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Future of Work: Navigating Digital Transformation with Drew Weiss

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About the Episode

Implementing new technology can take a lot of time, money, and effort—which leaves plenty of opportunity for things to go wrong. If you’ve suffered through a failed software implementation, you probably want to avoid experiencing that trauma again. Drew Weiss, VP of Global Business Technology Operations at VICE Media, joins us on this episode to help you do just that. Listen now to hear his advice on how to successfully introduce new technology to your organization, from gathering buy-in all the way through optimization.

Episode Highlights

Meet Our Guest

Drew Weiss has spent the last decade leading IT teams and scaling corporate technology at companies like Refinery29,, and VICE Media. His roles have included everything from Global Director of Internal Systems to VP of Technology Infrastructure. His passion is to help organizations improve operations, implement new technologies, and automate processes. As he’s grown his career, he’s always held onto the belief that people are at the core of what makes technology successful.

Episode Transcript

Lindsay: I'm Lindsay McGuire, and we want to change the narrative around the future of work. It's not about adapting. It's not about changing. It's about creating the future of work that works for your organization. So let's create it together. This is future of work, a ripple effects sub series from Formstack.

Digital transformation is something that can't happen overnight. You need internal. Buy-in a culture that embraces change and leaders who want to iterate, iterate, iterate. Drew Weiss is one of those leaders. He's the VP of global business technology operations at vice media. The world's largest independent youth media.

At a media company like vice there's an incredible balancing act going on on one hand, the company's always trying to be ahead of the game on technology tools, processes, and mediums. But on the other hand, they're a media company. So they're incredibly visible to the world, which means they've got to take risks and stride and know how to balance that risk with the rewards of being innovators and change makers.

here's drew giving us a peek into how vise approaches, implementations, 

Drew: our primary goal. Put in place best operational, uh, you know, practices, if we need to implement systems or technologies to go along with that, we will, but we really try to live within the confines of what vice RD uses and just use them to the best of our abilities.

So wa uh, a really good example of this is, you know, we will go to a. Line of business or department or team advice and say, we'd like to develop what we call a document of understanding with you on how your team works. Currently we'll develop all the workflows flow charts, things that you may not have in place.

From that we'll develop a strategic recommendations document. So those are usually programs or projects that we're recommending. We will gain buy-in on leadership. And then we'll go to the various stakeholders across the business, HR legal, it, gain their buy-in, make sure that we have their teams resource properly and then build out a full timeline on how we can.

Streamline what they do building in all automations where things are manual and implement new systems, or take better advantage of the systems that they already. 

Lindsay McGuire: I bet a lot of our listeners are so jealous right now, because that sounds like a fantastic piece to have built into a business or an organization.

 as your team is looking at the other departments, other areas of the business and trying to decide, you know, where can we assist? What can we do? There's a lot that goes into that. for you as the technology leader inside this department and this team, you know, what is the biggest thing on your mind at vice right.

Drew: Over the last couple of years, that one of the things that's really come to the forefront is how do we promote collaboration amongst our teams? Vices? Not without people who want. Make change and, and improve things. Like there's a million people that, you know, that want to do that and are very hungry for change.

Um, the problem is that everybody kind of does it through the lens of their own particular group or department. So one of the things that I brought to the forefront was, well, how do we make sure that we're all. Together and initiative that one team is taking on. Doesn't overlap with an initiative.

Another team is taking on that. We're not working against each other or kind of taking on redundant activities. So bringing everybody together and making sure that everybody is collaborating on these initiatives and is still the biggest challenge that we're tackling. So if something. In virtue, which is our agency arm wants to implement a new system.

They may, you know, previous to our team being in place. They may go sign a contract for that new system. Take that new thing on, implement it. And then down the line, they would go to our it team and say, oh, by the way, I need this system to integrate with XYZ. And it would say, well, we don't have the resources to do that at the moment.

And so we would sit on our hands and pay for a system that we weren't utilizing for an indefinite amount of time because we didn't gain that buy-in up front. So I guess, you know, that's a really long way to, to answer your question, to say that it's just collaboration is first and foremost, what we're looking to lean into advice and that's collaboration amongst our employees, but also kind of amongst our stakeholders, whether that be an it or HR information systems and so on.

Lindsay McGuire: Yeah, I think you brought up a really excellent point when talking about how one department might have one pain 0.1 issue that they are working tirelessly to fix. They come up with a solution. Think it's, it's going to be the perfect thing for what they're dealing with right now. But then we might not take into consideration the workloads of other departments or the priorities of other departments.

And it's really hard to. Get, I think, a full organization into that kind of thinking. So what advice do you have for people who are trying to figure out how to switch the thinking from only my team's problems or my department's problems and seeing your organization more holistically and doing what you said of thinking about all the pieces before you do the one solution for your.

Drew: That responsibility, I think kind of ends up falling on the business. You need to give people the platform to be able to vocal, you know, to, to vocalize issues that they're having to, to bring up, you know, pain points in their workflow. Because if you don't, what you'll find is that people will kind of circumvent the process to do.

Themselves. So one thing that I've really tried to instill advice is this opportunity that people have to gain the buy-in of other departments without necessarily needing to know who these two, those departments are. So there's kind of two separate ways that we're taking that on. Number one. You know, we have a centralized place where people can submit very broad strokes.

What the issue that they're facing is what the solution that they possibly want to implement is, and then it's on my team to go use that data to bring in other stakeholders, whether that be people who need to be on the project. Make it successful or just other people that we might think would benefit from it.

So for example, if we're implementing a new production payroll system, which I think is, has been a really great lift advice, we went from a very rudimentary manual system, paper time cards, paper, start work for all of our production staff to something that's very modern. Technologically up to date. And that was something that we rolled out specifically for production, but because it went through the lens of our business technology operations group, we were able to say, you know, who else?

I might be able to benefit from this, our marketing team, our, uh, our, our social team, our anybody else that kind of leverage is freelancers, but not necessarily production freelancers. And so we, in that way, we took it on ourselves to go out and find the other teams. Able to use this relevant piece.that we were only implementing for one department with advice.

So that's one is just like making sure that you have a team that can be the, the advocate for the person who wants to implement a new solution. And the second piece of that is making the data reporting available to everybody. So we've not only implemented quarterly town halls, where every team gets five minutes to talk about what they're working.

Mostly so that everybody else can hear what's going on at the business. And, and what comes out of that every single time is somebody raises their hand and says, oh, that thing that, that team is working on that would really benefit me. Can you help get us in touch? So that's something that's been really, really important and really helpful.

And then the other side of that is we also have a reporting dashboard that we've implemented. So now anybody can go to this dashboard and see. Any team is in their project lifecycle. So it's making those things available to everybody. That's been really key and helpful. Yeah. That 

Lindsay McGuire: data transparency can really assist across an organization.

It's amazing to talk to people who have done things like that and just how revolutionary that can be, because you just don't know what you don't know. 

Drew: Yeah, every time we have one of these town halls, I get 2, 3, 4, 5 emails from people that just like are clamoring to benefit from, from things that they've seen across the organization.

And that just didn't exist before we kicked off the. And I 

Lindsay McGuire: want to touch back to something you talked about just a little bit earlier with going from a very manual paper process that I would assume was a legacy process. It's something you've always done. One way. It hasn't been challenged.until your team took a look at it and said, wait a second.

So for these organizations who might be in the same situation where they have legacy systems, whether they are. Paper manual based, or they are legacy technology that is 10, 20 plus years old. How can these organizations approach innovation while also balancing the fact that it takes time to level up from these legacy systems and processes?

Drew: I think at the outset it's setting expectations. So there is often when you implement a new system, there's two sets of expectations you have to set. One is, you know, the people who want to see the change you need to set expectations on when you may actually be able to roll this out, how you're going to roll it out, who you're going to introduce it to first, how you're going to make sure that when it's in place.

It is in fact, a step in the right direction. I think there's this misconception that just because something is legacy it's bad, right? There's a lot of people who think that a legacy system has worked just fine for them and will continue to work fine. So they don't really know why you're trying to reinvent the wheel with their legacy systems.

So number one is, is, you know, setting expectations that what you're doing is actually going to be better for everybody and setting that expectation properly with the group. The second piece is setting expectations with people who are day-to-day users of the system. So again, kind of going back to that issue, that just because it's legacy doesn't mean it's bad.

If I've been doing something for. Years then I'm very comfortable with it. And now you're telling me that I have to, I have to reinvent the way that I do things. Well, how are you going to instill in me that this is actually not putting my job at risk, right? Like you're, you're automating something that somebody was doing manually.

So I think there's like being careful and making sure that you're addressing the risks and needs of everybody involved and kind of moving from a legacy to, and to an updated system is really important and being really. To the fact that just because you think that it's like, oh, I can't believe we still do this this way.

That everybody feels that way. I think that that's what really big lesson that I've learned in my career is, you know, when you come from technology and you, and you work in technology, You think that everybody's going to be excited for a new piece of technology as you are. And what you quickly realize is that not everybody has that mindset and a peak, especially people who work outside of technology or outside of it, they can often be very hesitant when it comes to change.

And so you need to be really sensitive of that. And it's something that I've learned over my career is, you know, I used to go in. Guns blazing saying like, we're going to change everything. We're going to make everything better. Look at how awesome this is going to be. When you know, we have all this new technology rolled out and everything is streamlined.

And very quickly you realize people say, well, you know, I really liked the old way of doing things. So you need to address that up front. And really that comes down to building trust with people and making sure that they understand that you have their best interest in mind, as well as the best interest of the organization.

Lindsay McGuire: Yeah, you're so right. The change management portion of that is so crucial. Um, I remember, uh, my first professional position was at a credit union and we had a SVP come in who was very tech minded and very forward-looking. And he brought in the idea and implement it. The idea of virtual tellers, where you could drive up to an ATM and virtually talk to a teller on a screen.

And let me tell you that shook some people to their core. But I think what he did successfully was cast the vision of why this was a great change, how this would be a great opportunity for not only their customers, but also the organization as a whole. So I'm interested in your advice on how should organizations approach those kind of hard situations about change management and when someone's been doing something.

One way for however long we've been doing it. And we want to approach us in a new way, but being sensitive, like you said, to their thoughts and their feelings and their job and, and kind of how they feel about their credibility and position in the organization, 

Drew: that's really important. And I think that it's what it really comes down to is gaining buy-in.

As early as you possibly can in the process, when people feel like they're part of discovery, when they're part of the initial roadmapping of a project, they feel like it's a collaboration and not something that's been put on them. So it's really, I mean, gaining that buy-in upfront, that's so important.

Um, and then building trust, right? Part of it is. Setting expectations and meeting those expectations. It's so important that when you talk to somebody at the outset and you say, this is what we're implementing, we want your help in implementing it. We want to understand what your current workflow is. so that we can make it easier gaining that buy-in is so important up front.

And then you need to make sure that you adhere to those things. So the worst thing I think you could do is go to somebody at upfront, bring them into our process. Try to build that trust only to break it later. So gaining that buy-in bringing somebody in upfront and then maintaining a relationship with your key stakeholders throughout the process.

I think we sometimes have a propensity to gain, buy in and then go run and build something. Once we think we've got it. And keeping people up to date and meeting deadlines is so important so that you continue to, to foster that, that trust that you built up. 

Lindsay McGuire: And you bring up a good point about, and this is a common thing.

I think we get caught up in that shiny new object, right. And the end that we're trying to chase or the solution we're after. And we lose the fact that really at the end of the day, people play just as much of a role, if not more in choosing your technology as the technical. 

Drew: Yeah, absolutely. This is like, you know, one of these things that I always think about with just, just like how we roll out technology, how we implement new technology.

And it's like, you know, I think there's been in our industry. There's been this. Top-down mentality for so long and it's changing, but you know that like change management needs to come from the top and you need to, you need to have a broad picture when putting in place any new piece of technology. But I will say that like some of the most successful implementations that I've seen.

A hundred percent organic where our development team wants a new tool and we say, okay, go for it. You can use it for 1520 users and it gains traction and other departments hear about it. And then all of a sudden you've got the whole company on something that is organically grown. And I think that that is sometimes so much easier and a more fruitful way of implementing a new piece of.

Lindsay McGuire: love that you brought up implementation because what we see with a lot of our customers, and I think not even just our customers, but just in the industry overall is a lot of organizations failing with software implementation. 

So what advice do you have for organizations on trying to smooth out that implementation process? 

Drew: Get as many stakeholders that you can bring into those initial discovery sessions is incredibly beneficial. So I think a lot of it is just err, on the side of involving too many people, rather than not involving enough people.

And again, there's a balance and align. You've got to walk there because you know, if you have 75 people helping you on the outset with discovery, you're, you're never going to get anywhere. But I always say I'd rather have too many people in the room than not. 

Lindsay McGuire: Always comes down to that clear communication and setting expectations.

And I want to dive back into this term digital transformation. So this is something that a lot of people can define a lot of different ways. So I want to know how you define digital 

Drew: transformation. The evolution of anything technology related. 

So, you know, advice, digital transformation for us is kind of trying to streamline. Operational workflows. So they fit best within our digital ecosystem. So it's taking the best advantage of the tools that we have at our disposal to automate what is manual. That's kind of how I think about digital transformation advice.

It's the, and this is obviously through the lens of what I'm doing currently, but it is the transformative impact on operations. 

Lindsay McGuire: I love that definition. And I think that is a really clear way to say that. And as we think about the future of work, you know, you brought up tools. What do you think are the tools that are going to become crucial for businesses?

As we look at the next year, two years, five years, you know, the workplace is so drastically changing. So what tools do you think organizations should be thinking about looking into if they haven't yet? I 

Drew: think that there's. Buckets as it were right there, the first is the collaboration tools. So things like slack, zoom, how those things interplay are going to be crucial and only going to get more important I've seen in my career in it and technology, just seeing the evolution of aim to Google, meet and Hangouts and chat to slack and Microsoft teams and just like all of them.

Ways that we started kind of collaborating just from a communications perspective are going to become even more important. And we're going to have to lean into more and more as we kind of move to this like high Rue way of working. The second piece of it is, you know, collaboration on projects. So, you know what you've seen.

The multitude of project management tools that are out there, um, right. Sauna, even like air table or Monday, just like all these suite of tools and when they're working their best, it is when you're promoting collaboration amongst those tools. So, you know, anybody can do a project plan. Excel document.

It's really not that difficult. What these tools provide you is the ability to collaborate on these projects in real time, pull in stakeholders, making sure you're holding people accountable in these tools. And I think that that's going to become more and more important as we go forward. So that that's, that's the second piece.

And then third piece, is kind of. Leaning into documentation and making sure that these things are available in real time. So, you know, we seen tools like notion, confluence, and trying to educate people on how to use a, what was kind of a developer tool for documentation and leveraging it for all documentation.

Full stop. Developing sites, uh, you know, that's something that we're really looking at and then having that live alongside ticketing, and then third is just, you know, platforms for making documentation readily available. And then having that live alongside things like ticketing platforms, you know, I think it's going to be really important then when I have a question.

Yeah. Pop that into something that gives me an FAQ. And then if that FAQ doesn't get me anywhere, I can reach out to the relevant stakeholder via ticket. That is kind of the, the other piece of that. And making sure that people can stay productive. 

Lindsay McGuire: Well, we formed sacker actually users. So quite a few of those tools too.

So I want to talk about the future of work. And I think the last few years have been very reactive. Many of us have been in reactive stages because of the way the world's been. We haven't known what was coming next and we've had to just react as things have changed and moved and developed. But I feel like where we are now, we're finally at a place where maybe organizations can start being a little bit more proactive.

So what do you think are ways that organizations can now start being more proactive in the technology landscape, going from. 

Drew: It's just giving people the tools that they need to do their jobs effectively and making sure that those, those tools are kind of at their fingertips. So one of the things that I really love that's come up, you know, when we talk about digital transformation over the last couple of years is the ability to easily integrate tools.

Previously, you know, I always said that we often try to square peg round hole things for our employees. So if we had chosen one specific system for completing the task, so let's say that the company uses a sauna. That's what we use for our project management. And that's your only option while we would have.

Hours and time trying to shoe horn people's processes into working in a sauna. And I think that one thing that we've seen with, with tools like Zapier, is that we don't have to do that anymore.

We can, you know, I mean, obviously cost being a consideration. Um, we can say, you know, if you prefer a different tool than what we are. I would rather you use the tool that you like and let's figure out how to integrate them. Let's use these, you know, off the shelf tools that have had these prebuilt connectors to make sure that the tools are talking right.

We don't want you in a silo, but we also don't necessarily want you to completely reinvent the way that you do. To shoehorn into, to something that you're, you're not in love with. So I always say that like my, from an it perspective, I like to, um, I have a, I have a yes. First model instead of a no first model.

So like let's work together to try to get to yes. On anything new that you want to implement. And these new, you know, off the shelf ways to integrate systems has. Made that a whole lot easier, because now you don't have people in silos. You know, you, they can work in separate tools, but their data can flow freely between them.

So I would say like really lean into a lot of these SAS tools that are out there that can make all of that possible. 

Lindsay McGuire: Yeah. I think the integration conversation is so crucial here because we do often see organizations that will adopt a tool and then they either can't integrate it. They don't integrate it, whatever the situation might be.

And all of a sudden, not only do you have a data silo there, but you also might eventually have an orphaned to SAS tool. And that is money left on the table. That's productivity that is wasted. So when companies are thinking about integrating their tools, do you have any best practices or advice? 

Drew: Do your discovery on, on what's possible.

Do your discovery on what's available off the shelf with these various tools? I think that the more points of integration of data integration that have been prebuilt, the less work that you have to do, and the more flexible you can make your. I want to 

Lindsay McGuire: shift into the conversation around digital maturity.

Uh, this is something that we have started talking about more and more, especially as we begin to see organizations shift from being reactive to proactive. So for those organizations who might have. Higher up on that maturity scale, that digital maturity, you know, what can they do to keep innovating if they don't see those huge gaps in their processes or those big data silos, things seem to be running effectively and efficiently.

And they've done a lot of the, let's say, heavy lifting. What should they be looking at since there's not those most like obvious issues I wanna say. 

Drew: The short answer to that. And it's this, it's a hard question to answer with that because I think every business is different and every use case is different.

So there's, there's not, I don't know that there's like a, a broad answer to that question, but the thing that I always look to first. Do you have everything documented? Do you fully understand your workflows? Um, do you have flow charts built out? Do you understand the way that people work fully? Because I think often there's a gap between thinking that things are running efficiently and smoothly and knowing that things are running efficiently and smoothly.

Lindsay McGuire: think you bring up a great point though that a lot of the times with digital transformation, once you finish or reach that in your mind finish line of this, project's done this project's implemented, everything's running. There does seem to be. Uh, pothole that people hit, where they forget that there is that maintenance, that ongoing maintenance that always happen.

So I think that's an excellent point to bring up because, you know, you reach your quote unquote finish line, and then you think you're done. And then you don't think about the fact that, but it's never really done. 

Drew: Right. Well, there's like, I talked to my team about this all the time, because we have this in the role that we're in.

You have to have a clear definition of done because otherwise you're going to support the system forever. But the thing that we've tried to get a lot better about, and we're still quite frankly, working through is like, what does our handoff process look like? Who owns this? When it's no longer our responsibility who owns this once it's implemented companies often forget that piece of it.

Well, you know, I'm going to, I'm going to implement this new piece of technology and, you know, once it's live somebody else's problem, but what you should rest on your shoulders as the person who's implementing the system is making sure that it's, it's fully supported going forward and not necessarily solely, solely supported by you or your team, but fully supported by the people that you're handing it off.

Lindsay McGuire: So for those organizations who might not be as digitally mature as they wish they were, you know, how can they get started? How can they maybe kind of figure out where, where to start what's tackle first, 

Drew: prioritize, prioritize, prioritize, figure out what your model for prioritizing. Systems technology is and use that in everything that you do.

So if you say our priorities are based on generating revenue and driving down costs that, okay, that's great. That's really broad. But use that through the lens at which you prioritize everything that you're working on. The key point, there is, you know, figure out how you want to prioritize things like have a model, have a, have a methodology for prioritization and use.

Every step of the way. I've seen a lot of companies, like we just want to identify low hanging fruit. and that's what we want to tackle first. That's great. But use that light and stick by it and make sure that everybody knows that that's how you're prioritizing things. 

Lindsay McGuire: Well, drew, I have one final question for you and we ask this of all of our guests on future of work and you can answer however you see fit.

But what comes to mind when you think about the future? 

Drew: It is giving people the tools to work efficiently, wherever they are. That's really the crux of it. And that's everything from communications to collaboration tools, to project management tools. It's just, you know, how do I make my employees as efficient as possible?

Yeah. If they're not sitting at a desk next to somebody else. 

Lindsay McGuire: So I think drew brought up a really phenomenal point that it's really at the end of the day, not about technology. It's about people. If you don't empower your employees, if you don't give them the resources, the freedom, the creative authority to invest in systems, processes, technology, new ideas, then you're really missing the mark.

I think he made a really excellent point that it's really putting people first. And that's the key to any success with any technology. So I want to bring up a few pointers that he said that really resonated with me. First 

I love that drew mentioned the power of organic implementation. Sometimes you just have to listen to the people inside of your organization to know what tools they want. And if the passion for the tools is there with the first few power users, soon enough, the tools spread through your entire organization.

And I love how he brought up that everything is iterative when it comes to digital transformation. When your organization is implementing new tools and processes, I know it's really easy for us to want to be in that, set it and forget it mindset, but it really, at the end of the day is not going to have as much ROI as we think.

Innovative organizations, embrace new tools, embrace new initiatives, and immediately start thinking about what's next. A great practice to start implementing is to never let a process get stale. Think about how you can audit your systems, your processes, your tools in an ongoing manner, so that you're getting the absolute most out of your investments and that the people on your teams are still getting the most out of them.

And last stop trying to square peg round hole, your employees into tools. Drew talked about how he'd much rather implement a ton of different tools than try to peg everyone in the organization into one tool that doesn't work for everyone. If your organization hasn't figured out how to easily integrate tons of tools yet, then you're doing your team and your productivity.

A disservice drew gave us an incredible foundation to build on with our future of work series. Having the right technology and tools in place is the first step to making sure you can meet all the needs of your customers. Next episode, we'll dive into the changing expectations of customers and how you can unleash your workforce in order to meet their ever-changing needs.

If you want an inside, look at how people are, re-imagining their world of work and making an impact head over to forward slash practically dash genius. We'll be back soon with more.

Hosted By
Lindsay McGuire
Senior Content Marketing Manager
Co-Hosted By
Ryan Greives
VP, Brand & Communications

Practically Genius is a show built for innovators championing digitization within their organization.

Hosts Lindsay McGuire and Ryan Greives host conversations with real-world innovators sharing stories of digital transformation while also providing helpful advice and insights to listeners.

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