SEASON 2 - EPISODE 155 - JUNE 4, 2025

The Case for Cover Letters

This week on The REWORK Podcast, host Kimberly Rhodes is joined by Jason Fried to talk about cover letters — what they say about a candidate, how they’re reviewed at 37signals, and why they still matter. Jason shares his take on the value of genuine effort, how AI can either help or hurt your chances, and why hiring should stay a human process.

Watch the full video episode on YouTube

Key Takeaways

00:13 - A cover letter says more about you than your résumé ever could
03:35 - How using AI the right (or wrong) way shows up in applications
06:04 - Why a pre-screening team reads every cover letter first
07:18 - A thoughtful effort is often what gets you to the short list
13:36 - It’s easier than you think to spot procrastination
16:50 - At 37signals, hiring decisions are made by people—not algorithms

Links & Resources

Transcript

Kimberly (00:00): Welcome to REWORK, a podcast by 37signals about the better way to work and run your business. I’m Kimberly Rhodes from the 37signals team, joined by the co-founder Jason Fried. We have Jason solo this week. I thought we would talk a little bit about cover letters. We’ve said for a long time when we are hiring the cover letter is super important. Jason, I know that you posted recently on X and LinkedIn about this and got a lot of feedback, so I thought we would talk a little bit more about it. First, before we kind of go into some of that feedback that you got, just give me the once over why you think a cover letter is so important in the application process.

Jason (00:34): So for us, we look at cover letters first. So first of all, we require them. So when we post the job ad, we say send us a cover letter.

Kimberly (00:41): Wait, lemme interrupt, ‘cause I thought, honestly, I thought everyone required a cover letter and then I saw some of this feedback saying, “No one asks for a cover letter anymore. This is ridiculous.” I was kind of surprised. I thought everybody asked for a cover letter.

Jason (00:55): Yeah, I think that’s kind of why we specifically ask for one because what I’ve learned too is that people don’t do that anymore generally, so we ask for one. And the reason we ask for one is for us it’s the first introduction to somebody and it’s a very specific introduction. So for example, if someone just sends a resume in, it’s not specific.

Kimberly (01:14): Right.

Jason (01:14): The resume talks about their past and it doesn’t actually talk about them, it just lists their past. So you don’t know much about the person. You know a lot about maybe where they worked. And some of the things they said they did you just have to dismiss that as not true. You just, like “Redesigned amazon.com.” It’s like no, you’re probably amongst 8,000 people who had a hand in that. Or like, “Sales increased 30% under my watch.” You didn’t do that probably. You may have been there while that happened. I don’t know. So I just dismiss all those things. The cover letter should be a personal letter to the company about you and about why you want this particular job and not just any job. That’s what a good covered letter should be. So this is a chance for someone to be themselves, to introduce themselves. It’s basically the first question in an interview or their first answer in a sense. So I think it’s incredibly important. It requires someone to think clearly, to present themselves clearly, to put themselves out there and to write something to you and it demonstrates whether or not this person wants this job at this company. You can tell if someone’s just blasting them out and there’s nothing specific about the role

(02:32): Or they’re just talking like dear hiring manager, which could be okay.

Kimberly (02:35): Is it though?

Jason (02:36): Let’s just say it can be, I don’t like that introduction, but let’s just say it can be if the rest of it is really about them and this specific position and you can tell because the things we talk about and the kind of job ads that we write, you should be able to respond to that job ad in a way that represents the fact that suggests that you read this and that you want this job. So anyway, that is the first line. And also most of our communication at 37signals is written. So this sort of is the first step. You have to be able to write. If you can’t write then you can’t communicate here because that’s primarily how we communicate and you’re not going to be a good fit right off the bat. So if you don’t write well, if you don’t make yourself clear well, we will throw you out basically even if your resume is impressive and whatever, I just don’t really care if you can’t get the first step right.

Kimberly (03:26): Okay, so your LinkedIn post about this mentioned AI, so talk me through how AI comes into this when it comes to cover letters and our screening process here.

Jason (03:38): A lot of people these days use AI to help them write, which I think is fine. I do sometimes, but I think you have to write something first and then you can use AI as an editor, as an assistant to maybe help you with a paragraph that feels a little bit kludgy or a point you can’t quite get across or is there another way to say this? But you can tell. You just can tell when you read through lots and lots and lots and lots of these. You can see patterns that emerge and you can tell when AI wrote the cover letter or when a human wrote the cover letter. You probably cannot tell when a human wrote it primarily with a little bit of help, which to me is fine. Historically, people would write a cover letter and ask their friend to look at it. Can you proofread this for me? Or have someone else who’s a good proofreader or whatever and give them, that’s totally, completely fair game.

(04:25): It would not be fair game in my opinion, to have your friend write your cover letter for you, just like you should not have AI write your cover letter for you. And if you have your friend write your cover letter for you and you change 5% of it, it’s not yours, it’s theirs. If AI wrote your cover letter and you change 5% of it, it’s not yours, it’s AI. And you just can see, the reason you can see is because of quantity. This is the difference. If you look at one thing, it might be a bit hard to tell, but you begin to see patterns emerge in the phrasing, in the structure, in some of the punctuation, in the way sentences are offered up, in the way points are made, in the way things are organized. You can go, I’ve seen that before, I’ve seen that before. And it may not be the exact same words, but there is a flavor that you can taste and something that you can see that, this is generated primarily by someone else. And when that happens, it’s again a bit of a turnoff, let’s just say, because you’re not representing you. I’m hiring you.

(05:22): If I’m going to hire the AI, why are you applying it all? I’m hiring you and I want to be able to see you in the letter. So I wrote this up of course, and some people would dispute the fact that you can tell, and all I can say is that, you can when you look at a large sample size. You may not be able to tell when you look at three things or five things or one thing because AI can write really, really well. It’s only when you have multiple things when you see patterns, which is true in anything. You see patterns across a sample size. You don’t necessarily see patterns in one thing. So that’s the advantage that we have is that when we get a thousand applications or more, you can begin to see these patterns emerge and you can tell who’s who and what’s what.

Kimberly (06:04): So our recent designer role that we are hiring for our hiring team is looking through a thousand. How many of those are you actually looking through cover letters for? I mean it was a lot this time I feel like.

Jason (06:18): The first batch we usually get cut it in half very, very quickly. So Andrea and Bethany typically will trim that down pretty quickly. There’s a variety of reasons why people just simply don’t follow directions. It’s obvious in the application this person’s unqualified. We get to like half or even let’s say a third or something like that. Then I’ll begin to start to look myself. I’m not involved in the first initial round of interviews which narrow that set even to maybe 50 or 20 or whatever it is, but I’m looking at that point and I’m going through them. That’s when you can basically very, very clearly see patterns. And also you can see the ones that are really, really good. It’s like, I like this person’s writing. I like how they represent themselves. I like their enthusiasm, I like the way they phrase things. You can see the things that stand out as well and you can see the people that stand out and that’s where I start to get excited about individual candidates and then I might look at other things. I do not look at resumes first. I look at cover letters first and only when I like the cover letter do I begin to dig any further or any deeper into their work at all.

Kimberly (07:18): Okay, so I saw some of the feedback on your recent post about cover letters and some of the people who felt strongly about cover letters or were like anti the cover letter were very much like, how do you expect as an employer for us applying to write these specific, individual cover letters for multiple jobs that we’re applying for? What are your thoughts about that? People were fired up about it I felt like.

Jason (07:47): Yeah, I mean look, you got to make an effort to get a job. I mean, which job do you want?

Kimberly (07:53): Right.

Jason (07:55): If you want any job, and that might be fine by the way, you might just want any job that you can get, you should blast out probably to as many places as you can because then it’s a law of large numbers and you’ll maybe get in somewhere. If there’s a few companies that you really, really like and you really, really want to work for and an opening opens up, put some time in, put some effort in. The fact that I even have to say this bothers me frankly. Why do I have to put any effort in to get a job at a company I want to work at? What? Are you serious? Yes you do. And by the way, if you do, you will have a very good shot because most people don’t put enough effort in. It’s not obvious that they’re putting effort in. When someone puts effort in, you’re like, oh my god. Wow, they really want this job. I’m going to give them more time, more consideration. I’m going to probably put them through certainly the next round, and they’re going to be on the short list. It doesn’t take that much to stand out because most people are like maybe the person you’re talking about or others who are like, when am I going to find the time to write something up?

(08:57): Someone will, that’s like someone else will and they’ll stand out. So if you want this job, you got to do the work.

Kimberly (09:03): Yeah. Okay, so the cover letter is obviously super important for all of our roles here. Are there any that are more important than others? I kind of think the answer is no.

Jason (09:14): All of our teams hire this way initially. Our entire hiring process is built around this method. Yeah, I don’t think there’s one that’s more important than another. I mean everybody here has to communicate with others like customer service, you’re doing a ton of writing.

(09:27): Maybe 50 to 75 tickets a day or whatever and you’re writing to customers. We really, really, really care about writing there because that’s outward focused, but all the inward focused writing too is very, very important. What’s interesting about the designer role specifically is that some designers will design their cover letter in a way where they’ll maybe make a mini site, a mini website. They’ll submit it maybe as a PDF or something of that, but they’ll also submit a link to it and they’ll sort of design an experience around the cover letter, which is something that we typically do not see in other roles because this is just this what designers do, like design an experience. And so I always enjoy seeing people who put in the extra effort to present themselves beyond just something they can email in, but actually something you can look at and you can link up and then we can go through an experience. We don’t ask anyone to do that…

Kimberly (10:22): Right

Jason (10:23): Because that’s work. It’s definitely a lot more work, but people who do that stand out. And this is like, you got to stand out. You have to understand that when you’re applying and a thousand people are going to apply or even 500 or 300, you’ve got to stand out if you want any shot whatsoever. So put in a little bit of effort, and I think you can go pretty far. We used to sometimes get people would respond by writing a cover letter and printing it out, mailing it in. That was another thing people used to do sometimes, which I thought was we don’t really have an address anymore so that they wouldn’t do that now, but they would write it up on really nice stock or hand write it, which is actually kind of interesting. So it is always nice to see that extra effort.

Kimberly (11:02): Yeah. It was interesting because one of the comments that I read from someone who was like, this is crazy that you’re asking this, was saying that in this competitive job market that we’re in, it is so difficult in this market, which also then goes to your point because it is so difficult, then you do need to take an extra step.

Jason (11:22): It is difficult, which is exactly why you need to put the extra work in. Sometimes I just wish people could see it from the other side because if you saw it from the other side, you’d go, oh, I know exactly what I need to do to stand out.

(11:34): Because all these people are phoning it in, like everyone’s phoning it in except 10%. 10% are really doing a little bit of extra work and then 5% are doing quite a bit more extra work and it may not even be that much extra work in terms of hours. It just might be thoughtful, considered work to stand out and make a point. And so if you could just see the other side, you’d understand what you’re up against. And the good news in that scenario is that, like I said, most people do phone it in and you see when you see those comments, why would I do this? Why would I do that? Well, most people have the same point of view that you have, which is why I’m not going to do that. Then you’re going to have a hard time. And so one of the things I do get, sometimes I do get emails from people asking, I’m having the hardest time finding a job.

(12:22): I feel like I’m good at what I do. Why is it so hard? And there can be a lot of different reasons for this and I understand that it is hard, but I’ll ask them, well, tell me about the last job you applied for. And it’s like, well, I sent ‘em my resume and I never heard back. It’s like a thousand people sent in the resume. Is your resume that good? Nothing personal, but is it truly, objectively? Is your history so extraordinary that people had to stop the presses and call you in? Or is your resume probably quite good, like most are, but recognizing that a lot of people have similar experience that you have? What are you going to do beyond that? And what’s interesting is that it just doesn’t dawn on people sometimes to do anything beyond that. They think their resume is enough, their experience is enough, and there are a lot of great people out there with a lot of great experience with similar experience or better experience or slightly worse experience, but still good enough that you’re just going to be thrown into the same pile which is like, they did what everyone else did. You got to do a little bit more.

(13:29): And again, I’m saying a little bit more at least. And then people who do a lot more really have a huge leg up, but a little more will get you pretty far.

Kimberly (13:36): One thing I do love about how we hire is that our job postings have a closing date, which some don’t. So I think people feel like I got to get it in now because it could close tomorrow or they could be the end of the process already. So there’s a sense of rush. What I love about ours is it is closing on this date at this time. It’s not a, you get it in first and you have a better chance than if you get it on the day that it’s due. I think that’s helpful to the user.

Jason (14:06): It is good to know. In fact, I would say that most people who get their applications in instantly, they didn’t put enough time. They just had something at the ready and they sent it in. And that’s not going to help you. It doesn’t help you to be first. It helps you to stand out and be better and take all the time you need, just get it in. Because another thing we run into, first of all, it’s very interesting. You get a lot of applications, it’s like a curve. You get like, well, it starts high, little bit goes way down in the middle and then huge spike at the end.

(14:34): And inevitably this always, always happens. We get a handful of people who beg to get in past the deadline because their time zone was wrong or they submitted it and they say they submitted it when we took the form down and it’s like, I’m sorry man. Maybe you’re right. Maybe it came down a second before because your clocks weren’t synchronized. I don’t know. You cannot take that risk. Get it in. Get it in the day of, get it in the night of. Don’t put yourself in a position to be at the point where it might not get in because of some technicality. That’s just pure procrastination and it also doesn’t look good. Think about this, and I’m sure you didn’t work the six weeks every day to get it in and you just ran out of time. It’s like you chose to wait till the end and the end, end, end.

(15:32): And if you didn’t get it in, the answer is I’m sorry, and I feel for you in a sense, but I also feel like, hey, you put yourself in that position and that doesn’t bode well for you in general. If you’re advertising that you procrastinated to the last possible second, it’s just not a good scene anyway. So I’m just trying to be real about this and I am real with people when they write me and they plead because I’m like, you had six weeks, you knew when the last day was, you cannot wait till the last second. Also, I can’t adjudicate. I don’t know what happened. I don’t know what happened in the last second. I can tell you that today we got 243 applications. So the system was working. I don’t know what happened the last minute. I don’t know and I can’t know. And the answer is no, unfortunately, because deadline passed.

Kimberly (16:22): That happens a lot?

Jason (16:23): It happens a lot.

Kimberly (16:24): Really?

Jason (16:25): It’s always this batch of people at the end with the same story. And again, this is like patterns. You see it. And again, look, I do feel for someone if it was legit and authentic, but again, these are the rules. You had plenty of time. And again, remember the signal that you’re sending, which is like I waited until the absolute last moment. It’s just not a good look.

Kimberly (16:49): Yeah. Okay. A little off topic of cover letters, but kind of not. I’m curious about your thoughts because of AI, there are many hiring companies that are using some sort of system AI of some sort to sort through all of these cover letters. Tell me your thoughts on that. What would you say to someone who is doing that about using that kind of system to find people for their organization?

Jason (17:17): I can just tell you what we feel about it. I don’t really like to tell, I mean, people would say, do this all day, I don’t really mean it this way, tell other companies what to do.

Kimberly (17:26): Sure,

Jason (17:26): Every scenario is different.

Kimberly (17:28): But there’s a reason that we do it this way versus other ways.

Jason (17:30): Yeah. My feeling is that if you’re going to hire a human, a human should hire a human. That’s just my general feeling on this. I don’t want some algorithm that first of all, we have not tuned to make decisions about who is worthy and who isn’t. If we were to sit down and really perhaps really tune that algorithm to really prime it for all the considerations we make, maybe that would be helpful in some way. But we also don’t hire that often. We have two incredibly good people who know this company really well, understand the kinds of people who work well here, who will do well here, the kind of people we want to work here. They have this in them. It’s like in their fabric, and they understand the preferences in that case, it would seem to be very, very, very hard to know how to convey this to a system and then trust that system and make the right decisions. I’d much rather have humans do it who really know us and really kind of feel us, even if they’re going to make some wrong decisions. I’m certain that we’ve let incredible candidates through, we’ve missed them. Of course you have when you have a thousand whatever, there’s going to be people in there that you just miss.

Kimberly (18:42): Yeah. But a system’s going to miss great people too.

Jason (18:45): System’s going to miss great people. Humans are going to miss great people. But I would say if we were hiring a hundred roles a month, we certainly could not do this with two people.

Kimberly (18:53): Right.

Jason (18:53): But we hire a few a year and we want to be very diligent, very careful, and very humane about the whole thing. And so for us, it works. Again, if you’re, I don’t know, Shopify or whatever, and you’re hiring so many people all the time, I can certainly imagine where a system that can be more systematized and faster and algorithmic would pay huge dividends for you. So that’s why it’s hard for me to say what each company should do, but for us, we want to make our own calls. Yeah.

Kimberly (19:25): I mean, I think your advice can translate well to another company of our size or smaller.

Jason (19:31): Yes. Especially if you’re building a company and you’re really small. You want to rub shoulders with everybody that you’re hiring. You don’t want to ever have some system in the way. In my opinion, hiring is a skill that you need to develop as well.

(19:46): And I think that if you offload that skill to a system, you’re not getting better yourself. And I think that’s a skill that you want to hone. And for the longest time, David and I did all the hiring here, and then eventually we moved it more to the teams to hire their own crew. And now we have two people who sort of sit in the front of that process to help whittle that down to make it more palatable for the teams. Otherwise it would be like a full-time job for them and we have work to do that’s different. So we have a system in place now, but it all began just like I used to do all the customer service before we hired our first customer service person. That was multiple years of me doing it. So I just think it’s good to do the work first, to understand the work, especially when you’re small, to be very, very attached to that work and to select the team by hand, not by machine, but by hand.

(20:35): Because this team is now going to be the team that makes the rest of your team. And that’s why it’s so important, I think, to be very, very intimately involved with the hiring process as often as you possibly can, especially in the early days, and especially when you’re small. It’s one of the advantages of being small is that you can be involved and to say, I don’t have time. This is the most important thing you do, is to hire the people who work at your company. There is a point where other people can start to do it, but if you don’t have the time to do that, I think you’ve got priority problem. And so I’d focus on that instead.

Kimberly (21:12): Okay. Well that is a great place to wrap it up. Rework is a production of 37signals. You can find show notes and transcripts on our website at 37signals.com/podcast. Full video episodes are on YouTube, and if you have a question for Jason or David about a better way to work, run your business, leave us a video. You can record or upload that at 37 signals.com/podcastquestion.