AI can be an effective brainstorming partner in a few different ways, whether that is helping you decide what narrative you want to present, what your most relevant experiences to mention would be, or serving as an editor and examining what you’ve put on the page. 

Alongside discussing the best practices listed above, this article will also examine the downsides and pitfalls to using AI to help write a cover letter. Keep reading to learn how to avoid those issues

Brainstorming partner 

AI can serve as a useful sounding board in a variety of ways. 

First, consider providing the AI tool with your resume and the job description for which you are writing the cover letter. Ask what your most relevant and compelling experiences on your resume are and use that as a foundation to brainstorm what experiences to discuss in the body paragraphs of your cover letter. 

The answer to that question could, for instance, point out that along with your technical qualifications, you also possess a variety of soft skills that the job description makes explicit mention of. This sort of insight allows you to not only highlight your technical skills, but also your unique ability to meet the non-technical needs of the role. That could be soft skills such as collaboration, communication, or project management, for instance.

A second interesting avenue for brainstorming could be to provide the AI tool with information about the company that you are applying for. This could include mission statement, values of the organization, or history, for instance. Once providing that information, you can then ask it to examine your resume for possible connections that your past experiences could make to those details about the organization.  

In short, utilize AI as a brainstorming partner to help you craft the strongest cover letter in your own words. From there, you can transition to the second stage of the writing process: fine tuning your draft and optimizing the cover letter.  

Editor at your fingertips 

Have you ever wanted to have insightful feedback at a moment’s notice? AI tools allow you to have that, but it’s a bit more complex than simply asking “how can I make this better?” Instead, consider using targeted prompts that aim to address the strength of your cover letter in key areas. Keep reading below for examples of the types of prompts that could yield interesting results.

The four prompts above are useful jumping off points for an interesting editing experience with the use of AI tools. While they can certainly be useful in this regard, also keep in mind that the use of these tools can have negative impacts on your application process, as well as your career development. The following downsides of AI use can occur if you are using the tool to completely write your cover letter and not using it as an aid for your own process. 

Using AI for your development 

While it can be tempting to ask AI to create, or directly edit your written material, this approach will not lead to sustained growth and learning.  

The more that AI directly creates material for you, the less you will be able to replicate that on your own in the future. The real power of AI is empowering us to act beyond our means while also supporting our development.  

In practice, you can adhere to the following guidelines to best support your development during your use of AI:  

Limit generated content

Place limits on the amount of content that AI directly generates for you

Actionable improvements

Ask for specific, actionable improvements that you, the user, can implement

Get explanations for feedback

Get explanations of why feedback is being provided, so you can learn for the future

By using these tips, you can find a balance of both using AI in your writing process, and furthering your own career development in cover letter writing.

Obviously AI 

The most immediate impact of submitting a cover letter written by AI is that there are obvious signs of this that a recruiter or hiring manager will quickly pick up on. People who review cover letters frequently become accustomed to the certain stylings of AI writing.  

A few different elements that can be identified are the use of dashes as punctuation marks (otherwise known as em dashes), a formulaic cover letter, and over polished writing that lacks a human touch. It is possible for something to be *too *perfect!  

An easy way to test this is if you ask the AI tool to write a few different cover letters for you, you’ll notice many similarities between them. If it is producing similar results for you, then you can be sure that it is producing similar results for other people using the same methods. You don’t want to be part of the group that is sending in half-hearted AI cover letters that are easily recognizable.  

Limited Knowledge 

Remember that you will always have more context about yourself than any AI tool that you are using. While providing your resume can give a fair amount of context, that context will lack the depth that you possess yourself.  

This can lead AI to make two different mistakes that can negatively impact your candidacy. First, it can oversell your qualifications and set you up for failure in the interview stages, or even once you are actually on the job. This can lead to expectations of your capabilities that will not be in line with reality, setting you and the employer up for failure.  

Even worse than overselling is hallucination. It has been well documented that AI can hallucinate facts to try and meet the needs of the prompt. An example is that if you are asking it to write a cover letter for you, it might take certain aspects of the job description and ensure that the cover letter meets those needs, regardless of whether you have those qualifications. To that end, it might make statements about your capabilities with no tangible evidence to back up those claims.  

Conclusion 

AI tools can be a powerful support for your cover letter writing when used intentionally. From helping you brainstorm relevant experiences to offering tailored, in-the-moment feedback on tone and structure, they can accelerate your process and sharpen your messaging. But that’s only if you’re guiding the tool rather than letting it take over. 

By using the strategies above, like giving AI clear prompts, asking it to explain its suggestions, and filtering all output through your own voice, you can get meaningful support while also building your own confidence as a writer. Your cover letter is your chance to connect the dots for an employer and show why you’re excited about the role. That story needs to come from you. 

If you’d like help workshopping your draft or want a second pair of human eyes, schedule an appointment – CAPD advisors are always here to help. 

Cross analysis: resume to job description

If you’ve met with a career advisor for a resume review, you may have been advised to use job postings of interest to help you tailor your resume. You can manually review a job posting to pick out the skills and qualifications an employer is looking for. Then, review your resume to see which of those you’ve already highlighted, which ones you haven’t emphasized, and which you may not have experience with yet.

This is a great step not just to help you present yourself effectively to potential employers, but also to help you recognize and prepare to discuss any gaps there may be between your experiences and what an employer is seeking. AI is a tool you can use to help with this process, and which could also provide an even greater depth of cross-analysis. 

As a start, one strategy is that you could use AI to compare action verbs between your resume and a job posting. For example, you might ask, “how can I make my resume align more with the language in the job posting”? One caveat here is that you may need to give AI some guidance on what part of the job posting you want it to focus on. For example, putting in a prompt to pay attention to “non-negotiable” vs. “preferred” sections. 

As a next step, you could ask AI more detailed questions to help you learn more about your fit for the job. For example, you could ask: 

• “Based on my resume, what aspects of this job do you think I would do well in?” 

• “Based on my resume, what aspects of this job do you think I have less experience in?” 

Questions like these can help you identify and prepare for possible areas of weakness in your application, but can also serve as a good reminder that sometimes experiences that seem to be less relevant can actually be great ways for you to highlight relevant skills. AI may also identify a weakness in your resume that you do already have experience with but hadn’t included or emphasized in your application materials, allowing you the opportunity to make mention of those skills. 

Working on bullet points

An effective use of AI tools is to edit your resume bullet points. Consider asking the tool to analyze factors such as redundancy between bullet points, or whether or not you are utilizing strong action verbs.  

It is important to provide instruction when asking for analysis. Consider instructing it to check if you are following PAR statement (project, action, result) framework, for instance. It can offer suggestions of ways you can better follow the PAR statement method.  

Another interesting prompt could be to describe to it how you want to come across via your different experiences. For instance, do you want to display your research capabilities, or that you can work well across disciplines? Or perhaps your communication skills are what set you apart? Describe this to the AI model and ask if you are effectively representing that version of yourself. With that insight, or “fresh pair of eyes,” you might realize that you aren’t describing yourself as you think you are.  

Setting guide rails

Setting instructions for the AI model is a must if you want to make the most of it and use it ethically. These rules, otherwise referred to as “system prompts,” allow you to mold the results that you receive into a form that makes the most sense for your needs. In essence, you are explaining to the model how you want a task to be completed. 

In addition, you can ask the model to make sure to incorporate your own voice in any edits that it suggests. If you ask it to analyze your own resume writing style, it can factor that into any recommendations that it makes. This can help to keep your resume feeling authentic to you and true to your voice.  

Becoming reliant and not being critical of results 

While AI can certainly be a valuable tool to help you prepare your job application materials, it’s best used as a starting point and to help you generate ideas. Being able to present yourself and your background, skills, and accomplishments is a valuable skill to learn and practice for yourself. While you can use AI to help you prepare, you will still need to be able to present yourself during interviews, career fairs, and networking conversations so be aware of becoming too reliant on AI’s help. 

One strategy to challenge yourself to use AI truly as a starting point is to ask it not to generate content. Instead, you might have AI help you to grow as a resume writer by asking you questions to help you reflect or expand on your experiences. Consider providing it with a system prompt that instructs it to serve in the role of advisor, asking it to be supportive and detailed in its feedback. You could also ask it to explain its reasoning, allowing you to build up your own understanding. 

Be sure to also carefully review any AI analysis as it may sometimes say something that is incorrect or doesn’t make sense. It may even make up an experience in order to fit your resume to a job posting, otherwise known as AI Hallucination. You certainly wouldn’t want to be asked in an interview about an experience that AI created but that you’ve never had, so be sure to review any AI analysis or content. 

Data protection

Data security is an important topic when it comes to working with AI tools, and that holds true when working on your resume. If you are uploading the contents of your resume into an AI model, it is worth considering ways to safeguard your data, as resumes can contain sensitive information, like contact information. 

Most mainstream AI tools have ways to ensure that your data is not saved in the system. For instance, ChatGPT allows you to turn off “Improve the model for everyone,” meaning that your data is not used to train the model in the future. Other models have similar systems. Regardless of the model, it is worth it to look into what data security options exist, and to always be mindful of what you are choosing to provide to these models.  

Conclusion 

AI can have tremendous benefits for your resume writing, assuming that you use it in an intentional and thoughtful manner. By using some of the tips above, you can get efficient help in the present while also growing as a resume writer for the future.  

If you want hands on help with your resume, schedule an appointment with CAPD – we’re happy to help! 

If you feel that you are constantly throwing your resume into a black-hole, there is a chance that your resume is not well-suited to make it through the ATS. Here are some tips to improve your odds of effectively navigating the ATS.

Need additional support on your resume, CV, cover letter or job application? Schedule an appointment with us.

*Although this article is about resumes, much of these tips can also apply to other documents you may upload including CVs and cover letters.

This guide will help provide the basics, and as you have specific questions not addressed in this guide, be sure to schedule an appointment with us in CAPD.

Alternatively, you can follow this more closely guided hands-on module!

Your resume

With your resume, you basically have an 8½ by 11-inch piece of real-estate to demonstrate to your prospective employer that you are a good fit for the position. Your resume is a marketing piece—you are the product. You want to be relevant, concise, and formatted. An unformatted, full description of everything you have done will not be helpful as your reader may spend only six seconds on initial review.

If you are completely lost as to where to begin, you may want to start by looking at example resumes, or here are some sample layouts (A, B) you can borrow.

Through this article, I want you to feel more confident about the message you are sending to your targeted reader. After all, it is your name that will be at the top of the document, so you should feel confident in what you put your name on.

Whether you are updating an existing resume or starting from scratch, here are some tips to help you write a stronger resume:

Relevance

The key to writing a successful resume is to keep in mind: “Who are you writing it for?” You will probably send your resume to a recruiter or hiring manager, a professor for a research opportunity, or the president of a student organization you wish to join. Depending on whom you send it to will determine several aspects of your resume.

Relevance is my short-hand for “consider your reader.” Throughout this post I will refer to relevancy and how it may impact your document. A couple of things that I think are beneficial to help you think about relevance can be located in the job description:

1. Action verbs
2. Job-specific terminology
3. Location in the description

Avoid being your own roadblock. If you have done something (or have an associated skill set or ability), try to make sure it is reflected on your resume. Pull from your:

• Past/current experiences
• Projects or coursework
• Skills you have developed on your own
• Past education
• Anything you have done

The job description is not the only place you can find information to leverage in your resume. You may also want to review other jobs at the organization, or language from the organization’s website. Likewise, having informational interviews with different contacts in the company (some of whom you may find through Advisors Hub, the Alumni Directory, or LinkedIn) may also highlight additional information you might want to include in your resume.

Basically, with your resume, you want to demonstrate that you understand what it may take to do the job that they need done. You want to be relevant to the position.

Content

The content of your resume is the key to being relevant. You will want to organize your content into different sections. Think of sections similar to a table of contents in a book or periodical—it will help the reader navigate to relevant sections faster. The most common sections are:

• Education
• Experience
• Skills

There are a host of other sections you may want to include depending on your background, and type of role you are targeting. You may also have multiple sections that are similar but that go by slightly different names (e.g. “Professional Experience” and “Volunteer Experience”).  You could have sections for awards/accomplishments, publications, licenses/certifications, trainings, projects, coursework, interests, and anything else you think might be relevant to your prospective employer.

Here are some of the different sections and some considerations for organizing content within a section. Remember that you will always want to make certain the most relevant content is presented to your reader.

Header

The goal of your header is to provide contact information and to efficiently use the space provided so that you can maximize the other sections of your resume.

At a minimum, you should include a contact email address and phone number. For your phone number, make sure you have a professional voicemail greeting. For your email address, make sure it is something that looks professional. Conventionally, you can include your address, or provide at least your city and state to provide a general geographic location if space is limited. You may also wish to include links to e-portfolios, professional websites, or online work samples if space permits.

Now, check your resume:

Education

The Education section can help the reader understand a bit more about what you know. In this section you can include degrees and completion information. You may also want to include coursework, test scores, awards, and activities. As a first-year student, you may want to keep high school or secondary school listed on your resume as a means to show additional coursework, test scores, or GPA. Over time, you may want to remove high school information as space is needed for more recent information on your resume.

Similar sections to education might include training, certifications, and licensure. Although you may see education at the top of most resumes, it might not always go there (especially after you graduate and build experience), but for most first-year students I recommend keeping it at the top.

Now, check your resume:

Experience

Experience is a broad term that basically encompasses things that you have done—so use that to your advantage. You could certainly have a single “Experience” section, but you may find it beneficial to think about clustering or grouping your experiences into meaningful sections. Sometimes I group experiences into two sections:

1. Relevant Experience; and
2. Additional Experience

Now, “Relevant” and “Additional” are just placeholder terms. Are you going for a computer science position? Consider having a “Computer Science Experience” section if you have some entries that will support that section title. You might have sections called “Projects”, “Leadership Experience”, “Service Projects”, etc.—basically, keep in mind how these sections are relevant to your end reader and curate your experiences that align with what they are looking for.

Each experience should have information on your job title or role, the organization/company, location, and dates (month and year). You may choose to clarify your experience through bulleted PAR (Project, Activity, Results) statements.

These bulleted PAR statements allow you to morph the experience into different directions depending on what you did in that role. For example, if you were a grocery bagger at a grocery store, you may not find it beneficial to have a bullet point that says you “bagged groceries”—since that may already be understood. However, if you assisted with analysis for inventory, or helped with asset protection, or maybe even supported cash-handling—those are the bullets that will help your reader achieve a deeper understanding of what you are capable of—provided they are relevant.

Here is a way to craft a PAR statement:

Start with an action verb, add in a relevant task and extend it to either an outcome or accomplishment. When possible, try to quantify your work and outcomes to help deepen the understanding for the reader. Estimations and approximations are fine at the start, but over time start to keep metrics around your experiences.

Now, check your resume:

Skills

Your skill section provides a quick way for your reader to see the different skills you have acquired over time, regardless of context. Yes, you can still mention the skills you used within your experience bullets, but a skills section provides a quick way for many readers to quickly identify if you have the skills needed for the role. Depending on the quantity of skills you choose to list, you may want to organize this section into sub-sections.

I do recommend keeping this list to technical, procedural, language, or laboratory skills, and avoid social or interpersonal skills that might benefit from the additional context of a bulleted experience (e.g. leadership, teamwork, etc.).

Now, check your resume:

Other sections

There is no limit to the sections you can have on your resume, provided you always keep in mind the interests of the end reader. You might have sections that cover awards, accomplishments, service work, publications, coursework, patents, interests, etc.

Now, check your resume:

Formatting & organization

Now that you have your sections, it is important to make certain that they are organized and formatted to help your reader see the content they find most relevant.

Formatting

No matter how impressive your background is, if your document is formatted poorly, it may make the reader think twice about reading your resume. Overall, your format should be easy to read for both your human reader and applicant tracking systems. Here are some key things to consider when formatting your resume:

Font

Is your font accessible and easy to read? Common fonts like Arial and Times New Roman are examples of fonts that can work, and avoid heavily stylized, curly, or silly fonts. You will want to make certain that your font is legible in print, so avoid going under a 10-point size (11-point works for most fonts). You can use text emphasis like bold, italics, or underline—but use them sparingly.

Margins & whitespace

Although relevant content is the star of your resume, avoid filling an entire page with it. Line breaks, margins, and indentations can help improve the readability of your document. Keep margins uniformly between ½ inch and 1 inch, and leave white space to make it easy to read and see the different content sections.

Consistency

Attention to detail is a sought-after ability by many employers, and a quick way to undermine that is to be inconsistent. If you use a specific date format, a specific font size for headers, or a specific shape of bullet—be consistent.

One area you do not have to be consistent with is in quantity of experience, bullets, or entries. Too many times I have seen students try to have exactly two bullets for each experience. If you feel that you only had one meaningful bullet from an experience, list one. If you feel you had three, list three.

Notes on Applicant Tracking Systems (ATS)

ATSs are systems (usually algorithms) that review an application before it is sent to and reviewed by a human being. Formatting your resume for an ATS is important so that your resume can get further into the process. Since ATS is an umbrella term for a suite of different software packages and in-house solutions, it is hard to find a uniform agreement as to how best to format a resume to get through to a human being. Here are some things that usually help:

• Avoid text boxes, templates, and tables
• Avoid colors, images, or graphics
• Focus on relevant content (specifically keywords)
• Use common, easy to read fonts
• Submit documents in DOC/DOCX or PDF

Here are additional tips to make your resume ATS-friendly.

Organization

Regardless of the sections you have, you will want to make certain you prioritize the sections from most-relevant to less relevant.

The key with the order you choose is to hold the reader’s attention and to keep delivering information that they consider relevant. The one section I recommend keeping fixed at the top is your header. Ultimately, this is your document and you can position sections where you see fit.

Within the sections, there are two ways you need to organize content:

• Dates
• Relevance

Some resume formats place a greater emphasis on relevance over dates, however the most common resume structure, Chronological, is what we are focusing on here. The rule of a Chronological resume is simple: if a section has dates, you will organize by dates; if not, you can organize by relevance.

Keep in mind that dates are listed in reverse chronological order, meaning you will start with the more recent (or current) items and work backwards.

Now, check your resume:

Final remarks

Now that you have written your resume, think about how you might modify it for different positions. You may find it beneficial tailor your resume if you are applying to different roles in different companies–really make certain you are being relevant to each position. Now, you may feel that this is a lot of additional work, but if you want your resume to get past the dreaded ATS and into the hands of a recruiter or hiring manager who will see your relevant attributes, you need to make certain you give them what they are looking for. In applying for positions, I recommend leaning more on the quality of your application more than the quantity of applications.

In the end, this document will carry your name so you should feel confident about it. If you are not feeling confident, or feel you might benefit from additional insight, I do encourage you to schedule an appointment with CAPD or an Alumni Advisor. You should keep in mind that if you show your resume to five different people, you might receive five different pieces of advice, so also incorporate your own view points into your finished document.

Many of us in Career Advising & Professional Development (CAPD) have had an opportunity to play around with the latest disruptive technology: ChatGPT from OpenAI. ChatGPT, a chatbot prototype launched in November 2022, has demonstrated use in reviewing code, compiling ideas, answering general questions, and writing full documents including poems, plays, letters, essays, and more. So, naturally, we wanted to factor in how ChatGPT may, or may not, be helpful with career related topics including resume writing, interview preparation, and personal statement writing.

Here are four considerations in deciding whether to leverage ChatGPT (or similar technology) for your career:

1. It’s only a tool

ChatGPT is a tool, and as such requires some guidance and constraints in using it for your career. You may find it helpful to develop resume templates, draft cover letters, or develop outreach emails, but when the template no longer suits your needs—it’s better to build upon it (or scrap it altogether). Make certain you take the time to present yourself as you would like to.  Use it to examine possibilities, but stop short of fully relying on it. ChatGPT is a starting point, do not let it be your finishing point.

2. Evaluate your sources

ChatGPT relies on a vast amount of input data, so it may be challenging to determine if the information you are getting is good or valid. There are also concerns about whether information is true or if it is copywritten. Cross reference the output of ChatGPT with insights you obtain from your network connections, recruiters/hiring managers, and other reliable resources. And trust your gut; if you feel that something is not right, it is healthy to be skeptical, ask additional questions, and seek deeper understanding of your topic.

3. Safe guard your privacy

This AI learns from having information added to it by both the developers and the users. If you share something with it, it can learn and retain this information for much longer than you may expect. You should read more about OpenAI’s privacy policies and consider whether you want to share potentially sensitive information with it. Be careful sharing—as the saying goes, diamonds are forever and the internet comes close.

4. Be an above-average human

Since ChatGPT indexes web pages to “learn” what to write, it is probably starting off with giving you a very basic and average response. We know that many of you seek to be above average (after all, you made it into MIT!), so take the time to share out what makes you shine! Allow ChatGPT to help you get started, but take time to create something worthy of your humanity. When I asked ChatGPT to write a resume for me, the result was less than impressive. The content lacked rich details, because it doesn’t know everything about me. I could coach it through things I contributed to or experiences I had, but that would take a lot more work. Likewise, as AI-generated documents become more common, organizations may use technology to counter it as well.

We understand that there are many tools available to assist your career, with new ones appearing all the time. Keep in mind that CAPD is one of them. Feel free to schedule an appointment with a Career Advisor to help you navigate these tools and your career.  

Working on your resume or other career documents?

Learn about resumes, CVs, portfolios, and other career writing.

You want to convince the reader that your interest in the job and company are genuine and specific. You also want to demonstrate ways that your experience has prepared you for the role by sharing a few brief stories that highlight your qualifications. This takes time and research; use the job description and the company’s web site or LinkedIn page to identify traits and skills the company values.

Cover letter structure and format

A cover letter should be no longer than one page with a font size between 10-12 points. Be sure to include your contact information and address it directly to the hiring manager, using their name. If you are not sure who to address the letter to, write “Dear Hiring Manager.” If the role you are applying for has a reference number or code, be sure to include it in your letter so that human resources is able to accurately track your application. The reference code is usually included

Cover letters typically take the following structure:

Additional cover letter tips

1. Be sure that each cover letter is specifically tailored to the company you are writing to. Research the company to help you determine your approach. Check the company’s website and other resources online. You can also use MIT’s extensive alumni network through the Alumni Advisors Hub to seek first-hand knowledge, advice, and insight about the company.
2. Are you seeking a position in a field or industry that does not have an obvious parallel or connection to your academic training? Be explicit about why you are interested in that particular field, organization or job, and what value you bring. For example, if you are an electrical engineer applying to a finance or consulting position, highlight your quantitative skills and ability to problem-solve.
3. If you are applying for a summer job or internship and do not yet have any experience that is directly related to the position, focus on transferable skills that will add value to the role – leadership, communication, problem-solving, project management, etc.
4. Lastly, cover letters are a chance to demonstrate the communication skills necessary to most jobs. Careful composing and revision are essential. To put your best foot forward and ensure your cover letter will be effective, watch this video on writing a cover letter and schedule an appointment with a CAPD career advisor.

Working on your resume or other career documents?

Learn about resumes, CVs, portfolios, and other career writing.