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

March 06, 2026 / 09:44

This episode discusses the impact of artificial intelligence on the labor market, specifically focusing on the evolving role of cover letters in job applications. Judd Kessler, Professor of Business, Economics and Public Policy at the Wharton School, shares insights on how technology is changing job application signals.

Kessler explains that the traditional cover letter, which once served as a strong indicator of a candidate's interest and fit for a position, is becoming less effective due to AI tools that make it easy to generate tailored letters. As a result, employers may no longer trust that a cover letter reflects genuine interest.

The conversation highlights the importance of networking and personal connections in the job search process. Kessler suggests that as AI simplifies the application process, real-world interactions will become more valuable signals to employers.

He notes that while cover letters are still a requirement, their significance is diminishing. Employers are likely to prioritize other signals, such as recommendations and prior work experience, which are harder to replicate with AI.

Kessler concludes by discussing the challenges faced by HR departments in adapting to these changes and the need for new strategies to identify suitable candidates in a crowded job market.

TL;DR

AI is changing job applications, making cover letters less effective and personal connections more important.

Episode

9:44
00:00:00
The labor market, like many other sectors, is dealing with
00:00:03
the influence coming from artificial intelligence. And one
00:00:07
component of the labor scenario that is changing is how people
00:00:11
go about promoting themselves to get a job, things like the old
00:00:16
fashioned cover letter. Judd Kessler is Professor of Business,
00:00:19
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
00:00:27
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
00:00:36
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
00:00:45
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
00:00:58
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,
00:01:07
I would imagine it becomes a lot easier to write a very good
00:01:12
cover letter because you have that extra assistance.
00:01:16
Yeah, and this is the problem. I mean, it's a little
00:01:18
counterintuitive. We made this thing very easy to write, and
00:01:21
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,
00:01:29
right, this is what we're trying to achieve with a cover letter.
00:01:32
We're trying to both show the employer that we are a good
00:01:40
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
00:01:46
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
00:01:55
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
00:02:04
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
00:02:13
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
00:02:19
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
00:02:27
thoughtful, detailed, tailored cover letter to every employer.
00:02:31
You only sent those to the ones you really, really cared about.
00:02:34
and that's just not true anymore.
00:02:36
So let's circle back here for a second. You talk about the
00:02:39
component of signals. And I guess when you're going for a
00:02:41
job, the cover letter is one of the signals that shows that
00:02:47
you're extremely interested about this position. You think
00:02:51
you would be a great candidate for this position. That's kind
00:02:53
of been the historic norm of what a cover letter was supposed
00:02:57
to do, correct? - Exactly.
00:02:58
And so that's— and the reason it was a
00:03:01
good signal, the reason that when a firm received a
00:03:04
thoughtful, detailed cover letter, they could be confident
00:03:08
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
00:03:16
letter like that. If it took hours to research the firm,
00:03:19
figure out exactly what they were doing, what they needed,
00:03:22
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
00:03:28
writing letters like that to every place you applied. You
00:03:32
were— you were selecting the places that were actually good
00:03:36
fits for you. But if ChatGPT or Claude Code or whatever your
00:03:40
preferred AI— generative AI model is can write hundreds of
00:03:45
those letters in a matter of seconds, then the firm that
00:03:50
receives that no longer can be confident that you actually
00:03:55
want to work there. They— you know, they might believe that
00:03:59
you're sending letters like that to all the places you apply, and
00:04:02
you very well might be.
00:04:04
So you actually suggest that the component of the job
00:04:09
recommendation may become even more important as we move
00:04:12
forward here. - Yeah.
00:04:13
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?
00:04:20
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
00:04:26
data coming out that is showing exactly this. That when
00:04:31
platforms, labor market platforms, introduce AI tools to
00:04:35
help people write their cover letters, the cover letters get
00:04:39
more tailored. They get more detailed, and, you know, better
00:04:43
fit matches— look like there is a better fit between the
00:04:47
applicant and the job posting. And those cover letters are
00:04:52
better. They're successful, but the firms that
00:04:55
are looking for candidates stop paying as much attention to
00:04:59
them. They kind of recognize, "Oh, I'm getting a lot
00:05:01
of these," and the cover letter becomes less important. What
00:05:04
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
00:05:13
experience and recommendations from prior employers or other
00:05:18
people who know you well, that might be written by AI. There's
00:05:22
nothing wrong with having the letter of recommendation be
00:05:25
written by AI, because the actual signal is not that the
00:05:29
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
00:05:35
in the real world believes you are a good fit for this firm.
00:05:38
So should the— for those that are out there looking for jobs, do
00:05:43
they bother with the cover letter at this point, or do you
00:05:47
make it just about those recommendations from other
00:05:50
companies, other employers?
00:05:51
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
00:06:00
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
00:06:06
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
00:06:13
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
00:06:23
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
00:06:32
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
00:06:37
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
00:06:44
having AI write a good cover letter for you. So yeah, I think
00:06:47
we're still in a time when we need to send a good quality
00:06:51
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
00:07:06
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
00:07:14
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
00:07:23
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
00:07:34
are happening in the real world. It's kind of this great irony of
00:07:39
AI, is that we're making things online just so easy, anything
00:07:43
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
00:07:52
cannot be replicated by AI. That are in the real world. And so
00:07:56
when I find somebody at a firm and offer to take them to coffee
00:08:01
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
00:08:07
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
00:08:15
become more important. And if what is happening is that the
00:08:21
cover letters or the referrals— oh, sorry, the letters of
00:08:25
recommendation or the referrals are going to replace the cover
00:08:27
letters, well, then, having more interpersonal connections,
00:08:31
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.
00:08:38
Is this just another— another change for the HR department
00:08:41
that's going through an incredible swirl of change right now?
00:08:45
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
00:08:53
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
00:09:00
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
00:09:06
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
00:09:13
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
00:09:18
the signals that actually are informative in this—
00:09:21
in this market today.
00:09:22
Judd, always great to chat. Thanks again for your time, sir.
00:09:25
Thanks so much for having me.
00:09:27
Thank you. Judd Kessler,
00:09:27
Professor of Business, Economics and Public Policy here at the
00:09:30
Wharton School.

Episode Highlights

  • The Future of Cover Letters
    As AI simplifies cover letter writing, their value in job applications diminishes.
    “The cover letter is kind of the prerequisite.”
    @ 06m 18s
    March 06, 2026
  • Networking's Rising Importance
    Real-world relationships will become more valuable as AI takes over simpler signals.
    “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 Evolution00:36
  • Networking Shift07:14
  • HR Challenges08:41

Words per Minute Over Time

Vibes Breakdown

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