In this episode, our guest Craig shares why, as a manager, it’s so important to create an environment where there’s psychological safety and strategies to help you create this beneficial environment in your workplace.
“The minute we start discounting someone as a number, as a product of their efforts, we don’t see them as human, we forget about all those different things. And when you don’t see someone as human, you reach a point of, I think, probably the most awful place you could be, be it personally or inside a business,” - Craig Handy
When you’re busy fighting for survival is there any room for growth?
When any failure means disaster, the stakes are too high for you to take risks — this means you’ll always choose the safe route.
Craig Handy leads a Global Revenue Operations team at Shopify, a fast growing startup, and he is also the founder of Jameson Strategies, his own RevOps consulting firm. He’s most passionate about how we can use psychology and human performance to dig deep and create team environments where high performers can thrive.
On episode #2, Craig shares why, as a manager, it’s so important to create an environment where there’s psychological safety and strategies to help you create this beneficial environment in your workplace.
We’ll also dive into the connection between psychological safety and trust and how it’s actually beneficial for different kinds of people to have different leadership styles instead of forcing people to fit in this one-size-fits-all leadership mold.
Tune in to hear all about how Craig’s leadership experiences and advice can help you improve your leadership style!
Team Lead at Shopify, Founder of Jameson Strategies Consulting
Craig is a trailblazer in the Revenue Operations field. His reputation has given him the honour of building diverse teams, globally.
Craig’s first and foremost passion is people. He taps into this fascination by learning about psychology and human performance. He likes to dig deep into these topics and utilizes his knowledge to create team environments where high performers can thrive.
He currently leads a Global Revenue Operations team at Shopify and is the founder of his own RevOps consulting firm, Jameson Strategies.
Outside of people management, Craig is a passionate hot sauce maker.
Craig (00:00):Psychological safety for me was this like perfect breeding ground for stretching what I didn't know, but naturally learning that. And, and I think that that was like light years of growth that I had in a very short period of time.
Fahd (00:24):Hello and welcome back to our unicorn leaders podcast. My name is Fahd Alhattab CEO and founder of unicorn labs. This is where we interview leaders on how they create high performing teams and high performing cultures. You just heard Craig handy team lead at Shopify and founder of Jameson strategies consulting. He has joined us today for our interview to learn about psychological safety. This podcast is brought to you by unicorn labs, and you can check us out unicornlabs.ca to learn all about the leadership development work that we do with startups on how we transform their managers into leaders. I'm really excited about today because psychological safety is the foundation in our model of the six levels of high performing teams, unicorn labs, we've researched a model of understanding what makes high performing teams in these small high growth startups. What elements, what ingredients, what steps do we need in order to be able to create that environment so that the, the, the sum of the individuals is greater than the parts where teams are truly high performing.
Fahd (01:29):And the foundation of the six levels of high performing teams is psychological safety. It actually comes from a really interesting study Google and their people, operations team love to do these data studies and they actually coded this project called project Aristotle. So project Aristotle was, was Google study and trying to understand what makes a highly effective team. They studied over 180 teams of different areas of business in marketing, engineering, and product. They looked at teams that had similar compositions different leaders. They looked at teams with different motivations and personalities. They looked at all these different teams to try and understand a cross section of what made a high performing team and whatever way they cut the data, whatever way they sliced the data. They couldn't seem to find certain patterns. They actually really struggled with finding patterns, cuz they saw, you know, some teams really engage in conflict.
Fahd (02:22):Some teams didn't engage in conflict. They saw some teams have different types of motivation incentives. They had different compositions, different sizes. There was a lot of different makeup, a lot of different pieces, but what was something that came out as they, as they, as they dug deeper, they came across this concept of psychological safety. This concept of psychological safety defined as an individual's perception of the consequences of taking risks and being vulnerable in front of their teammates. In other words, psychological safety is a belief that you won't be punished if you mess up. It, it, it it's perhaps known as in, in traits like conversational turn taking, you know, or your social sensitivity in a group. And it is what creates group culture, Harvard business professor, Amy Edmondson really defines this notion and she defines it as a shared belief, held by members of a team that the team is safe for interpersonal risk taking this was initially introduced and has become a really foundation piece in many startups today.
Fahd (03:30):And many successful companies is whether there is true psychological safety for our teams and for our employees. But I'm gonna take that one step further. I think psychological safety, isn't just important for your team. I think psychological safety is necessary for the leader because if a leader creates an environment that isn't psychologically safe, they in turn also have to act within that environment. And so then you end up having leaders who don't wanna say when they don't know that they don't have the right answer. They don't wanna say when they don't know, they don't wanna make a mistake. They don't know how to point their to the right direction. So they they're worried to go to their team. They're worried to ask for help, see a leader that creates a non psychologically safe environment for their team. Then you know, reaps what they sew.
Fahd (04:15):They, they don't end up having an environment that for themselves to be able to effectively empower. So psychological safety is equally as important for the leader as it is for the leader to create for their team. And I know personally, I, I reflect in this moment. I think I only realized how important psychological safety is when I was in a, I worked for a company right out of a university that was just toxic. They were in a bad spot financially, their product wasn't working. And I was there to try and help with some business development marketing. And the manager that I had was upset, angry, and frustrated about every single thing we did. I remember idea after idea that I shared, I was shut down. It was two weeks into the job. And I remember going to take a bathroom break to, to get a breather thinking like, holy shit, what the fuck am I doing here? Because of how challenging it was. And here I was like, I was a confident leader. I was, I was, I worked in technology. Like I had tons of work experience. Inuring university. It wasn't my first job. Like I, I knew how to work, but yet one manager was able to completely crush my confidence in a very quick, short period of time. And that is truly when I realized the power of psychological safety in leaders and what we create. So with that said, let's move over to another clip from Craig to hear his take.
Craig (05:32):You can be ambitious in things. You can be competitive in things, but the sake of doing things, because that's the way you are is like that's, that's, that's not doing it for you. That's not being creative. That's not being true to yourself. It's, it's, it's something that's more aligned with not having psychological safety.
Fahd (05:47):See when you're busy, fighting for survival. There there's not much room for growth. When any failure means disaster, the stakes are too high for you to take any risks. And in a startup environment, what we're doing is we're completely betting on risks. We're taking a bet that this one solution can outmaneuver the existing solution. We're taking risks, we're taking bets and we need our team to be able to be willing, to take those risks as often and as necessary as possible. Craig handy leads a global revenue operations team at Shopify, as well as being the founder of Jameson strategies, his own rev ops consulting firm. He's extremely passionate about how we can use psychology and human performance to dig deep and create team environments where high performers can thrive. You'll see that Craig and I really get into it and really go back and forth as we really both enjoy these concepts.
Fahd (06:34):On this episode, Craig shares why as a manager, it's important to create an environment where there's psychological safety and strategies that help you actually create beneficial environment in your workplace. How to create belonging and create belonging cues, which are essential to creating psychological safety. And we'll dive into the relationship of psychological safety, belonging, and trust and its benefit to people of all different leadership style, all different personalities, instead of trying to force a one size fits all in your leadership mold. So without further ado, let us have Craig handy and let us hear about his leadership experiences and how you can improve your leadership.
Fahd (07:19):Craig, I'm really excited to have you join us here on our unicorn leaders podcast, really excited for you to join us and, and share a few thoughts. And, and, you know, Craig, I think as I talked about, I really like to give our listeners a puzzle to start off with right away a challenge. And, and the topic that we're discussing today is psychological safety. And as someone who leads a team and you've got a team, a number of people you're currently working with a Shopify, I want to hear it from you. What role does psychological safety play practically in the day to day operations of a leader and of a team that is trying to grow and innovate at a high pace?
Craig (07:57):Yeah, well thanks for having me for head first of all. But yeah that's a great question because I feel like psychological safety in, in some regard is understood by many leaders, but it's not defined and it's not understood in it's encompassing environment. Right. I relate psychological safety back to, and I'm a, I'm a psychology fanatic back to Abraham nozzle's hierarchy of needs, right? And, and if you're familiar with the pyramid, you've got your psychological needs, your safety needs, your belongingness needs, your steam needs. And then you reach this element of self-actualization. And that seems so elusive. But I would say that psychological safety practically in a business standpoint, in a work standpoint is all of those things up until that self-actualization mm. And practically what you're trying to do is to eliminate all those things that your team, your employees, your organization worries about outside of the creativity process, the delivery process, the stretching into the new box type of process that, you know, things that are, are not conducive or constructive to them gets in the way of, and I, and I think that's about encompassing all of those elements and that's what base would you base psychological safety on practically?Craig (09:10):Yeah,Fahd (09:10):Yeah, yeah. I really like that. And, and, and I think you noted something in, in one of our pre-interviews you said something has to happen to the leader in order for them to be able to actually create psychological shift a shift, and you called it the introspective to the leader, kind of like that kind of, that, that transformation. Tell me what, how does, what does the need to happen to the manager, the leader themselves in order for them to be able to create that psychologically safe space for their team?Craig (09:33):Yeah. I mean, largely it starts with like a self-awareness right. It starts with, I mean, you and I have spoken before many times with emotional intelligence and it comes back largely to that perspective of that. If you don't understand it for your yourself, if you don't understand how this can impact you or, or, or things that you do or do not do that either contributes or doesn't to that type of an environment, then again, you, you, it, it's hard to create something that you can't imagine or that you don't contribute to yourself. And I think it starts with you as an individual before, before anything. Yeah.
Fahd (10:07):Yeah. That's that's, I, I like that. I like that. I think, I think that's it, that's a good piece. And, and I think you've, you've mentioned also how, you know, the sooner a leader gets over the fact that it's not about them. Hmm. Right. Tell me more about that. Tell me more about how that plays into yeah, well,Craig (10:25):Safety, I mean, I mean, I think like it's some regard of still trying to learn that piece, but yeah. I, I mean, you step into a leadership role and, and I remember like one of the first times that you know, you're given power and and it craps, it's like, ah, I'm in charge. I'm gonna, I'm gonna come in. I'm I'm, I'm in control of this. And part of that is like, I think in a snare, maybe, maybe it comes from excitement where it's like, oh, this is me. I've been selected for this, or I've earned this and I'm now in control. But the other part of it, I think becomes a fear of, oh, my name's on this and I want to do it my way. And I I'm responsible for this and I need this to be right. And that's not a human approach.
Craig (11:07):That's not a you know, anything other than a, a me related thing. It's not an us, it's not a, we, it's not a collective, it's just a me thing. And again, me, it's not a great fit for for a team. So I think like when, when you think about that, you, you, you're trying to say if, if I'm putting myself first as the leader, I'm not the leader, I'm not the leader that I, I should be. I'm not the leader for this team. That is, I mean, you hear like servant leadership or, or other different philosophies thrown around. But like, I think it comes back to the fact that if you're the leader you eat last, you, you have to look after your team, you have to do that. And that has to get outta your own head space. And it's not about you, as you say, it's, it's about the team, it's about the things the team is trying to achieve. And that has to be first and foremost.
Fahd (11:55):Yeah. And I think those two concepts are coupled, right. I think that, that in order to, for a leader, to be able to create that psychological safety, they, they need to be able to have worked through that ego. They need to have be, have be able to work past the self because psychological safety is to be human is, is to create, is to remove one's ego, to create the space enough for everyone else, Craig some brilliant insights. And, and, and I know you've got more for us and this is kind of what this episode is taking us. We're gonna unpack psychological safety, this leadership at concepts that go with it. But before we learn more about the insights I'm sure you, weren't always this brilliant I'm sure you, weren't always this you know a successful person that, that we have here today. Let's, let's go back to where Craig Handy. Where's Craig Handy from let's let's where were you from? Where'd you go to school? What's going on? Let's let's get a little story, a little background about you and, and, and let's carry that through. So, so tell me where, where are your humble beginnings? <Laugh>Craig (12:52):Yeah, I mean, I don't know. I wanna make one correction. I think I was born like this. I
Craig (12:57):I dunno what you're saying. Yeah. I've been this genius for, for the beginning. No,
Fahd (13:00):Yeah, yeah. For sure. I'm gonna ask mom and dad, I'm askingCraig (13:06):I'm an only child. So you, you can't blame me for some of this. You,
Craig (13:09):It's natural. Right. But no yeah, working. So I yeah, born and raised in a really Ontario and you know, went, went to school I guess. And I think I threw a lot of my growing up phase. Everything for me was about I had to do it all. I just couldn't sit one out. I was part of everything I could possibly do. I felt physically ill. I joined the choir. I hate singing. I hated choir.
Fahd (13:40): Wait, wait, wait, you joined the choir. Yeah, but
Craig (13:42):I said I had, I had to be there. Right. I had to try it for all the teams. Like I didn't <laugh> I thank God. I didn't, I never made the basketball team.
Fahd (13:51):But you're tall. That could have been,
Craig (13:52):I was six foot four and I was totally everybody else at that time, couldn't jump. And for whatever it was the only team I never made, I was like, thank God. Cause I can't stand basketball. <Laugh> so it was like, it was, it was almost like, please don't let me make something. Cause I don't wanna do it. But, but I just, it was like physically ill if I didn't step in and, and be part of things and, and, and whatnot. And so, you know, that, that preceded and I think my really first there was many throat throat growing up, but my real first foray into leadership let's say was I was in grade 10 and I was invited to go to what was called the rotary youth leadership awards. And it was a, a conference I guess you could call it for four young leaders out in Geneva park, it was a Y M C a facility near really. And and yeah, I was like, this is a gimmick, this is weird. Like, this is a cult, like what's going on
Fahd (14:44):Here? This is a cult.
Craig (14:45):And and I, I mean, it's great to, I think I cried when I left. Like it was, it was it was a pretty crazy experience to first step into a thing that was about to transform you the way you think. And, and the way you work was where I was introduced to the concept of disk which I know fed you're far too far too familiar with. And I'm sure we'll talk about later, but and really this whole thought of like, oh, a leader, not only is a leader, a, you know, just a thing that a skill that people display and, and a skill that people work on, but a leader is like a thing that you can do to contribute to both to your life, your, your loved ones, your friends, your family, your peers, your business, your career.
Craig (15:26):It was like, oh, leadership's like a thing. That's interesting. That's, that's new to me. But anyway, carried on with that university got into student politics, student leadership there's lines blurred between those two. So who, who knows what what's, what, but yeah. Did did that and came to, to Ottawa to go to carton university. And and then I never left. I met the love of my life here and she was from Ottawa, so I wasn't wasn't really allowed to move at that point, but here I
Fahd (15:58):Am. And, and you, you two, you two have have recently adopted a dog or you yes,
Craig (16:06):Yes. Yeah. Well, I, I wouldn't really call him a dog. He's a, he's a, he's a creature of some sort that lives in our house and he's somewhere between human and, and, and dog, but definitely more on the human side than dog. But
Fahd (16:17):Yeah, I think so. I think the way you treat him, Louis, right, Louis is, is definitely now you, you, you gave me hot sauce that was named after Louis, but I think the real story here is actually the hot sauce. So, so you are a gardener that as a hobby gardener, that makes his own hot sauce. Tell, tell, just like enlighten me and, and, and humor me, tell me a little bit about that. <Laugh>Craig (16:40):Yeah, so, so growing, I mean, I, it was something that I kind of stepped into in the last three years, but specifically growing up gardening was a huge huge part of my life. We always had a family garden and both of my grandmothers were avid garden gardeners, like green thumb, crazy with it. And I just, some of my fondest memories with them growing up in the summers is, you know, playing around in the garden and, you know, learning different lessons and whatnot from them. And then funny, I think it skips a generation cause my, my mom says she, she doesn't have a green thumb. She kills everything. And so she's a rock garden. That's, that's whatFahd (17:16):She does.
Craig (17:16):<Laugh> so, but anyway, it did fall on me and and I, you know, got into foray. I was like, all right, well, I'm, you know, bought a new house and got a backyard. Let's, let's make a garden and started plant a bunch of things. And, and too many things really I tried to do square foot gardening. So I made all these like square foot blocks and everything just flourished. And of course I waiting through like constant constant plants. But anyway grew two hot pepper plants decided to make my own hot sauce from it. It was huge success. So then the next year reduced a bunch of things, grew eight hot pepper plants and produced about 32 bottles of hot sauce all different varies. And I, and I love that creative process of like, you know, finding the different pepper, taking care of them, balancing the soil, balancing the care, trying to stress them at the end, get them hotter and then picking different fruits or flavors or types of vinegar. And there's, you never believe how many types of vinegars there are to, to use in the hot sauce. And then, and then you make that so fast tractor right now. I've got a little hydroponics going on here in the office.
Fahd (18:16):Oh, really?Craig (18:17):<Laugh> start, you know, growing things a little bit in the, in the winter time. And then this year planning on growing about 40 40 hot's just hop ever plants, 40 plants. My my guess is anywhere between 150 and 180 bottles of yield that, that I'll do so yeah,Fahd (18:34):You got a spreadsheet for it. You got a spreadsheet, you got the calculation.
Craig (18:37):Well, no, no, no, no, that's right. I mean, this is, this is the thing that I do, right? Like I'm a rev op person, so I'm gonna, I'm gonna get a Salesforce instance.
Fahd (18:44):You got a Salesforce
Craig (18:45):Salesforce instance, and I'm gonna monitor my plant growth and feeding schedules and, and the yield and everything all from, from Salesforce. So I, I'm gonna, I think I'm gonna blog it. I, I believe, or, or whatever, video, whatever,Fahd (18:57):Whatever, talk it, you gotta tick talk it.
Craig (19:00):Yeah. And and so I'm gonna do part of it is about, well, how you use Salesforce outside of the normal business perspective and nice little learning experience. And the other part will be well literally about hot peppers and how you make hot sauce and how you grow stuff. So, yeah, there's a little, little passion project to mind and yeah, loveFahd (19:16):It. I love that. I love that. That's awesome. Okay. So, so from, from gardening to rev op your, your first, your first kind of experience into, into, into sales kind of rev op really starts after university. You kind of take your, your leadership skills that you've developed at these, these youth leadership camps, which you and I both share, you know, spent many years in as camp counselors or youth leadership camp times. And, and, and even our time, you know, in, in student student government politics, student leadership when you take that into your first startup, you really enjoy the startup world, cuz you've, you've been in now a few startups. You, you have your own business also, but let's go through a bit of that career journey. You start with ascent compliance in that and you kinda learn about revenue operations. Tell me a little bit about that kind of experience and how that leads you to the next role.
Craig (20:06):Yeah. For, for sure. So, so actually like a an interesting point, I think going into that was was someone that, that I knew in university who told me being in, in student politics, student leadership was the best, worst thing that could ever happen to me. And, and the, and I was like, what do you mean? Like, this is good, but hi, his comment was, you know, here you are running some businesses you're responsible for a large group of employees. You're, you're, you know, you're on the top of your game here and you're gonna leave here and you're gonna go sit in a cubicle and you're gonna hate it. And it's good for you. You should do that. You should have that experience, but I'm telling you right now, you're gonna have difficulty with that adjustment. And I did.
Craig (20:44):And it was that scenario where coming into the, to a startup and I, I knew the folks there, it was a really cool environment St. Compliance. actually they just rebranded to just descent was an incredible place. And, and I associate a lot of my growth and, and challenges to what I thought was reality from my time being in there. But yeah, it was tough when you first started in there, cuz you're in a space that I'm not familiar with. I had, I, I didn't know what the term CRM was. I didn't know what marketing automation was. I was like, what is this stuff? You know, I thought sales was a bad job that people got and and I was just really arrogant to it. And I had to learn real quick and I had a lot of good mentors there.
Craig (21:24):A lot of good teachers there failed a lot. And that was really important, I think, to changing the mindset and then also stepping further and further into, into this space. So yeah, so the ascent journey really for me became I found myself in sort of like a, a business development selling role and I'd always wanted to do become an organizational psychologist. I loved the idea of how do you, when, when you evaluate two businesses that are, you know, equal access how do you get the margins and inches out of them? And that came down to actually, I did my, my thesis seminar in university on emotional intelligence and middle management. And this was this like fascination of again, how do you unlock those additional potential? And so for my mind, it was what, how, what does color of the walls impact the mood of the people?
Craig (22:15):What does the ambient temperature do? What about placing different apartments together? What about different like process and policies like that was kind of the space that I was in. But luckily I had a manager at the time who kind of identified, well, Hey, you can do that digitally inside these systems, SalesLoft Salesforce, and gave me an opportunity to step into it. And it was kind of love at first sight. At that point, I was like, Hey, you're right. I can do all these different things. And going through the experience, learning trial by fire being constantly challenged in that way, again, made me fall in love with this space of, okay, sure, this is digital, but I have people that are counting on me. I have a bunch of people who their day in and day out is using these tools, using these systems, using these processes for us to be successful and for the business to be successful and for our clients to be successful and what I chose to do and the way that I chose to do it could have a profound effect on them. And, and that I think was one of the real, you know, their stakes there, skin in the game here. And, and I need to be able to meet that. And so that, I think that was, that was a major turning point in my life. Is, is that first first step there?
Fahd (23:21):Yeah. You know, let me, let me kind of pull on this here. Craig once there's skin in the game and there's something to lose and you're trying to innovate a, you know, you're in a startup and you're trying to innovate a project, it, it seems that psychological safety plays even a bigger role because we've gotta be willing to take risks. What was the environment like for you? How, how did the environment allow you as a, kind of a new grad going into this, figuring it out, having no background in it allow you to thrive into what you've built today. Mm-Hmm
Craig (23:58):<Affirmative> yeah. So, so I think it, I think it comes to to two few major things. And, and so for me personally, at decent, I, I had a really strong line to the founders. I had a strong line to leadership. I had someone that had chosen to mentor me and and you know, look out for me. And that, to me created a space where like, I wasn't worried about things that, you know, were, were like, oh, am I gonna have a job? Or if I express an opinion, am I gonna be told that, that, you know, am I gonna be judged? If that opinion wasn't good? You know? It, it, things like that. Wasn't worried about that. I could, I could theorize, I could say wild things and, and I'd be like, Hey, yeah, I don't know if that's a good idea, but you know, feel free to think about it and explore it.
Craig (24:46):It wasn't, it wasn't criticized it didn't hold my career down. And that, I think early space that was given to me, gave me the room to stretch out and grow and, and, and explore things. And I think psychological safety also to many degrees is like, actually, you hear the word failure. You hear about like, you need, you need room to fail so that you learn how to succeed and you learn, you learn how to handle that failure. But when failure means disaster, the, the stakes are too high to do that. And so you take the safe route. It it's it's too risky or it's too dangerous, or it's too toxic to do that. And, and you don't, you just do enough that you can guarantee yourself success and that's not growth. That's getting by. I, I say, that's like, you know, we, we want to swim, but what you're trying to do is try not to drown.
Craig (25:36):And in the case of where my situation in particular was, you know, I didn't have to worry about like, failure didn't mean disaster failure didn't mean, you know, this absolute problem. This was like, failure is okay. I'm, I'm setting you up to fail as the mentor was. You're not gonna be able to figure this out, but nonetheless, go try. And when you mess up, that's okay, I'm here and I'll help you out and I'll, I'll fix it and I'll make it work. And then you're gonna go try again. And that psychological safety for me was this like perfect breeding ground for stretching what I didn't know, but naturally learning that. And, and I think that that was like light years of growth that I had in a very short period of time.
Fahd (26:15):Mm-Hmm, <affirmative>, mm-hmm <affirmative> and, and perhaps quite a juxtaposition to your time in student leadership and student politics, especially at the end, at the university level where, you know, you're a bit under a microscope and what projects you launch, if they fail, there's a lot of criticism and there is a big stake fail, failure doesn't seem like an option. And so then you tend to, you tend to not roll the dye as often, right? Mm-Hmm <affirmative> like you kind of pull back your punches maybe.
Craig (26:43):Well, yeah. And to, to avoid like getting into politics, but like, that's the thing that kind of, I think, translates to all politics is that when your major driver is, is that you're only guaranteed for the term that you, you want. And not even that sometimes the, the focal point is I'm doing things to ensure that I can stay here. I'm not doing things to ensure I grow. I'm not doing things to ensure that, you know, I'm, I'm providing some incredible experience I'm meeting those basic needs that have not been met due to the fact, there is no psychological safety in that type of space and that's toxic. And I mean, do I have a solution to it? No, I don't know. I mean, we talk for hours over that and, and see, but I think is very blatantly clear that that's an example where psychological safety has failed and failed again, and you see the results of it. It's, it's really poor.
Fahd (27:31):Yeah. I like that. As you said, you know, when you're, when you're, when you're busy fighting for survival, you're not, you're not trying to innovate. You're not trying to grow the next bit. You're simply trying to just stay alive and, and, and take us through that. Okay. So, so, so you took some of these lessons that you had in ascent, and you, you went off to Shopify kind of a nice, you know, entry wear and, and very quickly within your role at Shopify, you grew into a people manager mm-hmm <affirmative>. And I think that comes from some of the kind of leadership experiences that you had been accumulating all the way from leadership camps in high school university working a sentence. So, so, so tell me about that shift. Tell me about kind of the experience of becoming a, a people manager at a company, such a Shopify who was fast growing, maybe not so much a startup anymore, you know, at, at that rate, like let's, let's, you know, we, we won't call it that, but nonetheless, a fast growing technology company that is still innovating and pushing yeah.
Fahd (28:25):Tell me about that.
Craig (28:26):Yeah, for sure. So, so actually, like before I left ascent and actually on the cusp of that I had a team of 19 at that point and it, it was a great, it was a global team. It was international and it was a really interesting experience having gone from, and I, and I'm gonna foreshadow here for a second, having gone from, I know what it's like in a leadership situation, when you're all in the same room to then having a team that was not in the same country as me. And that was like, okay, how do I, how do I reach them best? How do I meet with them on a human level? How do I engage with them in a way that, that values them as not, you know, someone who's on a screen, you know, way away. And I mean, a lot of us now learn that,Fahd (29:10):Especially Craig, if I can, yeah. If I can point out, especially as a, as a strength for you, where, where, where you're, you're a communicator. Yeah. You're a charismatic communicator that wants to engage with people. And this is what a lot of managers are struggling with. Right? Like you, you might be chosen as a manager because you're good people's skill and you got the communication and all that. And suddenly you're behind the screen and your team is dispersed. And in your case, you know, the team across the world in different time zones. Yeah. Sorry to, to interrupt there, but I, I just, I think it was such, it's such a juxtaposition to your primary skill set, being challenged with this new mode and this new medium,Craig (29:47):It it's it's. And even like, even still to this day, it's a thing where, you know, I, I I've, I got feedback shortly after you know, going remote from COVID where like, Hey, yeah, you're, you're like documentation and communication is, is not as good, like what's happened. And I mean, the difference is, and truthfully the difference is, is like, I was never the person that was writing documents. I was the person that would go for a stroll down the hallway and bump into someone's office and be like, Hey, guess what? And that kind of conversation was the way that I always operated. It was, it was a very, like, I liked that human. I liked that face to face. I liked that I didn't like rigidity and the formality that you'd have of like booking meetings. I liked that engagement. That was, again, back on that human level where I don't need to book time with you, you and I, on the same team, we're the same entity we, we operate in the same direction.
Craig (30:33):So that first little scenario of like, I can't do that with my team at ascend was really good practice, but I'll tell you, I still, there's still those challenges that you have to face to do that. So, but anyway, your, your initial question, moving to Shopify, I go from a team to, to an individual contributor for about four and a half months or so. And, and that was fine. Cause I was coming into a space, the Shopify fulfillment network basically first rev op hire potentially actually in Shopify as a whole, but first rev op hire. And there was not a lot of nothing set up. And in that case it was a really strong sales leader, really strong marketing leader, but no team at this point. And again, so build it up. So it was, it was good figuring that out, coming up with the processes and then when the time came right to start adding folks to the team that was really exciting.
Craig (31:24):And the question then became, well, you know, how do we do this? It's a different caliber. At Shopify Shopify was a culture that was really important about, you know, building people up and really strong programs to, to develop talent. And so finding kind of the Shopify way, but also my way and the way that I've, I've developed a leadership skill, there's a lot of alignment. There's also some things that, that, that weren't. And so it, it was different, but it was exciting. And I think that that again is another turning point to say, this is a different caliber, this is a different type of of expectation requirement. So yeah, that's, that's, that's kind of what we did. So did that. And then I wanna say what a year and a half into the team getting up to, I think about four or five folks we we did this massive reorganization and that's where I've landed now, which is leading one of the major teams in the global rev tech and operations department.
Craig (32:22):And so I have a team, it kind of fluctuates through and through how things move, but anywhere between about 18 to, to 26 folks that, that we've had on that team. And it's, it's a global team, it's a remote team. It's so many different factors that are you know, different folks that have different skill sets and talents, engineering people business oriented people, trainers very heavy technical program management business system analysts. Like all of the things that would normally be in different teams are kind of mashed together with different personalities. And I find that thrilling that not only do we do it like that, but also the fact of just the lessons and experiences that we've had in, in that time. SoFahd (33:06):Yeah. Yeah. You've got, you've got an extremely cross-functional team Craig, right. And a global cross-functional team, different personalities, different time zones, different challenges. And, and this has been the the reality for many people in your role over the last kind of two years. And we'll continue to be as, as, you know, as we said, remote's not going away. Remote has its benefits, but remote has its challenges. And so perhaps perhaps let's start there as we kind of come back to the puzzle of psychological safety. How do you create that psychological safety in a remote world?Craig (33:43):Yeah, so, so that's like, that is the question, because I think in some cases it's easier and in others, it's, it's nearly impossible. And let me explain why that is in the easier perspective is when you're in your, and this is not, and I, I wanna be clear, this is not true for everybody. And everybody's situations, but generally you in your own home, in your own basement, in your own bedroom or your own kitchen, there's a natural, physical safety that that's had there. There's also the leveling of the playing field in many scenarios where, and I love what Shopify did here with this is like very early on. They said, this is every single person, one person per box. And what that meant was when you're on a Google hangout or for folks who use zoom, there, there will never be two people in the same box.
Craig (34:38):Everybody gets their own square and that's how we're gonna operate. And so it doesn't matter if you're in an office or you're there with someone else, you go to a separate room and you get on that. And somebody be like, oh, well, why is that? Well, the reason is, is that we're leveling out. And that's something I learned very early on actually youth leadership camps, Canada was this scenario of like, if you're speaking to somebody, you think the leader stands up and everybody sits down and listens, but how much more powerful when the leader sits with the group and it's about meeting people on their level. So this was like, it's a small thing and it's subtle, but it's the fact that the video platform made that no one had more access, technically mm-hmm <affirmative> to anybody. You weren't, you, you didn't sit by them, your office wasn't connected to them.
Craig (35:15):You weren't in this building. They were in that. But like, I remember coming to Shopify originally, there was folks that I worked with in Ottawa, but then there was folks that I needed to work with two different stakeholder groups that were in Toronto and Waterloo who would regularly travel back and forth and talk to each other. I can't help, but feel like, well, did they have a better relationship? Are they closer? Are they having better conversations? So this remote thing, leveled things out really strong mm-hmm <affirmative> however, where I think it actually became really difficult was how do you connect on that human level? And how do you create that, that trust and that, you know, am I doing a good job? And so many people from my experiences, when we went remote, you had a scenario where it's like, am, am I, am I performing well, am I not?Craig (35:58):Are people happy with me? Are they not? And it starts to, I think, create that, you know, what is it like paranoia around? I don't, I can't get the same level of feedback that I used to get by sitting around somebody and seeing how they react with me. Yes. And then, then I do now. And so that was, that was really difficult. So psychological safety had to become intentional. You had to create space for it. And, and I found too, like even through the interview process, one of the things that I ask always in every single interview I do is what is the type of environment that you need to be at your best, that you feel comfortable and that you feel is a, is a space for you. And what does that look like from your manager, from your peers, from your team, from the company, the culture, and I, and I want them, and I find many times like that, hasn't that answer hasn't been thought out, but I ask that question because I want to hear about it.
Craig (36:54):Not only like, is this a good fit for you, but also at the same time is when I do select you, or if you're the right person, I want to make sure that I know what matters to you coming in. Are you the kind of person that needs direct feedback? Are you the kind of person that wants their teammates to, to be honest, or are you the kind of person that takes feedback a little bit hard and you need it eased in and whatnot is, is, you know, so many other things in regards to, is it a reassurance for you or is it something that, you know, you, you, you want more opportunity and you want that to come, come to you and you don't have those conversations. So anyway, bottom line is it, it became an intentional thing. And we talk about it often, like my team shop right now, we talk about it. Often we talk, you know, how, how do we look at each other? We feel safe. Do we feel like this is a place where we can have conversation? Can we argue about topics? Can, can we be can we realign, can we, can we be honest and vulnerable with, with one another? So that to me is a priority and then has to be,
Fahd (37:54):Yeah. Yeah. I like that. I like that. Now, now to take us back a bit to your story, Craig, you know, you told me a little bit about this, but you, you really saw in your time in Shopify and with a new team, a personal transformation in yourself, in your leadership style. And, and it, it has to do a lot with kind of past learnings that we'll kind of get into, but tell me a little bit of that transformation. What, what kind of, you know, what had to be true for Craig handy to, to, to succeed in this larger leadership role in a remote world? Mm-Hmm <affirmative> what was that like for you?
Craig (38:29):So, so, and I'll, I'll caveat it too with it. Like it's something that I, I have lots to learn and lot to grow on. And maybe that's the first point is getting over yourself a little bit where you want to be or where you think you are. That's fine. But there is a reality where you actually are and it's, and it's, it's always somewhere where you can continue to grow. So, but I think for me, realistically, first of all, it was that focus on I there was, and I think for many people, this is why I'm trying to prove myself, or I'm trying to, trying to validate am I actually the leader? I think I am. And, and again, back down to, oh, I have things I need to deliver and I'm responsible for my name's on it. And I think that creates that sort of that panic.
Craig (39:12):But for me to be successful in this particular space is like, it has to become a shift towards the team. I'm not gonna get anywhere on my own without all of them, without them feeling line. If you have one of them that is upset, does that type of energy affect everybody else. And so it's not a matter of like, oh, you have a couple really good performers and you have some not like, no, that has to be, you know, you can't just like cut at that point. You have to invest in the people on your team. You have to take the time to have this conversation. And so for me, that's one of the major things that I did is, you know, really looking at, am I bringing myself into this conversation or am I actually having a conversation with someone where I'm, I'm listening to them, I'm hearing them out.
Craig (39:56):I'm not passing judgment. I'm not trying to push my ideals on someone else. As I'm trying to understand, where are you coming from? Why are you saying these things? Why do you feel this way? Why do you not feel this way? And use that type of information and conversation to coach rather than, rather than tell. And I think largely in some cases too, it's about finding why people want to be here. What's motivating them, what's driving them. And then making sure that, that aligns with them either does the company align with that? Does the team align with that? Can I align with that with them? And by doing that, I think that creates emotional investment. And that trust means that, oh, this is where you want to be. Like, do you trust me that I'm gonna help you get to that? Are you, do you trust me that I'm gonna help you achieve that? Or do you trust me that you can be open and honest with me and that for some people it's a given others, you gotta earn it. You gotta develop that. But I think that comes from dialogue. And again, coming and understanding the motivations and emotions of the people that are on your team first and foremost.
Fahd (40:54):Yeah. Yeah. Now I think that, that was, you know, I think what I'm hearing through a lot of that is, is the kind of complete dedication to the team is a, is a shift from a dedication of the self and the preservation of the self. And it's me as the leader to now it's about my team. It's about creating a team that is performing extremely well. Mm-Hmm <affirmative>. And that, that is really powerful. And that requires a serious amount of personal self growth, right? It requires an ability to reflect. And then I think as you get to, it is a real intention to understand the person, you mentioned two things, Greg, the real intention to understand the person and their individual needs and motivations and wants. And then you mention how that leads to trust. And I think there's a connection between psychological safety and trust.
Fahd (41:41):That's UN you cannot can't uncouple. Mm-Hmm, <affirmative> that by building trust, you create psychological safety by building psychological safety, you create trust, and you do that through a personalized approach. And you mentioned the personalized approach and it immediately took me back to kind of the disc story that you shared with me one time mm-hmm, <affirmative> on understanding using a model of human behavior to understand how to be personalized, right? Cause how do you, how do you understand how someone wants to be motivated? How do you understand how they want psychological safety, cuz the way they need trust is different than the way I need trust their safety is different than my safety. And that's just personality wise, add a layer of cultural complexity, add a layer of remote in a different part of the world. And you're sitting here playing a guessing game mm-hmm <affirmative> so, so you, you came across a tool at a young age and continue to use it. You're a big fan of it. Tell me a little bit of the story of kind of your, your learning about disk and, and how that, how, how you apply that today.
Craig (42:34):Yeah, so, so I think the most stark lesson was way back in the day. Back in that time when I was in high school and went to Tory, the, the rotary youth leadership event, we did the disc assessment and categorized people into de CNS. And it is you know, the D with saving, saving the audience for one thing, the, the DS are the dominance. The eye of the influence Sierra are like the calculated in the S are, let's say, I think it's steadiness, but it's very emotionally tuned and supported people focused. Yeah. So when I look across the room, I think my, my ignorant young self at that point is like, oh yeah, the D's in the eyes are, are the leaders, we're the ones in charge cuz either we're the ones that are commanding or the ones that are really social in light.
Craig (43:21):And those CS in the SS, well they're, they're here to be led they're they're the followers. And thank God that they've brought the followers for the leadership conference, otherwise who would we be leading? Right. <laugh> so that, that I think was my mindset and yeah, it's, it's, it's so twisted, but anyway so, so we do this do this low ropes course. And so those familiar, lower ropes course, like it's, it's you know, ropes twisted around, you have to climb through them or, or help each other get through it. And so a low ropes course, and we get together and they say, you're gonna do this ropes course. We're gonna time you go ahead and do it. And of course the the DS start making plans and directing people, telling people to do things and the eyes are rallying people out motivation, let's go.
Craig (44:00):And we go ahead and we do it and we we've succeeded great time. Excellent. You know, hurrah all done case in point here's the leaders, but then they said, all right, everybody come back. And these and I, you can't talk, what, what do you mean? What do you, we can't talk well, who's, who's gonna do this. We're not gonna get this done. I like, my eyes are like rolling in my head. How, how, how, why are they gonna do this to us? I don't want any part of this. And so anyway, they say, go, and we started a little bit slower. The the seas, they started figuring out a plan. They weren't telling people to do things they were coming up with. Well, what would be a good strategy? And the S are asking people what their strong suits are, where, where they would be best, you know, where they want to help out where they wanna do different things.
Craig (44:43):And I'm thinking like what the, what the heck's going on here. But anyway, plan set, people have been identified as where they should be, and we go ahead and we do it and we were successful and we did it in a faster time. And here's just like ego crisis going on with me like that. What has happened here? Like why did the followers do better than the leaders? And idiot me at the time is, is just ignorant to the fact that leaders come in all shapes and sizes. And primarily when I look at this, I, I think, you know, the CS provide leadership in, in a way that's entirely different than the eyes do. And the CS provide leadership entirely different than the, these there's not a right or wrong way to do it. But I can tell you right now that for some folks, there's stronger ways that it works for them.
Craig (45:26):Right. And to me then one of the most important things that we can do is, is two things. One stop telling people who are quiet or calculated or more emotionally inclined to, to folks stop telling them that they need to be loud and boisterous to be leaders. Mm-Hmm, <affirmative>, that's, that's silly. That's not the case. That's one way of leadership. It's not the universal leadership and I'd argue, it's not the strongest leadership at that. But the second thing is when we start to identify people and, and what they like and how they listen and how they learn is adapting your style to meet those people. And of course you can't just, you know, show up to, to someone and say I need you to fill out this, this survey. So I know what category you are. I mean company can walk around with the survey you don't.
Craig (46:12):Yeah, exactly. That's exactly. There's a, there's a company called crystal knows that I absolutely love. And they they try and read the way your, you write your emails and the way your LinkedIn is set up and try and like put a category on. And it's pretty cool. But again, like it's difficult when, when you're interacting with one on one. And so you, there are other ways to identify that. And I think it all stems largely from asking questions is, you know, what, how do you learn and what matters to you? And, and again, that question back to the, to the interview question, like, what ways do you find your successful? What environment do you need? How do you receive feedback and, and being able to not only like listen to that, but then respect it and then actually regurgitate it is, is that scenario where I think people and I, I'm gonna, I'm gonna make an assumption on people.
Craig (47:02):And I think it's very true for me is when you start to see someone act like that to you, it comes off as an investment in them. It comes off as an investment in me as, as a person, as part of the team. And that creates an energy that brings people together that creates that trust. That creates that I belong to this and I, and I'm valued in this. And when you feel like that, you're willing to go further, you're willing to push harder. You're willing to care about your neighbor more because you're invested emotionally in, in the, in this whole thing. And, and, and that, that's not just from the leader that has to be from the team amongst themselves as well. Yeah.
Fahd (47:42):Yeah. And that, that's it that I think there's, there's the, there's the beautiful summary and result of what a true investment that creates psychological safety can yield, right? Like that you get that, that piece, Craig. I, I love that. And, and I love these pieces now, Craig, you've, you've got some, you've got some, some, I'm gonna say controversial opinions. <Laugh> some more controversial opinions about, about certain commonly held beliefs. One around competition. I'm kinda laying this one up for you. Tell, tell me, tell me a little bit about that. Tell let's tell the audience a little bit about that.
Craig (48:15):Sure, sure. Yeah. So, so there's and actually you don't know more about this. The the leadership circle I think is is, is the, where this comes from, but they have a, a like creative and reactive tendencies. And when I first did the leadership circle, I was really angry about it because it said like ambition and competition and everything is reactive and that's, that's not good. And through more sessions and learning about that, I started to pick up the fact that. Okay. Well, it's, it's bad when that's the primary motivator, you can be ambitious in things. You can be competitive in things, but the sake of doing things, because that's the way you are is like that's, that's, that's not doing it for you. That's not being creative. That's not being true to yourself. It's, it's, it's something that's more aligned with not having psychological safety mm-hmm <affirmative> but when you look at competitiveness, I think competitiveness when used correctly and harnessed appropriately is one of the biggest drivers for a particular team.
Craig (49:12):And so case in point, when you are, let's say you're in a sports team, right? You have you, you have the goal to win. You want to beat the other team. And so the team gets really close and really tight because together they're in the same situation and they're looking to one another to perform at their absolute best. So in a business standpoint, how do you create that? And I think I've, and I've seen this firsthand so many times where the competition lies within the team and the view is, well, if that person does well and gets praised, they'll get promoted. And I won't, and I won't look good, and this is not good. So I need to make sure that I'm competing with them. And that creates this, I think, toxic environment, especially when that could be avoided. Instead, when you distribute the competition around this team wants to be like, okay, we're working the company's working on 15 projects and this team, well, we want our project to be the best project.
Craig (50:06):And so that competition is not necessarily against any other person, maybe friendly competition with another team. But the driver is, is that we collectively want to be successful. We don't want to be good. We want to be great. And when we do that, then we, again, we go further, we care for our neighbors and we are emotionally invested in the outcome. And that is the type of healthy competition that I think is what brings people together. Maybe sometimes that a necessity, but it brings them together with a shared goal, a shared outcome in mind. And, and that I feel is the tightest bonds in people. And so competition's good when it's done, right?
Fahd (50:46):Yeah. Yeah. I like that. And I, and I, I wanted to ask specifically about competition there, Craig, cause I think competition it, when, when left unchecked and when left it to be between individuals on the same team, it will, will quickly erode psychological safety, well quickly erode any of that cohesion that we just spent the last hour talking about. Right. Absolutely competition has. You need to really create that sense of comradery between the team members in order to get to that next level. And, and I think, you know, perhaps here's a, here's one of the last, one of the last bits I'll, I'll get to here with you. Craig is, you know, we, we start with psychological safety so that we can coach for performance. And I've, I heard you talk about coaching quite a bit here. And I think this is the bit that people kind of need to understand.
Fahd (51:32):We don't end with psychological safety. We start with it. It's when we start with coaching for performance, without psychological safety that people feel like, Ugh, I, I can't take, this is too much too high pressure. But if we stay at psychological safety and we don't coach for performance, we can kind of see it. Not, not, not fitting. We're not doing well, the team not. And I like where you said, you know, kind of competition within the can, can allow that coaching for performance. Cuz now when we're competing, I'm more open to that feedback. Oh, how do we do this better? How do we grow? How do we do this? And so I, I like how you've meld it brought these kind of topics in here together. Mm-Hmm <affirmative> so for our last question together Craig you know, I think you, you, you mentioned seeing the human, you mentioned in, in a key part of psychological safety, a key part of trust, a key part of leadership is about seeing the human that you are leading and that you are working with expand on that point for me.
Craig (52:26):Yeah. So, so this, this largely stems from I think initially with when hiring people and recruiting and then it, it, it translates I think, across the board, but you know, the, the, it, it becomes very easy to discount individuals as the, the product of their actions or to say like, oh, I don't like this person because they keep messing this project up. Or why is this person not, not helping? Ah, I don't like them. Like they, they suck at this. And the fact is that when you stop and take a breath about it and realize the fact that who we're actually referring to as a human or who we're actually engaging with as human. And so my example for this, with recruiting is this is not always the case. Some people, you know, throw all resume into a million places and they don't think twice about it.
Craig (53:13):But if you also think about someone applies for a job and maybe they told their mom and dad, maybe they told their, their child and they said all these different things and, and they apply, maybe they get the interview, they go on the interview, the hire is just like, okay, ask a few questions, not paying attention, whatever. And they go home. And, and the sense is, is like, maybe that person's, you know, son or daughters, like, you know, Hey mom or dad, like, how did the interview go? Because they just genuinely care so much about their parent mm-hmm <affirmative> or maybe they're in a scenario where, you know, they told their mom and their mom's like, oh, how did, how did go? Like, you know, I obviously mom thinks you're the you're the best, but you know, how did, how did it go? And they genuinely care about this person.
Craig (53:47):This person has hopes, dreams, feelings, and everything, and the least we can do for one another is to give each other the time of day, give each other. The benefit of the doubt, have a very human conversation with the person across from us. Cuz the minute we start discounting someone as a number, as a, as a product of their, their, their efforts, we don't see them as human. We forget about all those different things. And when you don't see one as human you've reached a point of, of, I think probably the most awful place that you could possibly be, be it personally, or, or inside a business. And so reminding yourself day in and day out that those people around you again, have have lives, have loved ones. And one thing I'll say on that too, is something that I had to, to adapt to as well is I found it was not good at it to begin with, but found it really, really effective and almost easy to do that for my team and my direct reports because I became very, not say protective of them, but it was very obvious that I was responsible for them.
Craig (54:50):And I, and, and if I didn't step up, I didn't do something. Then it was, it was them that suffered, but it became very easy to direct that ignorance to, to them being human to the folks that were external to the team. Mm. Especially if the clashes came between those particular groups, because then it became very productive. But again, you can't do that. You have to see, there's always something, somebody somewhere pushing and pulling in different types of initiatives. And I don't think anybody goes into something wanting to, to, to be poor or, or have you know, have an awful outcome. They want to be, be, be good and their situation circumstances change. So when you look for the human, you have a better opportunity to see those things and produce better outcomes. So that's, I think the most important thing about all like
That when you look for the human, you default to truth, you default to benefit of the doubt you, you default to believing in the inherent goodness of a person mm-hmm <affirmative>. And so then you look for the lacking skill that might be causing a situation or the situation, the event what's going on, why is this happening versus kind of the blame that we, we place some people. And, and I think that exactly, I think that's an inherent mindset in being able to, to create the environments of culture that we're talking about here and, and, and that we're getting at Craig, thank you. So much, this has been a, a, a fun conversation of hot sauce. <Laugh> fun conversation of leadership camp, low ropes disc tests and personalities, but fundamentally how to create psychological safety, how to build trust in our teams, create an environment where people are willing to try and innovate where is welcome and an environment where, how do we create psychological safety in a remote world. And, and we find the human in every person that we deal with by personalizing our leadership approach. Thank you, Craig. I really appreciated this conversation. This was a ton of fun, learned a lot, and I really had a great time.
Craig (56:40):Well, always great chatting with you and anytime.
Fahd (56:44):Awesome. Thanks Craig. Fantastic.
Thank you Craig handy for joining us and sharing all your insights, your wonderful stories. Thank you all the listeners for being, and, and being here and listening all the way through it is truly, always an honor, and a pleasure to be able to share this with you. And as always, if you've got any questions, you've got any topics that you'd like to have us discuss and have us unpack on our podcast. Please reach out to us on any of our social media on Twitter. You'll find me Fahd Alhattab or you want to email me email@example.com. That is it for today. Thank you so much for being part of our unicorn leaders podcast. You can find our show notes and transcript at unicornlabs.ca/Podcast. And if you've liked the content as always, please rate, review, subscribe, and sign up for notifications so that, you know, when the next episode is coming, please tell your friends and share it with fellow managers and share what you have learned from our podcast to get the word out. Thank you. And we'll leave you with this one final question to ponder what looks unsustainable in your team and leadership practice, but is actually a new trend that we haven't accepted yet. What perhaps looks unsustainable, but it's actually a new trend we haven't accepted yet. Thank you. And have a good day.