E200-People-First Leadership and Unconventional Practices with Shawn Stewart

200. People-First Leadership & Unconventional Practices – with Shawn Stewart

About this Podcast

Ep. 200 – Leadership is not just about setting direction; it’s also about revealing vulnerabilities. In this episode, Ramona and guest, Shawn Stewart, discuss the importance of transparency and vulnerability in leadership.

Shawn Stewart is a highly respected leader with substantial experience in the engineering sector. Currently holding the title of VP of Engineering at EcoCart, Shawn has spent over two decades mentoring, coaching, and leading in various capacities. Known for his people-first leadership style and critical thinking, Shawn is known for fostering environments of trust, collaboration, and shared success within his teams.

This conversation offers a playbook for new leaders aiming to establish themselves as trusted, competent managers.

A quick quote from the conversation: “High trust groups simply move faster and if you’re in a group that feels slow, that tends to be a signal that you don’t have high trust.”

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Episode 200 Transcript:

0:00:00 Ramona Shaw: Here’s the question. How do you successfully transition into your first official leadership role? Build the confidence and competence to lead your team successfully and establish yourself as a respected and trusted leader across the organization? That’s the question, and this show provides the answers. Welcome to The Manager Track podcast. I’m your host, Ramona Shaw, and I’m on a mission to create workplaces where work is not seen as a source of stress and drag, but as a source of contribution, connection, and fulfillment.

0:00:28 Ramona Shaw: And this transition starts with developing a new generation of leaders who know how to lead so everyone wins and grows. In the show, you’ll learn how to think, communicate, and act as the confident and competent leader you know you can be.

0:00:43 Ramona Shaw: Welcome to The Manager Track podcast. This is episode 200, which I’m very excited about. I remember vividly recording episode 100 with several of my clients who were all new managers and who were talking about their transition, moving into their first leadership role. So if you haven’t listened to that, by the way, check out episode 100. But today we’re here to record episode 200, which my very special guest, my partner, Shawn Stewart, is here with us today. And the amount of times that we sit with a glass of wine or a cup of coffee and chat about leadership and leadership experience would be mind boggling to most people. And there are so many gold nuggets that I pick up through our conversations because it’s so much easier to reflect on things with another person than to do this on my.

0:01:34 Ramona Shaw: So, you know, that’s what Shawn is for me. And I hope to bring some of that into this conversation today. I’m going know bombard him with some questions and see if it’s going to come out. What I can tell you up front, he is very well respected leader in the engineering space, and I’ve witnessed him through conversations and have seen his, I’m going to call this followership or the people that he’s mentored and coached and led over the course of the last 2030 years.

0:02:08 Ramona Shaw: What an impact he had on their career, on their life, and then personally. And Shawn is also someone who sees things somewhat controversially or applies a lot of critical thinking into his own leadership style and him as a human being overall. So that will come through here in a minute, too. Shawn, thank you so much for being here and doing this with me.

0:02:31 Shawn Stewart: Ramona, it’s a true pleasure to be here on number 200. I feel really honored and I’m happy to have this conversation. Bring on the questions.

0:02:41 Ramona Shaw: Okay, so I’m going to dive in with one that I remember when you first said this to me, and I think my jaw probably dropped visibly or not visibly, but I felt that way because I thought it was such a bold move. You said, oh, yeah. I shared my entire performance review unedited with my entire team. Tell us about that, and why do.

0:03:02 Shawn Stewart: You do I actually, this. This is not a new thing for me. I had another leader, frederick Bouli, who a lot of folks call Flee, who’s the CISO at Reddit right now. I worked with him at Gusto, and I’ve known him for quite a bit of time. He always did this, and I followed Flea’s lead by bringing my own version of this to my own team. And what I’ve learned is that my perspective is that I’m in the service of my team, and I go through a lot of conversations about their own personal performance, but really, the performance that really matters to their ability to achieve any of the goals that they’re setting forward or the goals I’m setting for them is my own performance.

0:04:02 Shawn Stewart: And it’s really important that my team understands how their servant leader is doing within their own realm of responsibilities and to be able to bring that forward for each of their teammates. So that’s the reason I do it. It’s to keep the conversations honest, authentic, actionable, and directly aligned with the type of outcomes that we want to have.

0:04:28 Ramona Shaw: I love how you tied us back to servant leadership, but it’s a pretty bold move because you’re really being vulnerable to your team saying, I got flaws, I got things, I’m not doing well, and here’s what that looks like. How does your team respond to this? What do you see happens or changes when they get your performance review?

0:04:50 Shawn Stewart: Yeah. The beauty here is that you have to make this decision the moment you start the job right, day one. And if you know that your intention is to share your performance unedited with your teammates, I think you’re going to perform with that responsibility in mind day in, day out, and it becomes a way better conversation with your teammates when you’re expecting them to do the same thing. So what I found for my team and the result of me doing this is a more transparent and honest work environment for myself and the folks that I work with daily.

0:05:39 Shawn Stewart: Another extension of this that I really believe in is shared goals for all of my teammates. We live in a competitive world as is, and this may not be a popular opinion, but I’ve been on teams before where maybe there’s a lead engineering role opening up and everyone wants the role and then we become really competitive. But the competition brings out a lot of the least admirable parts of ourselves because it’s secret.

0:06:21 Shawn Stewart: What I like to do is really have conversations with my teammates and be really clear around who I think is in the best position to be able to get to this role or not. Of course, being respectful to labor laws and the rights of every individual to apply for a role if they so choose. But the goal is if we can align as a team around what growth looks like for each individual. Right. We’re all trying to grow in different ways, and sometimes a promotion to a particular role doesn’t actually offer us the growth that we’re looking for. And if we can share that within the team, I think what we find is, what I found in my experience, is a lot of collaboration for every single person on that team to be successful.

0:07:19 Shawn Stewart: That’s one of those things that I’ve found that works really, really well just by simply being open, transparent about all the things that we want.

0:07:27 Ramona Shaw: I’m going to quickly call something out here that I talk a lot about on the podcast, which is that for the leaders that stand out and generate a lot of trust from their team are those who have very clear principles or behaviors that they know are part of the way that they lead. So I call those the leadership principles, or some might call or refer to this as a leadership philosophy, and they are clear about it. They communicate it. Like you said, you got to know about this day one, never too late to start. But your success or your likelihood of being successful with this will increase. If you are clear about it, you can communicate it. You tell people what they can expect, and then you live up to that expectation.

0:08:13 Ramona Shaw: That creates that sense of consistency, reliability, and predictability that you demonstrate as a leader. That makes it so much easier for everyone around to rally around this and get on board because they know what they can expect and how to succeed in your environment.

0:08:29 Shawn Stewart: Yeah, that’s exactly right. And I would add something else to it, which is that through that conversation, we really get to the point quickly that we all need to do work to get there. And if we can get the support from our teammates to help us accomplish this, it becomes more real. But there are no misgivings around the fact that any of this is entitled to anyone or predetermined. We all have to work at it collectively as a group in order to make this happen.

0:09:08 Shawn Stewart: And in my experience, a lot of folks that have worked with me can attest to this. But when these goals are achieved and accomplished, you have this really great celebration from everybody within the team because it really feels like it was a team win to get there.

0:09:29 Ramona Shaw: Yeah. Because everyone saw the goal and then they worked to achieve it.

0:09:33 Shawn Stewart: Yeah. They participated, they helped out. They contributed a little bit towards that person’s accomplishment.

0:09:39 Ramona Shaw: Right. The other thing that I want to quickly get back into is when you talked about the team seeing or creating this transparent approach to work when you shared a performance review, one thing that I see you do really well, and I’d love if you can explain more or describe your approach to this, is setting really high standards with your team, but also doing this with a very caring approach. And that is something that a lot of leaders and new managers struggle with, is how do I demand or ask for or set that high expectation? I want to generate this high performance on my team.

0:10:19 Ramona Shaw: They’re likely performance driven. They know that the pressure comes from their senior leaders, too, but at the same time, they also see that their team needs a lot of care and compassion, and they may really buy into this, too. They want to have this compassionate leadership style. How do you find that strike that right balance?

0:10:39 Shawn Stewart: Yeah, I think it’s from my own personal experience. I’ve had leaders that I reported into that pressed on my shortcomings or my gaps, and that was the focal point of our conversations. And then I had other leaders that really celebrated and really put a positive light on all of the great things that I was doing and used that as an anchor to kind of pull me and the rest of those other areas of focus forward. And I personally have gotten a lot better results working with the leaders who really focused on the positives over the ones that were a bit more critical and called out the shortcomings. And so I take that forward with my own teams.

0:11:37 Shawn Stewart: And I found, and large, that most people respond well to progressive encouragement. They want to know what’s working well and use that as the cornerstone of building out the other complementary skills that they might be lacking or falling a little bit behind on to round themselves out. So I’ve personally gotten great results from it in my own growth, and I just effectively just share my experience with other folks.

0:12:13 Shawn Stewart: The other thing that’s really critical here is in order for any of this to work, the goal that we’re trying to achieve has to be real. I have to be able to deliver on this. And so a huge part of it, regardless of whether I’m focused more critically on the areas that we need to develop or if I’m praising all of the great things and I’m hoping to continue to ramp us forward through that. I have to be able to deliver on exactly what I’ve promised, and so there’s a lot of work in it for me as well.

0:12:51 Shawn Stewart: My strategy around helping folks grow has to ultimately lead to me being able to deliver the thing that I promised. So I think for a leader, majority of the work is really on us to create the framework, the milestones, manage every bit of it, just as much as our team members who are trying to achieve these goals.

0:13:17 Ramona Shaw: So I get the sense that you’re, on one hand, strength focused, but also that you see how when you instill that sense of encouragement and confidence in others, you really see them rise to the occasion. And am I right to also read into this, that when then something doesn’t go well, like someone isn’t meeting the expectations, your approach would be to go in and say, here is what I know you can do, and here’s what needs to be done in order for you to achieve your goals.

0:13:46 Shawn Stewart: Absolutely. In my personal life, I have trackers all over me. I’ve got an oring and an apple watch. I really believe in setting the right metrics and the right processes to pull that data in real time. And so part of the conversation is not just establishing the goal, but it’s also establishing the metrics that would allow us to identify whether we’re making progress towards that goal or not. And so this is very clear for not just myself, but the folks that I manage.

0:14:23 Shawn Stewart: And so when we have the conversation, it’s really about looking at the data and talking through. I’ve found sometimes, a lot of times, actually, that a lot of management that my teammates need in order to accomplish their goals is really about whether I’m able to help them unlock the motivation and the aspiration on a day to day basis to get there. And sometimes it’s managing the detractors, the things that are maybe the things we didn’t plan for, that pop up at work or things that are going on with each individual at home.

0:15:01 Shawn Stewart: But no matter what, the goal has to accommodate all of these things, good and bad, and we have to be able to manage through it. And so it’s really an honest conversation about looking at the metrics, getting more contextual data about what’s affecting the outcomes that we’re looking at, and then making the adjustments, both from a manager’s perspective and the individual who’s trying to achieve this goal.

0:15:28 Ramona Shaw: So that’s the combination of the goals, the metrics, and then also your day to day interactions to check what are the detractors that would prevent them from being motivated to achieve those goals and live up to the metrics?

0:15:44 Shawn Stewart: Yeah, absolutely. I’ve had managers in my past, in my experience, who’ve asked me how well I’m doing, but I never felt as if they were connecting that back to day to day work or using that as an opportunity to really manage my work. Because how we show up at work is extremely important. Being able to manage your entire self so that you productive, really important. And I think a manager plays a huge role in that.

0:16:13 Ramona Shaw: And it goes both ways, right, of noticing, oh, someone may not be feeling well, and then how is that influencing work or work is not going well? What may be going on with the person.

0:16:24 Shawn Stewart: That’s exactly right.

0:16:26 Ramona Shaw: And then again, that transparency there that you’re trying to build through the tool.

0:16:29 Shawn Stewart: Yeah. A lot of trust is required in order to make this work.

0:16:33 Ramona Shaw: Right. Let’s take a bit of a more abstract, go to a more abstract level. When we look at, and you’ve coached and led and supported and championed many managers or high performing ics who wanted to become managers, and you support them through this transition, through your own leadership. When you look at the patterns that you’re observing, what are some of the things that you see other managers do well that help them move into leadership really well and quickly gain the respect from other people and sort of establish themselves as leaders? And what are things that make this transition a really bumpy road?

0:17:18 Shawn Stewart: I think I learned a lot of this. I’ve never met this person personally, but I’ve read a lot of their books. But Bill Campbell exemplifies a lot of this. You don’t have to know the domain that the person you’re managing is an expert in in order to properly coach them. What’s really important is that you have a great trust relationship with this individual where you can really understand the entire journey of what they’ve been putting into their professional career.

0:17:57 Shawn Stewart: Having an honest conversation around where we feel we fall short and then aligning that with the opportunities ahead of us. Having great people relationships, I think is absolutely critical for any manager. And so that’s something that I definitely really spend a lot of time analyzing and having conversations with future leaders about not just managing their direct reports, but managing up and across, really understanding where these leaders fit within a larger team, how they’re able to identify very quickly and support their teammates.

0:18:43 Shawn Stewart: Some leaders are really kind of paint by numbers leaders, right? They’ve got great frameworks and they follow the processes really well. But they lack that deep connection with the team that they’re working with. You really have to believe, in my opinion, you really have to believe that your futures are linked and tied between yourself and your team. I had an experience with an IC who once came to me, really great technical IC.

0:19:17 Shawn Stewart: They had moved up the ranks very quickly, got promoted into a lead engineer, and it was really natural for them to ask, hey, what would it take for me to be a manager? And what I saw from this individual was the way they went about becoming a lead engineer, building really great product, being very technically strong. They were almost thinking that it was about achieving some performance metric or goal, when in fact their team would be the one. Now the choice would actually live with their team, not with themselves.

0:19:55 Shawn Stewart: It’s not something that they could directly do. To get to this. I said, let’s call this person Tom. When I said, hey, Tom, what does your team think? Do you think your team sees you as the leader? If you became a manager right now, do you believe that your team would celebrate that promotion as a win for themselves, or would they see this as just simply a promotion for yourself? Because in order to become a really good manager, your team has to really believe that this individual who’s leading me is in the best position possible to make me very successful.

0:20:41 Shawn Stewart: And I think that’s something that a lot of folks don’t really understand.

0:20:46 Ramona Shaw: Yeah. And genuinely cares about their success and is able to translate that into the day to day work and the feedback and the conversations and all of that.

0:20:55 Shawn Stewart: I have this other really great story of an individual who wanted to become a software engineer, but they were a quality assurance engineer. It wasn’t seen as cool and as glamorous as being a full software engineer. And they came to me and they wanted to know, well, how do I become a software engineer? They were an intern, actually, and I said, well, I don’t have any software engineering roles for you right now, but we could get you started as a QA engineer, and I think what we could do with this opportunity, it’s the only opportunity I have.

0:21:39 Shawn Stewart: But I think that if you really leaned into being a quality assurance engineer and looked at all of the code that your fellow engineers were submitting, you could use this as a true opportunity to become the very best engineer that you could possibly be, and then it won’t matter if we have a role or not. And this individual trusted me, and they trusted the plan that I put forth for them. It wasn’t just an empty promise.

0:22:12 Shawn Stewart: I also told them that if they chose to do this, I would also commit myself to finding that opportunity to make sure that they would have it at the end of the term that we agreed upon. And to this day, that individual is one of the very best engineers that ever worked with. They really learned through that opportunity of being a QA engineer. They saw bad code, they saw great code. They used that as an opportunity to really propel themselves. Right now, they’re very strong engineer at a really great company.

0:22:50 Ramona Shaw: If I translate this to how it impacts all of us as we think about our own careers, that sometimes we may not have the ability to get promoted or to land that next role. But the mindset really then is how can I, with what I have or the level of influence that I have, how can I put myself in the best possible position so that the promotion will ultimately be inevitable? Because I’m, in essence, already doing the job that I’m aiming for now in my current role.

0:23:22 Shawn Stewart: Yeah, 100%. But it’s really hard for an IC to do this on their own. We need really great managers regardless of what level of management, right? We need really great managers. We need to build really great relationships. I think I’ve learned the hard way that the best relationship I can have is with my own manager. I have to be someone who really supports this person’s success and be very honest and direct about what I want.

0:23:51 Shawn Stewart: And we have shared goals together. The outcome of my boss directly affects me. So I want to make sure that my boss is as successful as possible and be real clear that I want them to be successful and I want them to help me become successful as well. And then I continue to create that type of environment for my team. And what I found is really, really great work environments I’ve been able to operate in as a result of this type of framework and environments where folks don’t feel blindsided or feel surprised, and just a lot of collaboration, support shared success.

0:24:40 Shawn Stewart: And even when things don’t work as well as we would like a lot of folks there to step in and help you out.

0:24:48 Ramona Shaw: Now, you emphasize relationships quite a bit here. Not only once you’re in a leadership role and how important that is then, but also how important it is to start building that. If you are thinking about becoming a leader, because your leadership will depend on your relationships with your fellow peers and across the then you also emphasize the importance of the relationship that you have with your boss.

0:25:10 Ramona Shaw: Are there certain things that, like we say, it takes a long time to build trust to do nurture relationships, but they can be broken within seconds what are some of the things that almost call, like, pitfalls or unaware mistakes that new managers specifically or leaders make that will compromise the relationships that they have in place? And I’m referring specifically to some of that office politics or the things that happen behind the scenes that many of us have to learn. And many of us, well, most of us have to learn, and some of us learn it the hard way because we step into one of those pitfalls and then realize, well, that backfired badly.

0:25:51 Shawn Stewart: Yeah. Steve Jobs had this really great quote where he said, you can’t fake being cool. And I’d like to extend that a bit and say, you can’t fake being honest. I think being trustworthy kind of feels like a feeling. Right. It’s not just the veracity of your claims and the things that you say or being. Aligning your actions with your words. Sometimes it’s about making people feel comfortable. And in order to make people feel comfortable, I think you have to lead with an honest assessment that you’re able to share with other folks about who you are and where you think you are.

0:26:39 Shawn Stewart: And really being open to feedback, like, solicit that feedback in a way that is truly meaningful. I like to, for example, go to my teammates and tell them about my goals. I really want to get to this place, and I think what’s getting in the way of me getting there are maybe items one, two, and three. I would love to get your own assessment of me as your leader. And this is why the performance sharing my performance review is so critical to all of these conversations, because the performance review is kind of the end of a long conversation that started at the very beginning about who I am, what I want.

0:27:25 Shawn Stewart: Right. And one on ones end up becoming a two way conversation where I’m talking to my teammates about how I can help them and how I also need them to help me and how we’re helping each other. There’s no framework to just simply ask the questions and not have your heart in it. You have to really believe that you’re on a worthy, purposeful path and that the people that you’re working with are part of that.

0:27:57 Shawn Stewart: And the goal is, in order for you to achieve what you’re looking for, you have to be able to help someone else achieve their objectives and their goal as well, whether that’s your boss or someone that reports them to you.

0:28:10 Ramona Shaw: Now I’m going to hone in on the question of what are some of the mistakes that you see people make that break relationships. Can you share a couple of examples that you’ve seen.

0:28:20 Shawn Stewart: Yeah, I think I see that. When folks don’t have a good relationship with their shortfalls or their inadequacies, if you’re afraid of your own professional gaps and it’s something you don’t want to share or you don’t want revealed, you might not be in a position to have the type of conversations I’m talking about or you might feel defensive about anybody else bringing up. Imagine you’re in this very trust, high trust group and everyone’s really leaning in to helping everyone out and you have a few folks that are not putting in as much.

0:29:13 Shawn Stewart: They might feel a bit triggered or defensive. If someone calls out for the benefit of the entire group, a gap that needs to be filled, they might take it personally. And so I’ve seen that as an example. I don’t think it hurts the entire team. I think the team, I’ve worked with a few individuals like this, it ends up becoming very apparent early that someone has not bought into working within the group and the results vary in terms of what happens after that.

0:29:47 Ramona Shaw: To add to that, I think there’s also something about not owning our own shortcomings or becoming defensive. That means sometimes you have to overcompensate because we feel like we don’t want anyone to see it. And that sense of I got to overcompensate or I got to pretend or keep up this facade then makes us overreact or take actions that are a little bit too aggressive almost, where a conversation behind closed doors with the person involved or an honest sharing with the team would resolve a lot of the issues at hand. But then we feel that need to go and be aggressive or to escalate quickly and to involve including CC on emails, right. In whatever degree involving a bunch of people in order to really make our case versus just pausing for a moment and letting things settle down and then acknowledging, yeah, what can we resolve here without this big escalation or reaction to it?

0:30:51 Shawn Stewart: Totally. Here’s a controversial statement. Potentially, I think I’ve been on my best behavior for you, Ramona. High trust groups simply move faster and if you’re in a group that feels slow, that tends to be a signal that you don’t have high trust. I think it’s based on my experience, it’s really that simple. The teams that raise their hands and say, well, yeah, I think I screwed up, or yeah, I really don’t know how to do that thing.

0:31:27 Shawn Stewart: I’d love to learn, but I don’t know how to do it move way faster and the teams that really embrace this, they move very quickly.

0:31:37 Ramona Shaw: There’s also way less drama and conflict. Right. That would slow things.

0:31:42 Shawn Stewart: Absolutely right. All the ccing and what have you, there’s a lot of overhead to manage and deal. Right. And it tends to be kind of an indication that, yeah, there’s not a lot of trust here.

0:31:53 Ramona Shaw: Before we wrap up, one final question. If you were to put yourself sort of in that mentor role or mentorship position where you have someone who’s new to leadership in the first couple of years, what would be a piece of advice that you’d want to share?

0:32:09 Shawn Stewart: That’s a great question. As you asked the question, I started thinking about a few folks that I’ve mentored, led, who are now sitting in leadership positions. I think that new leaders should really embrace the idea that their purpose is to really find a greater purpose for the folks that they work with. And so really understanding your people, getting to know them very, very intimately is really important.

0:32:43 Shawn Stewart: I had a boss, for example, I told this boss that I was going to Colombia for my birthday, and when I got back, my boss asked me, well, how was Brazil? Doesn’t make you feel good, right? So I think your number one job is to really dial in to each of your people, get to know them, really feel like they’re a critical part of your own personal success. And if you do that, I think you’re going to do really well.

0:33:17 Shawn Stewart: Make performance reviews about really assessing this person, not in terms of a compensation or punitive allocation of whatever your organization is deploying during that time of year, but really looking at it as a way of helping this person identify where they’re best and how they can become better and grow over time. If you can use performance management tools and have those conversations early and often, you’re going to get really great results out of your people. And ultimately, leaders get paid last.

0:33:58 Shawn Stewart: We eat the last slice of the pizza, but if we do a really good job, we get a pretty big slice.

0:34:06 Ramona Shaw: Pretty big pizza.

0:34:06 Shawn Stewart: That’s right.

0:34:09 Ramona Shaw: Thank you so much for sharing all this. And I think through the conversation, it’s obvious how much you care for the team and what your perspective is on leadership and what it means to be a leader. I think a lot of that reframing from moving for that mindset of how do I succeed as an IC versus how do I succeed, and what does it really mean to be a leader? Is the shift that so many of all of us in leadership roles have to go through.

0:34:35 Ramona Shaw: And sometimes that’s easy. Sometimes it’s hard, and it’s a process in a process that can take years to go. So thank you so much for sharing your perspective, and I hope that created some food for thought for other people as they’re reflecting on their own leadership philosophy and how they see their people and their role as a leader. Thank you for being on The Manager Track podcast.

0:34:54 Shawn Stewart: Yeah, thank you, Ramona. It was a true pleasure talking to you.

0:34:59 Ramona Shaw: If you enjoyed this episode, then check out two other awesome resources to help you become a leader people love to work with. This includes my best selling book, the confident and competent new manager, which you can find on Amazon or@ramonashaw.com slash book, and a free training on how to successfully lead as a new manager. You can check it out@ramonashaw.com slash masterclass these resources and a couple more you’ll find in the show notes down below.


  1. Why is trust so fundamental to effective teams and organizations? How can leaders build trust with their employees?
  2. How does modeling vulnerability, humility, and a willingness to learn help leaders connect with their teams?
  3. What unconventional practices does Shawn do that you found interesting and may want to implement in your own leadership philosophy?




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Are you in your first manager role and don’t want to mess it up? Watch our FREE Masterclass and discover the 4 shifts to become a leader people love to work for: ramonashaw.com/masterclass

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