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The Unusually Difficult system for applying to jobs

In this chapter, you’ll learn the overall structure of the Unusually Difficult system. Then, in the rest of the book, we’ll explore each step of this process so that you have clear and concrete actions to implement the system.

Some terms and why we need them

Before we get into discussing a better system for applying to jobs, we need to define two sets of terms, so that we can express some important concepts without explaining them over and over.

Warm vs. cold - a “warm” connection is to, or through, someone you already know. For example, if you have a friend named Harold, you could do a “warm reachout” to ask for his recommendation as you apply for the company he’s presently working at, or if he introduces you to a friend of his named Maria that would be a “warm introduction.” In contrast, if you don’t know someone, but look up his or her email address and send them a message, it’s a “cold reachout.”

Warm reachouts are usually more successful, but unless you know multiple people at every company you’re interested in, you’ll need to do cold reachout as well.

Assessment interviews vs. informational interviews - There are two major kinds of interviews we’ll discuss in this book.

“Assessment interviews” are what most people think of when they hear the word interview: part of a formal application process where your interviewer works at the company you’re interested in and is typically submitting written feedback to the recruiting team afterwards. Companies typically have multiple rounds of assessment interviews before they extend an offer.

On the other hand, “informational interviews” are much more flexible. I define these as an interview where learning is the main publicly stated goal, unlike assessment interviews where evaluating is the goal.

Informational interviews are characterized by not being a part of the formal application, and could be with anyone: people working at a company you’re interested in, people that used to work there, or just people you think could be helpful to your search. Your two most common goals in an informational interview will be learning, to gather information that helps your job search, and impressing, to get people to give you a warm recommendation for specific jobs you’re interested in. We’ll be exploring informational interviews in great detail later in the book.

Now that we’ve got our terms defined, let’s jump into the system.

The Unusually Difficult system

Quick overview

“Normal” way of looking for jobs:

Unusually Difficult system:

Step by step comparison

As we go through the system, don’t worry if you’re not sure how you’re going to do some of these things, like how to convince people you’ve never met to take the time to informationally interview you, or how to use an informational interview to get a personal recommendation. That’s what the rest of this book is for!

Starting the Unusually Difficult system is much like what you've probably been doing before: you'll start by finding a job description you think is interesting. However, at the next step is very different. Since there are so many problems with cold applying using only a resume and cover letter, we are going to take a different approach.

You're going to analyze the job description in order to figure out what sorts of people at your target company either have very similar jobs or might have information useful to you as you explore the job. Using that information, you'll then set up informational interviews with those people. Some of those interviews will be warm introductions, where you either know the person directly or know a friend of the person who can introduce you. Others will be cold reachout, where you're seeking to get people you don't know yet to spend some time talking with you. Many people find this intimidating, but cold reachout is extremely powerful when done well, since it allows you to collect information about companies even when you don't have a strong social network there.

When you have the informational interview, you’ll use that opportunity to learn more about the company and the position, as well as to make a positive impression upon the person you're talking to. If you make a good enough impression, you should be able to ask them for an introduction directly to the recruiter or hiring manager. The goal is that instead of applying online, you're applying with someone at the company looking out for you.

As we'll cover in the more detailed next section of the book, you're not going to try and get an introduction every time you do an informational interview. But by learning more about your target company every interview, you should be able to get an introduction fairly quickly.

Solving old problems and creating new ones

First, let’s talk about the good news. When you’re systematically manufacturing the chance to make warm applications, they solve the two big problems with cold applying that we found when we looked at the recruiter’s perspective last chapter.

Old problem 1: If you’re not a perfect fit, the recruiter has other options that look better on paper. That’s still true, but it doesn’t matter as much anymore for two reasons.

First, you’ve now earned the right to have someone think about your story. You’re no longer in the “30 second scan” pile, because you’re coming in through your recommender’s email or conversation with the recruiter. Even if you’re not a perfect on-paper fit, there’s someone on your side showing why you’re worth interviewing.

Second, and more importantly, most recommenders have more power than the recruiter. If a successful salesperson says you’re worth interviewing for sales, or a PM says you’re worth interviewing as a PM, you’ll get an interview nine times out of ten. The goal of the recruiter is to find one great candidate, and there’s no better sign that someone is a good possible fit than when the people involved in making the decision say so.

This is why it’s good to get a recommendation from someone close to the job role you want. A recommendation for a developer role from a nontechnical member of the customer support team doesn’t carry the same weight as getting a recommendation from another developer.

Old problem 2: It’s easy to reject a piece of paper but hard to reject a person. This problem is now taken care of.

Now that you’ve got a recommendation, it’s hard to avoid interviewing you. Instead of hitting a “reject” button in an Applicant Tracking System, the recruiter will have to personally say no to one of their colleagues who has said you’re worth interviewing.

This is rare not only because saying no is hard, but also because referrals are such a good source of quality applicants that the recruiter often doesn’t want to discourage future referrals. So even if someone is almost certainly unqualified, the interview may take place just to keep the culture of referrals going.

So, if you follow the Unusually Difficult system, you’ve solved two big problems that were holding you back from getting first-round interviews before. However, there’s a new problem: the trade-off you're making is that it takes much longer to do an informational interview and get a recommendation than it does to apply online.

New problem 1: The Unusually Difficult system is unusually difficult, in that it takes way more time per position to apply than sending out tons of online applications.

Between picking who to talk with, reaching out to them or a few other people, having an informational interview, and following up, you're probably only going to be applying to one company in the time it takes you to apply to 20 companies if you were only personalizing for a few minutes.

However, this strategy has a much higher success rate than cold applying, so if the cold applications aren't getting you the results you want, this is a great alternative. An important thing to keep in mind is that you’ll not only get more first-round interviews, but also more offers. These informational interviews equip you with more information about the company, which you can use to show that you’re the very best candidate in the later-round assessment interviews.

The rest of the book

Now that you’ve seen an overview of the strategy, the next chapters explore each step in more detail, to show exactly what steps you’ll need to implement the system, and what exercises you can go through to build your skills in these areas. Our goal is that by the end of this book you have a repeatable process allowing you to successfully get first-round interviews at the companies of your choice.

However, this book is called Unusually Difficult for a reason. This is much more work than applying cold, so you’re going to need to put in work to see the results my clients and I have seen.

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