Before You Hire an AI Company to Apply for Jobs for You, Ask These 10 Questions

At this point, you’d probably have to be living under a rock to not have heard about artificial intelligence (AI) and how it is disrupting industries, influencing executives, and driving hiring trends. AI is impacting my industry and transforming nearly every part of the job search. This won’t be about the ethics, industry standards within career development, nor the pros/cons of using AI in your job search. I frequently get asked about whether or not (or how) to use the latest AI technology within the context of building a meaningful career. I have very specific thoughts on how to effectively use it, but it all starts with your values. Beyond that, I’ve gone into the key questions you need to be asking before you leverage AI for your job search. Let’s dive in!

Setting the Stage

Today, beyond LLM tools like ChatGPT and Claude, a growing number of companies promise to automatically submit hundreds or even thousands of job applications on your behalf. This sounds like a dream for a burnt out, stressed out worker managing life, family, an overflowing inbox, and the day-to-day life stuff everyone has going on. Job searching can be emotionally exhausting and time-consuming. While AI can absolutely make parts of the process more efficient, it's worth taking a step back to ensure the AI tool matches your goals, strategy, and values before outsourcing your entire job search. Below are ten questions I recommend asking before hiring an AI-powered job application service to run your job search for you.

1. Does using AI align with your values? 

This should be no surprise coming from the creator of Values-Based Careers that this is the first recommended question. If you don’t know your values, I can help you to identify them or you can leverage one of the many free resources online.  

2. What is the company's actual job search strategy?

Applying to more jobs isn't necessarily the same as applying to better jobs and it is not necessarily the same as applying to jobs aligned to your goals. Research consistently shows that networking, internal referrals, and targeted applications remain among the most effective ways to secure interviews. Organizations such as National Career Development Association regularly emphasize the importance of aligning your experience with employer needs rather than relying solely on application volume. Make sure to ask yourself: Is this service helping me build a strategy? Or is it just increasing my volume of applications submitted (aka the “spray and pray” method)? 

3. Are applications customized for each role?

That depends on the tool. Make sure you know if the tool is leveraging templates, how many templates, if they are aligned to your job level, industry, and how much the tool will tailor your resume and cover letter. If you cannot review all materials before submission, consider if that is worth the risk of your personal reputation being influenced if the end product does not align with your personal standards. Templates are not inherently bad. Many career coaches and resume writers design templates that we use and customize for our clients. Templates can be effective, but employers often expect resumes and cover letters that clearly demonstrate how a candidate meets the specific qualifications for the position. Additionally, you will want to know how accurate the AI-generated responses are, what the QA process is, and what happens if incorrect information is submitted in your resume, cover letter, and application questions. 

4. Does the service help beyond submitting applications?

Submitting applications is only one part of a successful job search. Other important components include: networking, interview prep, personal branding, LinkedIn optimization, salary negotiation, and career decision-making. If the service only automates applications, make sure to consider whether you're investing in a tool or a complete job search strategy.

5. How are they protecting my personal information?

Before using an AI tool, please consider reading the privacy policies and understand how the tool uses your data. This includes whether or not it uses your information to train its models Throughout a job search, you will likely be sharing sensitive information intentionally or unintentionally including your employment history, resume details, contact information, login credentials, among other things. Consider whether or not the tool uses your personal information to train its models and before signing up, review the company's privacy policy carefully. 

Questions to ask include:

• Is my data stored? 

• Where is my data stored?

• Is it encrypted?

• Is information shared with third parties?

• Does the tool use my information to train its models? 

• Can I permanently delete my account?

6. What evidence supports their claims?

Marketing language, testimonials, and success stories are persuasive. Make sure to seek out information on success rates, client outcomes, refund policies, independent reviews, and know exactly how the technology works. 

7. Will this help me build long-term career skills?

A job search isn't only about finding your next position. (If this idea is new or foreign to you, let’s chat because there is a world of career development strategies I’d love to share with you that will help you now and in the future.)

A job search is an opportunity to develop skills you’ll use throughout your career and in the next job. These are things like professional networking, interviewing, communicating your value, understanding labor market trends, clarifying your goals, and so much more. These skills remain valuable long after you've accepted your next role and they will help you to benchmark your worth in the market, find a sponsor who will open doors for your next promotion, among many other benefits.

8. Is AI being used ethically?

As AI becomes more common in hiring, ethics should be at the forefront. Do you know how the AI tool you want to hire makes decisions? Are humans involved in quality control? Is the company transparent or murky when you are seeking these answers? 

9. Could another investment provide a better return?

Depending on your goals and the circumstances that you are coming into your job search, you may benefit more from investing in: career coaching, resume writing, interview coaching, professional development, certifications, networking, therapy, or something else entirely! Clarifying your goal(s) and aligning your strategies may create more opportunities than increasing your application count.

10. Does this approach align with my career goals?

Every career journey is different. If you're making a career pivot, targeting leadership positions, changing industries, or seeking work aligned with your values, a highly targeted approach may produce better results than mass applications. The best technology should support your goals, not define them.

My Perspective

I believe that AI is here to stay. I am a cautious, thoughtful experimenter with these tools at this point in time. I am actively researching the ethics and risks of these tools and anticipate changing my approach as I continue to learn new information. 

With that being said, I don't believe technology replaces thoughtful career planning. Your career is one of the largest investments you'll make over your lifetime, outside of your education, your family, and your home. It directly influences the quality of your life and can be the determining factor in whether or not you get to retire and how you spend your final years on this earth. 

Technology is powerful. It can increase efficiency and productivity. However, it will not replace human judgment, meaningful relationships, and intentional decision-making (at least for now) and those things are still what turn opportunities into fulfilling careers. If you're considering an AI job application service, don't just ask how many applications it can send. Ask whether it's helping you build your career. 

If you’ve gotten this far and your AI tool aligns with your values and it checks all of these boxes, that’s great! I love hearing stories about strategies that work for job seekers and welcome learning more about how you are leveraging these tools. If you read this and realized you need more support or want a human approach, I’d love to chat with you about what that looks like.