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Helen Kupp: ‘Once-in-a-Millennium Opportunity’ to Try Something Different

April 20, 2021 Digital Workplace
Simpler Media Logo
By SMG Events

As the director of product strategy and partnership at the Future Forum — a Slack consortium that collects and analyzes data such as employee preferences and organizational practices so that the partners it works with can stay competitive — Helen Kupp has done a lot of thinking and researching about the digital transformation organizations are undergoing. 

“We're moving into this era where you can't think of digital transformation separate from overall business transformation. They're just so interwoven together that it's not useful to think of them in isolation. We're all trying to figure out how to work differently and how to bring in more hybrid, flexible work.”

As companies try new tech and rethink what role digital solutions have in the future of work, Kupp said experimentation alone isn’t enough. 

“It's important to let teams experiment with new tools and processes that help them be productive, but also be thoughtful about how that integrates back into what your digital headquarters is. If you're using different tools as a team and you're experimenting with that, you still need to make that information accessible to the broader set of people within the organization.”

Slack is a sponsor of Simpler Media Group's Digital Workplace Experience Spring Event, taking place online on May 13. Kupp will present a breakout session during the event titled, "Re-Imagining Work: Building an Inclusive, Flexible and Connected Workplace."

We spoke with Kupp about what a hybrid work model might look like, how digital transformation can be paired with business transformation and how COVID-19 has given us a unique opportunity for experimentation rather than falling back on what strategies we’re already comfortable with. 

How Do We Weave Digital and In-Person Experiences Together?

Simpler Media Group: What makes an 'ideal' digital experience? How does that differ from what most organizations are doing, and how can those gaps be filled?

Helen Kupp: It's more than just the digital experience. What we're finding is that most organizations and people want some version of a hybrid work experience — where there's flexibility to work remotely but also come into a shared space when that's needed. Future Forum surveyed over 9,000 knowledge workers globally; we do this every quarter. Eighty-three percent of knowledge workers don't want to go back into the office five days a week. So the real question is, how can organizations be intentional about how the digital and in-person experiences weave together? 

That requires more than just thinking about the digital side of things. It often starts with: How do you think about the principles in which you want to operate, how you want to operate differently, and what guardrails you want to put in place to ensure that you don't snap back to old habits?

SMG: How can remote employees feel more part of the team once not everyone is on Zoom?

Kupp: I think this is going to be one of those things that we have to be even more intentional about as offices open up and we start to move from fully remote to hybrid. Fully remote and fully in the office are easier, right? There's a consistent set of expectations. When you move into hybrid, it becomes more complicated. How do we make sure this is equitable? How do we make sure that we're including everyone? And how do we also not make it feel like chaos? 

[One] of the principles that we're thinking about at Slack is that diversity alone isn't enough. Equity and belonging are critical. That translates into thinking about equitable access to opportunity, which becomes really important when you're hiring from different locations and trying to avoid creating a remote second class. You can do that by being thoughtful about guardrails that you implement as part of hybrid work. For example, something we talk about often at the Future Forum is 'if one person dials in, everyone dials in.' I think everyone has felt that the Zoom environment in many ways has leveled the playing field: We all have our own tile, we're all dialing in instead of the single zoom participant trying to hear what’s going on in the conference room. It’s made people feel like they've been able to be part of the conversation.

SMG: Face-to-face communication versus digital communication: Is one actually superior over the other? What has this past year of COVID taught us?

Kupp: Both are important for different reasons. The myths we had about face-to-face being absolutely necessary or the best solution for everything have been debunked. I think the biggest myth was, 'We need to be face-to-face to be productive.' In fact, we can be productive even while we're working remotely.

We just held our creativity and innovation research summit this past Tuesday. Most of us still hold onto this myth that the best way to generate ideas is to group brainstorm. It's the classic whiteboard, post-its, lots-of-people-in-the-room image, but decades of academic research actually tells us that that's not true. Group brainstorming often leads to groupthink, and you don't get the highest quality ideas. The best ideas come from when teams alternate between some individual work and some group work. 

That's a great example that I often think about in the context of face-to-face versus digital communication. When an individual can work offline by themselves, they come up with really great ideas. In many ways, digital ways of working and communicating actually open up our ability to include different voices that we typically don't hear.

We have this opportunity to be more intentional about when we should do digital work, when we should come back together and how we can make the best use of our time. There are cases where I think face-to-face is uniquely better, of course, that you’re never going to replicate digitally. But there's a lot of opportunity, like with brainstorming, to pair the two and think about how they work together to create a much better outcome and a better experience for more people.

DWX Leaders 2021. Helen  Kupp, Future Forum/Slack: "We have this opportunity to be more intentional about when we should do digital work, when we should come back together and how we can make the best use of our time."

'The Blueprint for the Future of Work Is Evolving'

SMG: How do you see digital experiences evolving in light of the pandemic? What does this accelerate for you? What does it hinder?

Kupp: One of the most interesting trends is that it has accelerated the adoption and comfort with virtual experiences. In the third quarter, when we released our research study — we call it the remote employee experience index — we saw that working from home was better on all dimensions, except for sense of belonging. But when we refreshed that in the fourth quarter, we actually saw that people were starting to settle into new ways of working and connecting with people in digital ways. Sense of belonging moved from negative to positive. 

I think it's interesting because we'll continue to see new technologies in the different ways that people develop relationships and connect with each other digitally. Leaders and organizations are recognizing the value of breaking down the geographical barriers of work and how we can pull more diverse perspectives into the mix. As companies lean into that hybrid model, I think we'll see more ways to connect without having to be in-person.

SMG: What are the biggest obstacles to creating and delivering on digital experience goals? How can companies leverage technology to help?

Kupp: There are two [barriers] that come to mind. The first is focusing on the technology before thinking about the overall outcomes you're driving toward. That goes back to that earlier point around principles and guardrails. Take a step back to think more holistically about the culture you want to put in place before thinking about the way that the digital experience needs to look.

The second is not recognizing that the blueprint for the future of work is evolving, and it's going to take experimentation and ongoing investment. So do things like listen to your employees to understand what is and isn't working, and pair that with finding practices that work and finding ways to continue to scale them. 

That first barrier is more around leadership alignment. The second one, around experimentation. Technology has a strong role to play in the organization's ability to experiment and share learnings transparently. The way I think about it is in this world of hybrid. Digital becomes so much more important as your central headquarters. Instead of having a physical headquarters, digital becomes the way in which you connect people, in which you ensure that information flows between teams and people who are no longer in the same location. But you also have to think about if [this method] incentivizes people to be transparent and share more information, not less. Without information sharing, you don't get that connectedness across different locations when people are working in a more distributed way.

SMG: On this need for transparency and information sharing: Do you think there's reluctance? Are there groups of people (like higher-ups, ground-level employees, etc.) who are more likely to feel reluctant? 

Kupp: It depends on the culture of the company. There are certainly senior leaders at Slack, for example, who are very transparent, who are always willing to broadcast in channels about what's going on. There are individual contributors at more technology-laggard companies who are like, 'We keep things within our team. We don't talk about this.'

SMG: There's this tendency in the media to over-generalize trends, especially now when we're trying to figure out what the future of work might look like. What type of research can we trust about this? How do we make sure that we don’t jump to conclusions?

Kupp: Media likes to take a headlining view of trends. Yes, there are broad studies, but your industry, your company, your employees — it's helpful to go deeper and understand what they want and how they’re feeling. [Regarding] one of the organizations that we've worked with on Future Forum, one of the best things they've done is just to talk to and survey their employees. 

Second, it's important to remember that we have this once in a millennium opportunity. We've been in remote work for a year now, and that means we're in this really sweet spot. We're all ready to try something different. It would be such a waste to just say, 'I'm going to give up.' Push through a little bit more and try something different. You can always go back to how you were working before.

The point around experimentation is important here because surveys can tell us only so much. Nobody has the complete plan for, 'This is exactly how hybrid is going to work.' We can communicate this to everyone that this is not the perfect answer, and that we will figure out what works as we step into an actual hybrid world. Because right now, we're still not hybrid. Some countries are, but for the most part, many of us are still in this fully remote work environment. So, we don't know what that looks like yet, and we will have to feel it out.

SMG: What advice do you have for organizations who want to overhaul their digital experience as part of a digital transformation initiative, but aren’t sure where to begin? How should they measure progress/success?

Kupp: We're still figuring out what's the right way to measure productivity. We have not cracked that code.The first step is to listen first, understand what is and isn't working for your employees — where there are gaps and where there are bright spots. 

Second, when there are gaps, evaluate if it's a process gap or a technology gap, and think about the ways that people need support. Too often we jump in and say, 'We need a new technology here,' before we understand if it's because we don't have the right training or the right culture in place for things to work. We can't think about digital transformation in isolation.

Third, be open to experimentation and just recognize [that] the blueprint hasn't been set yet. In terms of experimentation, I think we all want to measure productivity and outcomes. There are two measures that I think are important. One is understanding what outcomes you're driving to. What are those business goals and how are we tracking toward that goal? The second is employee engagement. Because ultimately, when we talk about the need to build a more flexible and connected work environment, it's because that's what people are looking for. Their expectations have changed, and it's about your ability to attract and retain the best talent. 

Register for your free pass to the Spring Digital Workplace Experience today.

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