Looks Good on Paper

Why 1,000 Applications Means You're Doing It Wrong - Anuj Rastogi (S2E3)

• Anita Chauhan • Season 2 • Episode 3

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Anuj Rastogi is a sales and revenue leader turned talent strategist who helps purpose-driven founders and HR leaders scale their teams. As Managing Director at BackStretch, he's seen firsthand how companies unknowingly sabotage their hiring by chasing the "obvious" candidate. In this conversation, Anuj breaks down the three critical hiring mistakes that even progressive companies make—and why the person who looks perfect on paper is often the wrong choice.

From a retail worker who became a top sales performer to developers hired without degrees who outperformed their credentialed peers, Anuj shares real stories that challenge everything we think we know about qualifications. He explains why job descriptions miss 97% of what the work actually entails, why hiring sequence matters as much as who you hire, and how the easy-apply era has created a volume crisis that's drowning out genuine talent. His advice? Stop optimizing for speed and start optimizing for the human connection that reveals true capability.

If you've ever wondered whether that stack of 1,000 applications is actually helping you find better people—or just creating more noise—this episode will make you rethink your entire approach. Anuj doesn't just critique the broken system; he offers a practical path forward that balances technology with the irreplaceable value of human judgment. Whether you're a founder building your first team or a talent leader drowning in resumes, this conversation will shift how you think about who deserves a shot.

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Show Resources

  • Willo: willo.video - The most cost-effective way to screen candidates at scale. Interview candidates anywhere & at any time
  • CV Free Toolkit: cvfree.me/join - Break up with the CV and get everything you need to modernize your hiring approach with skills-based assessments
  • Anita Chauhan: linkedin.com/in/anitachauhan - Connect with the host

This is looks go on paper, a podcast from Willo about flipping the script on traditional hiring. I'm Anita Chauhan and every episode I put big voices in hiring work culture through three quickfire questions, speed, dating style to get the habits, trends, and ideas that matter. Hi everyone, and welcome to the latest edition of the Looks Good On Paper Podcast. I'm your host, Anita Chauhan, and I'm here, uh, with Anuj Rastogi today, and I'm so excited to have you here. Um, you were one of the highlights of our super cut from Toronto Tech Week earlier this year that we just launched recently. Alright, so, um, Annu is a sales and revenue leader turned talent strategist who helps purpose-driven founders and HR leaders scale their teams as managing director at Backstretch, he built resilient talent pipelines and through YENZA3, he guides organizations on people-centric AI and knowledge transformations Alongside his work in HR and digital strategy, Anuj is also a podcast host. Amazing, uh, music producer and spoken word poet. So cool. Um, you're, I just, I'm, you're like so multidisciplinary. It's amazing. Uh, thank you so much for being here with me today. Yeah, no, my pleasure. Uh, it's, it's great to be back. It was great to meet you back in June at, at StartWell, that was a fun conversation and uh, I love how that Super Cut came together. Uh, it is really good to see all the people who are thinking deeply about these things kind of come together and people like you create space. awesome, so, you know the drill. It is the same three questions every single episode, but in this one season two, we actually have thrown in a different question. Um, we'll get to, it's the last one and I'll, I'll say it out loud when we get there, but we're gonna start from the top and rapid fire kind of speed dating style questions. So, what's the biggest hiring mistake companies keep making even though it's clearly not working? I am gonna cheat and I'm gonna give you three hiring mistakes, if that's okay. That's okay. Go for it. one, uh, the first one is that companies, uh, they're too quick to settle and to compromise on the talent that they bring into the organization. Uh, quality. Always should be the very first thing you're looking for. And the only thing that, that really matters, uh, and that can mean different things, but, uh, I think the too many people, uh, settle when they're hiring. The second is that they don't really understand the work, right? The job description is not the work. Uh, hiring somebody against just a job description. May actually turn out to be the wrong person for the organization and the work that needs to be done. And the third thing that I think is a, is a big miss is sequencing. Especially when people are hiring for entire teams or departments, the sequencing of what roles get hired when really matters because if you have all the right people in at the wrong time, they might start making some of the wrong decisions and it creates a, a downstream challenge for the rest of the organization. Yeah, I love that. That's such a good point. And this is the first time anyone said anything of that sort. And I think it's so interesting, right? It's like you might hire a leader and then the subsequent hires that that person brings in could also not be a good fit because that person themselves are not a good fit, right? If I can, if I can give an example, I, you know, 'cause a lot of my background was 20 years in the digital space. Um, uh. You need to build out a tech team or a development team. Uh, and I've seen this happen in the past where there might be 10 different openings. There's a bunch of full stack developers, front end developers, um, DevOps people, and there's also the need for a VP of IT or a, a technical architect, some of the people who are really gonna be laying the groundwork and the strategy for the stack. So if you hire a bunch of really fantastic world class developers and they're in exactly the right place. You should hire them. But if you hire them and they don't have some of the right technical strategy or the stack decided, or how the pipelines are actually gonna be configured, uh, what the quality practices are gonna be, they're gonna start making some of those decisions without necessarily thinking about it from a big picture standpoint, which creates a whole bunch of tech debt, um, down the road. So sometimes it actually makes sense to get that one key role in, um, and moving so that they can, they can lay the groundwork for everyone else's success. Yeah. Yeah, absolutely. Um, and you know, for your second point, you know about, you know, the job description. They don't know the job. What, how do we remedy that? What do you think? Like what do we do? So, so let, let me, let me expand on what I mean by that. Uh, most of what it takes to run any organization or company is not documented. It's not a bunch of SOPs and files sitting in SharePoint somewhere. Uh, when you take any company, however, large or small, most of what actually makes it run is sitting in tacit and tribal knowledge inside the heads of people and the loose agreements that they have with each other. And so if you think that the work is what's described in the job description. Actually, 97% of that work is not described in that job description because there's the relationships with different people across different departments. There's accepted cultural norms. Uh, there's specific nuances about how a thing is done here versus how it might be done elsewhere. And all those things aren't kind of written down anywhere. So if you just hire against. Purely a job description, thinking that that is the work, you'll actually miss the mark. So I think it really makes a lot of sense for, for talent acquisition professionals, for recruiters, anybody in the space of hiring to spend the time to really understand what that work is. And the people who know that best are usually the teams that you're hiring for the hiring managers. But some of it is just a matter of really understanding the questions beyond just what is the list of things in this job description. So having, I think that curiosity for the business and the work itself can help to elevate some of those conversations. Absolutely. Awesome. Thank you. So onto question two, and you know this is a little unfair 'cause you already answered this in person, but we're gonna go again. So what's a hidden bias companies unknowingly have even when they think they're being progressive in their hiring? We talked about this and it was in the Super cut. Uh, the most obvious hire is not necessarily the best hire for the organization. And what I mean by that is you think you need somebody who meets this job description a hundred percent. So they need to have 17 years of experience in, uh, healthcare quality assurance SaaS. Plus they need to be able to speak four languages. They need to be able to run an end-to-end sales pipeline using 50 different tools, some of which only launched two weeks ago, and on and on and on. And so they're, they're hiring against a set of criteria for which no individual exists. And even if that individual exists, they might not be the right fit because how that person works within the context of your organization really, really matters. So one of the things that I really can profess is we should be looking as much, if not more, at the capability of somebody as versus just the, the, the experience. It's not enough to just kinda look at how long they've been doing a thing. How long you've been doing a thing alone doesn't tell you how well you will do a thing in the future. A lot of people, especially new and emerging talents, or people who are changing careers partway through their career, um, they have so many different skill sets and they have so many things that they can bring to the table. Plus they might actually have a really unique passion for the thing. Um, I keep meeting a lot of people who. Are really motivated to either start companies or join companies with certain causes, either because they've seen family wrestle with a certain health issue, they're really committed and care about the environment. Maybe they care really deeply about, um. Improving the opportunities for creatives to find new streams of income, whatever those things might be. And if they have a raw capability and a bunch of skills, and then they have a level of passion for the thing that you're doing, the likelihood that they're gonna fit into the future of your organization is much greater than if they had 17 years of blah, blah, blah. And so. It's really important that we actually think about the person holistically. Um, and that means also giving people a chance who might not meet the criteria. Um, you know, if I may, I'll just reshare our story that I shared at Tech for canada. This is not my own story, but, uh, a friend of mine, uh, Sammy Singh, he had. He had met this woman at, uh, at a retail store. She was helping him out with picking out some clothing. Long story short, he just loved the way that she showed up and the way that she engaged and suggested that if she was ever looking to do anything outside of retail to reach out to him. Fast forward, she did reach out to him, eventually got, uh, an internship, if I'm not mistaken, and eventually a full-time role in the sales team and went on to become the top performing sales person in that organization. And she had none of that background in that industry. Absolutely. I know that story is so amazing. I just think like also. Good on Sammy to have that eye number one, and to see the things to be able to say like this person would be, I can see those skills, right? I can see that transferring over, I mean, for myself, like I run marketing departments and I actually don't have a marketing degree, and somebody, I was like in government and someone took a chance on me joining an AI company, a startup, and then it kicked off 10, 12 years of a career. I just constantly think like, how many good candidates are we missing with things like this? Yeah. And you hear these stories anecdotally all the time. I think all of us have encountered something like that. Whatever you do, a colleague of mine in a, in a previous, uh, digital firm that I worked in, and I used to run the BD onboarding, um, for new hires just to kind of introduce them to how sales and BD works there. And he introduced himself and he said, um, at the time that he was a little bit, I think just a little bit overwhelmed because he didn't actually have a university or college degree in software development. He had just kind of learned, um. Himself So I think we have to broaden our perspectives beyond just what's in a cv, um, and what's in the job description and the hiring criteria. Absolutely. Absolutely. And even more so now, right? I just think with all of the tools and the overloading in ai, we're actually moving further away from finding the right fits, but all right, onto question number three. Uh, this is our new one, and that's actually. Because of you and our conversation earlier this summer that, uh, we had this bright idea to offer this new question, which I think is really cool. So if you were to suddenly remove CVS from your current hiring process, what would that look like? I wanna delineate between a CV and a and a resume for a moment because I think a lot of those, those get conflated with each other. A cv, uh, is generally supposed to be a more exhaustive, thorough document that actually gives your education, your skills, and all of this other information about you. And a resume is this. Highly compressed contraction that you have to force fit yourself into two or three pages, and then you start messing around with margins and fonts. Uh, I've done all of that. Um, you have to be able to fit it in and, um, I, neither of them, first of all, is a fully accurate representation of who you are as a person. Um, but I do believe that a cv, if it's actually treated as a CV is, is a little bit of a more helpful document. Now, that said, I, I understand the need for them because when you're. You know, you have people that you need to hire, they need to have a certain degree of skill sets and familiarity with that thing. If you're doing software development, it sure helps to know how to do software development. Right. Um, being Kind of sorta, Yeah. Yeah. Being an incredible jazz musician, while that might have some use and purpose in there is not for that particular thing. Right. So I, I think it, it, it helps from that perspective, but I think what usually happens with people who are good at hiring and good at taking candidates through this process. That's sort of the first step. And then the rest of the interaction really is conversational. Um, it could be, uh, show and tell. It could be proving case studies. Um, from a sales and revenue perspective, I've seen a lot of case studies, how you present pitches, proposals, all of that sort of thing. And so what happens is we take that artifact of the CVR or the resume. We start there, we then cast it aside, and then we tend to go into a much more human interaction. Right. And so if we did away with cvs, and if we did away with resumes, I would suspect we would see, we would still see some sort of an artifact, but we would see more of a reliance on that human interaction with people, right? It would be a lot more conversational, It would be a lot more about building understanding about how does this person think, how do they operate? How will they actually show up? So I think a lot of those steps are already in the hiring process. Um, it's just that. The quality problem that we started with in this conversation, a lot of it comes down to the fact that we screen in some of the wrong people and we screen out too many of the right people too early on. So by the time we're getting into those conversations. We shouldn't even have been having those conversations in the first place. So we don't get the most outta those steps in the process. Um, so I, I'm not necessarily suggesting we do away with CVS and resumes, although that would be cool potentially. Um, what, what I am saying is that we need to actually really think about all of the human sides of the process. Yeah. Absolutely. I think like, yeah, like you were saying, quality, but then also like those people who can show up and actually show their passion and talk about things like, like even if they have a base. Line of, you know, I, I'm a software engineer. I, I did all these things, but also like I'm a good culture fit and I'm also a good fit for like the company. I'm gonna push this forward. And I have that passion. Like, but you can't get there just through like the online parts of things. Right. So it's. It's, it's tough though. But then I understand on the other side that ta like TA professionals, recruiters, they're tired. Like we know there's so much that they have to go through. So what's the balance? This is my wild card question for you. What is the balance and how would somebody, I know you do this a lot with back stretch and I know you consult with a lot of companies on this, so like what, how do talent professionals find the right fits with like so much volume right now? How do we do this the best way we can? So the volume, the, so there's always this push and pull between quantity and quality, right? And that that plays out no matter what the context is. And right now I feel like the pendulum is swung to. Quantity, it is so easy to apply for a job, right? The LinkedIn easy apply button, I'm sure indeed has an equivalent. Um, you know, people are firing off resume after resume, and it's not because they, they have ill intent. It's because a lot of people are either just desperately looking for work or they really are looking for a change or what have you. They really, I think most people mean well, but it's so competitive because it's so easy. To apply for jobs, right? So what that does is you post a job and all of a sudden 700 people in four days have applied to it. Now out of that 700 people, how many of them are really qualified, even would make the base cut? How many are, um. Qualified for that particular type of work are available to work, um, uh, in the country, even in the country at that point, uh, at any given point in time. And then out of that, um, which people should you really even talk to, right? So what we find is that there needs to be a balance between. The posting and, and kind of collecting people who are applying and then the proactive search. Proactive search is absolutely critical because a lot of the right people for a given organization may not be looking at that particular time. Or they may not have seen your post for whatever reason. You actually have to go to them and find them. And if they happen to be a great fit for this particular opportunity, and this opportunity happens to be a great fit for them, and there's a mutual benefit, uh, for it, it's just a matter of being able to communicate that to them. So I do think the proactive search is a, is a big mitigator. As far as the quantity thing, I think we have to get, uh, we have to step away from these vanity metrics of, I got a thousand applications for this job. Is that good or bad? I don't know. In most cases it's probably bad because it's actually creating a whole bunch of overhead for, uh, for you and the team to be able to search through. So I, I think that, you know, we have to find ways to use the technology to serve us instead of just serving the technology. And one way that to do that, I think is just to put quality. Front and center, right? Whatever your process, if it's heavily leaning on AI and tooling, if it's heavily leaning on people, uh, being human and analog, whatever that process is, if that process is not, um, if it doesn't have a bias and a focus for quality right from sourcing, um, all the rest of the process is gonna start to slip and, and fall. So, um, I don't know if that answers the question directly, but I would say like quantity should not be the goal. It should be quality. Absolutely. Absolutely. Awesome. Well, those are all my questions for you today. Thank you so much for joining us for a second time. Um, really happy to have heard all of your thoughts. I am really excited to share this with, uh, you know, the world. And, um, thank you everyone for tuning in to Looks, go on paper. We can't wait to see you next time. Alright, thank you for having me. Thanks for joining me on. Looks Good on Paper. Powered by Willo If today's three question Sprint gave you something new to think about, hit subscribe and share with your network. Because in hiring and really in life, it's never just about what looks good on paper.

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