Read an Excerpt from “Why You, Why Me, Why Now: The Mindset and Moves to Land that First Job, from Networking to Cover Letters, Resumes, and Interviews” by Rachel Toor | The Chicago Blog

Recruiters are filling many a campus job fair, and we’re entering that time of year when many soon-to-be graduates are contemplating the big question of what’s next. No matter what stage you’re at in your career, searching for a job can be hard and demoralizing work. But, in Why You, Why Me, Why Now, Rachel Toor delivers some good news. The most important thing is within your control — a mindset that shows you know the goals of the organization you want to work for and that you’re ready and eager to contribute. Toor provides, with compassion and enthusiasm, strategies to make it easy for hiring managers to say “yes.” In the excerpt from her new book below, Toor takes prospective candidates inside the mind of a busy hiring manager.

What it’s like on the other side of the hiring desk

Olivia is tired. So tired. Her voicemail is full, and the number of unread emails in her inbox is five digits. She’s up against a deadline, and because she’s down a staff member, she has to do both her job and that person’s job. Her boss is out of town, so she has to schedule and run meetings. Plus, her partner just had a baby so no one in the house is sleeping.

The staff member who’d been her assistant was super competent, so Olivia promoted them to another role. Olivia cares about the people she hires, and she goes out of her way to help folks advance in their careers, within her organization or elsewhere. She loves mentoring young people, and they appreciate how much they learn from her. Her most recent assistant helped write the job description so the new person would have the necessary skills to make Olivia’s life easier. But without that person? Olivia is drowning in work.

And she’s drowning in resumes. A listing on LinkedIn has netted more than two hundred resumes a week. Though the job ad said a cover letter was optional, Olivia prefers applicants who take the time to write one. Those letters help her understand the applicants’ personalities and decide if she wants to meet them. So she skims the letters first. She’s been doing this work for days now, and (Did I mention?) she’s tired.

Olivia doesn’t bother to read anything longer than one page. If she spots more than a few typos or spelling errors, into the trash the letter goes. Letters from applicants who say they are applying for a job at a different organization (oops) or don’t mention the specific job she listed-into the trash.

Each time she sees “I am the most qualified applicant for this job,” she snorts and puts the letter aside. No, you’re not, she thinks. You have no idea how strong the pool is.

When she reads how this job would be a good stepping-stone toward an applicant’s future plans, her colleague down the hall hears her exclaim, “No kidding! I know exactly why this job is good for you. Tell me why you’re good for this position. I need someone to help me get through this big honking pile of work!”

Her eyes glaze when she sees the same meaningless words and phrases: passionate, committed, hardworking, detail-oriented, driven. What on earth does that look like in the experiences you’ve had? And why didn’t you apply some of that passion to proofreading your materials, or ask a truly detail-oriented person for help?

These reactions may seem harsh. And to a degree they are. But if your application materials represent your best effort when you have loads of time to think about how you present yourself and could have taken advantage of opportunities to get help, mistakes in grammar and punctuation and spelling should not happen. If you can’t impress under these tame circumstances, how will you perform under pressure, on deadline, and when the organization’s reputation is on the line?

As with the cover letters, Olivia doesn’t read resumes longer than one page. If they don’t include contact info, or if it’s hard to find? Into the trash. If she can’t figure out how a candidate’s experience sets them up to do the job? Trash. She doesn’t try to decipher anything with fancy typefaces or lines of information that crawl vertically up the page. The trash bin is getting full.

If someone attended seven colleges before finally graduating? Well, Olivia understands life can get in the way of school. But if they’ve offered no explanation? Trash. If a candidate describes simple tasks with overblown language (“Escorted canines to relief stations”), she laughs and shows the document to the colleague down the hall, who will also find it hilarious. The resume goes into the trash, but Olivia knows they’ll mention “canine relief” to each other for years to come, whenever they see anyone walking a dog.

For those who take up valuable real estate on their resumes with lists of references, she feels sad and thinks, Why? We’re not at that stage yet! She also wonders about too much blank space. Surely a person did something-worked in a warehouse, operated a cash register, babysat a younger sibling. Those experiences could tell her a lot, especially if the candidate makes clear what they learned. Why wouldn’t those be listed?

If hobbies include riding dressage or earning a private pilot’s license or acquiring a PADI scuba certification, but the applicant lists no work experience or internships, Olivia figures the resume has come from a child of privilege who’s gotten everything they ever wanted and probably doesn’t need to work. She knows that’s her personal prejudice and knows, too, that other managers may see those hobbies and think, Hey, this person is just like me! She’s been in the business world long enough to know most people like applicants who remind them of themselves in some way. And she’s lived long enough to know that life isn’t fair.

Olivia’s job list includes “must haves” and “nice to haves.” She skims for the qualifications she knows she needs. If someone says they know Microsoft Excel or Adobe Illustrator, she wonders how proficient they are and why they haven’t listed experience to back up those claims. She gives a little cheer for applicants who’ve earned industry-recognized certifications.

When she’s winnowed the pile to a bunch of promising applicants, she gives up, turns off her computer, and leaves the office. She started out tired. Now she’s exhausted and, to be honest, kind of pissed off. As she walks to her car, she feels annoyed that so many recent college grads wrote only about what they wanted from the job. Few of them had done real research into her organization or even addressed their letters to her personally. How could you know you’re the right match or the “ideal candidate” and want to work here if you seem to know nothing about this job or company or the skills we painstakingly listed in the job description?

How did they get to be so self-centered? And cocky? Confidence is fine. It can be essential in many jobs, especially sales. But most of these applicants came off as downright arrogant. Who wants to work with someone who thinks they’re all that? Not Olivia. It’s not about you, she thinks before she drags herself to bed. I don’t care about you and what you want.

Yet. True, Olivia doesn’t give a hoot about applicants she will never meet. But she will come to care for the person she eventually hires. She always does. She works hard to find a good match, someone who shares the values of her organization and would be an asset. She knows they will come in without specific skills, and she’ll have to make an investment in teaching them before they can truly contribute. She values employees who ask lots of questions; those people she would mentor and promote.

Maybe, she thought as she lay awake, stressed because she needed to hire someone as soon as possible, these recent grads just don’t know what they don’t know when it comes to applying for jobs. Maybe no one taught them how to approach the process, how to be professional.

The next day, eager to give applicants the benefit of the doubt, and with the understanding that writing resumes and cover letters is hard for everyone (and realizing the ones who made it to the top of her pile had probably been smart enough to seek help), Olivia was excited to start talking to candidates. Normally she would send an email inviting an applicant to set up a time to talk, but she was desperate to get someone in place and, in any case, the job sometimes required cold-calling clients, so she skipped that step.

The first person’s phone rang and rang and finally went to voicemail. The outgoing message sounded as if it was recorded at a party. Olivia ended the call. She tried the next person and got no answer until an automated message informed her the voicemail was full. She finally got through to the fifth person on her list, who answered with “Yo!”

Once Olivia explained who she was and why she was calling, the applicant quickly changed tone. She asked, “So, why do you want to come work for us?” The answer: “Well, I need a job.” Thanks, but no thanks.

The next candidate seemed more promising, and they had a good chat-until Olivia asked if they had any questions and they said, “Can you tell me about your company?” Olivia thought, Seriously? as she ended the call.

The next person had a lot to say. So much, in fact, he interrupted and talked over her. Out.

She did get a panicked phone call asking if all the materials had been submitted and how they looked. That would have been fine if the caller had been the applicant. It wasn’t. The applicant’s mother was calling to check up on her son. Olivia wondered if Mom was planning to come to work with him too.

The series of ten-minute phone calls had given her a headache. After a few days Olivia had found some people she thought highly enough of to invite for interviews with her and a few members of her team.

The first person never showed. I’ve been ghosted, Olivia thought. No. Couldn’t be. When she called to see if he was okay, he said, “Oh, I got a better offer.” She made a note in her files in case he ever applied for another job at her organization.

The next person came in and impressed Olivia and her colleagues with her professionalism and the way she spoke about her experience. Before the interview, she had asked for a list of the people who would be questioning her, which Olivia was happy to provide. The poised young woman had clearly done research on each of them and asked smart and appropriate questions that led to a terrific conversation. But when Olivia asked the receptionist for her input, the longtime employee and valued team member said the applicant had failed to hold the door for someone coming in behind her with an armful of packages. Then she talked loudly on her phone while waiting for the interview. When the receptionist asked her to lower her voice, she was rude. Out.

Another person, even more qualified, gave a wowser of an interview. She spoke with excitement and dedication about what she wanted to do in her career and the mission that drove her. Unfortunately, none of what that candidate talked about had anything to do with the work at Olivia’s organization.

The next applicant was so anxious he sweated through his shirt. Everyone on the interview team told him it was fine to be nervous, completely understandable, and he could stop and take a breath. When he finally calmed down and was asked about the work-study job he had in college, he talked about how demanding his boss was and how unfairly he’d been treated. He said he’d hated every minute of working for that supervisor. Out.

A candidate whose resume listed an impressive achievement, when asked to explain what he’d contributed to the results, was forced to admit he’d been just one of a dozen team members, and it soon became clear he hadn’t actually understood the project. Out.

For another candidate, a quick reference check revealed they hadn’t even worked in the position listed on the resume.

One kept mentioning “our beach house in Cabo” and “our ski condo in Aspen.” By “our” they meant their parents’. Privilege is fine, Olivia thought. Entitlement isn’t.

Eventually the team narrowed the field to two promising candidates. In the final round of interviews, one said, “Just for funsies, when could I expect to be promoted?” Out.

The other finalist, whom they hired, showed up on the first day of work and said, “You know, I accepted the job, but I don’t think I’m being paid what I’m worth. I think I should be making a higher salary.” When they showed up the next day, Olivia told them it wasn’t going to work out.

And then the cute little robot had to start screening resumes all over again.

Rachel Toor, professor of creative writing at Eastern Washington University in Spokane is the author of six books of nonfiction, including Write Your Way In: Crafting an Unforgettable Admissions Essay, Admissions Confidential: An Insider’s Account of the Elite College Selection Process, and a young adult novel. Her work has appeared in the New York Times, Washington Post, Runner’s World, Glamour, and many other publications.

Why You, Why Me, Why Now is available now on our website or from your favorite bookseller.

Originally published at https://pressblog.uchicago.edu on March 4, 2024.