The Why Behind Team and Culture Investment

The Why Behind Team and Culture Investment - Future of Team Podcast Episode 001
The Why Behind Team and Culture Investment - Future of Team Podcast Episode 001
Future of Team
The Why Behind Team and Culture Investment

James: Welcome to the Future of Team Podcast. My name is James Giroux and I am joined by my cohost Dee Teal. This is a podcast where we are hoping to delve into the dynamics of HR, people ops, team building culture in particular at remote first companies I personally, and I think Dee as well, both of us have a background working in WordPress companies.

I’ve been working in the WordPress ecosystem for about 15 years, It is crazy to think it’s been that long. I mean WordPress is 20 years old so so I’ve been quite a seasoned vet, but part of what made WordPress really exciting early on was it was really one of these torchbearers or these early pioneers of remote first workplaces of being able to have your team distributed around the world.

I can remember in 2012, 2013, I think I was in San Francisco at the WordPress or the Automattic offices in San Francisco after WordCamp San Francisco at that time. And they were telling us that, yeah, this is the last time we’ll do it here and have an after party here because we’re getting rid of our office and going fully distributed.

So that’s a little bit of, of me. I’ve been in, yeah, the ecosystem for a while. Dee what about you? 

Dee: I think I started using WordPress in 2010, but found the community early on in 2011 at a WordCamp. I just went looking, I wonder if this conference is about WordPress and found this one that cost me 50 bucks.

So, so yeah, I’ve been around for a while and got deeply, deeply interested in the, in the whole community. And so I spent a lot of years as a WordCamp and WordPress meetup organizer. And yeah, through that community found my way into remote first workplaces and, and have worked with quite a few of the different agencies building great WordPress stuff since then.

James: Wow. I think that’s something we both share. So you’ve done a lot of agency work. I’ve been a lot on the product and service side. So I’ve worked for hosting companies and worked for, Product companies selling plugins and themes and marketplaces as well. I worked at Envato for a little while. He did.

And I guess like for, for me and, and probably for you as well, one of the things that happens is you start to see the way different teams structure themselves and as you get going, you kind of see the good and the bad, the ugly. As far as what goes on in workplaces. And I know for myself. One of the reasons why I wanted to do this podcast was to really help teams in WordPress and leaders in particular in WordPress who are managing these teams have conversations around the ideas of, People and culture and leadership.

And what does it take today to build a really thriving workplace for your team, especially as remote workplaces and remote work becomes the standard as opposed to the exception to the rule. And how does that flip a little bit of the way we do things? I think within WordPress, one of the things I’ve noticed and just in some of my own research is the, the average team size tends to be around 15 to 30 folks who are working at a place and, and when you’re that small ish it’s 15 is big to those of you that are, you know, solopreneurs, but you know, in the, in the grand scheme of things, 15 to 30 is small and you don’t really have somebody who is dedicated to, you know, HR or dedicated to people and culture.

If you have somebody passionate about it that’s really I think exciting. Dee how do you see this podcast contributing to the evolving narrative of team building and WordPress? 

Dee: It feels to me a little bit like it’s kind of a starting place. If people are starting to think about how are we actually going to make the experience of work.

better for the people here. I think the experience of work is becoming more and more critical. People are having more control over how they actually deliver their work and that they can be at home or they can be in an office. But the whole sense of how they feel about coming to work doesn’t just owe to To the tasks that they’re completing or the outcomes that they’re delivering.

It’s not just the website that’s on the other end of that contract. It’s the people that they’re working with. It’s the environment that the organization has created that contributes significantly to how they feel about going to work every day. And we’re in a volatile season at the moment, right?

There’s less work, potentially, we’ve, we’ve seen people be retrenched, they’ve been layoffs. There’s people that are just quietly doing their job, but mentally disengaging from what they’re doing. And a big part of that, I think, is how it feels to actually be in their workplace. And so, I feel like what we’re doing, or I’m hopeful that what we’re doing, is generating the conversation, giving people ideas, exploring what it means to create that space, where people not just are resourced to be able to complete the task, but actually also resourced to be able to enjoy going to work every day, to enjoy the experience of working with their teammates and to And, and to feel supported and free to be themselves or bring them best self, bring their best selves to the workplace.

James: I think that’s something we can. both agree on is that, yeah, how we work and the way we work is all rapidly changing. Or I think society or, or, or the greater work environment has been becoming more aware of our need to be more Employee centric, right? For many, many decades, it has been employer centric and we’ve been focused on, you know, things like what, you know, what are the benefits?

What are this, what are that? Right. And it’s just very employer centric. And so you’re, you’re lining them up that way. Where’s the best deal for me. And, you know, I know, I know for myself in the last number of years, I’ve seen, I remember when, you know, it was the whole bro culture of startups. With ping pong tables and video games and all of that kind of stuff.

And we, we made this really rapid transition to, you know, well, that’s actually not what people are after, right? People are after psychological safety. People are after, you know, fulfillment in their work career progression. People are after feedback that actually helps them grow. You know, like those types of things became the hallmarks of a great company, The foosball tables and, you know, the fizzy water in the, in the, in the kitchen.

So I think for us you know, the next stage of that obviously is, is this remote side of it. Right. And how do we do it remote when we no longer have the proximity to each other that we once used to enjoy. And WordPress, you know, like where, where our background and WordPress is, is maybe further along, but I think we’ve rested a little bit on the fact that we can work from anywhere that we can work from home.

Our, our commute is a minute, right? From, you know, the couch to the, to the, to the desk. And that really is okay. Right. But now that’s the standard, that’s the norm. So how do we move beyond that? So how, so that WordPress can stay competitive. And we can stay competitive as an, as an ecosystem and continue to grow the teams and the skills and abilities that we have so that we can deliver great products and projects to our clients and our customers.

Exactly. I’m, I’m interested. So like, so that’s sort of like the why of like, we’re doing this. And, but what specifically are we going to be talking about? I think for this podcast in particular, there’s lots of different things. The thing that I think of is like. Practical HR for growing teams. But with a WordPress perspective, right, we have a specific lens.

We do things a little bit differently here. Do you, do you have any thoughts on what you’re hoping our listeners will take away from this podcast? I 

Dee: think one of the things I’m keen for people to feel is resourced. to be able to go into their workplaces. So if you’re thinking about a small team that’s got 8, 10, 15 people and somebody’s going, I really want to improve the culture in our workspace.

It doesn’t necessarily have to come from the boss. I think I can even share an example. And the place that I work at the moment, we’re all predominantly remote. We have a hybrid office and we come in a couple of days a week. We do all of these we used to do these social things, you know, create a trivia night would do a social event and it would be trivia online.

We hadn’t done it for a while. And so I just took the opportunity to say, Hey, we haven’t got together just for the heck of it, just for fun. Let’s play Scribble. And we had the most ridiculous half hour meeting doing Scribble. So it can come from anybody. I guess where I’m going with that is that giving people who are in the workplace, Hey, here are some ideas.

For me to actually start this conversation or start doing little bits and pieces that can help kind of just get people thinking about it or building up that sense of, of culture, 

James: I think too, that’s part of it, I think. What else? Yeah, 

Dee: no, I think what’s an example of some of the insights you can see James about, 

James: but that’s exactly right.

And I think those are the kinds of things I hope people will, will get to hear as well from this stories from not just us, but from other leaders. Sure. And people all around the world. On their experiences it’s, and, and as you say, it’s not just about, you know, needing to be the leader and make the decisions from a top down perspective, but from a bottom up as well.

I’m a massive, massive believer that culture actually starts from the bottom as well as the top. Right. And we all have to have ownership of the place that we go to work and I can choose to allow the culture to happen to me as it is, or I can take steps to have it become the culture I want it to be.

There’s lots of, as I’m saying that I’m getting all the different reading in the back of my head. Well, no, you have to have top down leadership for, for it to work. And you, you know, one person can’t change the culture. Like all those things, those are all true to some degree. But it’s, it’s, it’s a both and it’s not an either or, yeah that 

Dee: makes sense to me. 

James: Yeah and I think too just even from, from my perspective, like having worked in smaller teams and larger teams there’s a breadth of The practical side of things that I think we can shed some light on, like maybe not everyone has heard of, you know, creating career progression plans for your teams or you know, maybe you’ve never had a management one on one course or understand what it is.

Actually means to do one on ones or to provide feedback or do a performance review. Like maybe there’s opportunities for us to have some conversations there, both as ourselves, and hopefully with some, some guests as well. With some ideas as you said, to put in the toolbox, right. That people can use as, and when they need them.

And scribble night is great. I remember quiz night at Envato. So good. My goodness. We don’t have like a pub night quiz night culture in North America in Canada or the US in particular. And that was one of the things I really, really loved was we’d all stay, stay after work. You know, we’d go into the main, the main meeting room, break up into teams and just have a blast.

It’s just something fun about that. 

Dee: Yeah, that’s, it’s crazy fun. We were, we were doing these on Kahoot and we, we had, so each team member who’s, you know, would pop on the roster to create their, their trivia quiz would pick some random topic. We had one on the apocalypse that was hysterical, you know, just like, but yeah, there’s some great stuff out there and great resources out there and it’s going to be fun to actually talk through and hear from other people, I think too, what the, what they’ve been doing.

James: I think that’s, what’s really neat about. Your experience and my experience as well as we’re actually kind of like HR adjacent. We’ve had leadership experience. We’ve had team experience But I know I speaking for myself. I Deeon’t have HR experience, which is crazy, right? Like that here I am championing team culture people hr all this stuff as a non hr person and that’s not to say You know I don’t value and respect all of the education and training that goes into that.

But you know, I just, I think there’s something neat about being outside of the regulation side, right. And the legal side of HR and looking at it from a different perspective. And I hope we’ll have people on who will be able to bring that legal perspective and speak to that a lot more. But yeah, how do you, how do you think our combined experiences are going to shape this conversation?

What are you excited about? 

Dee: I’m excited about the fact that you bring that perspective from the product side because that’s new to me. And I’ve had moments where I’ve kind of wanted to dive into that, but I just keep coming back that I love building these things for these clients and building that relationship.

So that sort of is kind of less so about the team and the culture that I’m in, but I’m really interested in how it differs on that side of the fence. I think that’ll be interesting. 

James: That’s a good point. And it’s something, it’s something I’m curious about too, because, you know, we, on the product side, you don’t ever get rid of your product, right?

Correct. You release, but then you keep it, you don’t let go. You don’t say goodbye. So you’ve, you’ve got to find a way to be okay. With the things that you’re killing your darlings, there is no done. 

Dee: Well, that’s the other thing too, is that an agency, your team is less likely to stay static so you can build the thing, the team that you’re working with, maybe the same people that you will.

I mean, we’ve, I’ve done projects that were eight or 12 months long and you’re working with the same team through that period, but then. The project changes or you go on to something else. And now you’re working with another team and you have to start building those relationships again in a, in a different way.

And I think the agency side of things gets informed a little bit by that too. 

James: That’s a really fascinating thing to think through because. Yeah. As, as you say, our, our teams tend to stick together longer. And so those team norms and ways of working and, and the culture of your individual team gets much more established and you can work through sort of the forming, storming and norming stages over time.

And as a new person comes in, cause it’s not going to be all at once. You don’t have to go as far back. into the process of, of building that, that safety up again. Whereas I would imagine on the agency side, you’ve got to figure out how to ramp up. You know, to productivity and working together and like that whole other, like, I would imagine your discipline around, you know, forming, forming that team and getting to that place is much more established.

Dee: Well, that’s the fun part. I’m a scrum master. As ended, you know, in a huge part of what a scrum master does, even in a, which is kind of weird in the, in an agency contest. And we can have a whole conversation about how you apply agile in an agency over a product. But yeah, this whole sense is we’ve got to get in there.

We’ve got to get moving, but then the other side of agencies. is also the situation I’m in at the moment is that I have a pool of devs, I have a project or a business as usual situation where I’ve got projects that are just humming along and I don’t have a big deadline that I’m moving towards and I’m just pulling people in, I’ll get you to do that beast.

And I’ll get you to do that piece and that there’s no working together. So there’s, there’s so many different dynamics, I guess, in an agency situation where, and how do you keep that sense of team when that’s how people are working, when everybody’s doing kind of ad hoc pieces of work. And there’s no, Hey, we’re, we’re all getting together.

Here’s how we’re going to get to this point next. I know that I’ve felt this. Possibilities are endless. 

James: It speaks a lot, I think, to you know, why we think it’s important to have these conversations. Obviously there’s different approaches, there’s different challenges and it’s neat. It’s neat to think about.

All of this and, and really, as you say, there’s, there’s complexity to it. There’s, there’s many different ways to approach how to do team and culture. I think one of the things that’s really interesting too, is the opportunity for us. Rather than relying on the traditional model of how work has been done and culture has been done.

Right. For us to explore some new ideas and new ways of thinking and ways of working. And to, to go, you know, like, like remote is new. It’s not, it’s not that new really. Like a lot of us have been telecommuting or tele teleworking. That’s the ancient term telework. Oh 

Dee: my goodness. I hadn’t heard it for so long.

I’d forgotten. 

James: So it’s always been, there’s always been an element of that. Right. Um, but much more prevalent now. And, and I think our systems are finally catching up. Right. And our, our stack, our tech stack and all of the things we do around it are finally catching up. To where our heads have been and our hearts have been for many years.

Pandemic, you know, definitely helped there. 

Dee: Yep. For sure. 

James: I mean, there are unique challenges as well to HR, right? What a small, medium sized teams. I think I think one of the things I’m keen to explore as well is how we can not just Not just focus on, you know, the basics of HR, like those things, but like how we set up our teams for longevity.

You and I have spoken a little bit about this. Dee, I’m curious to hear your thoughts on it. But, you know, from my perspective, one of the challenges I see is WordPress. Teams aren’t built for the longterm.

Dee: Now, I want to ask, how did you come to that conclusion? Yeah, 

James: no, fair, fair, fair. I think 

Dee: I’d start with that. I think, well, 

James: I guess when I look at the track record from a product side in particular, maybe that’s probably my lenses is skewed to product. It seems to be the end game is sell or acquire. Yeah.

And. For whatever reason, the space has been filled up with what we would consider successful teams and successful leaders burning out, tiring out, being done and ready to move on to the next thing. And instead of looking at their product companies as these 20, 40, 100 year, Yeah. Yeah. When I’m done, I’m leaving.

And, and this, to me, what’s interesting about that I think is, is the, the, the amount of influence or impact a single individual has on the state of a company.

Dee: So I hit, so then my next question is. I guess the things that I’m thinking around this are, if we’re talking about building these remote first companies with great cultures, a lot of it starts with what’s in the leader. And, and, and then the conversation is also, well, what am I building this for? I ran my own business for a while and, you know, was building WordPress websites, like a bunch of us did the solopreneur thing.

And I got to that point where I go, if I’m going to make this. They go, I’ll make more money. I need to make this a company. I need to make this a business. I don’t want to be a business person. I’m out. So that was me. And I wonder how many people kind of fell into that and go, well, I can do this and I want to make more money and I want to do more, but, and I will build the business.

And then the, but I wonder how many people actually came at it and go, Oh, this is what I have to do to get there. Rather than thinking, I want to build the business and I want to build this. I’m not sure if that, to what extent that contributes to this whole sense of, I guess where I’m going with this. And one of the things that I’m really interested in is the sense of what runs in the leader runs in the team.

And so that what we’re doing, and we’ve already talked about what we can do from the bottom up, but I’m also really interested in what people need from the top down. Hey, I’ve got this team, I’ve fallen into the situation where I’ve got 15 people. What am I going to do next? I don’t want to do this for the rest of my life.

How do we resource that change? How do we help people in that situation? How do we, yeah, I don’t know. I’m not sure if I’m, no, I think you’re right on it. 

James: And, and honestly, that’s a lot of the conversations I’ve seen happening, right? On the product side, it’s really interesting. What, what often happens is you see somebody who has a great idea.

For how to solve a problem in WordPress, right? Or solve a problem in, in tech. And so they go out and they build something and what they’re really good at is building with code or coding or engineering. And so they build this, this thing out and it solves this problem. And then, you know, maybe they go the free route, but maybe they also go the paid route and all of a sudden, you know, whether you’re free or paid doesn’t matter.

You end up with support. Right. And you end up in a situation of solving problems or fixing things for your user base. And that leads to feedback, which leads to a need for you know, more resourcing and, and over very quickly, you know, something that started out with, Hey, I just want to fix a problem or solve a problem can turn into, and I’ve got four support people on my team and two marketers and there’s myself and, you know, like got a sales funnel and we’re doing SEO and whatever else to try to grow, to, to, to what, to what end.


Dee: Yeah. Oh, Hey, I have a company now. Yeah. Maybe I should think about. I 

James: see this happen a lot with first time managers as well and maybe you’ve seen this where the transition from individual contributor to manager is a really difficult transition to make because you go from doing the work to managing the work and you go from output to To outcomes.

And that’s a really tough thing for a lot of folks to navigate. 

Dee: It’s hard to measure. It’s hard. It’s hard. It’s hard to hate you taken. I’ve been that person, right? I was a project manager and then managed a group of project managers and that sense of how do I feel productive if there’s not. And I’m, I’m just in meetings all day and I’m not even telling people what to do.

I’m asking how they are, how is that productive? And you know, a lot of that will come down the team go, oh de that’s the support of knowing somebody wondered how I was, you know, levels up the engagement. Like there’s all these things that are measurable, but that sense of, yeah, that transition is a really big one.

And I am fortunate that I was really well supported through that process with coaching and, and webinars and all these kinds of things. I know that not everybody else gets that. Maybe we can help with that too. 

James: I reckon that’s a great, great place for us to stop with that thought. So if you’re, if you’re keen on all of this, you know, like it’s, it’s a moving target for us, but the things that we’re definitely sure about is we believe that.

Culture, team, leadership, these are all things that are easy, that you can learn, right? And that you can try. You will definitely fail at, at some point. And I’ve got tons of failure stories that I’m excited to share. But through all those experiences, as you take these steps forward, the end result It is incredible, open people, first cultures where your teams are thriving.

They’re high performing. They’re getting things done, delivering at a level you never thought possible. And who knows? And they’re loving it. And they’re loving it and they’re sticking around. And yeah. You know, from my perspective, coming from a WordPress background, what I love is that the more WordPress companies are doing things like that, having conversations like that and have these kinds of tools in their toolbox, that’s going to leak into how we do community, how we do WordCamps and meetups and how we work on core together.

Oh, what an incredible thing that would be. 

Dee: Yeah. Awesome. 

James: Well thanks, 

Dee: James. This is fun. 

James: Yeah, I’m excited. I’m really excited. So if you haven’t yet, definitely make sure to subscribe to our channels. So you’ll be the first to hear when all of these new episodes come out. And I would really encourage you as well to contribute to the conversation.

So if something tweaks you or, or, you know, you’ve got a thought on something, definitely, Leave a comment, you know, send us a message, all those kinds of things. Cause we will reflect on that, add that in. We’ve got some really cool segments planned for bringing on some of that feedback and talking through that.

I’ve got, how do people 

Dee: find us James? 

James: Well I don’t know yet because we haven’t quite, I assume it’s going to be Future of Team. com forward slash podcast. You can find us on YouTube, Spotify, and wherever you listen to podcasts. 

Dee: Beautiful. 

James: Thank you so much, everyone. 

Dee: Thank you. 

James: Okay. I guess that’s it.

Dee: We did it.