Working Remotely and Organizational Culture with guest Joshua Siegal
25 Mar 2020 · 31 min
In this episode of the "This Feels Right" podcast, host Joel Silverstone interviews Joshua Siegel, Vice President of Organizational Effectiveness at Wave, about maintaining culture and connection in a decentralized, remote workforce. Siegel revisits his Disrupt HR talk, introducing the "4 Ts" framework—Technology, Travel, Training, and Talent—as levers for fostering human connection when employees are physically dispersed. He discusses how technology can approximate in‑person collaboration, the reduced relevance of travel during COVID‑19, the need for intentional remote‑work training, and the importance of empowering talent to act as cultural connectors. The conversation shifts to Siegel’s personal mission: training for the "Fight to End Cancer" boxing fundraiser, illustrating how storytelling, purpose, and a "yes‑and" improvisational mindset build resilience and motivate others. Siegel also shares insights on navigating Wave’s acquisition by H&R Block, emphasizing authentic communication, preserving startup values, and aligning employee value propositions post‑merger. Throughout, the dialogue highlights practical leadership tactics—active facilitation, purpose‑driven storytelling, and aligning individual motivations with organizational mission—to sustain engagement, culture, and growth in turbulent times.
Chapters
Hi there and welcome to TFR, This Feels Right. Before we jump in, we've got our first guest today with us, Joshua Siegel. So Joshua, let's check in and see how you're feeling today. How are you feeling today, Josh?
This is the COVID-19 update. Well, I can tell you physically I feel fantastic. Mentally, emotionally, maybe a small smidge of anxiety, but But you know what? I feel that's pretty pervasive in society right now, so we'll just work right through that and have some fun this afternoon.
You know what? Absolutely. This is such an anxious time, and if we can have fun, and we will have fun today, I promise you that, let's do that. And this is TFR, This Feels Right. I'm your host, Joel Silverstone. Again, this show is about bringing my 20 years of experience working with people in business and sometimes in life. on how to use their communication skills to be more influential, meaning to be able to shift behaviors, ideas, and actions without threats and without manipulation. Influencing is about speaking to the logic, to the data, but it's also, and most importantly, the forgotten piece is about connecting to the emotional side where the other person says, yeah, this feels right. And today's show is about culture in the workplace. And we've got today with us an expert on that. We've got Joshua Siegel, who is the Vice President of Organizational Effectiveness at Wave. And Wave is a software company based in Toronto. And he's going to talk to us a little bit more about some of the changes that are going on and how he's able to keep up the values and the missions, which is part of what he's responsible for, as well as the learning and development. Also, Joshua is also a speaker at Disrupt HR, so you can Look him up and find his videos there. And we're gonna be talking a little bit more about that because his talk was very timely. And we are also gonna talk about Josh's other mission. His other purpose is that he's one of 10 or 20, I can't remember now, participants who are professionals who are gonna be boxing to fight to end cancer. Yes, fight for the cure in our lifetime. Such a worthwhile cause. We're gonna be talking about that as well. So Josh, let me just pause right there. Did I get that right so far? Is that where you're at right now?
That was a pretty good summation of what's happening in my life. Not bad, Joel. Not bad at all.
Well, great. Thank you. So let's talk about this Disrupt HR talk, which was about the remote workforce. And, you know, it's changing day by day. And by the time this podcast rolls out, who knows where we're going to be at. But definitely at this time right now, there is, you know, companies are shutting down. People are working remotely. It's hard for a lot of people who are not used to it, who need that collaboration. who need feedback from people, who need those relationships. And your talk about the remote workforce was all about that. So let's share some thoughts here. Maybe can help listeners out who are maybe now transitioning into that remote workforce.
Yeah, it's interesting. So I don't think that I'm Nostradamus by any means, but the Disrupt HR talk happened well before this COVID-19 issue, and it was really focused about how do you create connection in a world that feels like it's getting so much more decentralized.
Yeah.
And, and the talk was really focused on the war for talent, that you need great people to drive great businesses. And in order to accomplish that, you need to rely on a global workforce, remote workers, work from home, whatever the case may be, to attract the right type of people. Now, obviously, the outcomes of that, a decentralized workplace, are the reality of what we're dealing with right now because of the coronavirus. But the talk really focused about how A basic human need, as basic as food, water, and warmth, is the need for human connection. And we're now moving into an environment where so many employees are going to be forced to work in isolated environments, not have that human connection. What are we going to be doing as people leaders or business leaders to foster that very important human need?
Yeah. So, so, so that— let me ask you that. So what, You know, because it's our motivators, right, for a lot of us. Some of us are fine to be alone and work alone. We function like that. We're maybe more achievement-driven or power-driven. We don't need it. But most of the people need affiliation. They need to feel part of something. So what can leaders do or people leaders do to help those people that need that connection? It's not just a, you know, an iMessage saying you're doing great. What can they do to make them feel still part of the team?
Yeah, so I'll certainly reference Disrupt HR in the talk that I did in answering that, because I think 75% of the answer that I provided back then still holds true today. And what I presented was what I call the 4 Ts of creating connection in a decentralized world. The first, which is going to be hyper-important as we move into a more robust remote workforce, is effectively leveraging technology. We're doing it right now. Obviously podcasts, digital communication, tools like Slack and Zoom are going to become much more pervasive. And we need to be really thoughtful on how we're leveraging the technological capabilities that we have to create as much connection as we can. Is it as good as face-to-face sitting in the same room collaborating? I'm going to argue definitively no, but we need to do whatever we can to get as close to that as possible through the technological lens. So that's the first of the 4 Ts. Number 2 is one that I will say is probably much less relevant in the world of COVID And I told HR leaders that they need to fight for travel. If you have remote employees, you need to be bringing them in, you need to be creating connection. Obviously, that's not something that's reasonable right now, nor is that something that organizations should be doing.
Right.
So let's kind of scrap that one of the 4 Ts in the dynamics of this particular world. T number 3 was training.
Mm-hmm.
And I think, and I can't underpin this enough, leading and doing work in a remote environment is not the same as doing it in an office. There's no casual bump-ins by the water cooler. You need to be really thoughtful about how and what you're communicating. You need to be thoughtful on how you check in on your employees. Are you micromanaging? Are you not managing enough? And understanding how you do that in a remote environment Incredibly important. Understanding how communication changes when the medium changes. You need to train your employees on this so that they understand the dynamics are fundamentally different. And if you want to be effective in a world that's fundamentally different, you need to operate differently. And the only way to do that is through effective training. And then the final T that I talked about at Disrupt HR was around talent. Great leaders find ways to keep people connected. And it's, it's an easy answer. Just put your best people in leadership roles and let them drive it. But it's an answer that makes a hell of a lot of sense. Trust your people, trust your great people leaders. They're the strongest connectors that you'll have in any organization.
I love it. And I think technology, you know, you say it's, maybe it's not quite sort of travel, maybe it's not quite so relevant right now, but technology has changed so rapidly. Like you and I right now are talking through this Zoom meeting. And it does, it feels like we're, we're much more connected. And if we had a team and we were working collaboratively on something, or we were having a training session or something, there's still, there's still that opportunity. Like, we're, we're looking at each other face to face. There's a connection versus the old conference call where people would be maybe zoning out because— and just putting their phones on mute.
Yeah, it's interesting. We had a great example of this at Wave this morning. So we had a meeting with about 13 individuals.
Yeah.
I would say 8 or 9 of them were in person in the same room and we were talking through it and we had 4 individuals on one huge screen in a conference room. This slide was kind of divided in 4. We could see all their faces. They could see us as a conference room. The other slide had a shared screen with all the data that we're looking at. So it's certainly more robust. You can engage, you can have discussions. I'll definitively say though that the in-person individuals found it easier to collaborate and communicate than the folks that are isolated at home. And so what you need is a phenomenal facilitator who's really cognizant and aware and pulling them in, ensuring they feel involved and connected. And how you moderate and foster that environment is going to be so unbelievably important moving forward.
Yeah, no, I agree. Absolutely. And, you know, interesting that you say that about the facilitator because That kind of leads me to my next question. With your background, you were a professor, you did a lot of teaching, you were involved in academia, you wore many hats after that. But, you know, what have you learned as someone who was in front of people and had to get different people and different thought processes and thought patterns engaged that you've now taken into your role in organizational effectiveness?
So I would say the biggest key that I got from my experience teaching at a few different Canadian universities is the importance of ensuring that your stakeholders, so either the students or employees, whatever the case may be, that they feel connected to what you're sharing, and you transmit the information in a way that matters to them. Essentially, you make it real. If it's not real, and it's just kind of academia or from the textbook, it's so easy to brush it off. not be connected, but the second you can tie it to something that's important to them, and for students I found a lot that was, here's what you're gonna need early on in your career. Here's some real-world challenges that I faced in my career and how these concepts tie into them. And the second I can make those real-world connections, you see the eyes open a little bit larger.
Yeah.
They start leaning forward and paying a bit more attention. You get more interaction in the classroom. And it translates— very effectively into the workforce as well, where again, you need to find out the basic needs and wants of your employees. Where do you want to grow and develop your career? Oh, you're sitting in the risk function right now, but eventually you want to go be a product manager. Okay, great knowledge for me, because now as I talk about your performance and how we grow you, I'm going to think through the lens of a product manager and really try to equip you with the skills and tools that will make you more effective today. But will also lead you on the path where you want to go. And being able to cater and tinker that to the basic needs and wants of the individual, there's nothing more powerful than that.
Josh, you make it sound easy. You know, and maybe these things are things that you already knew were natural. And I think it's, it's, it's, you're probably a very naturally curious person. You know, that helps a lot to actually be curious about the people that are in front of you. So you're not doing it for yourself. You're being of service mindset, which also helps a lot. And then relevance. Why should the people in front of you care? And if they could see— and again, it seems like you're very purpose-driven— if they could see the purpose of why they're coming to work, where they could go with this, or why they're studying this in a classroom, how is this going to change the world, or how can this have an effect on the world? There, your job is a lot easier. And that's what really influencing is, is to really find what is important to that other person and how to connect with them. Is that right?
If you're not tying into their specific end goals, yeah, what's their motivation to listen other than, I have to listen to this guy to keep my job, maybe, but you're never going to inspire or galvanize or create great work that way. But if you can align and show them, I'm with you, I care about what you're working towards, and I'm going to help you get there. You better believe you're gonna have an inspired student, employee, whatever the case may be, driving forward.
You know, my kids are in high school, and it just amazes me about the teachers that are successful are the ones that are keeping up with the times and really connecting with the kids and having a line of communication open. And the ones who are, of course, disconnected are the ones who are still doing it the same way as though it's 1985.
100%. You couldn't say it any better than that.
Yeah. So let's take a little break here. This is what I like to call improv or improve your communication style. And then when we come back, we're going to talk a bit about resilience and talk about the boxing and the fight to end cancer and how we could bring some of those mindsets towards the workforce. But let's take a little improv, improve your communication style break here. Josh, are you open to this?
I'm pretty much open to anything. So bring it on, Joel. Let's do this.
All right, terrific. Great. So we're going to do a little exercise. Let's, let's assume that, you know, speaking about the Boxing Fight to End Cancer, that you would like to recruit me to be one of the boxers to come in and try to help raise money as well as participate in the event. All right. So, uh, I'm also a fellow professional. You want to recruit me, um, just to let you know, uh, you'll shoot me some ideas. Um, I will always answer with yes, but just to let you know ahead of time. Does that make sense?
All righty.
Yeah.
Okay, great. I think so. We can iterate. We'll try it. We'll see what happens.
Yeah, absolutely. Whenever you're ready, start us off.
All right, Joel, very important question for you. Has anyone that you've been personally connected to been impacted by cancer?
Yes. But they, you know, they managed to beat it.
That's awesome. That's awesome. Could you imagine a world where you weren't that lucky? And that the folks that you knew weren't quite as resilient?
Yeah, but I guess I have, you know, I didn't go through it. I have difficulties connecting with it.
You know what? I can understand that. Joel, have you ever thought about your own personal fitness and and your own level of health?
Yeah, but I think I'm doing okay. All right, we'll pause right there. You're doing fantastic. You're actually making it very hard for me to say yes, but just so you know, you're making it very difficult, very difficult. Okay, good news, Josh. We're gonna go back in time. Do do do do do back in time. And now I'm going to answer everything with yes, and. Don't change anything. Ask the exact same questions. I'm going to answer everything with yes, and. Go ahead.
Joel, have you ever had friends or family be impacted by the horrible disease of cancer?
Yes. And it was my— it is my aunt and my cousin and a very good friend of mine.
I'm so sorry to hear that, Joel. Could you imagine a world where it's even more pervasive and 50% of Canadians are going to be diagnosed with cancer at some point in their life?
Yes. And I, you know, whatever I can do, Josh, to be a supporter and help out somehow, because it really, it's something that needs a lot of attention.
And Joel, on top of those horrific societal issues, have you thought about your own personal health, fitness, and wellbeing? Yeah.
And I definitely can, you know, can up it somehow.
Awesome. So I will see you at the Kingsway Boxing Club to start training for Fight Dan Cancer 2021.
All right, Drew, bravo. Good. All right, Josh, how did you feel the first time when I was giving you yes but? How did you feel?
It's a very frustrating experience. I did not enjoy it in one bit.
How did you feel then when we switched to be— you were being, uh, I was starting with Yes, And?
It was very open, made conversation easier. I got to be honest, Joel, it kind of felt right.
Say that again and so we can get the soundbite.
Joel, this just feels right.
Terrific, thank you. Absolutely. So Yes, And is exactly that. It's a mindset about collaboration. So everything that you're talking about before, Josh, about really connecting with someone else, it's It's not going with a yes-but mindset, which is, you know, how can I shoot this person down? How can I make this person, you know, embarrass this person or shame them or make them feel like they're really, you know, running up a hill basically against the wind? So yes, and maybe we don't agree on everything, but yes, and is let me just have an open mindset and I don't have to use those words. So thank you for participating in that.
My pleasure. I love a good improv game. Anytime.
Great. Well, let's keep the yes, and going in the sense of exactly what we were just talking about, about the fight to end cancer. So before we talk about the, you know, the purpose of it, what I'd love to know is, you know, I myself am very much, you know, sort of motivated. I do these Spartan obstacle course races, but I'd love to know the secret sauce because you're in organizational effectiveness, Josh. How do you take the fact that you are basically out there, I don't know what, 10, 20 hours a week with your wife, you're training, it obviously helps to have a purpose, But how do you take that kind of resilience and self-motivation and share some of that secret sauce of those, that mindset with your organization to have that kind of self-drive?
So first and foremost, the power of storytelling is unbelievable. So when I start sharing my fight to end cancer story and what I'm doing, why I'm doing it, the amount of dedication and effort that's going into this, this kind of 6-month ordeal, you see that story inspire others to think about what they can do. And so it immediately creates this ripple effect where one person doing good, driving change, fighting the good fight, if they share that story, that in and of itself starts to inspire. So, Yeah. one, storytelling, unbelievably important. 2, I think it goes back to something that we were talking about earlier. And it's all about connecting the dots. So when I think about it from a Wave perspective, the mission and purpose of Wave deeply resonates with me because I come from an entrepreneurial family. So when I hear our North Star, our big mission of propelling the brave entrepreneur to pursue their dreams and drive the world's economy, I get it. I wouldn't have been able to eat and go to school, have a roof over my head as a kid if it wasn't for brave entrepreneurs running small businesses, struggling to figure it out, and that's who Wave serves. So for me, the connection to the mission is easy to create. I just needed someone to kind of draw the sandbox, articulate it to me, and the connection was there. For other employees, it may not be as direct.
Yeah.
But through the power of storytelling and connecting different people together, you can get there. Joel, you're obviously an entrepreneur, so that's easy. But if you were a new employee on day 1 at Wave, we're sitting in a cohort room together and we're talking about our experiences, what brought us here, and it's show of hands, who's run their own small business before? A few hands go up, but some don't. For the individuals that don't, well, do you have any friends, family members who have done it? And you start to get them talking about the stories and all of a sudden the human empathy, the emotion, and the connection to what we're doing Comes to life. And that's the power of storytelling, connection, and true real purpose and mission.
It's true because, you know, even something as simple as, you know, people make resolutions and they say, oh, I'm gonna, I'm gonna lose weight. And, and it often falls off because if you're just trying to lose weight for the sake of losing weight, you're not gonna be motivated. But I like this idea of that, you know, again, if you've got a story, if you can, you can almost see see a vision of it and how it connects with you and what the purpose is. I want to lose weight because I want to have, you know, the cliché, I want to have more energy to be with my kids, or I want to run a marathon, or we basically, we do, we need a purpose to be doing this. And it can't just be for vanity. I want to look good.
It's just not— 100%. I couldn't have said it better myself. And when I think about what it took to get me to do the Fight to End Cancer, I love that you did the yes, but and yes, and exercise. And for the audience, I didn't know that was coming. So there's no way I could have created this segue.
No, it was improv. Yeah.
But when I think about the last 5 years of my life, maybe 6, back in 2014, I had an old friend of mine who did the Fight to End Cancer back then. And this is a very charitable individual. He volunteers at SickKids on a weekly basis, does a ton of things. And to this day, he talks about how Fight Dan Cancer was the most meaningful thing he's ever done in his life. And it deeply resonated with me. And I'm like, wow, I love the combat arts. I care about humanity. I should really do this, but I'm too busy. But I'm afraid of the fundraising commitments, but I don't have— like, there are so many buts. And then over the next 5 years, unfortunately, and the story that got me to Fight Dan Cancer was I lost both of my grandparents to the same type of lung cancer. And it was, Mm-hmm. A horrific battle for both of them. And I watched each of them struggle for a couple of years and their lives truly crumble because of this horrible disease. And I started thinking about, well, what can I do? How do I fight this disease? I'm not smart enough to be a doctor or a scientist. And I wanted to fall back into that whole but, but, but, and then I said, screw it. Yes, and maybe I'm not a doctor, but I can get punched in the face. I can raise awareness. I can raise funds. There's a fight that I can fight that will make a difference. I just had to be open to it as opposed to closing it down with the buts.
Well, I'm sorry to hear about your grandparents because that, you know, especially that it dragged on like that, which is obviously was not, not a good experience for anybody. And thank you for sharing that. Thank you for sharing, you know, what, what drove you to that and what, what the mission was and And I think that is. I think whatever it is that drives us is going to definitely help. And this is a great help for the fight to end cancer. And it is true. I mean, I do, I had my aunt and my cousin and a good friend of mine luckily have all survived cancer. So, thank you to Fight to End Cancer, who have obviously been a big part of that as well. Yeah. All right. So, before we, let's just to sort of wrap up the Fight to End Cancer, when is the event and how How can we be involved with that?
Yeah, absolutely. So we are, we're training our butts off right now to be ready for an Ontario boxing sanctioned match. So this is a real boxing fight with referees, judges, all of that fun stuff. The training culminates on May 30th with a big gala and 5 boxing matches. So there's 10 boxers participating, one of which is actually my wife. So she has her own fight, which is pretty awesome. It's fun training side by side with her. Now, obviously, we're monitoring the whole COVID-19 situation very closely. So Boxing Ontario has currently suspended all sanctioned matches. So there's a little bit of limbo right now, but we're hoping that it's all cleared up in time for the big event on May 30th. Obviously, it's a huge fundraiser. 100% of all funds raised as part of the Fight Day and Cancer go to the Princess Margaret Cancer Foundation. So it's an amazing cause that is doing life-changing work, world-class. Life-changing work. It's it's unreal some of the things that are developing, and and to learn more, obviously you can visit fightancancer.com, and I'm very active on social media sharing about the journey, the training, what I'm learning, and and what the whole experience has been like.
Okay, great. And where where is the site if we want to contribute to this?
Yeah, so so myself and my wife we have our own personal link, but the easiest place to go is. Fighttoendcancer.com. You can see all of the fighters that are participating, learn a little bit more of our individual stories, and then obviously you can connect to the donation pages through the Fight to End Cancer website. Right.
Okay, great. All right. Well, thank you for sharing that. And hopefully the fight will go through and yeah, for many reasons that hopefully— Please, please, please. Yeah. That life can go back to normal in that sense. So before we wrap up, let's just talk— let's just go back to WAVE for a second because you were talking about, you know, the mission, the purpose, and the values of that. You know, you came into WAVE within the past year. It's been taken over by a larger organization. So what has been your role to keep or even drive new initiatives around keeping people engaged and driven towards a purpose?
Yeah, phenomenal question. So I'll provide some more definitive context. So I joined Wave about 7-ish, 8 months ago, and H&R Block, so obviously a giant American firm, purchased us about a couple of months before I joined.
Mm-hmm.
So I joined after the acquisition, and I've seen a lot of M&A activity throughout my career, and I've been on both sides of the purchaser and the acquired side. So I understand the complexities that come in that environment.
Yeah.
I can definitively say that H&R Block has made my job way easier than I thought it would be by being phenomenal acquirers. So they purchased us for our growth. So Wave's been growing pretty much 60% year over year for the past few years. And H&R Block clearly saw us as some rocket fuel and a growth engine that they could strap onto their very consistent business. to drive some growth. With that in mind, they've recognized that staying out of our way is probably the smartest way to keep the fast growth going. So they really want us to operate in the same kind of startup mentality, be nimble, be fast. You're still Wave, you're still Canadian success story. Like none of those things has changed post-acquisition, which has been unbelievably refreshing.
Yeah.
And I would definitively say that we're very lucky to have gone through an acquisition process quite like this. That being said, there's still a whole bunch of challenges that come anytime an acquisition happens. So you have to help employees through the whole image versus identity challenge on, well, who are we now?
Yeah.
We used to be this startup where everyone had stock options and controlled their own destiny, which is kind of true, but there's also the whole venture capital thing which complicates the whole picture. And now we can't call ourselves a startup. startup anymore. We just got bought for half a billion dollars.
Right.
So it's a different dynamic. We're part of this larger public company. So as much as the feel and what we do within Wave HQ really hasn't fundamentally changed much, I think the perception and the mental models that either our employees or prospective employees has, has certainly shifted. And we've had to do some learning over the past few months on How do we communicate that in a really authentic, meaningful way? How do we position that? What does it mean about our employee value proposition? And we're still working through that. And how do we continually communicate with our employee base so that they feel comfortable raising concerns about what's important to them and what they want to maintain, and that they also have as much visibility as possible? And what are the new paradigms and what does it mean?
Yeah, because I think that's one of the challenges when you are in a sort of startup type of organization or even a small company and all sudden you're this huge change being bought by a bigger company. Everyone's afraid of what's going to happen here, what's going to happen to my job, what's going to happen to my role, are we still that. But what I'm hearing is that what H&R Block understood was that the reason for your success is that there's some values, there's some mission that helps people to still feel that there's a commitment. And as you said, it is about a growth mindset, I think, versus a fixed mindset, which is how can all of us grow within this organization. And this is This is— we want to grow and we want to also be of service to that entrepreneur, to that small business, and continue to help them thrive.
Absolutely. One thing we always say is that we live in a very, very dynamic world. It's really the nature of fintech and software. So things are constantly changing. The one thing that doesn't change is growth. That's the one constant that we have that we know is gonna happen. And that growth fuels a lot of amazing things when it comes to opportunities, The reality is our revenues are nowhere near big enough to value us at half a billion dollars. It's our growth that drives that. That's why H&R Block purchased us, and that's what we're gonna continue to deliver.
Love the story. Great, great. Thank you for sharing that. So before we go off, Josh, where can we connect more with you or maybe follow you?
Yeah, absolutely. So I'm very active on social media. My favorite platform is LinkedIn. So feel free to just search up Joshua Siegel. Happy to create some new connections. Have some good conversations there.
Terrific. Joshua Siegal, Siegal with an A at the end.
S-I-E-G-A-L, no relation to Steven Seagal, although we both like the martial arts.
Great. Well, thank you so much for being a guest on TFR. This has been really good about, you know, and timely that, as you said, you know, months ago you had talked about the remote workforce. And, you know, I think the theme that comes out of today is that if we want to have a influence others and keep the culture and missions in our workforce. It's important that we connect with everybody, that we keep them engaged and find out what's relevant to them and how they could feel a part of something. And then in the end, it is about growth, whether we are looking to fight den cancer or we are working in a startup organization that's been taken over by a larger organization. It is important as leaders and people, people developers that we continue to connect and engage. So thank you, Joshua Siegel, and this has been TFR, This Feels Right. We will see you next week on our podcast. And if you'd like to connect with me, you can also connect with me on LinkedIn or our Facebook page, This Feels Right Podcast. And of course, you can also watch us on our YouTube page, which is also This Feels Right Podcast on YouTube. So thank you very much, and we'll see you next week.
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