The Happy Engineer Podcast

053: Grit and Failure – Being Tested Beyond Your Limits with Dana Sherrell

PASSION or GRIT? Which one will help you build the engineering career of your dreams? What are leaders made of?

And if it’s both, what does that really look like?

In this episode, meet Vice President of Engineering at Boulevard, Dana Sherrell. Her leadership success spans a variety of technology companies including SendGrid, Advatech Pacific, Optivus Technology, and Senior Director of Engineering at Twilio where she oversaw their entire email platform group.

Dana understands the challenges of building technology for massive scale. We’re talking BILLIONS of emails.

She also understands the challenges of building a career for meaning, impact, and happiness in your zone of genius.

One of those challenges is your ego. Dana explains how ego almost derailed her career and how to deal with it. She also gives some sage advice on how passion and grit show up in the workplace.

So press play and let’s chat… it’s time for the genius in you to come out!


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7 billion emails in a day. Holy cow! 

And that’s just one company that does marketing automation and emails

I’ve never actually thought about the scale of email in numbers before this conversation with Dana.

Perception is reality

Story time with Zach once again here. Back in 2011, I was working at Whirlpool corporation as a test engineer. And there was another test engineer on the team. We both reported to the same boss. 

I did everything I could to plug in on all the active projects, and that included projects that had been assigned to my peer, this other test engineer.

And I knew which projects were mine and worked doubly hard on those, but I really wanted to help out and just provide support in any way that I could. And so I would contribute with ideas, provide my thoughts and input, attend a couple of meetings in the lab on those other projects and all in the spirit of just wanting to help.

I was focused on building my career and delivering great results. 

And, I thought my boss would appreciate it. And so would my team as well.

Except, my colleague, the person I was helping directly, did not!

They thought that I was stepping on their toes, that I was trying to take credit for the success of their projects, that I was encroaching on their territory. 

Their perception of my actions was really negative. And I started to notice that they were avoiding me in the hallways. They weren’t responding to my emails very quickly or at all.

And the dynamic around the office got really awkward with this person. And I didn’t understand why. 

Looking back, I was really naive. I was not aware I wasn’t paying any attention. I was only thinking about my perceptions and my beliefs about what was happening. And I hadn’t even posed the question or considered what might someone else think.

Here’s the truth. Your reputation at work matters

Getting opportunities. Receiving promotions, increasing your income, increasing your influence… It all depends on having a great reputation.

And that is built on the back of what other people perceive, not what you think. 

If everybody else thinks that what you’re doing is negative, harmful, rude, fill in the blank. Not something good, then it doesn’t matter. It really doesn’t matter. So it’s so important that you become aware of this.

Your perception of others is how you create their reputation and others’ perception of you is how your reputation is built. 

Dana was spot-on about this.

But how about…

The Art of Not Giving F@#k?

Yeah, there’s that book, right? 

But my point is that If we recognize that our reputation depends on other people’s perception, where does this notion of not giving any cares to what others think about ourselves fit into all this?

I think we would both agree about the idea that we should not care about what other people think about us.

Well, I want to just point out that these are not talking about the same thing, the idea of ignoring or not giving any attention to what other people think is a really important principle when it comes to self-image, self-worth and self-esteem. 

If somebody doesn’t like you, disagrees with you, rejects you, or doesn’t share the same beliefs as you… that has nothing to do with your esteem, value or worth as a human being. 

And when we allow what other people think to dictate our own self-esteem, that is a problem. 

But if we take that concept and copy and paste it into our career and say, therefore, I don’t care what anybody else in this office thinks about me because my self worth doesn’t depend on them.

Well, you’re confounding two ideas that are not meant to be in opposition to each other. They’re both true. 

Your worth and value does not depend on what other people think. But your ability to lead an influence and create results, increase your income and impact at work and your career absolutely does depend on your reputation and your reputation absolutely does depend on other people’s perception of your reality. 

These are both true. It’s not an either, or. 

Find People’s Zones of Genius: Observe and Ask

This leads well into what Dana talked about in the catalyst to her ultimate, explosive growth as a people leader and dynamic technology leader in her career, which was finding people’s genius. 

Understanding them and then being able to influence them. And these ideas are closely tied. Your understanding of people’s perception is directly related to how well you understand them. And that understanding will precede your ability to influence.

So, if you want to lead at a higher level you need to master these things. 

If you want to get better at finding people’s genius and understanding them so that you become more influential, first observe.

Observation is the core of all science. 

Observe the people and the situations around you. Ask yourself, when did that person on your team do their best work? What were the conditions surrounding that? Who were they working with? What were they working on? What was the dynamic like? 

Then, ask

This is where we tend to overthink things. No, you’re not being inquisitive, or wanting to pry into people’s personal lives.

Getting curious and asking people questions really does work. 

Anyway, now, don’t overthink it and…

Shoot me a message

Quick reminder for you before I let you go. We’re getting some amazing questions sent in for our Q&A. I’d love it for you to join that conversation, so shoot me a note at my personal email [email protected]. So if you want your career growth or career happiness questions answered on the podcast, shoot me an email. 

Hey, keep crushing comfort, creating courage, and I’ll see you next time..


Previous Episode 052: Why to Celebrate Change and Disruption with The Tao of TA-DA Joel Zeff




Dana Sherrell is vice president of engineering at Boulevard, where she leads a global team responsible for the development of the company’s client experience platform. Before joining Boulevard, Dana was senior director of software engineering for Twilio, where she oversaw the organization’s email platform group.

Her career also includes leadership positions with a variety of technology companies including SendGrid, Advatech Pacific, and Optivus Technology. Dana holds multiple patents as well as a Bachelor of Science specializing in Computer Science from the University of California, Riverside.





Please note the full transcript is 90-95% accuracy. Reference the podcast audio to confirm exact quotations.

[00:00:00] Zach White: Dana. Awesome to have you on The Happy Engineer Podcast. Thank you so much for making time to be with us today. 

[00:00:08] Dana Sherrell: And thank you for having me. I’m excited to be here. 

Expand to Read Full Transcript

[00:00:10] Zach White: It’s so great. There’s a million places we could go and looking at your bio. It’s like, wow, where do we begin? So many amazing things, all the VP and CTO and CEO level leaders that have come on, the happy engineer podcast have come from the mechanical engineering discipline, which is my Alma mater as an engineer. And I realized like, wow, Donna’s.

[00:00:35] Senior level leader who comes from the world of software and tech, which okay. All engineering has experienced tremendous change in the last couple of decades. That’s for sure. But I think a fair argument can be made that software and hardware in it and the space like you were at the tip of the spear for what drove so much of that change.

[00:00:55] So would you be willing to take us back to comment out of school in the world of software? In the late nineties, early two thousands, when boom and all this stuff that like, what was that like to be there right when this whole field just exploded. 

[00:01:13] so I graduated in 1998 and. It was interesting. I had so many opportunities in terms of where should I go next? That it was kind of unclear where to start. I didn’t particularly have, let’s say an industry in mind. And as we all have come to know, this space is very industry agnostic and the opportunities are limitless.

[00:01:38] Dana Sherrell: And so I actually just did the easy thing, the low friction thing, I just stayed below. And research companies that were local. And I found an interesting company really because of their mission, optimists, or was the company’s name, they’re local here out in, uh, Riverside Burr, Redlands San Bernardino county.

[00:01:55] basically what this company did is they Howard the proton beam cancer treatment therapy center at Loma Linda. treating cancer patients. And it was an interesting technology that was not conventional. And so I got really interested in that and just the idea of Hey, something that I’m going to be doing in terms of the purpose is directly going to be, helping people’s health and, you know, saving people’s lives.

[00:02:16] Dana Sherrell: So I found that to be really interesting. And I jumped right into that for the next five years of my career. Wow. 

[00:02:22] Zach White: I love that. So tell me a little bit, let’s see if we can geek out for just a moment on, I noticed you have a couple of patents in this space, and I was curious how it connected to what you do now, but now it makes sense.

[00:02:35] The world of proton beam control systems. Am I right? tell us what are the patents? What was the work you were. Yeah at that time. 

[00:02:44] I’m really grateful to have this job as my first experience out of school.

[00:02:49] for many reasons, it was an opportunity to really jump in broad all over the place in the stack. I was like doing device driver level code for power supply controllers. I was doing network level, you know, client server side, Control code. And then, even some kind of like front end UI.

[00:03:10] Dana Sherrell: So I was pretty much all over the stack. And at the same time, we were a pretty small team. not a lot of, maturity in terms of a product driven company, really more of a very specific mission and purpose and, make sure you keep the system up and running safely in terms of, safety mechanisms, you know, you’re, you’re dealing with, humans and people’s lives, right? So a lot of very mission, critical type stuff. very real time driven, extremely distributed system. So it was just this crazy breadth of, experiences and areas to just delve into and learn. Kind of sink or swim a little bit too.

[00:03:48] but from a patent perspective, really what we were doing is building a system that would deliver this treatment that is still even today non-conventional, proton therapy, the way that the radiation is delivered, it’s actually very targeted based on the energy level to the site of the tumor. And so you’re minimizing the impact and in the entry point to the healthy tissue, and you’re really targeting where the tumor site is, and this is what. patients to be able to do this as like an outpatient therapy, not get sick, not lose their hair, not have some of these kinds of big side effects that you have with conventional radiation.

[00:04:26] the patents were really centered around the control system that we built both from a software perspective and getting into the even hardware component level of all of the many things that went into play to deliver. This 2.2 second beam cycle over the course of a treatment that may run 10 or 15 minutes.

[00:04:47] Zach White: Interesting. W where are we at in the life cycle or maybe the adoption curve, I should say for that technology and medical treatment was this before that was even offered to patients that you were doing the work or was it already kind of mainstream and you were just improving and optimizing it? Like, where does.

[00:05:05] That technology. Yeah. 

[00:05:06] it was a little bit of both because we were also experimenting on being able to treat a broader range. so for example, when I first joined the company, we could not treat the metastatic cancers. we’re talking about a big mass that isn’t spreading through lymph nodes and things like that.

[00:05:23] , but the next big project. On was around being able to have more of a. Uh, steering capability and, uh, much thinner, beam that would go in and treat, areas like cancers within, lymph nodes and things like that.

[00:05:37] Dana Sherrell: So like potentially one day, breast cancer, unfortunately, the technol, I don’t think it’s the technology. That was the problem. It’s probably more administration and that sort of thing. That was the challenge in terms of, it’s just not conventional approach and it still isn’t today. There’s very few.

[00:05:53] Proton cancer treatment centers, across the world, actually. And I think probably the big reason why it didn’t really take off and become more of a common treatment probably has to do with. Kara Chrissy and politics more than anything. 

[00:06:05] Zach White: Wow. Well, for those who have benefited from that technology, thank you, Donna.

[00:06:10] And your team for the amazing work you did. I want to go back to a comment you made though about how you felt lucky. This was your first job, because you got to touch so much of the full stack and doing work. And I’m curious for you today, do you still believe that is.

[00:06:25] best or a recommended way for somebody to think about starting a career in software development and this space now, or is that something that it worked, in the late nineties, two thousands to do it that way, but you would recommend a different approach with your teams that work for you today, for example.

[00:06:44] I think it’s a combination of, you know, you know, yourself as an individual and how you’re going to respond to certain situations and types of challenges. And I think for me initially, it was actually pretty overwhelming, but. I’ve said this to someone else recently, I kind of equate it to a fight or flight scenario when you’re in a moment that, may seem like stressful and you, your brain 

[00:07:10] Dana Sherrell: You know, subconsciously takes over it. It’s more of like, what is your reflex reaction going to be? You don’t necessarily think about it too hard or control it. It’s just how you respond in this situation is for me, I think, fight kicks in and I just buckle down and go, no, I’m going to figure this out.

[00:07:25] this is a challenge. I get it. It’s scary. It sucks. but I’m gonna prove it to myself that I can do it. And so I think when you. Are considering, Hey, how do I want to start out? I’m new early in career. I think you should know yourself very well and understand what are the types of challenges that are going to motivate.

[00:07:45] Dana Sherrell: Versus maybe potentially not motivate you. And if you feel like something that is more focused in succinct around, like, Hey, I have a real passion for distributed systems. I have a real passion or really interested in, experiencing that journey of the front end. UX side of the house, then you may want to kind of spend some time building up that experience and considering yourself, you know, a subject matter expert.

[00:08:09] but you might also say, Hey, I tend to get bored easy. And so I’m looking for something with a little bit of a broader scope Maybe there’s an area where I’m really focusing, but there is an opportunity to be able to test those boundaries and get involved in other, in, in other parts of the system or other parts of the stack.

[00:08:25] Dana Sherrell: But I would say typically what I’ve found, and this industry is more often than not, that’s going to happen anyway. you’re going to join a team of people. You’re going to have a mission of like, Hey, this is the, the charter we have and what we need to support and what you’re going to find as you jump in and start experiencing that is even if you stay within a particular discipline.

[00:08:49] Back end front end. What have you, you’re going to be stretched, and challenged to continue to go beyond that edge of your knowledge and, pick up new technologies, pick up new frameworks, pick up new approaches to doing things. And so I just feel like there’s always been a plethora of opportunity, no matter what.

[00:09:05] Zach White: Yes. So fast-forwarding through your career journey then, Donna, what were the points that you would highlight where you had to pay. a new building block. this was one of the challenges or the things that I encountered at this stage of my career, where I had to really buckle down into one of those tough moments.

[00:09:24] Does any things stand out to you as those kinds of peaks of here’s where I had to really go after it? What are those moments? there was a few that 

[00:09:32] Dana Sherrell: actually stand out, I would say maybe the next one that really stands out for me is when I joined SendGrid. And, um, you know, SendGrid is, uh, uh, can say was an email service provider.

[00:09:44] We were acquired. soon after we IPO owed by Twilio, in 2018. And when I first joined the company, it was my first experience and huge scale. So I’d had the distributed experience. I had, that level, which was applicable, but, really first time going into a scale that I’ve never seen before.

[00:10:04] When I first joined the company, we were sending about 140 million emails per day on behalf of our customers. And I thought that was a lot of scale. And when I left the company, we were sending over 3.5 billion emails per day. on behalf of our customers. 

[00:10:19] Zach White: The mechanical engineer is like, what are you talking about?

[00:10:22] Billions of emails a day. Can you just set the stage? Like how big is that total market in term? I mean, if you took what now Twilio is doing, plus all these others, do you have any sense of the scale in its entirety? How many emails get sent? 

[00:10:37] Dana Sherrell: So when I left the company, our average was around 3.2 billion emails, 3.2, 3.3.

[00:10:44] But, every year when the black Friday season comes, you can basically expect that number in the course of about two days to immediately almost double. And so we were projecting to be sending over 7 billion emails per day on this last, black Friday. Just insane scale. Like it’s hard to get your mind around it.

[00:11:04] Yeah. Through the years as we were growing really fast and, you know, volume and in, infrastructure, just the things that we have to constantly like plan to prepare for that and make sure that we can do it. this is something, a lot of people probably wouldn’t expect. We weren’t in the.

[00:11:20] Our pipeline was not on like an AWS, you know, a hosted solution. We were actually an on-prem data center. So, you know, you have to do all this planning around having the hardware there to, you know, be able to support that. And there’s lead times. And when COVID hit, that was interesting because the whole supply chain kind of stopped for a minute.

[00:11:38] Right. So, a lot of challenges there, a lot of really interesting, you not just scaling challenges, but even just. from a team aspect, how your team is evolving to be able to keep up with that and, be able to even stay ahead of it, right? Like you need to stay ahead of it. It’s not even just about keeping up, but being able to stay ahead.

[00:11:57] And just a lot of the experiences that we went through there as a group and how to evolve things, to be able to support that type of scale, I would say. A lot of people did a lot of growth. Like a lot of people learned a lot of things and picked up a lot of new skillsets and, I really do consider that a, an experience where it’s had a lot of career defining moments for me.

[00:12:20] And then that was also the company where I transitioned from more of the IC tech lead role into. my, my journey through, crossing over and getting into more people in org, leadership and, pursuing, a leadership career in that respect. 

[00:12:35] Zach White: Yeah. I definitely want to talk about that transition, but before we go there, can you share your tips or at least your own methodology for how you go into deep learning and growth mode while you still need to deliver?

[00:12:51] In your day-to-day work. There’s a ton to learn and you’re stretching yourself and you’re challenging yourself. It’s like being back in school again almost, but you’ve got a job to do right now. How does Donna approach doing that? do you set aside time, every day to study? Did you practice, did you take courses, get coaches?

[00:13:06] Like how did you do that? a lot of it is really by experience and working with your team. yeah, there’s these moments where it’s like, okay, this is the problem we need to solve for what might exist out in the world that can help with this. And then, yeah, you’re spending a ton of time researching a particular technology, right.

[00:13:28] Dana Sherrell: That is going to enable you to achieve an outcome that you, we are shooting for. but I wouldn’t say it was like, I think this planned or organized thing, I’m going to go take these courses. I’m, that kind of thing. It’s, really more, every situation that arises where, okay, there’s a thing I don’t know.

[00:13:46] Or there’s a thing that we, as a team don’t know, then you’re the gears are like, okay, how are we all working together to figure out how to take on this challenge? And who’s going to take ownership of what geese and go research that and come back with their findings. And a lot of it is trial and error type of stuff.

[00:14:01] When you are. POC something and, build these prototypes and that sort of stuff. But, I think maybe just at the crux of it, for me has always just been, what is the challenge that’s facing me at the moment. Okay. What do I need to go do to figure out how to get to the other side?

[00:14:17] And it’s often a balance of, maybe some unique things, but like very similar you’re working with other people. To, you know, figure things out to prove to yourself that, yep. You’re still on the right track. Or if you’re not, how do we need to pivot? But a lot of it is just honestly, it’s teamwork, it’s collaboration.

[00:14:34] and then it’s some experimentation. 

[00:14:36] Zach White: I love that. So there was a point at which Donna, the individual contributor, the IC crushing it on projects, you got picked or you wanted to move into. leading the teams, being that manager now, obviously a vice-president and we’ll talk more about the high levels of leadership, but can you take us to that moment or what it is that created the transition for you into leading teams and starting to develop that side of your career?

[00:15:02] It was actually originally unintentional and supposed to be temporary. Yeah. We were growing really fast at the time and we were a really flat organization and, I had just been picking up. Areas to help support the team, or there have been some gaps in terms of just, you know, we didn’t have engineering managers in place.

[00:15:22] Dana Sherrell: Right. And, I think, leadership at the time just observed that and said, Hey, you seem to have an app for this. Would you like to do it? And I was like, no, I really love coding. And I want to continue to code and you know, all this stuff. and I really tied my worth to what I was contributing to the team, to what I was deploying and production.

[00:15:40] Right. And so it was actually a little bit intimidating. to think about that changing and, I was also like, Hey, I want to help the company, whatever the company needs me to do. I’ll do it’s cool until we hire people and then I can go back, 

[00:15:54] But that’s not what 

[00:15:54] Dana Sherrell: happened.

[00:15:55] I actually, uh, as I got into the role, um, it was bumpy at first I made mistakes. I think there’s. There’s a switch that needs to go off. If you’re not already thinking about it, if this wasn’t something that you were already working towards, where you have to realize how you support and enable your teams, your participation.

[00:16:13] It’s different, as a manager than it is as a individual contributor. And so it’s less about your hands on keyboard and it’s more about how are you empowering and enabling your team to achieve the things that they need to achieve. So they need your support in different way. There’s still obviously technical mentorship.

[00:16:31] There’s still obviously, you know, rolling up your sleeves and digging in and helping troubleshoot when the team needs it and asks for it. But, a lot of what you’re doing is figuring. Hey, these are the individuals that are on my team. this is each individual’s particular, genius or, strength areas and you know, how they help kind of level up others on the team, in that area.

[00:16:51] And everybody’s got that mix of, I’ve got some growth areas and I’ve got some areas that are, you know, more subject matter expertise. Right. And so you, you really need to understand that. And also understand what kind of motivates each individual on your team. And, you know, those are tools that you gain to help you figure out, okay, how do we best work with each other as a group and make sure people are getting the right opportunities.

[00:17:16] make sure people are being challenged in the right ways and you know, together we’re going to achieve the outcomes we’re looking for. And so it took me some bad experiences to, to realize that. And as I said, we didn’t really have other like engineering leaders in the company. So it’s not like there’s somebody there that’s mentoring me and saying like, Hey, this is how you should be thinking about this.

[00:17:35] Dana Sherrell: Right. So, figured it out. when I did, it became a much more enjoyable experience. And then I just realized I really, really enjoy. The feeling that I get, like, I get so proud of individuals when I see the journey that we’re all going through together. And I see the outcome on the other side and what we’ve all been able to accomplish together.

[00:17:54] And it just makes me so proud. I didn’t realize this was a thing that I valued years and years ago, but then when I experienced it, it’s, it’s, it’s a joy for sure. 

[00:18:04] Zach White: So Donna, tell us about your worst mistake and that first manager job. Ah, just one, um, one or two or however many. What were your mistakes?

[00:18:16] I think I just was, so I was still so focused and in the, in the mode of, you know, I’m in the, board, I’m in the JIRA board, I’m picking up a ticket, you know, I’m looking at people’s code and doing code reviews and, you know, it’s D book it’s different. The way you’ve set up the relationship and trust with the team is that like, the team would like your input and wants you to get some feedback versus.

[00:18:40] Dana Sherrell: You’re doing it and you’re giving people feedback and they’re like, does Donna not trust us that we know how to code? And we can have quality code reviews amongst ourselves. And it wasn’t that I was like, I don’t have that trust. And I’m, I’m checking on what everybody’s doing. It was more like I’m helping the team out, because this is the stuff that I was doing already, you know, as being, an IC on the team.

[00:19:02] And, I think it was stuff like that. So it wasn’t one huge thing, but it was more of being involved at that level still versus being involved in a different way where I was trying to understand like, Hey, where, where do you need help? How can I help you? What are your challenges? What’s going well, what’s not going well.

[00:19:20] instead of just inserting myself and thinking I’m helping, but really it’s creating this trust factor with the team or the team is feeling like, okay, Donna doesn’t trust that we know what we’re doing. So that’s one example of how that showed up, but there was a few other ways in which that was happening and it did, really come back we all do our engagement surveys, right.

[00:19:40] Dana Sherrell: It really did come back in the feedback of, The way that I was supporting the team, wasn’t really showing up as support, but really more showing up as 

[00:19:49] Zach White: lack of trust. This is a really common challenge. You know, the engineering leaders I coach shows up constantly and especially that first manager job, Don.

[00:19:58] My first engineering manager job, I had the same thing now, different world in mechanical and project stuff that I was doing, but that tendency to want to flex the muscle that made me a great IC and, just go help and check. 

[00:20:13] Dana Sherrell: Well, and that’s the comfortable thing to do. Cause that’s what you know.

[00:20:16] Right. 

[00:20:16] Zach White: Exactly. And the question. I ask myself now and I challenged my clients in and I encourage everybody. If you’re new to management to get curious about is who is that action truly in service of, because we. Trick ourselves into thinking that it’s in service of the team, but really I’m doing it in service of myself.

[00:20:39] It’s my own insecurity perhaps, or my own habits. And it’s something that makes me feel good about I’m doing work that I’m good at, but it’s not actually in service of the team at all. So I get curious with my clients, you know, Hey, who’s that really in service of that behavior that you’ve got so well, you mentioned like I figured it out.

[00:21:00] I had that moment. I got good at. And then I really fell in love with it. Can you tell us one or two things that helped catalyze figuring it out? did a mentor come alongside or was there a resource or something you just learned the hard way through enough mistakes? Like how did that shift from failure, failure, failure to, oh, now I get it.

[00:21:22] Where did that happen? 

[00:21:23] it was two things and I’m a little bit embarrassed to say. I don’t remember the actual ebook that I read. but what had happened was we had the engagement survey, the results came back. It was really hard seeing the comments. It was really difficult for me to see what the team was giving feedback, and how it was making them feel.

[00:21:46] Dana Sherrell: And in my head thinking. Geez. I’m putting in 150% to try to be there for everybody. And nobody appreciates the hard work that I’m doing. And it was kind of in that moment, it took me a few days of really mulling over that. And just being crushed that my team was like, we don’t like her, you know? at some moment of that, I just kind of like, I remember I was like driving home.

[00:22:10] I had such a long commute and I was like driving home and I’m sitting in traffic and I’m all grumpy about it. And then I just said to myself, you know what? It doesn’t matter how hard I’m working. It doesn’t matter that I think I’m helping, like these things don’t matter. What matters is the perception?

[00:22:26] The perception that’s there is not what I intended. It’s not what I was hoping, would be the outcome of this. And so something’s wrong and checked my ego a little bit. Not that I feel like I have this ego, but really more of like, why am I I’m I’m worried so much about my own feelings, right on the fact that I’m really putting in all this effort in the snap, but like, if it’s not working, it’s not working.

[00:22:47] So there’s something that has to change. the things that I used to be appreciated for are not what is needed of me in this new role. I got to figure out, what, what am I missing here? Right. And that’s when I went and I listened to this ebook and I can see this was, almost 15 years ago.

[00:23:05] So it was. Um, I can see the book it’s, it’s this yellow book with like a light bulb on it. that’s, that’s where I heard the term, for the first time, finding people’s genius. And that was one of the key messages in that book of, as a, you know, someone who is aspiring to be a great leader, two things that came out of that, right?

[00:23:26] your ability to influence others and your ability to understand others, because that’s going to be a factor in how well you can also influence and the understanding others part, the finding other people’s genius was all around that. The crux of that was, need to know the people on your team.

[00:23:45] Dana Sherrell: You need to understand them and you need to understand what drives them and what motivates them. And, People will respond in different ways to different ways of being challenged. And so it’s just really focusing on individuals and understanding, how they like to work and how, what environments are going to make them or situations like the most set up for success, does really matter because.

[00:24:05] We’re all individuals, world, we’re all different. We respond differently in what might work with, one person that you work with is not going to necessarily work with the next person. And so that book was really helpful for me. And it’s, it’s kind of weird to hear myself saying like, oh, it was this book and it was magical.

[00:24:21] And all of a sudden I was this great leader. That’s not what it was, but that was kind of the impetus for that realization. And then going, okay. Now let me take a step back and start thinking about how do I actually. start changing in these ways. And that’s when I also started engaging with other leaders and just having those conversations and it wasn’t necessarily an engineering, 

[00:24:41] It was, you know, across the company in different teams and orcs of, their thoughts and perspectives on what works well, what doesn’t, necessarily, and that sort of thing. But I think that was, the starting point. That’s such 

[00:24:52] Zach White: a great story. You’ve made a comment about having to set your ego to the side a bit.

[00:24:57] And I can say for myself, and I know for many of the engineering leaders, I’ve coached that the ego is a sneaky thing. It gets in the way. We don’t always notice that. Do you have any thoughts or tips for somebody? If you know, if an engineering leader is hearing this conversation and they want to do a self-assessment like, is my ego a problem right now?

[00:25:17] What would you encourage somebody to consider whether or not that might be. Blocking them from the awareness they need to make the kind of changes you made. first I would say, ask yourself how you show up. So how are you showing up to a discussion? How are you showing up to a situation?

[00:25:35] just in general, how do you show up? Are you. Receptive. Are you listening to what other people are saying? Or are you just so focused on what you’re going to say next? You’re not really hearing the voices in the room and, you’re just kind of focused on, okay. Here’s what I want to say and what I want to get out.

[00:25:52] Dana Sherrell: I think those are all signs of, you’re really focused on, on you and what’s going on in your head and what’s going on with you and not actually the broader picture and the broader situation. And so, thinking. the moments just in your day or what happened yesterday. And if you were in a design discussion with the team, or if you were on an incident with the team or whatever the discussion was, were you encouraging others to participate?

[00:26:19] Were you challenging others to participate where you really listening to what the other recommendations were? And even if you like your own better, where you trying to understand, because there’s often more than one solution to a problem. Do you actually give way for others to, bring that solution to the table and try it and not stick to your.

[00:26:38] too much 

[00:26:39] Zach White: all the time. That’s really powerful. obviously Donna, you have developed this skill in spades because the, comments about you and the leadership you’ve created since then is, is just tremendous. And I’m curious for this idea. Finding genius influencing and understanding some of those core things that got you started on this path.

[00:27:01] Now at the, you know, you’ve done director, senior director, VP level roles. Is there anything that’s different at this upper echelon of the company really leading the enterprise and the strategy and the vision from the VP seat that is different in terms of those core ideas? Or is it the same? How do you think about finding genius?

[00:27:21] And influenced now at this level, versus then when it was sort of a beginning catalyst to managing, 

[00:27:29] I think at the, at the core of it, it’s still the same, right? Because I think the common element is always us as people and it doesn’t matter, honestly, what role we’re in and who our team is in the end.

[00:27:45] Dana Sherrell: We’re all working together to achieve something. We succeed it’s because we did it together. And if we failed it’s cause we did it together. Um, and so I, I think, you know, those base principles of, being open understanding other’s points of view, and even just pushing on questions like. What are we aligning around?

[00:28:07] what are we trying to achieve together? Is that clear for everybody? That definitely becomes more important. I think, as you get, to different levels of leadership, because if that isn’t there and you make a mistake, the impact of that is probably going to be much bigger than if it happens within, the cone of a single team or, yeah.

[00:28:25] Dana Sherrell: It’s gonna be painful for the team and maybe for some of the boundaries in the team, but you know, recovery from that mistake is probably. Easier than recovering from a broader level mistake. And so the stakes are higher for sure. but I think, just fundamentally it’s the same type of thing, you know, just what are we aligning around listening to other people’s perspectives?

[00:28:48] You know, being open, if you have an opinion. Yes. You should share it. You should stand behind it, but don’t always be so tied to that opinion that. you can’t be open to anything else. Don’t die on Hills. You shouldn’t be dying on kind of thing. Um, but yeah, I think for the most part, it doesn’t change.

[00:29:05] I just think you need to be aware of the stakes as the decisions that you’re responsible for are bigger decisions. 

[00:29:12] Zach White: Yeah. A lot of people are scared of high stakes, you know, it’s like, whoa, I don’t know if I want to be responsible for that. And certainly takes a certain willingness from yourself to.

[00:29:25] Put yourself in those environments where, Hey, I’m, I’m willing to put it all out there and take that risk for you. Donna, what is the driving force for that? Why is it worth it for you? What, motivates you to just keep pushing and keep growing and take those risks in your career and in your life and with the business and your teams?

[00:29:43] what is it that lights the fire for you? Yeah. 

[00:29:48] I’d say one of the main things is. You get a lot of reward or I D a lot of reward out of being able to participate in something with a group of individuals where there is a clear, like this is my previous CEO used to call it a Beehag big, hairy, audacious goal.

[00:30:11] Dana Sherrell: And, you know, we’re all gonna rally around this thing and work on it together. And. It’s scary. Yes. And you don’t as an individual, have all the answers check. but I think there’s an exciting piece to, you know, a team of people getting together to figure this stuff out. And, one of the key reasons that I joined Boulevard recently is because I realized that, okay, I’ve gotten to a place and in my career with, Toyo where just, things happen, company dynamics change as the company grows and, when I first started, we were, I was like employee number 54, uh, back in 2012.

[00:30:45] And when I left, you know, we were over 7,000 people, you know, the company hadn’t had really grown, and the opportunity with Boulevard to come back to a, earlier stage company that needs to go through these stages. Right. And iterate, um, you know, towards them, it was super exciting. Cause it’s like you’re coming back to a smaller group.

[00:31:05] The impact is going to be. The impact is going to be more company-wide and, you could take that experience that you you’ve gained in this previous role and see what you can bring to the table, because, you’ve been there and done that, right. And say, Hey, let’s see what my learnings, let’s put these learnings to the test and see what works, you know, not everything’s going to work.

[00:31:26] And we’re all still gonna make mistakes where people were going to make mistakes. But, if you’re going to be afraid of making a mistake, then you’re never going to challenge yourself. And you’re never going to see what you can achieve, beyond what you’ve already achieved. And if you make a mistake, it’s not the end of the world.

[00:31:42] I guess you have to get comfortable with that at some point. And it’s not like, oh, no big deal. We made a mistake, if you’re not going to be okay with failing, sometimes then you’re. You’re not going to learn. So 

[00:31:55] Zach White: if you’re not okay with failing, sometimes you’re never going to learn.

[00:31:58] I think that’s every 

[00:32:00] Dana Sherrell: time you 

[00:32:02] Zach White: fail every time you don’t make it to vice-president. But if you’re going to fail sometimes, um, I’m curious Donna, with everything that you’ve experienced in your career and just knowing what you know now, is there anything you would really want to tell? Uh, younger, you know, software developer or engineer from any discipline for that matter, but just, that Sage wisdom of what got me here, you know, it was these kinds of things.

[00:32:26] And this is what you need to think about. Does anything come to mind that you’re really passionate about sharing with young engineers? first of all, this is just assuming people are doing the thing that they love and they’re passionate about it. And so if that’s the case, I think for me, it came down to grit.

[00:32:43] Dana Sherrell: And I know sometimes when people say grit, some people smirk a little bit and go oh, grit’s not going to, get you necessarily to where you want to go, but it shouldn’t be minimized. if you enjoy what you’re doing and you are going through these, whatever the challenge or the hurdle might be, it might not be a technical challenge.

[00:33:02] It might be. Teen challenge. maybe right now, you’re not necessarily getting along with your manager or some folks on the team, or, maybe you’re not working on the thing that you want to be working on. whatever the challenge is, you can avoid it and kind of become, lackadaisical about it.

[00:33:19] Right. And just be like, pretend it’s not there deal with it, or you can challenge it and you can say like, okay, I want to change this. You do have. Some power within you to change the situation. You might not be able to control something a hundred percent, but there’s typically something you can do about it, whether it’s changing your perspective or outlook on it, whether it’s trying to approach it from a different angle, whatever it is.

[00:33:39] But the point is is that you’re going to push yourself outside of your comfort zone to do something a little bit different, to see if the outcome feels better for you. And I think a lot of times people can. It’s easy to lean on and look towards others to own all of that for you. Like my manager should fix this, or so-and-so should not act like that.

[00:33:59] But a lot of times it’s all of us, whoever’s involved in the situation and some of it, you can control some of it. You can influence some of it. There’s things you can do differently. And, it does take a big person to realize that I think, and you know, it takes a little bit of humbleness to say, okay, I’m going to kind of stretch myself a little bit and see if this helps improve whatever the situation is.

[00:34:23] Um, or helps me gain some knowledge in some particular way. But yeah, that means you have to work at it and that means you have to not give up. And some of the times you’re going to be happy that you, buckled down and did that. And other times you’re going to realize, okay, well, I did do my best and it’s still not a situation I’m happy with, but yeah.

[00:34:40] That’s kind of how life works sometimes. Right. And we have to be okay. Accepting some things. Um, just as long as there’s a good balance of, you know, that. Okay, great. A situation got better versus, you know, okay. Maybe not this time. Next 

[00:34:53] Zach White: time, really powerful. I love the assumption that you’re in an area of passion and loving what you do.

[00:34:59] Big assumption,

[00:35:03] no amount of grit make up for hating what you do. So make sure that’s clear, but I think you take that concept. And then my other thing I talk about with clients all the time. Then a sense of radical responsibility. Like I refuse to be a victim to these things, whether I can or can’t control them, but I’ll take whatever agency and choice I have and go after it and just keep pushing forward.

[00:35:23] I think such a, an important thing. So I love that. Donna, what are you most excited about for the future? what are you seeing? What’s uh, you know, whether it’s in technology or just in your life in general, what are you looking forward to these days? So 

[00:35:40] Dana Sherrell: in my life in general. Um, so I have two sons and one is entering high school.

[00:35:46] One’s in high school graduating next year just started driving. So a lot of really exciting times, my two boys. It’s just really awesome. Just seeing the change that they’re going through and how they’re growing. And a part of it is really scary because pretty soon they’re, you know, they’re going to be off doing their own thing, but just kind of thinking about parenthood and my relationship with my boys and you know, how that’s going is, is, you know, something that.

[00:36:11] I really enjoy being a parent. Um, and then professionally, I’m really excited to be with Boulevard. I’ve been here for about eight months, eight and a half months maybe. And we’re growing so fast. And when I joined, I think we were somewhere around, somewhere between 150, 15 to 120 people in the company.

[00:36:29] Dana Sherrell: And now we’re. Above two 70. So, you know, quite a bit of growth in the last eight months or so. Andpeople listening to this might think like, okay, wow. That’s like, over a hundred people to add to a small group, it’s not like we were 5,000 people and we hired 200 people. You absorb that really easily.

[00:36:45] Right. So, um, as you can imagine, you know, we’re doing a lot right now in terms of just, planning and preparing to enable teams to be set up for success. And so we’re really. preparing for the second half of the year, to just kinda realign everybody around, like, Hey, here’s our goals and objectives.

[00:37:04] We want to go out and, achieve and succeed on together. And how are we positioning ourselves to do that? And what’s that gonna look like? And, just a ton of stuff that goes into. Getting all of that prepared and being able to share it with a group of people that a lot of them are fairly new, you know, just weeks to months in with the company.

[00:37:23] getting everyone positioned to go off and build some really great stuff for our customers. So I’m really excited about that because that is, something that, you can get your arms around in the next foreseeable future and know that if we all have the right level of focus and purpose, like we’re going to be able to really achieve these things and, you know, see what impact that it has on our customers and all that good stuff.

[00:37:45] Dana Sherrell: And I think I’m just hungry for that right now because, um, you know, it’s, it’s been a little while in terms of just coming from a larger organization where that was kind of slowing down a little bit. Um, so I’m excited about, that opportunity here, 

[00:37:56] Zach White: so cool. And what a perfect place to. Bring this to a close.

[00:38:03] I know that vision and being in the role that you’re in to have the opportunity to cast that vision and to influence and impact all of the people who are going to join your team at Boulevard. And you know, they’re going to be under great leadership with you and your peers there in the company. But I know there’s engineering leaders everywhere who want that chance to be where you’re at.

[00:38:23] so Donna, if you were speaking to them, one of the things I’m passionate about. Questions lead answers follow. And if the answer they’re looking for is big success and vice-president opportunities in their career, what question would Donna leave them with today to help them kickstart that journey?

[00:38:47] Dana Sherrell: ask yourself, what am I doing for myself to challenge myself? To move myself or to, to move in that next, take that next step in the direction. Right. So, you know, do I feel like I have the right leader supporting me? Do I feel like I understand what it’s going to take to go to the next level?

[00:39:09] Do I have the right opportunities? How my engaging to show that, you know, I want that next layer of ownership or that next layer of expanded scope. What am I doing to demonstrate. And if you’re really comfortable in your role, you probably want to reevaluate, maybe you’re, you’re not doing enough and you might not have the answers.

[00:39:29] It’s like why? I’m not really sure. Then what that looks like or what to do. And, at that point, you should probably be leaning on your leaders and mentors and asking for some constructive feedback on, okay. You know, what are the missing pieces? What do I need to do to, to challenge myself, to be able to demonstrate like, Hey, I’m ready for this?

[00:39:46] Um, so yeah, just a little bit of a self evaluation, maybe. 

[00:39:50] Zach White: Brilliant. So what am I doing to demonstrate. And prepare myself for that next level. And if the answer is nothing time to get curious about what I need to start doing with leaders, I think a lot of, I 

[00:40:03] Dana Sherrell: think a lot of times it can just be a natural state for us.

[00:40:07] I think something’s going to come if we’re doing a particular thing, but we own our careers. As much as our leaders are there to support us and enabling us to keep moving in our career. Right. but we own them individually. What is it that you want? How are you going after it? How are you having those conversations with your leaders to make sure that you guys are on the same page and working towards it together versus thinking, okay, my leaders are going to come and all of a sudden there’s a promotion or something.

[00:40:34] Zach White: Donna. I know people are gonna wanna follow you and your work. Maybe get curious about what Boulevard is up to as you scale and grow your impact as an organization. Where can people connect with you or find out more about what you’re up to. 

[00:40:49] everybody should go check out, join Blvd dot. At, or actually I should say, I’m sorry.

[00:40:53] Dana Sherrell: our website, and feel free to please reach out to me on LinkedIn. You can find me very easily I’d love to hear from anyone who’s interested in. 

[00:41:04] Zach White: Yeah, it sounds like if you’re looking for a great opportunity Boulevard might be hiring, so definitely check it out. Yes. 

[00:41:11] Dana Sherrell: I’d love to hear 

[00:41:12] Zach White: from people.

[00:41:12] Yeah. And we’ll put all those links in the show notes. So you know where to find [email protected]. Donna, thanks again for making all this time. It’s been awesome. I appreciate you. Yeah.