The Difference Between a Leader and a Boss

Episode Transcript

Aydin Mirzaee 2:20

Kirstine, welcome to the show.

Kirstine Stewart  2:18  

Hi, thanks, Aydin. Nice to see you.

Aydin Mirzaee 2:20  

Yeah, this is going to be fun. I’m very excited to have this chat with you today. , you obviously have a very extensive career in leadership at all sorts of different companies, obviously, you lead the CBC, you’ve held executive positions at Twitter, and now you’re at the World Economic Forum. 

And for obviously, those that still haven’t read your book, Our Turn, which we definitely recommend, is another thing, so you’ve also been an author. 

So one of the things I wanted to do before we get into the nitty gritty of it was just basically go back in time and ask you, who was your personal favorite manager or leader, or someone that you reported to earlier in your career?

Kirstine Stewart  3:11  

Now that I’ve had quite a few years under my belt, it’s interesting to think back on the kind of past that led me here and all of the twists and turns along the way. 

I always say that part of the benefit that I’ve felt in terms of how I’ve grown as a leader is because I’ve had the benefit of having all kinds of bosses, because I worked my way out. I was someone who started out literally as a, what they call a Girl Friday, back in the day. And that was someone who did everything from file papers, when we used to have papers, to, faxing, to changing the water bottles in the water coolers.

So starting from that kind of position and working my way up. I had a number of bosses along the way. And I think sometimes you actually learn as much, if not more from some of the bosses that are challenged, and maybe aren’t as confident or good at their jobs as the ones who are fantastic. 

And so I think, the journey is what I kind of look at as a culmination. And I have had fantastic bosses like the very first boss that I had out of school in that job where I was a Girl Friday and then quickly moved on to a Sales Executive position within the company was a woman who had a small business, but a really impactful one. It was a global international television distribution business. And she gave me a lot of opportunities. She recognized that I was a go getter from the start and really supported my own growth and gave me challenges along the way. 

So I think what I learned was the importance of , leadership, provided access to a path, not necessarily building that path for you and that ability to support. You as someone coming into a role or learning your own way, and building your own career as a support rather than, a lot of people talk about mentorship. 

Although I understand the benefits of having someone as a particular role model, I like to build a whole cabinet of characters who kind of guide me through the process of what is life because hearing, you need to open all kinds of levels. 

So other than the first boss that I had at Paragon when I was starting out in my first executive roles, I would say it’s kind of a combination of all pieces of great leaders and maybe not so great leaders that have given me the framework to build my own sense of what a leader needs to be.

Aydin Mirzaee 5:56  

Yeah, and talking about what a leader needs. Was your first leadership role in that first company?

Kirstine Stewart  6:05  

Yeah, it was actually when I started. It was one of my longest 10 years at any one company. I was there for seven years. I started out at like 19-20 years old graduating right out of university and as a Girl Friday, and by the time my time at Paragon was done, I was president of the company. 

So I had started off as the receptionist and Girl Friday, and then we moved along to different positions, and the company grew at the time, and when the president left, she, obviously needed someone to replace her. I’d been working at her side for so many years. I think I made a lot of sense at the time to pass it to me and it gave me an opportunity to really grow because the business grew even past that. And so it was, it was, a series of different jobs, but it ended up being… and the result was I was the president of the company, which is kind of cool.

Aydin Mirzaee 7:03  

Yeah, that’s awesome. That’s usually the sort of thing you watch in a movie or something. But this happened in real life. So I have to ask you, basically starting out in those very early days, I mean, you talked about this person, how she was great at noticing that you were a go-getter and giving you more and more responsibility. And you obviously, being able to take that on.

What would you say changed in your own leadership style from those very early days that you first took on management responsibilities to obviously where you are today, what would you say is the biggest difference or the biggest change that you’ve noticed in yourself?

Kirstine Stewart  7:45  

I think for a lot of folks, as I watch out there, people embrace leadership for the first time and what it’s like to be a manager. We all get caught up in this, not necessarily understanding the difference between being a manager and a leader and being a boss. 

I think some of the mistakes I made early on were, thinking that I had to be a certain kind of person, especially being younger in those manager roles and met leading people who were older than I was and more experienced than I was in terms of their years of working in the business. 

I think sometimes you build up this persona that you have to be right all the time, or you have to know the answer, instead of understanding that actually, part of leadership is tapping into the great brain power and skill set of the folks that you are leading, and helping them unlock and unleash that to contribute to a bigger picture. 

You’re there to really think about what the direction is of something as opposed to knowing all the answers. Actually, the best role a manager or a leader can have is to ask all the right questions. And particularly today, when , Google gives you a lot of the answers. , I think great leaders are the ones you can ask them and really challenge their teams to rise to different crap. 

What are the questions that we need to answer? So I think, a lot of what I probably did in my early days was think that a manager was a boss, and a boss was someone who told people what to do. And that’s not the best way to lead. I know that. 

I learned that from my own experience, as I said, working my way out, I had a number of different bosses. And those were not the ones that I thrive the most, and are the ones who were the kinds of leaders that opened up doorways and opportunities and provided guidance and not instruction were the best ones. 

I think that that was what I learned not just as a manager myself, but being managed, that there’s certain ways to motivate people… and telling them what to do is not one of them.

Aydin Mirzaee 9:57  

Yeah, I think that is so important. I just have to emphasize it. Because oftentimes when you are starting out and you’re an individual contributor, it is very much about having the answers or finding the answers. And all of a sudden, there’s this transition. And yes, it might be, obviously a promotion to and , you have a title and things, but it is a shift in role. So it’s actually not the same thing. And I love what you said, which is like your job is to ask the right questions. I think that’s incredibly powerful.

Kirstine Stewart  10:32  

And you have to be okay with ambiguity. You have to be okay, that sometimes there is no right answer. Because a lot of this world especially right now, like we’ve seen how quickly industries move, how, how things change, and no one predicted the situation that we’re in right now with this pandemic. 

So the ways that businesses need to be flexible and agile and not get caught up in what they thought should happen and just be prepared for anything could happen. I think that’s when you have to be okay with not knowing all the answers, but being ready to explore all the opportunities.

Aydin Mirzaee 11:08  

Yeah, totally agree. And so, thinking about this concept of, obviously this is not just a promotion, one of the things that you’ve said in the past is “altitude is not the only way to measure success. You can choose to be a leader in whatever work you do, because leadership is a mindset.” I wanted to ask you. What is a leadership mindset, in your opinion?

Kirstine Stewart  11:37  

I think, especially today, I feel for people entering the workforce, where there doesn’t look like there’s necessarily an easy path of like this upward trajectory of this idea, like when you said the beginning, it sounded like a movie like it’s… I think people enter the workforce thinking that one job will lead to another, will lead to another, and by the time I’m 30, I will be X. And that’s not necessarily anybody’s path, it wasn’t my path, you have to accept that was going to be a bit of a jungle gym that you have to reach for this and you might be getting that. And the path isn’t always a straight line, I can be quite meandering and I can go backward sometimes. 

And so I think the challenge of kind of applying yourself and making sure that the path fits you is one that’s most important. I think that’s why sometimes if you look ahead and you think that title is not necessarily matching what you thought you’d be at the particular time of your life or a time in your career, you recognize what leadership is, is not necessarily in a title. It’s in your impact. 

It’s in the strength of your impact and that strength of impact. Sure you can be the boss of an industry, you can be the boss of a company. You can leave a project, you can leave, something right at your own desk. And I think that impact that you make is one that is measured. That’s what you should be looking at as a measure as opposed to the title that you have. Because it will leave that impact that you have in a particular role that you’re playing, whether it is, the leader of an idea or project within a bigger system, that can lead to the next step very quickly. 

It is also an opportunity for you to kind of flex those muscles and learn what you’re good at, and where you can apply yourself so that you can create the most impact. So I think leading where you are is an important sense of that leaders mindset. 

I was at an event once and it was soon after I had written the book. Our turn. Random House (the publisher) had sent me on a book tour and I had done a few events where I was speaking to large groups of particularly younger women. Who were looking at what would be opportunities for their own careers? And afterwards I got a question from one who said, Look, it’s all great what you’re talking about, but  you are a boss you are a leader. So what do I do? I am and she told me her situation she was a researcher in a large sales company in a sales unit. So I said,describe for me your day, what does it look like? 

And she said, she often sat at meetings where she was the source of a lot of information because she was the researcher and the sales guys mostly guys sitting around the table, we kind of just pepper her with questions and at the end of it, she just felt like she was just being kind of used for the information and didn’t really feel like she was creating any kind of impact. 

So I said, look, try this next time. Those sales guys need your information. You actually have a lot of power. You have a lot of strength, and need the information that you have, you obviously have some ideas about some of the information that you’re gathering, you’re not just there to spew out detail, you actually probably start to notice, given your breadth of experience with all this data, you’re probably seeing trends or you’re probably seeing things that are happening that you might want to present to that group. So why don’t you next time, say instead of sitting in the meeting as a kind of repository of information that you’re just being tapped into? Why don’t you suggest to the group leader that in the next meeting, you’ve noticed this data, the other thing, and the data that you’re that you’re examining, and that you want to present it to the team as a strategy or as an idea, and in that way, you could lead with the data as opposed to just kind of doling it out. 

And she followed up with me afterwards and she said she did that and she said that completely changed the way her relationship worked with the sales team. She was someone leading a sales team with ideas and strategies because she wasn’t just giving out the information she was analyzing it and, and coming up with ideas based on the data. So, in those ways, that’s, I think, an example of how you can actually step up and lead because you actually have a benefit or advantage. Why not use it?

Aydin Mirzaee 16:22  

Yeah, I love that. I mean, so many valuable points there, obviously focusing on impact above all else, and also seeing how you can actually drive information not waiting to be asked questions, but figuring out insights and then distributing them elsewhere. So I thought that was super valuable. 

So just following up on that last point, one of the things, I thought you’d be a great person to talk to you about was this concept of a leadership mindset and, some of the points that you made, what are some things at a larger organization that you can do to foster that mindset?

 So for example, when you were leading large teams, how did you make sure that that kind of a mindset actually flowed through to everybody else in the organization?

Kirstine Stewart  17:16  

I think as a leader, it’s important again, to recognize that you’re not there to be the only leader at the table you’re actually there to empower others to lead as well. So the opportunity you have as a leader particularly in a big organization, or with a big team is to understand where your skill set is and what who the others that are around you. What are their particular skills and benefits because ultimately, you’re assembling a team and you’re only as good as the team and how they work together. 

So tapping into their strengths and their skills is an important skill of your own as a leader and then empowering them to lead themselves is important as well. 

So I think you hear a lot about delegation and people who are good delegators and bad delegators. And I think sometimes it’s a matter of understanding, it’s a control issue, that some leaders are maybe not confident in their ability to let go of the reins a bit and really empower their teams to, to lead and come up with their own kind of strategies. I think as a leader, the important thing you do is is empowering others is to understand what their skills are and how they fit in with your, how they fill in the gaps that you don’t have, necessarily how they, how you as a team functions all together is how you can empower that group that works with you to really kind of rise and really kind of flex those muscles around what their particular skill set is and where they fill in gaps that you don’t have and that others don’t have around you. 

So it’s, I think it really is an understanding of the group dynamics, the skill set of the people that you’re pulling together as a team, and how to optimize them and how to really kind of give them the road. We’ve always said the best thing a leader does is kind of set the vision, like you have a leader, you have a responsibility to, to view the future and to really kind of set an idea that people can get behind. And so that they feel that they understand what success looks like. 

Once you determine what that meaning of success is, and what that vision for the future is, you, as a leader are supposed to provide the team with the kind of tools or assets that they need to get there. And then you gotta get out of the way. So it’s like setting the vision, bringing the tools, and then getting out of the way. And I think that’s really the best kind of guidance that you can give to a leader is that that is the role that they play is not necessarily to sit down and everything but to actually embolden others to take up what they can do in terms of their skill set, and really rise above.

Aydin Mirzaee 19:57  

Yeah, no, this is really interesting. And I know you Talk about this in the book as well, when I guess the Sochi Olympics were happening, just to reiterate for for the audience here, you have this framework of obviously set the vision, build the tools to lead the team to success, set goals, and then get out of the way. So this Get out of the way thing is actually probably more important than then people would think, because of, because I think that most people don’t do a good job of getting out of the way. So, just to ask the, maybe novice question here, if you’re getting out of the way, how do you kind of balance that in terms of feeling that you have an impact and feeling that you were able to contribute to the success?

Kirstine Stewart  20:47  

Sure. And I think too, it’s a convenient security thing and that you can trust the team to if you get out of their way can you trust the team to keep following what you set out as an initial vision and it is a fine balance. It is a matter of checking in. It’s great communication. And it’s trust. 

Essentially, the trust that you build with your team is two way. You need to trust in your team that they’re going to be able to manage and carry out the vision that you have set overall, with what they’re implementing and what they’re doing on a kind of practical basis day to day. And then they have to trust you that should something go wrong for them along that way, or should they have a challenge? Or should they need something else that you, only you, can provide them as a leader, that they can come to you for that and so that that two way trust is really important.

I think places where I’ve known in my past where I’ve struggled the most with leadership that I’ve worked with I don’t necessarily trust them. And that’s not good. I think in order for things like innovation, and trying new things to thrive, you need to believe that your leader has your back if things don’t go well and so on. It’s  the responsibility of the leader to provide that safety net, to provide that sense, that feeling of camaraderie and that belief that look, we’re all in this together. 

And we’re all going to try new things. And they’re not all going to work. But we’re going to learn as we try new things. And if they don’t work, we’re going to learn from those mistakes, and we’re going to recover quickly and move to something that does work. And in that failure, if you call it that, in that sense of, you might be moving backwards, we’re all going to be in this together and no one’s going to stand out and take a fall like we decided to take a risk together. We all win together, we all together. But eventually we will all win because we’ll learn from that failure. 

So I think a lot of a lot of the challenges that come up in the dynamics of leadership and kind of getting out of the way is establishing good trust because you need as a leader to trust that once you step away from the day to day and the and the kind of minutiae of the of the things that need to happen on our lives. That the work is still being done and still being done in a way that leads up to the bigger vision. You need to feel trust that the person you’re leaving that under you is going to keep following your vision and execute properly. But they also need to trust in you that you’re not going to abandon them, you’re not going to abdicate and you’re not going to leave them should something else. It’s something that worked out. They need to know that they can keep coming back to you and that you’re involved in a way that helps them move forward. But that doesn’t get in their way.

Aydin Mirzaee 23:36  

Yeah, I think that’s so important just this concept of having that psychological safety so that if you do fail the first time you fail, you’re not out the door.

Kirstine Stewart  23:46  

Yeah, I think we’ve all felt it right? Like I’ve been, I’ve had occasions where someone, I felt really emboldened because I had a leader who was great and said, hey, go out and try it. When I went out and tried it and it didn’t work. I also suddenly felt I was wearing it as opposed to us. It was a moment in time where I went, wait a minute, I thought we’d all agree we were doing this. And when it didn’t work, great, we would take that manage risks together, no one was doing anything ridiculous, it was all something that hadn’t been decided to manage risk. But when it didn’t work, I felt like I was the one being hung out to dry, and that did not, did not help me build a trust back to that leader, and I didn’t feel like I could then try anything new. And that leader ends up failing in a way because they can’t, if they’re not able to tap into everything that their team can do, then they’re not optimizing it.

Aydin Mirzaee 24:44  

Yeah, totally makes sense. Then everybody plays it safe, and then, you get mediocre outcomes.

Aydin Mirzaee 24:51  

So one of the things that you’ve definitely talked about in the book and more broadly is that the way of leadership has really changed over time. And modern day leadership requires a lot of skills and traits that women tend to more naturally exhibit. 

So I’d love to talk to you about what is that modern style of leadership? 

What are some of those characteristics and why women are better positioned to fill some of those leadership roles as a result?

Kirstine Stewart  25:24  

Sure. And yeah, when I wrote the book, Our Turn, I think there was a sense that leadership was changing, because this was a few years ago when I had the book together. It was published about five years ago at this point, but I think it’s true today, that although I wasn’t really focused on female leadership, in particular, the focus was or the view was looking at leaders who didn’t typify the white male leadership from a corner office who did kind of a command type of leading those that have the kind of personalities or the mindset of leadership that can actually lead better today with the type of workforce that we have generationally, geographically because the word world is more global. And the pace at which we work, there’s a, it’s kind of borne out in some of the evidence we’re seeing now in female leaders of countries that are doing really well through this pandemic, there’s a sense that, they haven’t been taken by surprise by something that really shouldn’t have taken everyone by surprise or actually feel more equipped because they are quick to react, and more empathetic. They’re more empathetic. They are more attuned to science and make science based decisions, because they take input from others. 

So like all of those attributes, in terms of you checking in and listening to others, these are all I think skill sets have in the past been considered to be soft skills. Like you might do you well as someone on a team, but maybe not as a leader, I think what we’re seeing now is that leadership has changed because it isn’t so kind of command and deliver from a corner office and because leadership is, is more connected to a team and to the world around it.

You need to have an ability to look outside of yourself and take advantage of the world around you and I think that’s what leaders of today who succeed the best. That’s really what they tap into.

Aydin Mirzaee 27:38  

Yeah, I love that. We’ve definitely noticed this. This concept of it used to be a lot about command and control. And as we’ve all matured and industries have matured, it’s much more about like a coaching style leadership. I’ve been evidence gathering and yeah, totally agree with you that it’s definitely shifted. 

One of the other things that I found really interesting in the book is this example that you talked about where I think you were at Twitter, and there is a company town hall that happened all throughout time. And one of the things that you noticed was that there were less questions coming from the women employees. And I think that the reason I wanted to emphasize this is I think that for most people, they would look at this situation and say, Yeah, well, that kind of makes sense. I mean, it’s a tech company. So there’s more men, so naturally more questions from them. And they would have probably just brushed it aside and left it at that. 

But I think you looked at this and said that it was actually a very serious issue. I’d love for you to talk about why you thought this was an important thing for you to dedicate your attention to.

Kirstine Stewart  29:00  

Sure, well, I think sharing a voice is really important. And it goes back to this whole idea that you can’t be what you can’t see. 

And so even back in my days at the CBC I had, I was the first woman to have the role that I had at the CBC, the first person under 40, at the time to have it. So I was not typical at all, I wasn’t what they had expected. And I remember trying to kind of establish myself as a leader, there was an interesting challenge, because I was also not a life for CBC or I was someone from the outside. And so establishing myself in my kind of leadership position. And having that kind of authority that you need to make the big decisions was not easy, it wasn’t an easy road to get there. 

And I remember particularly feeling I was struggling when I was and I hadn’t there was a particular event that happened that I write about in the book around an advertising upfront that went really well that you’ll find is when you pitch what the new shows are to a bunch of advertisers who come to us even once a year, kind of like when you see these big tech events, and then unveil things you do that in, in television as well. And then the event went really well.

 But afterwards, there was a newspaper journalist who kind of was more focused on what I looked like and what I was wearing on the stage than what I was presenting, which totally threw me off. And I felt very disillusioned by the whole situation. So, I was walking through the halls of the CBC, like a day or two later thinking, I want to change my appearance, I’m gonna have to fit in with what’s expected of me as a leader, and tone things down, so to speak, I guess. 

And there was a younger woman who, who came up to me and said, are you interested in them to visit? Yes, I am. And I visit because it’s a huge building with a lot of people who walked through it. And she said, Look, I just want to say, we really like that you’re here. You look like we look, you talk like we talk, we actually think we can be you someday. And I was quite young at the time. And now that I’ve had a few years under my belt in terms of understanding what your impact can be, I didn’t know what my impact was of being someone who could be seen, and that people could picture themselves in the role because they saw me in the role. I didn’t realize how important that was until that moment. 

So when it came time to move over to the tech space, where as you rightly point out, it’s a huge gap between the opportunity for women, people of color. it’s still a very kind of white male run business, which is unfortunate because it’s a new business, you kind of was hoping that he kind of were hoping as the industry they’d be able to remake the rules, but they kind of fell along the lines of some of the older businesses. 

Creating opportunity and room for voice and space for leaders who don’t again, look like most of the people who are around them is really important and you have to put effort behind it. And that effort in this case was a group of. We called ourselves SWAT, the senior women at Twitter, decided that this lack of voice in public events like town halls, we actually had to put a concerted effort behind supporting young women who we thought would be able to contribute to a situation like a town hall or an event like a town hall in a meaningful way. 

Again, not like setting up anything artificial, but just knowing that there were folks who had ideas, and great thoughts that could be contributed at a town hall and go to them before the town hall and support them and say, “hey, look, we noticed you didn’t say anything last Town Hall. We know that you’re working on this. And wouldn’t it be great to share that with the team? And wouldn’t it be good for everyone to hear what you’re working on because I think it’s to everyone’s benefit to hear your voice”.

That kind of backing and support then led to more women feeling like they could take the microphone at the town hall. So it’s being present in the time that you’re in and understand anything that you’re representing something bigger than yourself when you’re a leader, who is a woman or a person of color. You’re not the typical, white, straight male in the corner office. It’s understanding the impact that you’re making just by being there and, and what people see when they see you.

And then there’s also the role that you play in kind of reaching out and letting others come into that tent and also have a voice and have visibility at levels that make an impact as well, so that you’re not alone. I think the one thing I learned was being the only woman to do this or being the only woman on that panel.Maybe that’s a nice notch in your belt, but it’s not one that you can be that proud of, because you actually end up being quite lonely. Your role, your obligation, I think when you get to that position is to expand that table and make sure that others come to it as well. So doing things like supporting young women at Twitter was an important thing for all of us who were senior women. To pass that torch along.

Aydin Mirzaee 34:02  

Yeah, that makes a lot of sense. And I think you almost have to look at yourself at this meta level to say, I have a lot more purpose and responsibility here than just this, I guess narrow field or whatever it is my role job. So that’s really interesting. 

Kirstine this has been really, really awesome. So many great insights. Just to ask, the final question here is for all those managers and leaders out there looking to get better at their craft to become better leaders. Obviously, we want them all to read your book, Our Turn, but what other resources or tips or guidance would you give them to kind of take note of over the coming years?

Kirstine Stewart  34:54  

I think what’s important right now you’ve seen a lot of activism in the past few months. It’s probably been a bit overdue. And I think things like the pandemic kind of shine a light on some inequalities that have been sustained over time and maybe gotten worse instead of getting better. 

And I wrote the book Our Turn five, six years ago at this point, and you’d be hoping that at this, at this stage, the points that are in it wouldn’t be as relevant anymore, but unfortunately, they still are, because we haven’t come as far as you’d hoped we would have in the last five or six years.

So I would recommend for those who are looking to see how can they round out, what it is they’re doing and how they can provide impact is, with this, all the social activism that’s going on around them is to is to learn a bit more about it, whether it’s a matter of getting in getting right into right into it and and and participating in it physically or whether it’s supporting it and learning more about it and educating yourself on things that  you are not necessarily as familiar with.

I think a lot of us when we look at activism… particularly for myself, I’m a white female, I would look at what, what I could do to help others who were like me, because we felt that we were not necessarily being seen. There’s a lot more people who are not being seen. 

And I think sometimes we need to expand what our view is of that and, and help others who are also not being seen. And so I think right now is a really good time to think about your own situation. Think about your own biases and where you can actually be helpful to others who are also not necessarily getting ahead. So taking advantage of this time with social activism, I think we can all play a really important role.

Aydin Mirzaee 36:40  

That’s great advice, and a great way to end the discussion. Kirstine, thank you so much for doing this.

Kirstine Stewart  36:47  

Thank you, Aydin.