Why Shopify Asks Every Candidate to Tell Their Life Story

Anita Chauhan (00:17)

Hi, and welcome to this week's edition of the Looks Good On Paper podcast, powered by Willo. Today I have Simran Siddhu joining us. She is a people and talent leader who has spent her career building the hiring and people functions as startups and scale-ups from the ground up. She's currently at Shopify where she leads talent acquisition on the commercial side, and before that held roles spanning talent acquisition and people operations at companies including Relay, Pocket HR, and Out of Office HR.

She's deeply involved in the HR and talent community across Toronto, which is also crazy because I haven't met her until this moment and we've both been in the space. But what I really love about what I've seen online and what I've heard about you, Simran is that you're known for your transparency around career breaks, burnout, and what it actually means to build a career that doesn't consume the rest of your life.

Did I miss anything in your intro? How did you get here?

Simran Sidhu (01:11)

No, that's awesome. That was a perfect intro. Yeah, I'm super excited to be here. Thank you for having me. Yeah, I've been in the people in talent space for a while. So much more to learn, but really excited to share what I've learned so far.

Anita Chauhan (01:25)

Amazing amazing and I know it's kind of like one of those things where it's like Talent it's just like the people that we work with they it changes and the needs change. So, you know I see I have some really great people from the community on, from North America from the EU from UK, on the podcast and it's so interesting because all of them no matter how long they've been in the game will always be like I'm still learning.

Simran Sidhu (01:50)

Yeah, yeah, especially with AI coming up. It's like, it almost feels like you put your head down to work for a week and you're like almost behind. I'm like, well, what happened in the week? And I'm like, my God, I missed the new tool or something. So it's changing and just even year to year, it's like wild to see the change.

Anita Chauhan (02:26)

What's the biggest hiring mistake companies keep making even though it's clearly not working?

Simran Sidhu (02:31)

Yeah, this one's so interesting. I took some time to think about this because it feels like there's so many. But for me, what I've noticed is just moving too slowly on decisions. And let me expand on that. So a lot of hiring managers fall into the trap of like, I just want to keep looking. Like I want to see what else is out there and maybe someone better is coming.

But the best candidates don't always wait around and indecision can be really costly. So a big part of that issue is hiring managers aren't often calibrated on what great looks like before they kick off their process and start interviewing. What I see happen really often is we get a strong first batch of candidates. I'm sourcing, I have other sources going after a brand new talent pool, but the hiring manager hasn't developed their bar yet of what great looks like. So they don't get that urgency they deserve. And it's only after you've met a few not so aligned candidates that they look back and they're like, that first batch was actually really strong. And by then, these people have moved on or we've rejected them because we weren't sure.

Simran Sidhu (03:32)

So I thought, what is the fix for this? And I think it's simple in theory, but do the work upfront to think through what great really looks like for the role. So that way, when you see it, you recognize it and you can move quickly. You're like, I know that's the person I want to hire. And you have to think through what does great look like in terms of skills — really iron that out. And then on the flip side as well, what does great look like in terms of fit, whether that's culture, team environment, like what traits does this person need to possess for them to be successful here? And having a really clear scorecard and really noodling on it with your team of like who's the right person that's gonna succeed in the role — that way when you interview them you're like hell yes versus like yeah I'm not sure and then you do this song and dance for months.

Anita Chauhan (04:58)

Are they always able to even tie that back to the business itself?

Simran Sidhu (05:02)

Yeah. It's also like, what do you need immediately, but what do you need a year from now when the business changes? Two years from now, like is this person still the same person? So just having to like zoom in and zoom out and be like, what's the immediate problem and the future problems that this person will solve and be able to get clear on that. And yeah, it takes a bit of reflection and you really have to encourage that upfront with your hiring managers.

Anita Chauhan (05:26)

Absolutely. And I think it's like also, I've been a hiring manager as well. Each individual business function within a company has their own needs to fulfill. So these are the things that we have to balance. I really appreciate that because during the last three seasons no one's actually had this answer. We're hearing it more too — you're gonna turn someone down if they don't seem good up front and then you're gonna go back to them eventually? That does not look good from an employer branding perspective. And then I'm seeing on Reddit forums and posts like that where it's like you know I went through and was waiting months to hear back. So this is not just a problem for the business, it is the external branding that gets impacted too.

Simran Sidhu (06:22)

Yes, and yeah and like that's why you sometimes hear people saying like I've seen this job posted for months and it keeps getting reposted and sometimes that's because the hiring manager isn't calibrated right? That can also answer candidates' questions of like, why is this job always up? But it's like sometimes you're just — you've had this problem up front and it has implications onwards. So then you're really looking for the needle in the haystack when you really should have been set up better from the start.

Anita Chauhan (07:32)

Alright, now moving on to question number two. What's a hidden bias companies unknowingly have even when they think that they're being progressive in their hiring?

Simran Sidhu (07:42)

Yeah, I've seen this so often, but I feel like it's less so now, but the assumption of like big tech is the best breeding ground for talent. I think it made sense many years ago when those organizations were leaner and you could have outsized impact there. But many of these companies now have lots of layers and organizational complexity, which makes it really hard to develop the kind of scrappy, high-impact skills you might be looking for.

So you end up with a lot of concentration of solid, middle-of-the-pack performers rather than standout talent. And I've spent my time interviewing a lot of them, so I'm just like, they just feel meh for such a great logo behind them. And I think my encouragement to hiring managers is always to just broaden the search. Sure, you could want somebody from here and there, but let's go out and just talk to all these different industries and sizes and just focus on the core skills and traits that the role demands. And industry background can be a factor, but it shouldn't be a filter that narrows down your pool so early. At Shopify, we do a really good job of that — talking to candidates across all industries and companies, because to us, what matters more is just the proven impact they were able to make.

Simran Sidhu (09:05)

And just a personal story — I remember earlier in my talent career, I was hiring for a senior role and leadership was really set on finding somebody that came from a consultancy background. Their reasoning made good sense on the surface. Consultants work really hard. They're adaptable and they can get up to speed in a new industry really quickly. But I kept flagging as I interviewed more and more consultants — they just weren't really aligned on the impact and execution. Consultants are really great at doing all the work and proposing all the solutions, but then they move on. That's the nature of their work. So we kept seeing that gap come up in the interviews. We ended up making the hire, and sure enough, the same concern surfaced once the person joined.

And I think it was a really good learning opportunity for the manager and for me. Now if I saw that again, I'd come with the why of this — why this might not work and why we should broaden the search. Just a reminder that clarity on what the role actually demands comes before any preference of where someone comes from.

Anita Chauhan (12:22)

Alright, so thank you. And moving on to number three — if you were to suddenly remove CVs from your hiring process, what would that look like?

Simran Sidhu (12:33)

I love this question because it's actually a really big reason why I joined Shopify. And I feel like it would look like what Shopify's done with what we call our life story interview. So it's really moving that focus away from job titles and company names and towards the things that actually predict success. I want to hear the candidate's story. Like what did they go to school for? Why did they choose to study that? What were some of those first jobs they had? Really thinking through how they've made decisions, what they're proud of, where they failed and what they took from it, and just going through their whole journey.

The reasoning behind this is that past behavior and history are amongst the strongest signals we have for future performance. A resume kind of flattens that into logos, and those biases come up.

Simran Sidhu (13:24)

And honestly, something we talk about at Shopify a lot is with AI now, most people can do a decent job at most things. We expect you to be able to do the job and do it well — you have a whole tool that will help you. So what I'm really vetting for when I do these life story interviews is taste, judgment, agency — people who can articulate the why behind their decisions and not just the what.

You can throw something into Claude or ChatGPT, but do you really understand why you're prompting that? Can you then take that and deliver it to a leadership team? What do they want to see versus what does your team want to see? How a candidate thinks now is just as important as what they've done.

Simran Sidhu (14:11)

So the real question I'm trying to get out of those interviews is: based on everything I'm hearing about how this person has operated, the impact they've had, the calls they've made, how they've grown — do I have enough evidence to believe that they'll succeed here? And if the answer is yes, the company name becomes a lot less relevant. I've hired some people from companies I have no idea about, but the life stories were phenomenal and all the traits and skills were there.

And that interview at Shopify is such a big data point. When I go to leadership and say hey, I gave this person a hell yes on their life story interview, that holds a lot of weight. It's such a fun interview to do as well — it's so non-conventional. I get to sit and talk to somebody about their story for an hour and it's a really nice thing to do. I actually really enjoy it. I don't find it draining. And I get a lot of feedback from candidates like, wow, I felt so treated like a human. People want to know about me. I hope more companies really follow suit because it's a really great way to hire.

Anita Chauhan (17:08)

Alright. Now moving on to our wild card question. We know that there's a massive boom with AI. Companies are using it to screen, candidates are using it to apply. It's really tough to pick up on good signals about who could be a good hire. How would you increase trust in hiring? Like how do you know that you're hiring the right person or what type of signals do you see right now?

Simran Sidhu (17:34)

Yeah, I think there's a few things. It sounds so funny to say, but if I see a human and I get a human response — like, I don't even care if there's a spelling mistake, I'm like okay great — I can almost tell when you've used AI. When I go through applications, everybody's saying the same things and all the resumes are starting to look the same.

So I've added optional video so I can get to see the person, what they have to say — and the people that do it, I'm just like, I'm so glad you did this. It's almost like a way in because I'm like, I can tell you're human. You don't even have to follow a script. And then the same in some of our screens — we had a discussion as a team like, hey, now we can start seeing candidates' eyes going like this and they're reading off a script or they have an AI bot that is also in the call telling them what to say after every question.

Simran Sidhu (18:30)

Even just calling that out, just like, hey, I can see you're reading from something or are you using a tool? And some candidates get really defensive. But actually what we would love to hear is like, hey yeah, I'm actually using this tool and here's what it does. We would actually really prefer that honesty and that excitement about an AI tool. Because that's kind of aligned with Shopify's values. We want people that are excited and want to use AI, but just be open upfront about how you're using it.

And also just a reminder to be human. There's so much discourse about fraud applications, candidates that you talk to that aren't even real. So people are now looking for humans. The more you can just show up and be yourself and ditch the script is really important.

Simran Sidhu (19:18)

In our process at Shopify, we even say we expect you to use AI. Please use AI in your assignments. But talk to us about how you used it. What did you use it for? How did you prompt it? We want to hear about that too. Versus somebody who's just like, no, I didn't do it — well, we know you did.

Anita Chauhan (20:09)

Absolutely. You know, the best companies will understand that AI is an enabler and it does not replace, and you can be human still throughout the whole process. Well, those are all my questions. Thank you so much, Simran. This has been amazing. I love the way you think about hiring and the process and I'm really excited to have this out in the world. Thank you again for joining me.

Simran Sidhu (20:26)

Thank you for having me. This was so fun. I really, really enjoyed it.