you build trust and make what you say interesting?

This isn’t a creative writing course so let’s just keep it simple. Take it back to 7th-grade English.

Your cover letter should have an introduction, a body that restates the problem (the job to be solved and a few key points about how you fit in there), and a conclusion.

All of this will need to be custom to the organization/job you’re applying to. Sorry. If you fake it, it’s insanely easy to spot.

We’re talking 3–4 tight paragraphs here. Long enough to say something meaningful, but not too long that it becomes burdensome to read. Remember, we’re trying to get the founder to the next step of actually bothering to open your resume.

How to format your cover letter

These days, it’s best to have your email be your cover letter. No need for it to be formally formatted inside a doc/pdf. In fact, it’s better to not require employers to take that extra step of having to open a document.

Link it up

I love seeing a few well-placed links in a cover letter. Have a really impressive project you’ve worked on? Link it. Have a website you keep up to date? Link it.

At the very least link up Twitter and LinkedIn profiles. I’m going to search for those things anyway, put them right there and save me a step.

Often, if the cover letter is good I might search on the person before reading the resume. Lead me to your best stuff.

The Resume

Resume file titles

As the hiring authority, I’m going to be getting a lot of emails and resumes. Not being able to tell which resume is which is a big problem for me. It means you might simply get misplaced. It also shows a lack of common sense. Examples of what I get all the time.

> resume.docx
> resume (updated) v2.docx
> cv.doc
> 2014bob.doc
> Resume 1 (4).docx

These are real! If you’re this sloppy with your resume file name how are you going to treat my customers?

Examples of good resume titles

> Ian Landsman — Resume.pdf
> Ian Landsman.pdf

That’s pretty much it. Some variation of your name and maybe the word resume or cv.

Resume file format

Resumes should be in PDF format OR be a dedicated site that you link to. On a Mac seeing a docx makes me cry, if the person is on Windows they’re worried about opening random Word docs from strangers. Just make it a PDF and save everyone the trouble.

Yes, that’s one more step you’ll have to take to convert your Word doc. Yes, see the pattern here?

How long should your resume be?

For some reason, people are taught to keep their resume’s short. I suppose there are some personal preferences here, but I’d rather it be too long than too short.

Don’t worry about silly rules like fitting it all on one page. This isn’t 1986; nobody is going to misplace page 2 of your PDF.

The thing to understand is that if I’m looking at your resume I already have some trust and interest in you from the cover letter. That means, unless you do something really stupid in your resume I’m probably going to interview you.

The interview is really what the resume is all about. The resume brings me up to speed on your background so that we actually have something to talk about in the interview. The more details in the resume, the more questions I can formulate ahead as well as allowing me to skip over other areas that I can see are covered.

Make sure the content of your resumes gives potential interviewers enough facts and details to build a conversation around. Also, please don’t load it with keywords. When you’re applying for to a small company a short section on the technology you know is fine. Save the huge list of every tech you’ve ever touched for The Man.

How much should your resume be customized per job?

Unlike the cover letter which should be nearly 100% custom, the resume can be pretty generic. Your history is what it is.

I often see people who have obviously replaced some other bullet point for one that seems more fitting for the job they’re applying for. That can be OK, however, removing an impressive accomplishment for a mediocre job relevant point may not be a win.

Formatting your resume

This is a biggie. First, your resume needs to be easy to read. Echoing the above, don’t shoehorn everything onto one page just because. Keep proper line spacing and readable font sizes.

Break up your sections into logical groups for easy scanning and reference during an interview.

I’m personally a big fan of using some color on your resume. Just a touch helps you stand out and can make the resume more readable and memorable. A photo or some other element is also OK.

Education, top or bottom?

The eternal question. Unless you’re directly out of school education goes below experience. Even then, if you’ve had some good internships or other job experience, it might make sense to put it above education.

We’re moving to a world where what you know is more important than what a school’s name implies you know.

Going above and beyond

You don’t have to do this, but if you really have a dream job you’re going after think of ways to go above and beyond. Can you build a custom website for just the job as Adam Wathan did here? It may be over the top but it’s not THAT much work and if you’ve done a good job on your cover email it’s likely to get looked at and make a huge impression.

A word about objectives

At best an objective won’t hurt your chances. On the flip side, it often conveys the genericness of your job search. Applying for a job in support with an objective of being a software engineer? Trash.

Instead of an objective, I’d rather see a well written About section. A sort of overview of who you are. Use it as a place to convey important information about yourself that isn’t present in the other resume sections or to emphasize something extremely important.

Following Up

If you put in a really good effort on your cover letter but haven’t heard back be sure to follow up. People get busy, email gets lost. It can’t hurt to follow up.

If you just sent an email that says here’s my resume, of course don’t bother.

Random Bits

* You should have a professional email address with your name in it. Not peewee79.
* If you’re looking for a job in tech, I’d go farther and have an email on your own domain ([email protected]) or at least a solid gmail address. Weird AOL emails and the like are going to be a negative.
* Get an introduction if you can. It’s always a huge leg up to be presented to the hiring person by a trusted source (that word again!).

I Put The Effort In, But Get No Results

Well then, better keep pushing! A founder of a small company has gone through YEARS of personal sacrifice. Are you upset nobody responded to your cover letter? Try harder. Try something different. Apply to different jobs. Get some more experience. Present a new angle of yourself. Find something that works. We did, you can to.

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