Using generative AI in your job search:

Resources and prompts

Pamela S. H. Bogart, Lecturer IV
University of Michigan English Language Institute
[email protected]

You are welcome to share and remix any part of this document for non-commercial
purposes if you include a full citation:

(Bogart, P.S.H. (2024). Using AI in your job search: Resources and suggested
prompts. [Google doc]. Creative Commons license Creative Commons
Attribution-NonCommercial-ShareAlike 4.0 International.)

This document can be accessed at the link https://bit.ly/useAIjobsearch

Introduction
Greetings. I’m glad that you have found this document. My name is Pamela
Bogart. I’m a Lecturer at the University of Michigan English Language
Institute.

Dozens of my graduate and undergraduate students have been exploring

how to leverage generative AI in effective and ethical ways to support their
job search process. This document is a work in progress, seeking to compile
the insights from many job-seekers in one place.

Whether you are applying for an internship, a part-time job while in school,
or the next step in your professional career, I hope that this summary of
approaches and set of example prompts will be helpful to you.

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
1
 Table of Contents
Introduction 1
What is generative AI? 3
Tips for prompting generative AI tools 3
Comparison table: Generative AI platforms 4
What can I do with generative AI in my job search? 5
Preparing for interviews 5
Generating interview questions 5
Brainstorming answers to interview questions 5
Responding to a custom question 6
Responding to “Tell us a little about yourself” (aka the elevator
pitch) 6
Responding to “What questions do you have for us?” 6
Learning about an employer and position 7
Networking in your chosen field of work 7
Mock interviewing 8
Practicing behavioral questions for a specific job 8
Practicing questions about your resume for a specific job 8
Asking the employer your questions 9
Practicing small talk in an anticipated interview setting 9
Building written applications 10
Structuring a cover letter 10
Getting feedback on a cover letter 11
Revising a cover letter for a specific position 11
Editing a resume or CV 12
Other job search activities 13
Writing an interview thank-you note 13

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
2
What is generative AI?
Generative AI is a subset of “artificial intelligence,” “machine learning,” and
“natural language processing.” Generative AI tools produce language, sound,
images, and video that sound and look similar to the language, sound,
images, and video produced by humans. There are lots of terrific resources
on this topic, so I’ll refer you to some of these, rather than spending a lot of
time on that here. The remainder of this document offers sample prompts to
use primarily with text and speech generative AI, but you could extend the
advice here to practice with video avatars as well.
● McKinsey & Company: What is generative AI?
● Eliza Strickland at IEEE Spectrum: What is generative AI?
● Ethan and Lilach Mollick: Practical AI videos
● University of Michigan: Generative AI terminology

Tips for prompting generative AI tools

The prompts in this document are just example starting places to inspire
you. In each case, the prompt includes
1. a human role the user wants the generative AI tool to play
(e.g. a human resources representative conducting a screening
interview)
2. the human role the user will play
(e.g. a recent college graduate job applicant with 3 years relevant
work experience)
3. the context for the communication
(e.g. a 20-minute screening interview conducted via Zoom)
4. the purpose for the communication
(e.g. answering behavioral questions in a screening interview)
5. rules of participation
(e.g. “wait until I answer a question before asking another question”
or “ask me at least one follow-up question after every answer I
supply”)

You will see that many prompts among the following examples set up a
conversation to help you brainstorm your own ideas and to practice language
you can use to describe yourself professionally. Often, your first prompt

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
3
won’t quite get exactly what you want, so you should expect to need to
redirect your AI tool to produce something closer to what you want to do.

Comparison table: Generative AI platforms

This table indicates some of the strengths and limitations of a few popular
generative AI tools, with an emphasis on free options.

Name and Advantages Privacy Access/cost

link protection

Pi ● optimized for poor free; requires

conversation free login after
● great voice initial trial
synthesis with access; may
multiple identities change due to
and accents Microsoft
● voice input on acquisition
mobile only

UM GPT ● free access to excellent free and

ChatGPT’s most available to
recent text version University of
Michigan only

Windows ● free access to restricted to free; requires

Copilot ChatGPT’s best Microsoft when Microsoft or U-M
version using login
● can reference live institutional
websites login, may erase Can also be
history of accessed on
content deemed Windows desktop
“sensitive” when and in the Edge
logged in with browser.
institutional
credentials

Claude by ● designed to reduce input and output free for

Anthropic hallucinations and are not private slower/less
bias but Anthropic advanced
● strength in seeks to prevent versions;

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
4
 academic language harm to pricing structure
● handles uploaded individuals due subject to
files well to data shared change.
● offers “agents”
(premium only)

Google ● can reference live poor May require login

Gemini websites with a
● good voice input non-institutional
● supplies feedback gmail;
on voice input Basic level is free

Chat GPT ● multi-modal poor Some limited

● fast speech capability for free
response
● fast roll out of new
capabilities
● offers “GPTs”
agents (premium
only)

What can I do with generative AI in my job search?

Let’s divide the answer to this question into three parts. First, we’ll explore
preparing for interviews, then we will explore building written applications.
Finally, we’ll look at other elements of the job search, such as sending thank
you notes after interviews.

Sample prompts can be found in

boxes like this.
Each sample prompt includes dropdown lists for you to select from and
[variables in bold in brackets] to fill in with your own details.

Preparing for interviews

Generating interview questions
To generate questions that you can contemplate before doing a mock (or
real) interview, try the following prompt. This prompt imagines a traditional

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
5
interview, so if you anticipate special experiences like a group of candidates
together, doing some problem-solving, or doing a day-long campus visit with
multiple types of events, you can add this context to your prompt.

I am preparing for an interview for the job posting pasted below. The text
of my resume is pasted below too. Please generate a list of 20 interview
questions that I am likely to be asked. Please include a mix of different
types of questions (e.g. behavioral, skills, prior experience, etc.).
[paste in text of job description]
[paste in text of resume]

Brainstorming answers to interview questions

If there is a question you anticipate and are not sure how to answer, you can
use your generative AI tool as a brainstorming partner. When doing this, it is
incredibly important that you analyze the AI suggestions critically, using this
interaction as a process to plan your responses, not as a response to
memorize. Adapt words and ideas you like to your own unique story.
Responding to a custom question

You are a Choose role preparing for a Choose length -minute

Choose mode interview for the job posting pasted below. The text of
your resume is pasted below too. You are trying to brainstorm ways to
respond to the question [type question here]. You will produce three
possible answers, one using the STAR answer structure, and two others
with an alternative emphasis and structure. In all three your voice should
sound polite and professional but not too formal, and consistent with who
you are.
[paste in text of job description]
[paste in text of resume]

Responding to “Tell us a little about yourself” (aka the elevator pitch)

You are a Choose role job applicant preparing to interview for a position
as a [job title.] The job posting is pasted below. Your resume is pasted

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
6
 below. Your cover letter is pasted below. The interview will total
Choose length minutes long, and is conducted Choose mode . You
know that one of the first questions they are likely to ask you is “Tell us a
little about yourself.” Given your skills, experience, and future aspirations,
brainstorm four different ways you might answer this question. All answers
should be about one minute long, should be polite, professional, but not
super formal, and should showcase what makes you a unique candidate for
this position.
[paste in text of job description]
[paste in resume]
[paste in cover letter]

Responding to “What questions do you have for us?”

You are a Choose role job applicant preparing to interview

Choose mode for a position as a [job title.] The job posting is pasted
below. The interview will total Choose length minutes long. The last 10
minutes of the interview are dedicated to time for you to ask questions.
Brainstorm 10 appropriate questions to ask the employer, and provide a
rationale for each of these questions.
[paste in text of job description]

Learning about an employer and position

Part of preparing for an interview is learning about the organization you are
applying to. This prompt offers a way to check out the organization’s
website, imagining the employer’s point of view. This requires a generative
AI tool that can read a live website, e.g. Google Gemini or Windows Copilot.
This is basically a fun way to get going on researching an employer.

You are a [job title] at [firm name or type]. You are going to interview
four candidates for a position as a [job title.] Your manager asks you to
answer the following three questions in detail:
1. What kinds of information do you think the best candidates will
already know about your organization? Why?
2. How could they find this information out?

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
7
 3. What pages on your website will be most important for them to read
in advance? Why?
Your website URL is [paste in link to website].

Networking in your chosen field of work

Networking has massive benefits in the job search process, including but not
limited to
● building relationships that might turn into job offers
● learning about possible job roles and responsibilities
● practicing talking about yourself, your experience, and your aspirations
This prompt is designed to help you to develop networking questions.

You are a Choose role preparing for the job market, looking for a
position as a [job title] in [industry.] Your resume is pasted below.
You are getting ready for two kinds of networking conversations: both
networking events sponsored by [your school/other organization] and
informational interviews you have been able to secure with alumni of your
college. But you’ve never intentionally had a networking conversation
before! Create a conversation between a university career center coach
and yourself where the career center coach helps you to generate at least
six questions that you could meaningfully and productively ask in at least
one of these networking settings. The coach should only offer one question
at a time, with at least some conversation to generate each one. The coach
should ask questions to their client to learn more from them, and then
base a suggested question on this conversation.

Your resume:
[paste in resume]

Mock interviewing
The sample prompts here are designed to set your generative AI tool up to
have a mock interview conversation with you. You can repeat these practice
interviews as often as you wish, generating a different conversation each
time. Since interviews are usually spoken, this rehearsal will be closest to
your real interview experience if you choose an AI tool where you can

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
8
respond by speaking, not writing, and where you hear the questions with an
AI voice you find good enough. At the present time, Pi’s mobile app and
Microsoft Copilot in the Edge browser using your computer’s speech voices
(e.g. the Windows U.S. English language pack) seem to be particularly good
at voice input and output. Gemini is quite good at speech input, but you may
need to change settings on your browser or computer to get more realistic
voice output.
Practicing behavioral questions for a specific job

You are a [job title] at [firm name or type]. You are going to interview
me for a position as a [job title.] The job posting is pasted below. The
interview is Choose length minutes long, and is conducted
Choose mode . In the section of the interview we will do today, greet me
and then ask me behavioral questions, and follow-up questions in response
to my answers. Ask only one question at a time, and wait for my response
before following up.
[paste in text of job description]

Practicing questions about your resume for a specific job

Note: Because many genAI interfaces limit input to 2000-4000 characters,
this prompt is set up for multiple phases of input. You can change the
instructions in blue based on what extra contextual information you will be
pasting in, and how many characters long it is.
I will give you this prompt in three more parts.
Part 1: First, ask me to give you a job description. Then, after I submit
that to you, go on to Part 2.
Part 2: Ask me to give you my resume. Then after I paste in my resume,
go on to Part 3.
Part 3: you will ask me for instructions on how we will conduct a mock
interview. I will give you a detailed prompt to guide the mock interview.
Wait to start the mock interview until after you have all three parts from
me.
Please let me know if you have any questions about this process.

Part 1: [paste in text of job description]

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
9
 Part 2: [paste in resume]

Part 3: [paste in directions for the mock interview]

You are a [job title] at [firm name or type]. You are going to interview
me for a position as a [job title.] You have the job posting and my
resume. The interview is Choose length minutes long, and is conducted
Choose mode . In the section of the interview we will do today, greet me
and then ask one question at a time in reference to my resume. Do not
include any follow-up questions until I answer. Wait for my response to
each question, and then ask a follow-up question in response to me, before
asking another question. Always ask only one question at a time.

Asking the employer your questions

The point of this practice is to get another way to think about how your
questions might land and might be interpreted, which can help you refine
your questions.

You are a [job title] at [firm name or type]. You have been interviewing
me, a Choose role for a position as a [job title.] The job posting is
pasted below. The interview will total Choose length minutes long, and
is conducted Choose mode . The last 10 minutes of the interview are
dedicated to time for me to ask you questions. To start this segment of
the interview, you will ask me, “What questions do you have for us?”
Please supply realistic answers to each of my questions. After responding
to each one of my questions, wait for me to ask you another question
before supplying more information or commentary.
[paste in text of job description]

Practicing small talk in an anticipated interview setting

One of the most difficult elements of job interviewing can be making small
talk with strangers right before and after the interview, or between interview
events. This prompt may need more tweaking than others, depending on the
LLM (Large Language Model) that your AI tool is relying on, which is why Pi
is my current favorite for generating conversational language. Even in Pi, it

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
10
was necessary to add the reminders at the end of this prompt about
appropriate topics and turn length.

You are a [job title] at [firm name or type]. You are in the lobby of your
office building in [city]. I have a job interview scheduled with you in 15
minutes, and I have just arrived at your front door. My name is [Name to
use in this mock conversation]. I am a Choose role interviewing for
a position in your organization as a [job title.] This is my first time
meeting you. Before the interview starts, let’s have a 5-minute friendly
chat where you start by welcoming me to your firm. Do not ask me any
typical interview questions yet; save those for the interview scheduled to
start in 15 minutes. Keep turns in the conversation very short, like an
informal social conversation. Do you have any questions about this
conversation before we start?

Building written applications

Structuring a cover letter
Getting an AI tool to write you a cover letter from scratch or even based on
your resume and a job description is unlikely to produce an effective letter,
because the tone and style will likely sound either weird or generic, and are
highly unlikely to match your voice. This prompt proposes getting AI to help
out with figuring out the sequence of ideas, not generating full paragraphs
for you. Also, this prompt helps you break down the content of your cover
letter into small, manageable parts, which is helpful for getting started.

You are a business English teacher with long experience helping college
graduates formulate job applications. One thing you like to do is to help
job candidates polish their cover letters to clearly identify what makes
them especially qualified for a given job. You also are reader-oriented, in
that you can help a writer to look carefully at how they organize
information and supply the right level of detail for their intended readers.

One of your clients, a Choose role named [name you want the AI
tool to call you] is applying for a job in [work industry] as a [job title]

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
11
 and comes to you to brainstorm ideas for what to include in their cover
letter. Don’t tell them exactly what to write. Instead, ask them questions to
find out what makes them an especially good fit for the position. Ask only
one question at a time, and wait for their answer before asking the next
question. After at least 12 question-answer turns, offer them two outlines
with a suggested content flow for a cover letter, and describe the strengths
of each of these options.

Getting feedback on a cover letter

It is pretty straightforward to get a tool like Grammarly or Quillbot to use AI
to give you grammar and wording suggestions for clarity, accuracy, and
tone, so this prompt does something different. Here, the idea is to generate
ideas to enrich your cover letter, content that a (fictional) hiring manager
wishes the letter had included.

You are a hiring manager at [firm name or type]. You are going to select
four finalists to be interviewed for a position as a [job title.] One of the
things that often frustrates you is how job candidates leave out the most
useful, interesting information from their cover letters. But now you have a
chance to fix this! You have access to (pasted below) a cover letter that
you can supply feedback on, in the form of questions indicating what you
would like to know more about, and what content seems entirely missing.
Ask ten questions to elicit the content you wish were there. For your
convenience, the job posting is pasted below. The same candidate’s
resume is pasted below. You will post this cover letter, resume, and your
questions on your Careers page to indicate to applicants what you are
seeking in a good cover letter.
Cover letter: [paste in cover letter]
Job description: [paste in text of job description]
Resume: [paste in resume]

Revising a cover letter for a specific position

One of the most important features of a cover letter, especially if it is going
to stand out from the rest, is that the writer demonstrates a keen knowledge

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
12
of the specific position at the specific firm. To do this, each cover letter
needs to be adjusted to signal both knowledge of the position/organization
and a specific investment in doing that particular job. This prompt seeks to
brainstorm ideas to tailor a cover letter for a specific position.

You lead a team at [firm name or type], where you have worked for 17
years. Now your brother tells you that his young adult kid is going to apply
to a different group in your firm as a [job title], and asks you to look over
their cover letter to supply feedback. He sends you the job description
(pasted below.) You agree to do this for your brother, since you will not be
part of the hiring process for this job. One of the things that often
frustrates you is how job candidates, even very good ones, send the same
cover letter everywhere, making it hard to tell how serious they are about
working this specific job in your firm. Your niece’s cover letter is adequate
in most ways but is not tailored for this specific job, so you identify
sections of the letter that could be revised to reflect knowledge of this job
at your firm. Make at least five suggestions for revision, and provide a
rationale for each suggestion. For your convenience, the job posting is
pasted below. The same candidate’s resume is pasted below.
Cover letter: [paste in cover letter]
Job description: [paste in text of job description]
Resume: [paste in resume]

Editing a resume or CV
Like with a cover letter, it is pretty straightforward to get feedback from a
tool like Grammarly or Quillbot about grammatical accuracy and consistency
on a resume. To offer a complementary way to improve your resume, this
suggested prompt focuses on boosting evidence of skills and
accomplishments by asking questions about the resume.

You are a hiring manager at [firm name or type]. You are preparing your
questions for three finalists for a position as a [job title.] The job
description is pasted in below. To prepare to interview these candidates,
you make a list of what information seems weak, unsupported, and
missing in each resume, so that you can ask candidates about these items

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
13
 during the upcoming interviews. Make a list of at least 10 questions for
each resume. You are just brainstorming here; you may not ask all
questions during the interview. The first candidate’s resume is pasted
below.
Job description: [paste in text of job description]
Resume: [paste in resume]

Other job search activities

Writing an interview thank-you note

Caution is recommended when using AI to generate an email thank-you note
after an interview, for two reasons. First, today’s AI tools tend to generate
language that is comically over-formal. Second, the AI tool was not in the
interview, so unless prompted, it has no specific memories from the
interview that it can call on to remind the interviewer of what made the
interviewee a great match for the job. This prompt, therefore, seeks to
collaborate with AI to give shape to an email where the tone is appropriate
and the content is unique.

You are a Business English teacher with 32 years experience providing

feedback to job seekers on their professional communications, including
email. One of your students shares this draft email with you (pasted
below) to seek your feedback. They are writing to the hiring manager at
[Employer] where they interviewed yesterday for a position as a [job
title], to thank them for the opportunity to interview. Engage this student
in a conversation about their interview to seek an additional tidbit of
information about the interview conversation itself that they could work
into the email, for two reasons: (1) to make their thank-you note unique to
this interview and (2) to have another opportunity to exhibit a particular
skill or attitude. Ask at least five questions. Then, after learning more
about the interview, make three suggestions to the student for ways they
could work in elements of the interview experience. Remember that
professional emails should be brief, polite but not overly formal,
enthusiastic but not exaggerated, and very well organized.
Draft email [paste in draft email]

Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
14
Using AI in your job search: Resources and suggested prompts © 2024 by Pamela S. H. Bogart
is licensed under Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International
15