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Is AI Making Cover Letters Obsolete in Today’s Job Market?

March 06, 2026 / 09:44

This episode discusses the changing role of cover letters in the job application process, the impact of artificial intelligence on job seeking, and the importance of networking.

Judd Kessler, a Professor of Business, Economics and Public Policy at the Wharton School, shares insights on how technology is transforming traditional job application methods. He notes that while cover letters have been a staple for centuries, their effectiveness is diminishing as AI makes them easier to produce.

Kessler explains that the ease of generating cover letters with AI leads to a lack of confidence from employers regarding an applicant's genuine interest in a position. He suggests that as cover letters become less significant, other signals, such as personal recommendations and networking, will gain importance in the hiring process.

The conversation highlights the irony of AI simplifying online applications while making real-world relationships more valuable. Kessler emphasizes that building interpersonal connections will be crucial for job seekers in the evolving labor market.

As firms adapt to the influx of AI-generated applications, Kessler believes that HR departments will need to identify new, effective signals to evaluate candidates.

TLDR

AI is changing job applications, making cover letters less relevant and emphasizing the importance of networking.

Episode

9:44
00:00:00
The labor market, like many other sectors, is dealing with the influence coming from artificial intelligence. And one
00:00:07
component of the labor scenario that is changing is how people go about promoting themselves to get a job, things like the old
00:00:16
fashioned cover letter. Judd Kessler is Professor of Business, Economics and Public Policy here at the Wharton School. He's also
00:00:22
author of the book <i>Lucky By Design</i>. He wrote recently about the cover letter going away, and he joins us right now. Judd,
00:00:32
this is an interesting topic, and I guess, like many things in life, even the cover letter changes over a period of time.
00:00:41
It's been around for hundreds of years. So it's— you know, dates back to the 15, 1600s, that era. But you know, technology
00:00:51
changes. And what is a useful signal of your interest in a firm and your fit for a firm, it changes as technology changes.
00:01:02
Right. And obviously, in this day and age of artificial intelligence, I would imagine it becomes a lot easier to write a very good
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cover letter because you have that extra assistance. Yeah, and this is the problem. I mean, it's a little
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counterintuitive. We made this thing very easy to write, and now it's not useful anymore. But that's exactly how signals work
00:01:26
in the labor market. So you know, to paint the picture, right, this is what we're trying to achieve with a cover letter.
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We're trying to both show the employer that we are a good catch, that we're high quality, that we're producing high level
00:01:43
work, and we're also trying to signal to them that we are actually interested in this job. And one of the reasons that
00:01:50
second one is so important is it's become very easy to apply to many jobs at once. So a job application that you send to a
00:02:01
firm, you might be sending out 1000 applications like that. So the firm has to decide, is this person worth investing time and
00:02:08
energy in evaluating? If we recruit them, are they actually going to want to be here? Are they going to be looking over
00:02:15
their shoulder for their next opportunity? And a good, well thought out detailed cover letter used to provide that
00:02:22
assurance, because it was hard to write, and you couldn't write a thoughtful, detailed, tailored cover letter to every employer.
00:02:31
You only sent those to the ones you really, really cared about. and that's just not true anymore.
00:02:36
So let's circle back here for a second. You talk about the component of signals. And I guess when you're going for a
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job, the cover letter is one of the signals that shows that you're extremely interested about this position. You think
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you would be a great candidate for this position. That's kind of been the historic norm of what a cover letter was supposed
00:02:57
to do, correct? - Exactly. And so that's— and the reason it was a good signal, the reason that when a firm received a
00:03:04
thoughtful, detailed cover letter, they could be confident that you really were a good fit for the firm, believed the firm
00:03:12
was a good fit for you, was that it was hard to write a cover letter like that. If it took hours to research the firm,
00:03:19
figure out exactly what they were doing, what they needed, and how you fit in, then, you know— if it took hours to do
00:03:25
that, the firm could be confident that you weren't writing letters like that to every place you applied. You
00:03:32
were— you were selecting the places that were actually good fits for you. But if ChatGPT or Claude Code or whatever your
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preferred AI— generative AI model is can write hundreds of those letters in a matter of seconds, then the firm that
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receives that no longer can be confident that you actually want to work there. They— you know, they might believe that
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you're sending letters like that to all the places you apply, and you very well might be.
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So you actually suggest that the component of the job recommendation may become even more important as we move
00:04:12
forward here. - Yeah. I mean, the question is, what is going to be a useful signal for
00:04:17
the labor market to identify folks who are really good fits? And I should say, you know, I'm not just— when I wrote my book, I
00:04:23
was kind of speculating that this would happen, but there's data coming out that is showing exactly this. That when
00:04:31
platforms, labor market platforms, introduce AI tools to help people write their cover letters, the cover letters get
00:04:39
more tailored. They get more detailed, and, you know, better fit matches— look like there is a better fit between the
00:04:47
applicant and the job posting. And those cover letters are better. They're successful, but the firms that
00:04:55
are looking for candidates stop paying as much attention to them. They kind of recognize, "Oh, I'm getting a lot
00:05:01
of these," and the cover letter becomes less important. What becomes more important? Well, the signals that are not as easy
00:05:08
for a candidate to generate with AI. Things like your prior work experience and recommendations from prior employers or other
00:05:18
people who know you well, that might be written by AI. There's nothing wrong with having the letter of recommendation be
00:05:25
written by AI, because the actual signal is not that the letter is good. The actual signal is that you got somebody
00:05:32
to write the letter on your behalf, that somebody out there in the real world believes you are a good fit for this firm.
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So should the— for those that are out there looking for jobs, do they bother with the cover letter at this point, or do you
00:05:47
make it just about those recommendations from other companies, other employers? So I think we're in a transition period where you actually do
00:05:55
still need the cover letter, unless a firm stops asking for it, which is where I think we're going. Eventually the firm will
00:06:03
realize this is pointless. We're having AI write these cover letters. And, you know, many firms now are using AI to read
00:06:09
the cover letters. And so the whole— the whole process is a little silly. But right now, the cover letter is kind of the
00:06:18
prerequisite. It's no longer the differentiator, because if you decide not to send a cover letter, or you send a bad cover
00:06:27
letter, then the firm has to think like, "Well, why didn't they send— why didn't they just put it through one of these
00:06:35
generative AI models? It's so easy to write a good cover letter, they must really not care, if they're not bothering to
00:06:41
even do that, even do the kind of lowest-cost thing of having AI write a good cover letter for you. So yeah, I think
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we're still in a time when we need to send a good quality cover letter, but I think you can be confident that the firm's
00:06:56
not really looking at them. And later on, you know, this won't be necessary.
00:07:01
You also talk in your article about the importance of networking and how that kind of plays into— obviously, people
00:07:11
have done networking for a long period of time, but how does that get impacted by this shift that's going on?
00:07:17
Yeah. The issue is when AI comes and makes a lot of the signals that we used to send less costly, easier to send,
00:07:29
then the signals that will take over are going to be ones that are happening in the real world. It's kind of this great irony of
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AI, is that we're making things online just so easy, anything that a computer can aid you with has become very, very easy to
00:07:48
do. And so the signals that will be effective are ones that cannot be replicated by AI. That are in the real world. And so
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when I find somebody at a firm and offer to take them to coffee and spend half an hour with them, chatting with them, that
00:08:05
is a signal that I'm interested in the firm. That is a relationship that I am building that cannot be replicated with
00:08:11
AI. And as a result, those types of relationships are going to become more important. And if what is happening is that the
00:08:21
cover letters or the referrals— oh, sorry, the letters of recommendation or the referrals are going to replace the cover
00:08:27
letters, well, then, having more interpersonal connections, having more relationships, having more folks who are
00:08:34
willing to go to bat for you, is going to be all the more powerful. Is this just another— another change for the HR department
00:08:41
that's going through an incredible swirl of change right now? I think they're gonna settle on this. I think, you know, when you
00:08:48
are flooded by hundreds or 1000s of applicants for each position that you have open, and they're getting better and better, and
00:08:56
you're having trouble sorting through them, right, you're going to need to figure out, what is the alternative way that
00:09:02
I'm going to cut through this noise? And I think that HR firms are getting there, and you see it in the data from the papers
00:09:09
that are coming out looking at this. But yeah. It's— it's a period of change. I do not envy those folks. But it's—
00:09:16
it's going to get better once they figure out, what are the signals that actually are informative in this—
00:09:21
in this market today. Judd, always great to chat. Thanks again for your time, sir.
00:09:25
Thanks so much for having me. Thank you. Judd Kessler, Professor of Business, Economics and Public Policy here at the
00:09:30
Wharton School.

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Episode Highlights

  • The Evolution of Cover Letters
    Cover letters are becoming less significant as AI makes them easier to write.
    “The cover letter is kind of the prerequisite.”
    @ 06m 18s
    March 06, 2026
  • Networking in the Age of AI
    Real-world relationships are becoming more important as online signals lose value.
    “Those types of relationships are going to become more important.”
    @ 08m 15s
    March 06, 2026

Episode Quotes

  • The cover letter is kind of the prerequisite.
    Is AI Making Cover Letters Obsolete in Today’s Job Market?
  • AI makes things online just so easy.
    Is AI Making Cover Letters Obsolete in Today’s Job Market?

Key Moments

  • AI Impact00:03
  • Cover Letter Decline01:12
  • Networking Importance08:15
  • HR Challenges08:45

Tension Over Time

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