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Stories, target qualities, resumes, and cover letters

Why most of this chapter isn’t about resumes and cover letters

Some approaches to job searching place a heavy emphasis on creating the perfect resume. The theory is that if your document can stand out from other people’s documents, then you'll be selected by the recruiter for an interview.

It's certainly true that a substantially better resume will lead to more first-round interviews when you cold apply. However, this approach does not solve the two problems we talked about with how most people apply: even if you send in a great resume, if you don't have more experience in your field than other applicants, you're still at a major disadvantage. Additionally, because you have no relationship with the recruiter or company, you're easy to reject.

In many ways, resumes and cover letters are the least important things we’ll discuss in this chapter. Understanding your strengths and your best stories, on the other hand, allows you to shine in informational and assessment interviews. Developing a strong sense of what hiring managers are looking for in your target role will affect every answer you have when they ask you questions. So if you spend time on the material in this chapter, focus most of that time on understanding yourself and understanding what companies want, not on playing with fonts, formats, and minor wording changes in your resume.

In this chapter, we’ll follow a four-step process to get you ready to apply.

After this, we’ll wrap up with a simple cover letter layout.

Because my expertise focuses on using informational interviews to make your resume as irrelevant as possible (due to the strong personal connections you’ll make), I link out to several expert sources over the course of this chapter who know more about resumes than I do.

Finally, we’re trying to make a great resume for humans, so there’s nothing here about getting the right keywords for automatic resume screening software. By getting intros using the rest of this book, you’ll skip the automated keyword screenings.

The dangers of feeling safe

The material in this chapter is valuable, but has a possible problem. Unlike most other topics in the Unusually Difficult System, working on stories and resumes feels very safe. When you write out a story or make edits to your resume format, you are not asking for informational interviews, talking to people, or doing anything else that exposes you to the possibility of rejection. Over half the clients I work with have used this internally-focused work as an emotionally safe refuge from more effective tactics like reaching out for informational interviews, and it’s likely you’ll be tempted also.

So, because the tactics in the rest of this book focus on systematically developing personal connections that decrease the importance of the resume and cover letter, the goal of this chapter is to make sure your resumes and cover letters are good enough, not to make sure that they’re great. This lets you focus your effort on areas that matter more. I encourage you to get through your first resume edits within a few days so that you can start the more meaningful part of your job search, especially because you can always go back and edit documents later.

Four steps to a resume

1 - Stories

Developing your best stories is an exercise that helps a lot with both resume writing and interview success. I strongly recommend thinking hard about the best stories you have from former jobs and activities before you begin writing or editing a resume.

The goal here is to make sure that these stories are prominently featured in your resume, for two reasons. First, it increases the chance of getting an interview in the first place, since you’ll be showcasing interesting accomplishments. Second, when you feature your best achievements, an interviewer trying to come up with questions about your resume is more likely to ask the exact question you want to hear: an invitation to tell your strongest and most comfortable stories.

Because these stories are valuable during every step of the application process, so far I have always spent more time developing and refining my clients’ stories than I have on directly changing their resumes.

The following personal branding exercise is heavily inspired by the excellent 1992 reprint of In Transition.

Brainstorming story ideas

By emphasizing different parts of the same story, you can use the same events in your life to prove different strengths or values. For example, a story about how you helped save a failing project at your last job could be used in a question about leadership, or a question about overcoming a difficult situation.

Because stories are flexible, our focus will be on finding excellent stories first, and matching with employers’ target qualities second. Please try not to think about “what employers want” until you get to the Target Qualities section of this exercise.

This part of the exercise will take about 10 minutes to understand and 20 minutes to complete. To prepare, get one or more old resumes if you have any, and find a job description similar to your last job. Have those physically nearby or already open on your computer.

You’re soon going to write down story ideas. Make sure every story idea you write down fits these three criteria:

I’d suggest writing down your ideas as phrases, so they are easy to remember later: “Canceling the website redesign project that was going to fail” is better than “Cancel project”, for example.

If you are brainstorming and don’t think of anything for a minute or two, read over an old resume or a job description similar to your previous job (not the one you’re aiming for) and see if that creates any ideas. Or use some of these questions to help think of stories:

Now it’s time to start! To start the exercise, set a timer for 20 minutes, and start writing down story ideas from your past jobs and hobbies.

Once you have 20+ possible stories or have spent 20 minutes, whichever comes first, move to the next step. Keep this output, since you might revisit it when you know more about what employers want, and when you’re preparing for interviews.

2 - Target qualities

There are two major ways of finding out what hiring managers care about most: reading job descriptions, and informationally interviewing people who have the job you want.

Throughout your job search, I strongly recommend you keep a document on “What I believe people who hire for {your role here} are looking for”. This should live in the Reflection folder of your organizational system. Don’t do this once and forget about it--as you do more interviews, come back and update it, since what employers want should affect everything from your resume and cover letter to how you present yourself in the interviews.

Please make a blank document in your folder now, so that you have something to update when you add content.

Reading job descriptions

The best directions I’ve read of how to read a job description are from Kai Davis’s article, How To Write a Kick-Ass Resume. If you read the article from the beginning up to the “Deconstructing the perfect resume (and my resume writing template)” heading, that will give you specific directions on how to read a job description and extract what an employer wants.

That process is great but extremely time-consuming, so I’d recommend doing it once or twice per job role you’re looking for (so if you’re not sure if you want to work in a sales job or a marketing job, you’d do double the work). Update your “What I believe” document with what you learn, and then focus most of your time on informational interviews.

Informationally interviewing people who have the job you want

No matter how many job descriptions you read, there’s no substitute for talking to the kind of people that would hire you and finding out what’s important to them. A huge part of this book is about reaching out to people for informational interviews and what to do in those interviews. So, don’t worry if you’re not sure how to find people to talk with, since that is covered in future chapters.

If, for example, you want to work in customer support, you’re going to contact customer support representatives and managers. Your goal will be to understand how they decide if someone else is good at their job. Some helpful questions to ask in these interviews include:

Take your “What I believe” document and tell or show it to the person you’re speaking with. See what they add or remove.

Eventually, people will start agreeing with and being impressed by your “What I believe” document. At that point, you know you’ve got a great idea of what qualities and skills interviewers will be looking for.

3 - Linking stories and qualities

From steps 1 and 2, you’ve now got a list of what you’ve done best in the past and what employers probably want when they hire for the job role you’re interested in.

The next step is to see where these lists intersect. Ideally, you’ll be able to take the most important themes from what employers are hiring for, like “creative problem solver” or “leadership experience”, and adapt one or more of your best stories to show how you fit that theme.

Run through the three or four most important things employers are hiring for and find a story that at least touches on that quality, if you can. You might be left with a gap or two, and that’s OK. You can handle this during the interviews by having a good plan, which you’re ready to share out loud, explaining how you’ll learn or develop the missing skill.

Take the stories you just selected because employers want them, and add your most impressive one or two stories, even if they don’t perfectly fit the job. You now have a list of stories that you want to tell during interviews, which is the main input you need to craft a good resume.

4 - Resume creation

At this point, you’ve done the most important work, by getting your stories ready and learning what employers want when they hire people like you.

I’d recommend you use a simple template, like this one from the Kai Davis article I’ll link below.

Please remember two things as you make a resume using the linked guide of your choice:

Here are three good guides covering how to make a resume:

A simple cover letter layout

In addition to your resume, most applications give you a place to write about why you’re interested in the job. This could be attaching a full cover letter, or could be typing a few lines of text on LinkedIn or AngelList.

While a great cover letter can help an application and a terrible one can ruin it, cover letters generally matter less than resumes or interviews, so this is probably not the best place to focus large amounts of effort.

Key cover letter elements

A simple cover letter might have two major paragraphs.

In the first paragraph, you’ll want to quickly point out the position you’re applying to, and spend most of the time talking about why you’re interested in the company in a very personalized way. If the text is generic enough that you could use it for multiple companies, it is not specific enough to send.

In the second paragraph, you’ll explore why you’re a good applicant. Take two or three of the target qualities the employer is looking for and briefly point out why you fit each one.

Surround these paragraphs with a quick intro and conclusion, and you’ve got a solid cover letter!

An example cover letter

Here’s an example I might have used earlier in my career, when I had no product management experience and was applying to be a PM for the first time. We’ll use Pocket Gems, a mobile gaming company I applied to at the time, as an example.

Dear [Recruiter name],

Hi, I’m Matthew Du Pont, and I’d like to be your next Associate Product Manager. I’ve been an avid gamer ever since I first tried Candyland, and found Tap Farm (note: an old game from Pocket Gems) both entertaining and deep enough that I started to investigate your company. When I interviewed [PM name] about your company culture, I was excited to hear how everyone’s ideas are taken seriously, and how you not only use data to make decisions but go back and check if those decisions were correct afterwards.

I believe you’re looking for a highly analytical APM who can work in environments of extreme uncertainty. I’ve built up expertise as the person to turn to when you need to make a complex model in my BCG class (note: a consulting firm), and have successfully managed client teams during periods of massive change at three Fortune 100 companies.

Thank you for considering my application. I look forward to hearing from you soon!

This isn’t a perfect letter, but there are a few key characteristics:

When to revisit your resume

The goal of this chapter has been to get some great stories about your past work, a great idea of what employers are looking for, and a good enough resume and cover letter that they won’t hold up your job search as you focus your effort into higher-impact activities like informational interviews.

However, there are three main scenarios when you should revisit your resume and do more work there.

Now that you’ve got a resume and some target companies, let’s look into how you can select which companies and jobs would be the best fit for you.

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