🎧 5 PM Job Search Mistakes Keeping You Stuck
If your PM job search feels stuck…
This episode is for you! 🫶
Most PM job searches don’t fail from lack of effort. Usually, they're stuck because of a few well-intentioned mistakes that are sabotaging their traction.
In this episode, I share the 5 PM job search mistakes I’m seeing everywhere right now (and, of course, what to do instead):
Being “open to anything” is undermining your credibility
Thinking of your interview as a test, not a pitch
Applying to roles you’re overqualified for
Expecting consistent interviews when you lose momentum
Confusing volume with a clear application strategy
Ready to land your next awesome Product role? ✨
SPRINT helps you position yourself as a top-tier Product candidate so you can land high-quality interviews consistently and confidently - without guesswork, burnout, or wasting months applying into the void.
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Jess Sherlock (00:00)
Most of these things are super well-intentioned and they make logical sense, but I've just seen over and over again that they end up being really short-sighted and often have unintended consequences.
Hey everyone, I hope you're having a great start to the new year. I can't believe we're halfway through Q1 already I wanted to share some of the patterns and themes that I've been noticing with what is not working in job searches for folks so that
Hopefully you can take some notes here and avoid the same fate.
So as we go through these mistakes, just know that these are not meant to call you out. So if any of these resonate, I want you to know that Most of these things are super well-intentioned and they make logical sense, but I've just seen over and over again that they end up being really short-sighted and often have unintended consequences.
So my goal here is to share what those mistakes are and more importantly,
you see why these might lead you astray. And so hopefully you take away at least one thing that you can do in your job search if you're job searching right now, or one thing that you can avoid if and when you do have a job search. So let's dive in. These are the top five mistakes that I've been seeing with PM job searches recently.
All right, number one, and this one, man, I swear I've done no less than 10 podcasts about this probably in one form or the but
continue to hear about folks that are expanding their job search. what this will look like is folks will tell me, well, I'm really open to anything. I'm applying to PM roles, senior PM roles, director roles. And if need be, I'm open to program management and maybe even prod ops. And
I think the goal is that you think you're expanding your options, right? You're casting a wider net. But here's what I want you to know is from the other side, from someone who's looking at your profile on LinkedIn, maybe a recruiter, or as a hiring manager, which I was,
When I would get folks like this talking to me and I'd be saying, tell me what's got you looking or tell me why you think you're a fit for this role, what folks don't realize is that this seemingly well-intentioned goal of expanding your search and targeting a lot of different types of roles, while you think it makes you more compelling or you're giving yourself more chances, it's actually making you look less committed and less clear.
And it's making you come across as indecisive or kind of like, I don't know, short-sighted really. And so the analogy that I always make is let's imagine that you're dating, okay? And you know for sure that you are looking to get married. You know that you wanna have kids and you're on a date with someone who says, you know, I'm open to kids, maybe marriage or not, you know, what do you want? How would that land?
When you're super sure of what you want and the person that you're talking to is trying to be flexible or they're trying to be open to your input, it's actually kind of frustrating. It's like, well, I know that this is what I want, but it's not coming across that you're clear that that's what you want. And maybe it's what you want, but do I really want to bet on that? And so this is what you sound like to the hiring team.
when you say, well, I'm really open to anything or I'm really open having a conversation about whatever you might have open, it undermines the strength of your positioning. It undermines your unique value proposition. And quite honestly, it makes you seem not committed to the job search. so if you find that you are looking for multiple roles, I think some flexibility is okay. So for example,
I have some folks right now in SPRINT program, who are looking at maybe PM roles or senior PM roles. And they're aware of the fact that they're not going to be across the board super qualified for all senior PM roles, but that they might be well qualified if they have on the job experience with product roles.
And it's in a particular industry here in a particular problem space or for you know building for a particular type of customer and so that is an example of how you can still be Flexible right and not being like so specific in your job search strategy that you don't have any options But it's much different to say okay. I'm gonna be applying to mostly PM some senior PM if it hits certain criteria versus saying
I'm open to PM, I'm open to Prod Ops or I'm open to program management. Those are literally three different roles. Those are literally going to be three different interview processes. They're gonna be different job descriptions. They're going to require different resumes. So my encouragement to you is to recognize if you're casting a wide net that might actually be
diminishing your strength from what is your core qualification? And so if you're PM, position yourself as a PM. If you wanna go after Prod Ops position yourself as Prod Ops. But trying to do all of the above is where you're just going to undermine your own strength and the candidacy for that role.
Okay, pitfall number two that I've been seeing a lot, and it's something that I even see with folks inside the SPRINT program when I'm coaching them in a one-on-one mock interview session is I think we have this tendency to focus on accuracy and recency when we are deciding on the stories that we want to tell in our interviews, right? So we're practicing things like, tell me about a time you failed or tell me about a recent feature that you worked on from initial
insight all the way out to launch or any of these behavioral type questions, sometimes product sense, but I see it more in these behavioral questions is for whatever reason, maybe it's recency bias ⁓ or a tendency to believe that recent stories are better or accuracy is better. What I coach on constantly is we want to identify stories that are relevant. And I'll put an asterisk on that,
Ideally, the stories that you're picking are from within the last few years. So certainly the hiring team is going to admire and respect the work that you've done fairly recently, but it doesn't have to be the most recent thing that you worked on, okay? So in your interview stories, even on your resume, when you're thinking about the bullets to include or the stories that you use in your answers, relevance is usually going to be the winner.
So this is relevance to your unique value proposition. So here's an example. If you are trying to say that you are a career expert in banking products for entrepreneurs and small businesses, then
it's going to be smart for you to choose the stories from your experience that are gonna be most relevant to that. So let's just say for the sake of example that your most recent role took you away from FinTech, right? So you had years and years of experience in FinTech and then for whatever reason you wanted to try this new role, maybe it was a health tech role and you thought that that's what you wanted for your career, you wanted to broaden, but when you landed there you found it to be less exciting, less interesting and so.
you decided to pivot back to FinTech, back to payments, okay? So in your interview, if you're interviewing now for a payments role, the tendency is to say, well, my most recent role was in HealthTech, so I have to talk about that. No, you don't. No, you absolutely don't. And I'll tell you right now, it's not gonna help you, right? Because...
As much as we like to think that everybody you're talking to in the interview process is going to remember your resume exactly and they're going to remember that you had all these years of experience in payments before your most recent role, you're doing yourself a disservice and you're undermining your own credibility if you go into that interview and you're telling stories about your most recent job. Now, it is okay to share recent stories if for some reason you think that that's important, but in general, my advice to you is to always pick the most
relevant stories. And that's because interviews are not a test. I think the tendency when you're prepping for interviews is to go in thinking that there is a right answer to these questions, you're gonna get asked, and you have to plan the perfect answer, right? The A student in all of us comes out where we're like, all right, I gotta prep for any question I might possibly get, and I gotta get it right. And instead, I want you to not think of your interviews as a test.
but think of them as a pitch. I'm gonna say it again, because it's that important. We don't wanna think of our interviews as a test whereby every answer we give is either right or wrong. We want to think of the interview as a pitch where every answer that we're giving is building our credibility. It's our job as the candidate to tell strong, relevant stories that help the hiring team see you as the obvious choice.
to make sure that they see that we are experienced in exactly what they need and we don't want to try to make them piece it together. We want all of our answers to build this compelling pitch that they couldn't possibly fill this role with anyone but you.
Okay, mistake number three, and this one, whew, I see this in every industry. This is not just PMs. I think this is a job search myth that showed up at some point and it just won't go away.
So the tendency that I get is your job searching for a while, maybe you're getting traction, maybe you're not, and you think to yourself, you know what, I'm just, screw it. I'm just going to start applying to jobs I'm overqualified for because surely then I'm going to beat the other candidates, right?
If you're a lead PM, maybe you're like, you know what, I'm just gonna start applying to PM roles. Or if you're a senior PM, you're like, oh, I just need a paycheck, I'm gonna start applying to associate PM roles. Do not do this! Because here's the reality, and I have been on the other side as a hiring manager who's reviewing resumes when I didn't have a recruiter, and I will tell you for sure, when I saw someone who was clearly overqualified for a role, it made me raise an eyebrow.
because it's a risk and it raises question marks. So first and foremost, the most practical reason why you might get denied or rejected when you apply to these jobs you're overqualified for is they just may immediately assume that you're too expensive for their budget. If their budget is really strict and they have zero upside, like sometimes I knew that I could go up
for a really strong candidate, but many times I had a fixed budget. It wasn't a budget I could go outside of. And so considering an overqualified candidate, right from the very beginning, I knew that, okay, at best I'm gonna come in right at the top of my budget, but this person likely will be a flight risk, either because I'm not able to come up to their market rate. So when they get a job offer from somebody else that's more in line with their market value, they're gonna leave.
or they're not gonna be challenged in this role. As I'm looking at the things that you've been doing and I'm looking at the requirements for this role. You are either gonna be immediately angling for a promotion that I'm not gonna be able to provide and therefore you may leave, or like I said, I'm not gonna be able to come up to your market rate for you as a talented individual. And so I know that you're gonna continue looking and you're likely to
Just remember, hiring teams ideally want to hire people that they think are gonna stick around at least for a year or two, because hiring's expensive, training is expensive.
it's a distraction to the rest of the team to be consumed with hiring and training new people.
So anyways, I would caution you against applying to jobs that you're overqualified for. Not only is it just a waste of your time, most likely, but if you do land the role, you're probably gonna be underwhelmed by the offer.
And you may just continue job searching anyway. That is what I have to say about that.
Alright, mistake number four.
If you are not being consistent with the volume of applications that you're putting out, with the amount of outreach that you're doing, you cannot expect consistent results.
Interviews are not happening by accident. They happen as a result of your applications and your outreach activities. So if you're doing no applications or no outreach or reducing the volume of your applications or outreach,
you can't be surprised when you're not getting interviews or you're getting lower numbers of interviews, right? Now, here's the thing, if you are applying and doing outreach and you're not getting any traction, that's a sign of something else. We'll get to that in just a minute. if you find yourself saying things like, just don't have any interviews this week or I feel like I'm not moving forward at all in my job search,
I actually want you to look back at last week or even the week before last week because typically the lack of interviews or the lack of results has a direct connection back to what you were or more likely were not doing one or two weeks ago. And so that is the change of mindset that I want to encourage you to have is you control than you give yourself credit for typically in that.
If you are able to keep up with the consistency over time of your applications and your outreach or whatever those activities are that you're doing that are leading to results in terms of interviews or informationals, and you stop doing those things, you have the ability to pick those things back up and we would expect to see the same or better level of results. Now, like I said, I wanna get to this other piece, which is if you are doing all of these activities.
and you are applying, you're doing outreach, and you're just not getting any traction, then that's going to be typically a result or a sign of this last mistake, which is you may need a clearer application strategy. So the problem may be is that maybe you're applying to anything and everything. Maybe you are falling into the trap of updating your narrative, updating your resume for every single job. If you
aren't sure of where your unique value proposition is, then it is likely that no matter what you're applying to, you're not an attractive candidate for those roles and therefore you aren't getting traction. So this is that important differentiator, which is when we're not getting traction, we want to look back because traction is the result of those upfront activities. And so ideally you have a clear application strategy that is
something that you feel excited and energized by, but is also realistic of where the demand will be for your skill set and your actual hands-on experience. And so if you have a clear application strategy that tells you these are the sorts of job titles that you would be most qualified for, these are the types of industries you have experience in, these are the types of customers that you are accustomed to solving problems for. In other words, what is your unique value proposition to the hiring teams?
and your application's and outreach or an alignment with that strategy, then traction should follow, okay? And if you don't, if you feel like, I'm just applying to anything and everything, I'm just focused on quantity and not quality, that's your sign. That's a recipe for burnout, I'm gonna tell you that right now. Because a clear application strategy is gonna allow you to, first and foremost, have a single resume, a strong, compelling resume that represents all of your strengths that you're using for
95%, 98 % of your applications. There will be an occasional application where you may wanna make some adjustments for, maybe it's a passion apply. My clients sometimes have wild card jobs, like for the most part, I wanna apply to EdTech, because that's where my strengths are. But there was this one job at The Farmer's Dog and I just really loved dogs, right? So in that case, you might edit your resume.
But for the majority of your applications, right, they should be in alignment with your actual strengths, skills, and experience. And you're using that resume for basically all of your applications. Now, your LinkedIn, therefore, would be optimized for all of those same things. So it's also representing your unique value proposition. It's clear about the types of roles that you are interested in because those are the ones you are most qualified for. And because you've done a good job optimizing your LinkedIn,
you should be attracting inbound requests from recruiters for informationals or interviews as well. so a clear application strategy, finally, is going to let you spend your time on higher ROI activities. So what I always tell people is like, listen, there's definitely a school of thought that you should be editing your resume for every single job, right? That you should be taking and uploading your resume and a job description into some magic AI tool and having it spit out the perfect result.
But here's what I'm going tell you is when you do that, your resume ends up looking like everyone else's. Recruiters can tell when AI wrote your resume, and you can do it. But my personal philosophy is that I want you spending time on higher ROI activities because I just don't believe that adjusting some adjective on your resume or some verb on your resume is going to be the difference in the traction in your job search.
I think a really strong resume that works for the grand majority of your applications is the best use of your time initially. And then ongoing during your job search, I strongly recommend that you put that time and energy towards the things that I think actually result in better ROI for you. Things like personalized outreach, right? So that you're not sending the same exact message to every person you wanna have an informational with.
That you are setting up why you're an obvious choice in every message that you send. That you're taking the time to nurture those connections from previous jobs or people in your community who might be hiring or know someone who is. You're spending time monitoring for new job posts so that you are applying within 24 hours of that new job coming up so you can be in the top of the stack. Better yet, if you're getting referrals because you're spending time on personalized outreach.
You're spending time on informational calls and your energy and enthusiasm's high because you haven't just been staring at AI output from ChatGPT of your 400th change to a resume and storing that nicely in a bunch of folders labeled for every single job you've applied to with 500 different versions of your resume. It's just crazy to me. ⁓ Another super high ROI activity would be analyzing your job search data so that
If you do need to make tweaks, that's fine, but let's make them based on data. If you're noticing that certain jobs that you really believe you're highly qualified for and you're not getting traction, let's actually analyze the data we do have to make some assumptions on why and try a new test. So we can edit our resume, but I would encourage you to not do it with every single job because it's kind of like changing your control in an A-B test. You can't ever have...
anything fixed to base your experiments off of.
If you're noticing that you're not getting traction even though you are doing these activities, I would encourage you to look back at your application strategy and really start to question the types of jobs that you're applying to because you may be telling a great story but to the wrong people or you may not be telling the right story to anyone. And so the calibration that we wanna be doing is we wanna be telling a great story, AKA your application and resume.
to the right people, which is the application strategy and the types of roles, the types of companies, the types of teams, the types of problems that you should be applying to. So if that alignment is strong, then it should result in traction. So those are the top five mistakes that I am seeing here in 2026. Many of these I've been seeing for years when folks are job searching. And so if these mistakes are resonating for you, you feel like you could use some help with these.
then absolutely we should chat about my SPRINT program. It's designed specifically for PM job searchers. And SPRINT is cool because it helps you position yourself as a top tier product candidate so that you can land those high quality interviews consistently and be able to handle them confidently. My goal is that you do this without guesswork, without burnout, and without months and months and months just applying into the void and going crazy. Because nobody wants that. I don't want that for you.
So if you'd like my help, if you'd like to learn more about the SPRINT program, you can go to jesssherlock.com/sprint. You can learn all about it and there's a link right on that page where you can schedule time for us to chat.
Or you can find me on LinkedIn, send me a DM. I always love to hear your questions. We can get the conversation started, see if you might be a great fit for the SPRINT program, So I hope you enjoyed this episode, and I'll see you next time on AFTER THE CERT.
