Episode 7

How to Foster a Culture of Development to Improve Your Team’s Performance with Brittany Forsyth

In this episode, our guest Brittany shares how her leadership journey and styles grew and evolved as she rose through the ranks to eventually becoming Chief Talent Officer of Shopify. She shares her lessons along the way and how they all helped her build her leadership confidence to succeed at a unicorn level company.

Listen now on your favourite platform

My favourite thing as a leader that I probably learned during that time is the notion of like, everyone's a teacher and a student at the same time. And so, yes, I could be a teacher, I could guide, I could lead, but I also was allowed and should be a student from the people on my team, from others. And there's a vulnerability and confidence that has to come with that notion. And that was a massive piece that unlocked leadership for me than going forward.

In this episode

What does leadership mean to you? Ex-Shopify Chief Talent Officer Brittany Forsyth, used to think it was the same thing as management. Over the years and various leadership roles she realized it means creating a following and driving that following towards a common shared goal. In episode 7 she gives us insight into how she recognized her natural leadership tendencies and how they helped her land different roles - from managing a bar to becoming a C-suite executive.

She also shares the tricks she learned firsthand to manage a team and create the best dynamic possible.

She made lots of mistakes along her leadership journey and doesn’t shy away from sharing what they were and how to eliminate them.

Her main piece of advice: figure out what’s in your leadership toolbox and constantly add things to it throughout your leadership journey.

Tune in to hear all about how Brittany’s leadership experiences and advice can help you improve your leadership style!

Time Stamps

2:37 Leadership Levels

6:37 Leadership Styles

14:24 Differences between managing and leading

16:43 Leadership Toolbox

18:00 Reframing Feedback into Confidence

19:33 Journey to Shopify

29:54 Coaches aren’t just for athletes and leaders need them too

31:39 If you wanna look in a mirror, look at the culture of your organization and that's your leadership style

33:56 Digital by design

39:33 Leadership Common Mistakes

42:19 Angel Investing in Women and Non-Binary

45:33 Unpopular Leadership Opinions

Brittany Forstyh

Previously Shopify's Chief Talent Officer, and current Founding Partner and Active Angel Investor of Backbone Angels

Guest Bio

BRITTANY FORSYTH has unique expertise in hyper growth, talent and driving culture evolutions that she acquired as the Chief Talent Officer of Shopify (2010-2021). She played a critical role as the HR and talent leader for the company as it grew from a 20 employee startup when she started, to an international team of over 10,000 employees of a world leading public tech company. She excels in her role as adviser to founders, Board member and is an active angel investor in high growth companies on their journey towards impact.

During her time at Shopify, she built and scaled the Talent and Culture organisation from the ground up to eight (8) divisions including over 500 employees: Talent Acquisition, Strategic Leadership, Talent Operations, Diversity & Belonging, Development & Growth, Culture, Environment as a product, and People Analytics. She was integral to Shopify’s IPO in 2015. As an outspoken leader in the space, Brittany’s vision and her focus on development, growth and innovation are key elements which have helped firmly cement Shopify as one of Canada’s top employers.

In March of 2021, Brittany launched Backbone Angels, as the founding partner, along with 9 other brilliant minds. An angel collective aimed at providing more opportunities to women and non-binary founders. Since launch, Brittany has invested in over ten (10) companies.

Brittany has been an active and trusted advisor and mentor to countless founders. She has partnered with Bessemer Ventures as an Operating Advisor and continues to advise leaders across sectors. In her role as advisor, Brittany has helped CEOs, Executive leaders and Talent professionals to design environments and talent teams that drive growth and scalability through a strategic culture and a data-informed approach.


Brittany (00:00):

My favorite things as a leader that I probably learned during that time is that the notion of like, everyone's a teacher and a student at the same time. And so, yes, I could be a teacher, I could guide, I could lead, but I also was allowed and should be a student from the people on my team, from others. And there's a vulnerability and confidence that has to come with that notion. And that was a massive piece that unlocked leadership for me than going forward.

Fahd (00:36):

Hello and welcome back to the Unicorn Leaders Podcast. My name's Fahd. I'm your host. And on this podcast, we interview startup leaders on their journey of creating a high performing team on their journey of leadership and improvement. And, and we try to, to really pull out the insights, the mistakes, the stories. Our goal is to bring you the tools in order so that you can learn from them and you can learn from them on your leadership journey and how you are building your own high performing team. This podcast is brought to you by Unicorn Labs. That's www.unicornlabs.ca. Feel free to check us out. We're all about helping develop leaders that create high performing teams and help companies scale. And today's guest did exactly just that. This is Brittany Forsyth. She has got a unique expertise in hyper growth in talent, in driving culture and evolution, where she was the chief talent officer of Shopify from 2010, 2021.

Fahd (01:37):

She helped the company grow from when it was a 20 employee startup all the way to an international team of over 10,000 employees. And we're gonna learn about her leadership journey, uh, her insights in developing culture, her insights in being a leader of her own team. When we interviewed Brittany, it really, uh, uh, had me come to two different insights. It reminded me of two different frameworks that are so extremely crucial to all the leaders that are listening to this podcast. It's about understanding our own leadership journeys and where we are with it. There's, uh, what we call the levels of leadership, and then there are the styles of leadership, leadership style. So as leadership levels, leadership levels are kind of the degree of a relationship that one has with their team and with each individual, we're at a different leadership level because your degree of your relationship with that individual is likely different depending on who it is, how much time you spent with them, and how much you've worked with them.

Fahd (02:37):

Leadership styles, on the other hand, are kind of like golf clubs. You, you choose the right golf club for the right moment, the right leadership style based on what context is needed. So let me take you into leadership, uh, levels for a sec. And this concept is brought to us by, by John Maxwell. He, he writes a lot about this, and I found it really interesting because as Brittany takes us through her journey, she talks about how she moved from being an individual contributor, a contributor to a manager, to a director, and how she had to evolve her, her leadership levels and her style at the same time at different ways. When it comes to leadership levels, most of us, uh, assume that we've become a leader. Once we've gotten a position, once we've are like, Okay, you're now named the manager. And so you've got a position, you've got some authority, and if you're leading from that first leadership level, then you're leading from a level of authority where your own people are only doing what you want them to do because you have authority over them.

Fahd (03:34):

And that's really the lowest level of leadership. That's the lowest level of engagement, simply because you have authority over someone and you can give consequences. So they're gonna listen and do what you ask, but they're gonna do it to the minimum that they can get away with. That's typical positional leadership. It's all about authority. Typically, we start there when we're young and we're trying to figure out our way into manager and how that works. And then we dive into the second level. Many of us stay at the second level of leadership. Second level of leadership. Maxwell calls it permission leadership. It's really all about relationships. You have a relationship and a friendship with your colleagues and they follow you because you're the manager. You're in charge from authority perspective, but also because they like you. Cuz you're kind and and you've got ideas and you listen to them and you have a relationship with them and they trust you.

Fahd (04:20):

And so trust is really established at the second level of leadership based on relationships. And that's really where we start to develop. Most of us kind of stick around that level. We use a relationships level. Leadership now to continue to evolve in our leadership. We have to move past that. Level three is, uh, Maxwell calls it production. This is, this is when you got results. This is when people follow you because of the results that you've created. You're known in the team, you're known in the company as the guy who gets the most sales, as the person who's developed the entire app for the product that we have. The person who's, uh, built out an entire marketing campaign. And you've gotten results. When you start to get results, people follow you because you're the person who knows or you're the, the expertise. And so you evolve beyond just the relationship.

Fahd (05:09):

You become a person of knowledge that people seek out. The fourth level of leadership is people development. This level is when you start to use your time and your talents to actually coach your teammates, help them become better, help them find opportunities and make your team better. When you become a coach, you enter the fourth level of leadership, which I would argue is the level each and every one of us want to be at. When we're able to develop our team members, we're no longer just a manager. We're not just managing projects and managing budgets, but we're actually helping them get better. We're giving them opportunities, we're coaching them, we're using a coach approach. In how we give feedback and how we help them advance. This perhaps is the most underutilized opportunity in Maxwell's model. The fifth level is what's called pinnacle.

Fahd (05:54):

And this one is usually based on reputation. And it's kind of this elusive, You follow the people based on what they represent. So for example, you might have never met Obama. He doesn't have any authority over you. He don't have a relationship with him. You probably can't tell me what the results are of what he's done as an individual aside from become president. Most people don't know the, the specifics of it. And he's never coached you, but you believe in the idea of what he represents. And so that, that is pinnacle. Typically, most leaders don't enter that stage. There's a certain level of fame, a certain level, you know, Nelson Mandela, Martin Luther King, Jr. The ones that you can name off the top of your head. Most of us get to the point and the opportunity where we can develop other people, where we can use our coaching skills.

Fahd (06:37):

Those are the different levels of leadership. So I want you to ask yourself, when you think about your team, what level of leadership am I at with my team? With each individual, with each person that I work with? Am I at different levels? Now, depending on the different levels and depending on the different contexts, you need to have a certain amount of fluidity in your style of leadership. There are six key styles of leadership that we get from Daniel Goldman and I and I and I love them when I list them out here for you. The first one is visionary. This is one many of us have heard of. Visionary is when a person has a big idea, they're able to paint a vision of where you want to go, where we're headed. They don't take it day by day, but they have the skill of painting the future of where you want to be in a year, two years, three years.

Fahd (07:18):

And they're able to, to provide enough emotion to move us towards that vision. The second one is democratic. This is someone who always likes to involve everyone in their democratic style. You know, asking for opinions, consulting, bringing people in, really engaging democratic style of leadership, really trying to build a certain level of consensus. If it's not full consensus, it's a majority of people who believe in the idea that's going forward. Another style, The third style is the affiliative. This is the relationship based style. This is the person who, you know, wants to be the friend and wants to learn to lead from a friend's perspective and really building that relationship, getting to know you at a human level. The fourth style is the coaching style. This is the one I was referring to earlier where both you can see the level and the style, uh, uh, you know, cross over here.

Fahd (08:07):

The coaching style is when you take time to help people actually improve on their performance. There's coaching for performance or coaching for development. And one helps people with actually get into the answer in solution while other gives them the space necessary to fail and experiment. And the guideposts, those four styles tend to be really positive and effective styles. But the other two styles are probably the most common that we see in startups and the most common default styles. The fifth style is called pace setter. This is when your go go go that I will run faster. So my people run fast with me. I will push as hard as I can and I will work really hard so that other people work too. The pace setter, a style sets a pace because we've gotta hit a certain deadline. The pace setter style can be really powerful in certain moments, but can be destructive in the long run.

Fahd (08:55):

The sixth default style that happens is the commander style. This is the, you know, do as I say, style. I know what needs to be done. I know the strategy, I know what has to happen and I've gotta tell you what needs to be done. You need to follow. Now often people will look at pace setter and commander and say, Well, those two are negative, we should never use those. But that's not true. The secret is that we have to be able to use every single leadership style at a different moment. You don't want a democratic leader if there the building is on fire. We're not sitting here debating on, we should vote on how we should try and save people while the building's on fire. No, you want a commanding leader that says, Go here, do this. Nobody asks questions run during a, a very difficult moment.

Fahd (09:37):

A commanding leader is definitely needed in, in, in, in times where there is very short deadlines where you're competing for, for a big contract. A pace setting style could be really powerful cuz it can get everyone rowing in the same way at a really high speed. But if that's held for too long, that could be dangerous. We can see how the different styles show up based on different needs. A visionary style is key when we're setting direction of a big team. However, in, in, in small conversation, one-on-one conversations, a coaching style is really powerful. This is a key concept that we want to implement as we listen to Brittany's conversation, as we learn from Brittany and her insights as a leader, how she navigates the different leadership style, how she navigates the different leadership levels as she grows throughout her career. From an individual contributor, uh, contributor to a team lead to a manager, to a director, and finally to the chief talent officer of one of the biggest companies in Canada. So without further ado, let's hear another clip from Brittany.

Brittany (10:44):

Amazing leaders take risks. They say no, they, they put themselves out there. And that was something like we're talking probably in the last five years that I really started to do. Like it wasn't in the first eight years. But once you can start to do that, I think the team then really builds trust in you and you can take risks on your own and you can do more things.

Fahd (11:07):

What's the difference between leadership and management? That was the question that Brittany started to really ponder when she realized that. They used to think that, she used to think they were the same thing over the years, various leadership roles. She realized that being a leader means creating a following, driving that, following towards a common shared goal. And in this episode, she gives us insight in how she recognized her natural leadership tendencies, How they helped her to land different roles from managing a bar to becoming a C-suite executive. Uh, she also shares the tricks she learned firsthand to manage a team and create the best dynamic possible. She made a lot of mistakes along her leadership journey and she doesn't shy away from telling us all about it and really bringing us through that journey and how to actually eliminate them. Her main piece of advice is figure out what's in your leadership toolbox and constantly add things to it throughout your leadership journey. It's giving us that analogy of the golf clubs in our leadership styles. Can we add more golf clubs and know when to use which style, at what level in each other relationships that we have? So, tune in to hear all about Brittany's leadership experiences, advice that can help us improve our teams and our leadership styles.

Fahd (12:29):

Hello Brittany. And, and welcome to our Unicorn Leaders podcast. I'm really excited to have you. This, this has been an episode I've been really looking forward to having with

Brittany (12:38):

I appreciate you having me here.

Fahd (12:40):

Um, so, so Brittany, our our episode today as we've discussed is gonna be all about leadership and leadership styles, whether that's the coaching leadership style or whether it's how leadership styles evolve over time. And I like to kind of kick us off right away to get some of your thoughts on that. What are some, I guess what are your, what's your biggest insight on the importance of leadership styles and how they evolve throughout your career?

Brittany (13:06):

Yeah, it's a great question. Um, you know, I think over the time at Shopify and even prior to that in other jobs, um, early on, I always thought there was kind of one way to lead. Um, and I actually thought managing and leading was the exact same thing. And over the past decade I've really realized that one, there's like no perfect fit. There's multiple ways to lead. Um, leading is actually different than managing and there's just a lot of nuance to it. And so, um, I think I always look at it as each leader kind of has a toolbox and you need to pull out different tools depending on who you're leading, um, who you're bringing with you, what the skill sets are and also just the context around you. And so, um, for me, I like to think that I've really expanded that toolbox over, over, you know, the past decade and a half. Um, but it's been quite a journey to do so.

Fahd (14:02):

Yeah, I love that. You mentioned two things that I wanna pick on. Brittany, you said, you know, there's a big difference between managing and leading. Let's, let's, let's unpack that one right away like that. There we're probably getting some eyebrows here of like, ah, I felt like they were the same. What, the difference between managing, leading? How do, how do you differentiate them and, and you know, there's a need for both and when do they show up?

Brittany (14:24):

Yeah, and I'll only speak from my perspective. I mean, I went to school and did HR at university and did all these things, but, um, and so there's a lot of research that you can go out and go into, but I'll speak from my perspective and my experience. Um, so when I think about Leadering, like I realize now when I look back, it's always easier to look back in the rear view mirror. But I realize that I led far beyond my job at Shopify. I led in my friendships, I led when I worked at a bar, went from the hostess to the bartender and manager. Um, and to me what leading is is creating a following. It's driving towards a common shared goal and really, um, making sure that you're all aligned, getting it done and moving forward. I think managing is actually one of the tactics of how you get there.

Brittany (15:12):

I think managing is, you know, ensuring that people are at their top performance, that are having the impact desired. It is the feedback and um, you know, performance management that comes through it. Um, I think leading can come naturally, but if you don't know how to manage people, you kinda lose them along the way. And I think I did that early on. Um, I gave too much autonomy. I didn't give clear direction. I didn't give feedback cuz it was hard. I didn't let people go because they weren't performing because that was really hard. Um, but I was really good at leading throughout those times. And so I think the true, I mean, I think what we all aspire to be is a strong leader that can also manage and through both of those things, ideally grow a business, grow a team, and have impact.

Fahd (16:03):

Yeah, yeah. Yeah. I love that. I love that. That's, that's, I like how you've separated it too. I think is, is really, it's really powerful. You know, leading is, is taking, putting a stake in the ground, right? This is, this is what I believe in and this is where we're going and managing is being able to manage that group of people to actually get them there. Right? And, and the pieces. Yeah. You also mentioned a toolbox. You said, you know, you've gotta you gotta build your toolbox, you gotta collect your tools. I love that analogy cuz I think, I think that's, that's really what we're, what we're saying. There are tools for leaders and there are tools for managers. You gotta collect it. What are some of the, some of the tools that you've collected, I guess in your journey? Let's kinda unpack that analogy and, and set stage

Brittany (16:43):

For it. Yeah, I mean, on the leadership front, early on I was always, um, pretty strong one to one. Meaning like if there was someone, um, a friend or, you know, at Shopify, one of my employees on my team, um, a coworker, et cetera, I could one on one, you know, have a really charismatic, engaging conversation. I get very excited. Uh, I personally, so I get very excited and so like I can kind of create the hype and then we get in the hype together and it's like, Hey, we're gonna do this. What I couldn't do was one to many meaning like, funny enough. But if I think back to early days, like I would very often not have team meetings. I would have one on one meetings with all my team leaders or my team employees on my team, team members, let's say. Um, and I did that because it was easier to guide, it was easier to engage.

Brittany (17:35):

And so one of the tools that I built in my toolbox was like, influence to many. How do you clearly succinctly get up there, talk about vision, um, talk about goals and, and really create the track for everyone to come along. And it's just a different skill set. And like that took a while to build and I would still fall back on like my earlier skill, which was one to one. But there's a lot of problems that happened with that miscommunication, lack of alignment. And so like I really had to build that next level and that new tool. I mean, another one is like just probably a human trait, but is really a strong leadership trait, but is like receiving feedback. I think it's so easy, especially when, um, we're young and, and trying to develop ourselves to get defensive when we don't like what we hear.

Brittany (18:22):

I mean, we're humans after all. And so I had to build a capacity to receive feedback and like in real talk it's like, here's something you don't like and actually hear it and then like improve it and actually say thank you for that because it's gonna make me a better person. Like, that is hard. And so that was something you have to build up. Um, I think we all have like imposter syndrome. So sometimes when you hear the negative it's like, Oh my gosh, they were all right. I can't do it. And it's like, no, you gotta build confidence around that. But there's so many tools you build over time and it's all relative also to just the surroundings and what's required, whether it's like your company size goals, um, team size, what you gotta do, you know? Yeah.

Fahd (19:04):

Yeah. And I love that. I think you've mentioned that is that our, our leadership style and our leadership stage depends on where we are with our company, where our company's at. And so you've gone through quite an evolution yourself and I'd love to, I'd love to hear and learn about that. Um, yeah. So, so take to take me back a little bit, where did your leadership, uh, journey begin? Where, where, what's Brittany's story? Tell me a little bit about Brittany and let's go, let's go through a little bit of your leadership journey.

Brittany (19:33):

Yeah, I, I, So before Shopify, I would never say that I was a leader. Um, and now like I said, looking back, it's kind of easier to see, oh, some of the, the strengths and traits and skills that I have were there before, probably a little bit value based meaning like, um, just certain things that show up now showed up all the way through my life. And that is, you know, why when I was younger, I always had a group of friends that we were really tight and, and we would move forward together. And I probably led a bit there or why I went from kind of the bottom of entry level role in every company I've ever worked and then kind of made it up to a manager or the top mm-hmm. I've had four careers in my life and each one, whether it was Canadian diabetes, where I started as someone who called for donations to then became the supervisor for the shift and manager there, or the bar that I worked at hostess to bartender and manager, which is kind of the top of what I was able to do.

Brittany (20:27):

Or Shopify where I started as office manager and ended up as chief Talent Officer. I think for me, I always went in with extreme curiosity, a drive to do more and just a high, high level of respect and, um, care for the people around me. And I think those things kind of together allowed me to lead. Um, but what happened over the 11 year, 11 and bit year period at Shopify was I built that out so much more, like we said in the toolbox. Like cuz it was just required. You can't, it's different lead two people versus a team of 600. Yeah. Um, and so, and then also I will say there's a difference between leading your team directly down, but leading an organization. And so when we were smaller and I was just the HR manager, I was leading, you know, my team to then better Shopify.

Brittany (21:28):

But as we got bigger and as part of the executive team, you're leading the whole company. You're trying to create a vision of what should be. And so, um, it doesn't just happen overnight. Like, that's the other thing I think that you have to be extremely self-aware. That's probably other magic ingredient to it. I think you have to be really self-aware and realize what you need to grow and then constantly want to work through it. One of the things that, um, that's actually been the biggest driver towards leadership and growth is a growth mindset. And before Shopify would say, I had a more fixed mindset. And so that's probably the thing that unlocked me during my time there and really helped me expand throughout my roles at Shopify. But, uh, but it kind of is like each day is a new problem set and you challenge your opportunity rather, and you just kinda, you gotta show up and then do the work to be able to do it.

Fahd (22:22):

Brittany, I I love, I love how you have kind of talked about, uh, the different e pieces of your leadership and, and how it evolved. You know, you mentioned the one-to-one, one to many, how that was different when you first started Shopify, when you know, later on. I wanna actually go through those stages in more detail. If, if you don't mind me. So let, let's let's say, okay, fir starting a Shopify first. What was the first role? What was, Uh,

Brittany (22:45):

So when I first started Shopify, I was the office manager with a dash of hr, meaning they hired me as the office manager and I convinced them I could do HR stuff and for free. So I did that after hours.

Fahd (22:57):

That happens so often in startups, right? It's kinda like office manager, We need someone to do some HR stuff. Yeah. You wanna take care of it. Um, what leadership style was required of you in that role?

Brittany (23:08):

I mean, the only thing I would say is, um, a self starter. Like I had to find my own work. Um, because like when I joined, I remember telling Toby I wanted to do HR because sidebar, when I joined shop, I was looking to build up my HR resume. I didn't think I was gonna be there. I thought I would then leave and get an HR job. Little did we know. Um, but because that I convinced him like, let's do hr. And he's like, What is HR heart rate? And I was like, No, it's human resources. Anyways. So then I had to say, okay, what does this work look like? And so I think I had to like, the first one was just leading myself. Like it was like finding the work and doing the work and then presenting it. But that was it.

Fahd (23:47):

I love that. I I love it cuz cuz you know, there's a notion we talk about the title of leadership typically lags the action of leadership. Once you start leading and you start taking initiative and doing things, then people say, Oh, I think she be a great leader. Right? It typically lags. Yeah. So, so, so you know, if you're listening to this and, and you're in a role where you wanna be a leader, it really is take that initiative, be a self starter, find the problem and go like you went to Toby, it was like, you have a problem here with hr, let me help, let me do this. Right? Yeah. Like I love that. So that was kind of the self leadership, that super initiative, uh, kind of taking piece. What was the next role at Shopify?

Brittany (24:23):

Yeah, it's a good question. The next one was probably, um, I would say the next chapter would be where I hired my first few people on my team. Um, and where the HR was becoming more full circle. Uh, we went from, I was employee 22. We went from 22 to like 48 in like six months cuz we got our series A raise. Yeah. Um, so we all of a sudden had to, well I all of a sudden had to do a lot of work but lead a team. And so, um, I'd probably classify that as a very rocky start on the leadership cuz I don't think I knew what I was doing. Oh, I know I didn't. But it really was, um, it was like defining goals. Like, it was just like as simple as like, okay, I no longer am leading just myself, now I have to lead others. Like what is the outcome? Like what do we need to do here? And getting people on board to that. I don't think I was getting necessarily the best outta them, although they are amazing humans and they were self starters. But like what I was trying to do was just get us all on the same page.

Fahd (25:26):

Right. Right. I love that. If, if I may, I'll probably classify that as almost team building, right? You you kind of went to like, I've gotta build a team, I've gotta get them roll rolling in the same direction. Yeah. But I have to actually talk about my goals now. Cause before when you're self starter, a lot of stuff are in your head, Right? I'm gonna do that, I'm gonna do that. But now it's like aligning people and getting them to actually buy into it. Like that's the next step. That's the next phase.

Brittany (25:46):

And you make it sound so beautiful. But it wasn't cuz it was like one to one aligning. It was like one to one team building. Like it was a shaky time. Let me be honest.

Fahd (25:55):

Yeah. Well no, I appreciate you and usually I have to ask like, what were the next mistake you made during that phase? But like you're just blisten them out for us. And I appreciate that. Cause I think that's, I mean, as much as we, we can learn about leadership and we can, we can teach it, It's, you can't, you can't read about what a banana tastes like.

Brittany (26:12):


Fahd (26:13):

And, and at some point you can't just read about leadership, but it's, it's going through it and those mistakes and that pendulum of, of swinging one way to the other. Right? Yeah. You were super one to one and you, you know, you, we gotta swing you to one to many. Some people are super one to many have no one on ones. Right. And, and, and we're all kind of going through that swing and I really appreciate that. So then next chapter,

Brittany (26:35):

The next chapter for me was, okay, so I built a team. We were growing, we were continuing to raise money for the company. So like growth overall. Um, and I think it was probably around confidence to be honest. I was doing all these things, but yet I was so afraid to fail and I was failing less be honest, like you're, you can't help but break multiple times over in a hyper growth. Yeah. But I wouldn't admit it. And so I, I think the next piece was actually probably a Brittany piece, which was like confidence in self. Again. Like it's funny how it ebbs and flows from me to we, to me, to we, um, or did for me anyways. And it was confidence in what that allowed me then was to be vulnerable with the team and say, Here's some things we messed up at.

Brittany (27:19):

Or once again yeah, share feedback with me cuz we can do this better. And one of my favorite things as a leader that I probably learned during that time is that the notion of like, everyone's a teacher and a student at the same time. And so yes, I could be a teacher, I could guide, I could lead, but I also was allowed and should be a student from the people on my team, from others. And there's a vulnerability and confidence that has to come with that notion. And that was a massive piece that unlocked leadership for me than going forward.

Fahd (27:48):

I love that. I love that. That's such a good little clip there too, right? Like <laugh>, I just, such a good notion. Everyone can be a student and a teacher at the same time. And I think, you know, one of the concepts that we, we discuss and some of these podcasts is the idea of creating psychological safety for our team. One of the kind of reverse ones and and you just hit the nail in the head for me, was well we also create psychological safety for our leaders.

Brittany (28:10):


Fahd (28:12):

Cause if, if, if I don't create it for my team where they have a safe space, then I feel like I always have to be right and, and know what I'm doing. And I can't be like, I actually we're making this up as we go <laugh>. You know?

Brittany (28:22):

Um, and for me that journey, like it, you make me realize even, which is, this is the fun part of what doing a podcast is you can you become so aware of self and you know, your own journey. But I had to figure it out on my, my own. And so like whether it was, um, doing it yourself versus then doing it with a team or here, which is building my own confidence. Then I was able, I'd say that next chapter was building confidence in psychological safety in the team. Which was, I can, I can hold this. And also the, the combination was with risk. Like I could take bigger risks. Cause I think amazing leaders take risks. They say no, they, they put themselves out there. And that was something like we're talking probably in the last five years that I really started to do. Like it wasn't in the first eight years. Yeah. But once you can start to do that, I think the team then really builds trust in you. And you can take risks on your own and you can do more things. And maybe it happened a bit along the way or else I don't think we would've been as innovative, but we really ied in anyways with the team until later on was something that had to be worked on.

Fahd (29:30):

Yeah. Yeah. I love that. I love that. And I love how you talk about the you know, it goes from team to self and team to self. And I think what's, you know, when I kind of see that from a third party perspective, what we always say is that, um, managers at one point leaders realize that teams hit a capacity based on their own leadership capacity.

Brittany (29:48):

Hundred percent.

Fahd (29:48):

Right? And so when you hit that, you're like, Oh, I gotta go back and work on myself. Cuz right now the limit is me.

Brittany (29:54):

Yeah. The limit is, most of the time I had a coach from uh, like my first few months of Shopify all the way to the end. I had few different coaches. And I think it's so important. Like I remember early on Toby said to me, um, the best athletes in the world have coaches, so why wouldn't we? And it was so simple. And so I've been lucky enough to have four amazing coaches over my career at Shopify and I still seek coaches now. Um, but the most annoying thing is you always, when you're in tough situations or you feel like you're breaking as a human with your team, whatever it might be, you go to your coach to like, go bitch, let's be honest. You like, this isn't working, da da da. And I can guarantee you that the end of each of these sessions, the coach is always like talking to you. And then in the end you realize, oh, it's all me. It's me that has the power to, which is, which is amazing cuz you have the power to fix it. But it's also like just that repeat that you need to hear that it starts with self. Um, Yeah. It's so, so important.

Fahd (30:56):

I love that. I love that. It's uh, that's such a good one. And, and it it is us and I think that, you know, leaders like yourself, Brittany, who've who've gone through some of the challenges and, and have found success, have the humility to realize it to me, right? Yeah. Like there's a certain self-awareness and there's a certain humility I say where you don't believe in your own bullshit. Right? At some point when you're part of a super high growth startup, things are succeeding. You know, there's, there's the trap of Oh, we're so amazing. It's all us. Look at what we're doing, look at what we're building. But the fact that you had the humility to have a coach, the humility to recognize it was you, I think is such an important character trait that that is part of that leadership journey. And, and genuinely kudos to you. Right. So thank you.

Brittany (31:39):

I appreciate that. But I completely agree on how it ties to being a strong leader. That would probably be the next chapter or piece some along the way, which is like the awareness and the culture you create on your team, which then allows that. Like I think that as a leader, we used to talk about culture. That was, culture is such a passion of mine. What I really think it is. You know, the one product that an HR person gets to build, which is the environment in which we build and how people show up. And so I was always very passionate about that. And the first thing you realize when you think about culture when you dig into it, is it's led by example. So like leadership is critical in any culture. And when you look at Shopify, the culture is built by Toby the founder, by the executive by the leaders. And if you tried to say any different but then didn't walk, the talk culture was broken right away. Yeah. And so, like, if you wanna look in a mirror, look at the culture of your organization and that's your leadership style.

Fahd (32:40):

That's, that's so powerful. I love that rn I love that you, you've hit the, Cause there's a lot of talk about, ah, you can't create culture, you can't dictate it. And it's, it's, it's true. You can't create it in that sense. Right. It's not a, it's not a product. You can't just make it a policy. You can't, but you

Brittany (32:56):

You can involve it, you can, you can definitely, Culture shouldn't be stagnant. You can't just like set it and oh, here it is. Like you can definitely, you can build a nurture culture. You just can't, you can't just say it just like what you said earlier, which is you can't just all a sudden say, I'm a leader now follow me <laugh>. That doesn't work. You can't be like, my culture is innovative now let's innovate. Like that doesn't work. It has to be a representation with a little bit of a nudge towards something better. Yeah,

Fahd (33:24):

Yeah. We always joke about demanding psychological safety. <laugh>. I demand that you feel safe. Um, you know, Yeah. And the idea of that, but our leaders, leaders by example. I love that. And so, kind of you're taking us through that next chapter, which was you had to start to realize, I'm not just responsible for myself or my team, but responsible for the culture of the organization and the examples that we're setting. And so what did that do for your leadership style?

Brittany (33:56):

Um, I think the interesting thing about like evolution of the leadership style as it's almost full circle moments. Yeah. Because at that point it almost went back to self and then many, and then like the, the vulnerability and the confidence piece again and you know, it, it really goes through that. But just at a whole new scale. Um, and so you're, you're relearning things. You're expanding the notion of it. Um, and so, I mean there's so many like small things daily that you would learn, but I think that it's like instead of just taking risks for um, hr, you're taking risks for whole company. You're leading a vision of what you think should be. I mean, so two and a half years ago when we said, or however, yeah. Two and a half years ago when we said we're gonna be designed digital by design cuz of covid, we're gonna all go from working in offices to now working from home. I love that.

Fahd (34:50):

That was goal. That was early.

Brittany (34:51):

Yeah. Yeah,

Fahd (34:52):

Yeah. Yeah. Not too many companies haddone that was very early on in the pandemic. Sorry, I'm jumping in there. But No, to kind of like, because I think a lot of companies are saying that now and, and it's like, okay, yeah. But let's, let's talk about that bold decision that was made Yeah. Very early on. And it wasn't loved by everyone either. No, right?

Brittany (35:09):

Like, no, there's many people, One of the things I think you need to know as a leader is that if you're only to your point earlier, but if you're only hearing that, that's so great and that's all good. Like you've either peanut buttered the whole decision. So like, it's not actually impactful, it's just man or else you're not hearing something. And so when we launched that, I mean, that was like, I can't take full accountability. It really was a leadership of like Shopify decision, but I was leading it on behalf of that. And so I had to go out and say all the things, talk, the strategy, go through it, and people hated it. And it's so easy to wanna get sucked into that and say, we gotta change. I think you gotta be bold, you gotta be brave. You got to remind yourself of the true core of why you're doing something and what it's supposed to be.

Brittany (35:55):

Cuz the, the how is gonna change and evolve. But I think you can't get out of track. Like you need to really drive something forward. And so there's a perseverance or a dedication to the why that is so critical. Mm-hmm. Um, and I remember hearing so much negative, and by the way, so much positive people loved it and hated it. There was just no really in between. Yeah. And that to me is a sign of a good decision. Yeah. It's that it's divisive, that it's gonna, and then you can work from there and move it forward. Well

Fahd (36:23):

You took a bet. Right. And I think, I think that there's that part of it, right? Yeah. There's so many companies try and straddle like, we'll fit everything. And as you kind of said, put peanut butter all over, you've done nothing. Right? Like you, you're not taking, you're not taking an opinion. And you guys said, No, we believe this opinion, this be is the way forward. And I mean, look at all the companies that are followed, like, you know, that was a, a clear, clear piece.

Brittany (36:46):

And there's gonna be so much that evolves from that. And they're probably like, I think major change always overs, swings and it comes back to the right balance. Mm-hmm. So like I'm really intrigued to just watch the industry and how things will ebb and flow. But like I always go back to just a core belief, which is like, no change is the easiest. So in uncertain times when you don't have all the information, the easiest and the most comfortable thing to do is to just stay the same. And I fundamentally believe that is the wrong outcome. So how can you take all the information, I used to say, take the data points, evolve your thinking, it will come, but how do you start to make better decisions? And I think it's being like uncomfortable is a good sign. Um, and I think as a leader, as a manager, as a human, you know, these are the type of things you need to build when you wanna innovate. Um, and so over many, many years I was able to cultivate some of those skill sets and they showed up at the right time for the digital by design.

Fahd (37:46):

I love that. I love that. And, and, and that's, that's really cool. And I think, I think, you know, that's kind of the, the accumulation of the leadership journey, you know, that you've been on makes you have the confidence, the right culture in order to take these bets in order to feel that you can, you know, we can, we can make a bet, we can make a play. We know we're gonna upset some people, but we know that we have a culture that allows for that discussion, that debate and uh, and people to engage in.

Brittany (38:11):

And the only thing I would add there is cuz we're, we're talking, um, so much on leadership. I think the non-negotiables for me in regards to management that needs to follow this and really should be from day one to the end, although I was pretty crappy at it in day one. But, you know, work towards it is like, you need to have clarity of expectations. I think that's nonnegotiable as a manager, you need to provide timely and accurate feedback. I think that's non-negotiable. If something isn't working, you should hear about it right away. And if you don't, that's on you as a manager. And I think you have to like, I I was gonna say cut the fat, but that's not a great term. Like I think you have to believe in a weak link system, meaning your team is only as strong as the weakest member on it. Oh yeah. So use that as a guiding principle to what is your standard of performance and impact. And I think obviously that's over simplistic, but if you have those three things, I think you'll be able to manage over time. And that's critical to then go hand in hand with how you lead. Mm-hmm.

Fahd (39:12):

And I mean on this, on this topic as we're kind of adding some tools here to people's toolbox, right? Kind of what you're mentioning. Yeah. What's, what are some of the biggest mistakes that you commonly see happen in as, people develop their leadership skills, right? So you on different leadership journeys, as they develop their leadership skills, what's some of the common mistakes?

Brittany (39:33):

Well, I'll speak from my own experience. I think when you start to be able to share a vision, speak one to many people are starting to say, Oh, I wanna do that too. It feels so good that you forget that you have to manage them. You assume they're doing what you're saying and you're not checking in, you're not providing feedback. Um, you're not saying what you actually expect cuz it's sometimes hard to say what you actually expect. It's kind of believed within. Um, I think it's, you know, when you go from a team of 10 to 50 that you forget to onboard people. Like I know I did that. I was like, Wait, you weren't here two years ago when we made that decision and you don't know exactly why we made it. Of course not Brittany. So like, I think, I think there's plenty of pitfalls, which is like context is is key.

Brittany (40:17):

So like, whether that's through feedback, whether that's through setting expectations, whether that's just through a context behind a decision. I think context is key to moving forward. And so that was one that I lost because I thought everyone had the same context and that's obviously not the case. Um, but then, like, I still remember the first time I had to fire someone. And I see this all the time, like, people hate firing people for good reason. It sucks. You are impacting their life. But I always remember that, you know, it's kind of like a, a relationship, like someone you both know it's not working. Someone has to make the call and then you both kind of take that breath of relief like, oh, now we can move on. And so instead of a bad relationship, um, because really what employment is, is it's a, a two-way relationship that has, you know, ins and outs from it. Like have the conversation and think of the bigger team and company and what you need to do. But I mean, high performance and, and letting people go is probably something that just people challenge with the most. Yeah.

Fahd (41:21):

Yeah. Yeah. I appreciate, I appreciate those insights and I, I really like how we created a little bit of, of a theme here right. Between management and leadership and we kinda keep getting back to it. And I really like it cause cuz what we're talking about is a swing between the two. If, if you're a really good leader, but you're missing some of the management skills you've kind of mentioned here, make sure we're doing these things, feedback, exciting expectations and so forth. You, and we get some really good managers who fail to have some leadership skills and they over process things and they, like, all they do is set processes and systems and templates in place, but then there is no vision. Where are we going? Where are we headed? What's exciting? There's, you said, you know, you can get people hype, like that's a right, can we get people excited over something? Right? So kind of that, that swing between the those two, um, is, is so key. I I love that. Now, now Brittany, you've, you've kind of concluded some of your time at Shopify and you've moved on to some new projects. Let's hear about that. What have you been doing out in the community now? You've had some really interesting projects.

Brittany (42:19):

Can you tell I'm excited. It just went from like normal face to a big smile when you asked that question. Um, so when I was still at Shopify, myself and nine other amazing women at Shopify decided to create an angel collective to invest, um, in women non-binary. Um, and really just people that aren't able to get, uh, angel investing early stages and due to minorities or just. Um, we wanted to, I mean, tldr we wanted to give opportunities to people that weren't getting opportunities. Yeah. Um, and so we launched Backbone Angels in March of 2020 and or March, 2021, Oh gosh, now I'm gonna mess this up. I'm gonna just say March a year ago, <laugh>. Um, and uh, the best part is we have invested in so many companies and they're all women led, um, or one of the founders is women. And so it's just so cool to see, um, the opportunities that you can provide.

Brittany (43:22):

It's close to my heart. I get to do what we're doing here, which is I get to advise and talk through how to build companies. I get to help where I can and honestly, I get to learn so much. So that pinnacle of being both a student and teacher to me, I'm in the perfect match of that where I get to just like, learn about industries I would've never been able to deep dive into. Um, but then I get to teach from my experience, which is humans, which is leading, which is growing a company. Um, and it's just badass to see so many, you know, women, but also all minority groups getting funding and building companies. Because when you go talk to VCs and you're like, Okay, what's your split? And we'll just talk gender to start, what's your split? And they're like, Oh, we invest in women too. And then you ask for numbers and it's just like depressing. Yeah. Um, so they're out there, uh, and we're helping to give opportunities there. And I gotta work with 10, nine other amazing women that I just deeply adore, which is fun. I

Fahd (44:16):

Love that. I love that. I'm, I'm gonna give that some snaps here. Yeah. Just, you know, some, some true love. I think that's such phenomenal work that you're doing and that's, that's you continuing your leadership journey, right? Like that's, that's taking an opinion, taking a stake, finding a problem in our community that you want to work towards and, and, and creating solutions. And I think that's fundamentally what leadership is, Right. Taking that initiative kind of full circle back to Yeah. That HR office manager moment, Right. Of like, I see a problem, I see something that I can help fix and here's what I'm gonna do about it. So I that's, I love that. I love that. Well, well, Brittany, we're almost at the end of our, our episode. I like to, uh, kind of leave things off with, uh, a bit of a, uh, maybe some questions to think about for, for our audience.

Fahd (45:01):

Some things to leave them, pondering about what we've shared. Yeah. And so, uh, you know, what, what are, what are some, some last pieces of thoughts, maybe, maybe controversial, unpopular opinions about leadership, You know, maybe some, some opinions that are not heard enough and, and kind of get the pot stirring about what we should expect of ourselves when we're building companies, building cultures, when we're building leaders. Or if, if, you know, you're a VP of talent listening to this, you know, what you should do to invest in your leaders and your companies.

Brittany (45:33):

Yeah. Maybe I'll take the stance just of what you should ask yourself. Um, but maybe, I mean, it probably goes to what you should ask of your other leaders as well, but I think, um, I think one question is just like, are you getting feedback as a leader? Like, what do you not know? Like if you think you're doing great and you're only getting positive praise, I can almost guarantee you that you're not listening to someone who's probably the most honest. Cuz nobody's perfect and no one should be aspired to be perfect cuz that's an illusion. So I think that's just the first one. And then I think it's, you know, how are you setting up your leadership style? What are you growing in for so long? I tried to be a leader that I wasn't. I tried to be a corporate exact leader and I was failing.

Brittany (46:22):

Like, I, I remember someone came to me one time and just said, Where did Brittany go? Like, you don't seem like yourself. And it was, yeah, it was a little upsetting, but it was probably the best feedback I could have ever gone cuz I realized I'm trying to be this persona of, you know, Canada's top company executive. Like, that's not me. My real me is authentic, it's real. I'm gonna tell you the good, the bad, the ugly, and then I'm gonna tell you what we're gonna do to fix it. And it's gonna be big and bold and like, I just, I yeah, ask yourself who are you trying to be? But who are you really? I think authentic leadership is probably the most powerful leadership out there. And so yeah, just check in with yourself. Yeah.

Fahd (47:04):

Yeah. I love that. I love that. I think that's such a powerful message for us to end with today. Uh, who are you as a leader? I think that's, that's kind of what you were, you know, where did Brittany go? That that's what they were asking? Who are you? Like, where, where was the leader? We got to know? And thank you for sharing that. Thank you for being vulnerable, Brittany, thank you for being on our show today at Unicorn Labs. Such a phenomenal guest. Such a phenomenal conversation. Thank you so much for being here and, uh, we look forward to hearing from you again. Maybe having you on another episode with another John Baker, seen all the amazing work that you're doing and hearing more about the community of leaders that you're helping build, uh, through your angel group.

Brittany (47:47):

Well, thank you. It was a lot of fun and good, uh, good time. Kind of reliving all of that. It's always nice.

Fahd (47:53):

Thank you Brittany, so much for joining us in this podcast. It was wonderful to be able to have a conversation and really, uh, understand the journey of building a high performing team at Shopify, Building culture and her own leadership experiences. Thank you to all the listeners who've made it all the way through. You are fantastic. You're awesome. Love that you are making it through our episodes and you're enjoying it. If you've got any questions, if you've got topics that you're interested in, please, please, please find us on social media. You can find me @fahdalhattab, you can find us on Unicorn Labs or you can email me directly fahd@unicornlabs.ca and you can find us on LinkedIn, on Twitter, on Instagram and everywhere possible. That is it for today. If you wanna learn more about Brittany and her adventures, feel free to jump on our website and look at Unicorn Labs podcast.

Fahd (48:42):

You'll find a detailed transcript of the episode, all the show notes and details about her bio and all the, uh, more recent adventures that she's been on, um, where she's launched. Uh, Backbone Angels, she's a founding member with, uh, nine other brilliant minds. She sits on several different, uh, boards and is a, an advisor and a mentor. Many different startups, which just super cool to see, so you can find those show notes, find that transcript at unicornlabs.ca/podcast. If you like the content, be sure to rate it, review it, subscribe, send it along to some friends, some managers, other folks who could learn from this content. Maybe share it on social media and give us a tag. I wanna leave you with this last question to think about for today. What is your default leadership style? Not the style that you would like to think you have, but the one that you default to.

Fahd (49:35):

I know for me and fortunate, I default to commanding style. When things get tough, I just kind of say, This is what needs to be done and this is where we gotta go with it, and I gotta spend a bit more time in coaching. I gotta spend a bit more time and affiliative, and I can recognize that and I can see it. And I want to ask you, what default style do you fall into when you're under pressure, when things are tough? Do you have a default style? And what style would you like to work towards? Give that a thought. And with that, I'll leave you there. Tell everyone and we'll see you again. Bye.

Subscribe Now