Leadership Is a Skill, Not a Personality Trait feat. Jen Silva Boucher

What if leadership isn’t something you’re born with? In this episode, Alyssa sits down with Jen Silva Boucher to explore why leadership is a skill you can learn, practice, and grow.

Jen shares her own origin story of moving from individual contributor to people leader, the struggles of being a first-time manager, and how she built For the Middle Academy to support others in the same place. Alyssa and Jen talk openly about the mindset shifts, the importance of communication, and why middle managers are often the most overlooked but most important leaders inside a company.

This conversation will challenge how you think about leadership and leave you with practical ideas you can use right away.

3 key takeaways:

1. Leadership is not a personality trait — it’s a set of skills that can be developed.
2. Middle managers need resources and support just as much as executives and individual contributors.
3. Great leaders adapt to their teams instead of expecting teams to adapt to them.

It's time to say "goodbye" to the Sunday Scaries.

Connect with Alyssa
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Transcript

0:01

Hey everyone. Welcome back to taking back Monday where we are saying goodbye to the Sunday scaries. And hello to the brand new future of work. My name is Alyssa Nolte And I'm Jen Sila Boucher. and we are going to have a great conversation today. So, Jen, tell us what is your origin story? Yeah. When I think of my origin story, I actually hear a voice saying six words. They don't know what you do. So talking, going back like 13 years ago in the middle of like a corporate reorg, I was probably lower entry level and trying to decide where I should go.'cause this department was essentially being split in two. So the leader that was taking over this new area had talked to the executive team and come to find out my current manager really never. Escalated what, or talked about what their team members did. And actually when I got into it a little bit more, actually seemed like a lot of some, the work that we provided was also even passed off as if it was their work. So hearing those words at the time. It was like a lot of emotions all at once. Um, I think the one that wrote to the top was like, shame and embarrassment because I allowed that to happen. Um, but then anger, um, you know, foolishness, um, then, you know, how was this new leader coming in gonna think of me if people don't know what I did? So there was a lot of emotions and I think at that point I remember thinking. If I ever get into management and people leadership, I am. This is like never the way I want. Someone that I work with, collaborate with reports me every day to feel so. Moving forward. A few years into when I got my first time manager role, it was kind of a startup environment, so we were doing a lot of different things in a lot of different directions. Um, I knew what I was doing as an individual contributor, but looking back on that, I always felt like, did I really do, like, did I grow my team enough? Did I coach them? Did I mentor them? You know, part of it was the environment, right? But I probably could have done more looking back on that, but I didn't get any kind of training or resources or anything. It's like, Hey, you're good at what you do now. Go lead a team. So, you know, I'd say the last like, you know, six to eight years is really when I dove into my learning and growth and really, um, people leadership, um. Taking time to really grow my team, see what gets behind their performance, what motivates them, what drives them. Um, and that's kind of where the genesis of, for the Middle, for the Middle Academy came up. Um, just noticing the gap in resources, especially for first time managers. Um, and anybody in the middle or people leadership role. We have things coming down, you know, a lot of different directions and. Those are the people that usually get the least amount of resources and why. Um, so, you know, leaning into my leadership communications, um, made my communications marketing background. I developed. A program of things that have worked for me, um, and now I am talking to people and trying to build this community for middle managers and people, leaders to really thrive in not what they also do, but then also grow and mentor their teams. Unfortunately, I think that, uh, your origin story is something that we hear from a lot of people, right? Like they found out. Out that a, a leader, uh, was taking credit for their work that wasn't escalating, that wasn't kind of being that insulating layer. But one of the things that you said that really resonated with me, and I I'm sure, resonate with a lot of the people who listen to this podcast, particularly the women, you said something like, I looked back and asked myself if I did enough, if I did enough coaching, if I did enough opportunities for my teammate, if I did enough growth. I think simply having that thought in your head means that you probably did.'cause a majority of leaders won't even have enough care, and I shouldn't say leaders, that's probably the wrong word. The majority of people in management roles. Would not even care enough to do a retrospective and wonder if they did enough. They're only worried about what the, the fire or the mess that's in front of them. And so I think a lot of us as people who are trying to be true leaders with a capital L and live up to that expectation that we've created for ourselves and that we want other people to view us as we look back and say, I didn't do enough. When in reality we're probably just doing like 10 x more than every manager that most people are encountering. That's interesting. I definitely have never really thought of it that way, but I can definitely see that. And that's probably one of the strengths, um, that some people, as the great leaders really have is that. Care. Right. So, and that's another thing I like to focus on. We all have different strengths, right? What are the strengths that you, as that middle manager or people manager can lean into? Um, it's really hard to change, you know, say like you're super analytical person, like, it, it's really hard to lean into things that aren't your strengths. Uh, but what are those strengths? And what are those like leadership roots like do you have like a really good senses of awareness? Do you have a really good ability to provide clarity? You know, give people autonomy, provide trust. Those things are all great. Right? So, but how are you also communicating and conveying those things? Um, I think that's sometimes what's missing. There's varying levels of communication or lack thereof. And I'm not just talking about communication, right. It's like you can talk to people, but I'm talking, you know. Really articulating, advocating, um, using, you know, even if it's body language, even, it's like the written word, you know, emails alone, you can get like people's hair rising on the back of their neck, right? So how do we get in front of these people? Figure out what their strengths are and then teach them a way to communicate that will elevate their team members to higher performance and then obviously will grow them as a leader as well. And it's not always easy. And I think that's what happens is, and I think that's also why leadership sometimes doesn't wanna tackle management because you know, you hear things, oh well, you know, people don't change, or you know what's gonna really move the needle? It's really consistency. Communication. I, I mean, I really believe that as long as you have consistency in communication and having open dialogue and that really like care for each individual contributor, I think that is what moves the needle. But it doesn't come overnight, but nothing successful does, right? We all know that anything that is worth it. Building a business, building a career, it takes time and it takes consistency. Yeah, the time thing I think is especially important, like if you look at the, the history of an employee, right? You go to college for four years and you spend four years becoming a, a, a pre-professional, someone who's ready to graduate. You go through all this training and all of this stuff, and you go to lectures and you do workshops, and then you spend an X number, let's just say five years. Becoming an individual contributor and you go to all the trainings and they teach you everything you need to know, and it takes years to develop and become like a really good individual contributor. And then you get approximately zero minutes to become a great manager because it's almost like people think you can just flip this switch and become a great people leader. But I have seen great individual contributors be absolutely horrendous people leaders because they don't have the skills. To do it. And I use the word skills specifically 'cause leadership's not a personality trait. It is a set of skills. So take us through how you help people in that middle moment where they're no longer an individual contributor, but they're not giving, given the time, space, or resources to become a truly great manager. Right. I think the first thing that gets missed in, people might think, oh, it's not really important. It might not be like, you know, say an actionable thing, but really is like. Clarifying the change in mindset that is needed. So you are no longer primarily an individual contributor, like you have to realize Yes. Well, you have your own tasks, right, that are a little bit higher function, administrative, you know, um, managing up. Absolutely. But I think one of the biggest mistakes I see a lot. Of first time managers and I've actually seen people even in higher up positions because I think they've never either brought awareness to it or never been trained that taking so much on. That their team is not growing and they're not getting as much done because they still have that mindset that they need to know what everybody is doing at every second, or, um, jump in and do these things because you know, you're the manager and you're responsible. Now you're responsible to know what the goals are of the business and figure out everybody's strengths on your team, including your own, and how to push those levers and how to help people grow. Give them trust. Trust them with new assignments. Hey, they're gonna make mistakes. As long as you're not making this like huge mistake, that's like losing billions of dollars, you know? I feel like, and I think it, it comes from school, right? We have this such aversion to making a mistake. And I really think that comes from like years and years of like just traditional school, you know, like taking tests. You don't wanna make a mistake, right? Because then you get bad grades and showing that even like smaller missteps. Is a learning experience. So I think primarily I start talking about like mind shifts, mind shift shifts that need to be taken. Um, and then talking, then going into a little bit more of channels to communication frameworks, cadences to meet with your team. Um, gets a little bit more like granular and planning and, and action based. But the first thing that's most important is the mindset shift for sure. So I'm gonna ask you a, a two part question. I'm gonna give you both parts because they might intersect, but I want to hear kind of the, the frame from both. So if someone is hearing this. And they are either one, a brand new manager who just got put into this situation where they have moved from individual contributor and they are ready to lead a team. And they are hearing this and saying, okay, I, I'm hearing the call to action. I, I know that I need to do something. Um, what is the one thing you would have them start doing in order to. Head down this path of great leadership. And then on the flip side, if I am an upper level leader and I'm about ready to promote a new manager into this role, what should I do to ensure that the environment they step into is the best possible outcome for them and their team? Okay, so let's go to the first one. So talk, looking at it from the lens of like the first time manager. So, you know, after kind of having some of the conversations about mindset, I think it's. Going in and really talking, okay, here's your team. What are the functions? What are the roles? Right? How do you communicate with them to say, move certain goals over the needle? Okay, what is the framework? Are we gonna develop cadences for team meetings? Do we need a team meeting? Maybe we don't. Do we wanna develop a cadence for like 30 minute hot seat discussions, just so everybody's on the same page? You know, I think it's. Talking and figuring out what the goal is of not only the department, but then each role and developing that plan so they can thrive. Because I think a lot of times too, they just don't have a plan. Like, you know, Hey, we got this project coming up. We'll have a meeting about it and then well, are you talking to each individual and then telling the, then going to another individual and telling them what they're doing. Sometimes that that's, that's not really the best way. You think it's the best way, but it, maybe it's not the best way because then maybe some people also like to be more involved in the conversation. They like to generate ideas and that can only come, you know, with group sessions. So it's really. Talking through what that plan is based on the manager's role and goal. Um. Yeah, I think sometimes people assume like it's intuitive. Over being clear. And I do this with my own kids. Like I, I learned so many leadership lessons from, uh, my children and my family and my personal life that I take over into my work life. So I have, um, a two story house and I am notorious for putting stuff on the stairs. And to me, stuff on the stairs, like on the bottom of the stairs means, and we're gonna take this up. Like it's on the bottom of the stairs and you're walking up the stairs, you should grab it and take it up. Right. Um, it is not intuitive for my husband or my children because I will set stuff on the stairs and it sits there for like. For like weeks until someone brings it up. And it finally occurred to me like, oh, I intuitively know that I want this to go up as the quote unquote leader of the house. And my children do not intuitively know that I want this to go up. And if I just say, Hey, if you see stuff on the stairs, you gotta bring it up. But I had to articulate that out loud and have a conversation with them, even as something as small as like, Hey, when we eat some Cheetos, we throw the trash away. We don't just leave it on the side table, but saying it out loud, what's intuitive to me is not necessarily intuitive to everyone else that I'm talking to. Absolutely. And I think it's funny 'cause I've actually had that same exact steer discussion with my family and my kids because I do the same thing, put stuff on the stairs, I, I take it up. Everybody else just walks by their stuff and you're It. hmm. But, so I'm laughing on that part, but yeah, that's exactly true. I mean, even when it comes to, especially, say if you're a new manager and either you're building a team or if you're coming in as a new manager and there's an existing team sitting down, how do you guys like to each individual at first, like, how do you like to be communicated and led to? I've had people that, you know, they're like, Hey, I love like giving me a project. Tell me the goals. I'll hit the ground running and then I'll check in with you once a week. Perfect. I have other people that if I, they're like, well, I, I need a little bit more face time. Right. So it's, I wanna make sure I'm on the track, my track more often. Okay, that's good. So where that other person, if I checked in with them more often, felt I was micromanaging them. Right. But then I have other people that. If I don't check in with them, they see it as a lack of leadership and support. So that's why I'm saying like the communication is really where I see the breakdown a lot. Um, and really knowing the strengths and how it's really almost being like that leadership chameleon. But unfortunately, that's kind of the name of the game. If you want to be successful, you need to become the leader they need, not so funny. So you can't see my notebook. I have a notebook on my, on my desk that I literally just wrote as you were talking. Uh, the ultimate leader adapts to the team, not the other way around. And then you said leadership chameleon. And so like if two people are independently coming to this conclusion, it has to be right, right? That's the universe saying this is correct, this is the right answer. And. I, you know, I really believe it. I, I do too. And I, uh, in my very limited spare time, I also coach a team of dancers. And so I've done that for 15 years and we're on a high school dance team. So if you think about it, I've had probably several hundred 14 to 18 year olds who. I've, um, coached and taught and built relationships with, and one of the things I always tell my assistant coaches when they come in for the first time is that you will think that you're gonna be a leader in a very specific way, and you'll have expectations and you're gonna enforce them and blah, blah, blah, blah, blah. But I'm like, you're gonna find that you will have to be a different coach to all 20 girls on the team. You're a coach, this kind of coach for that girl and this kind of coach for that girl, and it feels hard, and it might not even feel fair sometimes that you have to be 20 different people for 20 different other people. But that is how you build a truly great team culture because you are who they need you to be and not the other way around. Right. I mean that really is, you know, if you talk about like even like sports, why are we so attracted to sports? Because you have that great coach or few coaches that can bring this team together for one common goal and you don't see a lot of the back, but like. It's a lot of work and the really great ones also love it because. You know, they like that connection. And I think that's what it is too. I think some of the great leaders really value connection, um, and really knowing and caring about their people. Um, and I think that's kind of a shift. I'm also seeing, you know, we see all the stuff about the demographics, like what does Gen Z want? And things like that. And, you know, and the boomers are like hating on Gen Z and vice versa because I mean, there has been a shift and it's time for us, even just like as corporate America to adapt. The younger workforce is coming in and not saying like, oh, I got a job. Like whatever I punch in, I punch out. They're coming in saying like, okay, I wanna add value here. Am I moving the needle needle? Or am my con contributions being either valued or listened to or advocated? And, um, they want more purpose at work. And honestly, what is wrong with that? That's, we spend so much time at work, that's what makes us feel well at work. That was, that's what makes us. Be better contributors. So I think the time is, I, like I I is now to really find where the gap is in some of these trainings, which I know it is, like there's, there's studies that's like, you know, your average first time manager is 30. The average age that they get their first leadership training is 42. I mean, that's a big gap here. Yeah. And let's, let's go back to the second part of my question. Because I think that that is a gap that we have to address, right? Nobody wakes up in the morning on Monday and says, you know what? I'm really looking forward to being undervalued today, and I can't wait to have zero purpose in my life. And you know, I really get a lot of joy from doing something that doesn't matter, like no human being. We're not wired that way, right? We wanna do things that matter and. If I'm a leader, I, I'm, I'm the 42-year-old leader. I got the training that I needed, or I'm in, I'm in my fifties. I've, I've hit that VP level. I'm about ready to promote that 30-year-old individual contributor into a manager. What kinds of things should I be doing to ensure that they have the resources that I didn't get when I was first promoted? Yeah, I mean, I think it's really trying to find some leadership training P programs at the get go. Not waiting until there's an issue, because that's another thing I see a lot of times too. Well, and I've actually had conversations with certain people. I love hr, I love you guys. But like, sometimes like, well, you know, we offer the classes, um, but you know, the people that probably should take it don't sign up for it, but they're there. So what are we gonna do? Well, maybe it's, Hey, you have a new role. You know, there's onboarding for almost every role, but it's more technical. Right? And then your benefits and all the, like, why isn't there onboarding for managers, especially if you're finding out this is like a first time manager. There should be some onboarding, you know, a couple hours a week. You have some either, you know, training or some webinars, something that helps them, because another thing, you know, I've had this conversation with other mid-level managers. Sometimes it's the loneliest job in the world because. You also have to not only help your team, but you have to learn how to also collaborate with your peers in a way that is helpful and that your makes it easier for your team members to collaborate, say with their team members. So. There's a lot to it, but I think just addressing that there is a need and trying to find out how we can communicate better and give support is the first step for sure. And if someone is like hearing this and they say, okay, I, I'm so far down the road, I do need help. Is it too late for them to turn it around with their team? I don't think so. And but I think that person really has to go like, okay, this is just not working. I want it to work. You can change. I think it's like with anything right, you can make, we have our innate personalities and our innate strengths and weaknesses. But if there's something that you really want to do, you can find the resources, learn how to do something new. It is a skill, like it leading teams is a skill because that's not something that you're just born knowing how to do. And again, like you mentioned, you know, college, you have training, you have all this for this individual work. Nobody tells, like, okay, you know, you have to even craft out your day and your week like most of your stuff or your daily work is probably not gonna be your daily work. Like, be prepared for that. Like, you might get like an hour or two and you have to carve that out over the week. Knowing just things like that, I think is helpful. You know, how to prioritize and just how to speak to people, you know, and shift priorities where needed without coming across as, um, you know, just kind of like a micromanager. I, I think is just. Again, like there is a lot of pieces to it and I don't think there's a one size fits all approach, but acknowledging that we need to communicate better to our teams and give the middle managers, and specifically the people manager support is important. Um, especially as you know, they get promoted to the top because you hope then at least the leadership. People that are running the organization, um, value also like their team members, you know, across all levels of the organization. So I think that's another thing too, is like getting in at that time period before people, you know, become the, the C-suite is truly where you're gonna see, um, change in corporate culture. And considering all of the incredible people that you know or that you aspire to know who is leading the charge, who is taking back Monday. Hmm. So it's interesting, um, I think at the end of the day. I know people probably throw out names. I think we all need to take back Monday. I think it's everyone's everyday contributions. I am seeing like a lot of people talking more about what it really means to be a successful people leader, especially on LinkedIn. Like, and I think this is a conversation that is so important to have where we didn't have these conversations 10 years ago, right? Nobody wanted to rock the boat. Um, you know, happy to. Be the, the, the worker be, and you know, we want, want to stay employed obviously. But I think it's great that I think collectively you are seeing a shift in thinking, um, especially when it comes to corporate America and people management and middle management. Um, and I think we all have a piece to take back that Monday for sure. And if someone is hearing this and they are really connecting with you, they wanna learn more, they, they wanna check out some of your, um, content or your opportunities or what you've got going on, where can they find you online? Yeah, absolutely. Um, so they can find me on my website for the middle academy.com. Um, it'll have some information on coaching and. Speaking. Um, there are some upcoming, uh, leadership communication series workshops, um, and then they can also find me on LinkedIn under, uh, Jen Silva Boucher. Awesome. Well, thank you so much for taking back Monday with me. Thank you so much, Alyssa. It was great conversation.