💻 Future of Work Feature: Helen Kupp
Senior Director and co-founder of Future Forum at Slack | co-author of "How The Future Works"
In This Edition
🍼 How motherhood impacted her professional journey
🧡 Why reinventing how we work can make it more inclusive
🧪 The importance of embracing a culture of experimentation
About Helen
Helen Kupp is Senior Director and co-founder of Future Forum. She has led many of Slack's largest cross-functional and growth initiatives, and is the creator of many of Future Forum's playbooks, tapping Future Forum’s research and networks along with her experiences at Slack, Bain & Company, startups, and her MBA from Harvard Business School. She is also co-author of How The Future Works: Leading Flexible Teams to Do the Best Work of Their Lives. Helen is the lucky mom of two wonderful children.
What sparked your professional path to the work you're leading now?
For most of my career, I’ve been in a business strategy and operations role where I focused on scaling a company, looking at new opportunities and using data to drive that work.
When I had my first child in January of 2020, it was a very unique moment — my big life moment of becoming a mom coincided with the world’s big life moment of the pandemic. Returning from maternity leave, I reevaluated my priorities, specifically my professional and life aspirations.
As I was figuring out how I wanted to show up as a mom, we were asking these same questions as a society — how do we better integrate work and life while trying to manage this major health crisis?
This collision of forces was an unexpected opportunity for me to take my skills and try to help answer this big ambitious question — how do we define the new ways we work and make flexible, distributed work successful?
What inspired you to co-author "How The Future Works"?
Writing a book was always on my bucket list, but I didn’t imagine it would be at this stage of my career! When we started, it wasn’t to write a book — it was to figure out the shifting preferences around the world of work and how to tap into this really big moment to make it successful for the future.
Along with Brian Elliott and Sheela Subramanian, I founded Future Forum within Slack. We had worked together previously at Slack and knew that we brought together complementary skillsets. Early on, we realized that the way we work wasn’t going to return to what it was like before the pandemic. We saw this big opportunity to re-think and re-design how work happens, a mission and vision that brought us all to Slack initially. But with Future Forum, we were able to pair our product expertise with the behaviors, organizational changes and processes to make this change happen in a monumental way.
As data nerds, we began with the research and focused much of our energy publishing the Future Forum Pulse — quarterly research of over 10,000 desk workers around the world. It became a running index to track how work was changing. We were having conversations with leaders who acknowledged these shifts, some were experimenting, but many kept asking us — what’s the blueprint for making these changes?
We realized that we were developing best practices, templates and tools to make these changes possible through our data and dialogue with leaders. That’s when we realized it would be really helpful if we published an end-to-end playbook for how to build flexible teams. We decided to co-author How the Future Works and bring all of these learnings into a shared resource for others to access.
What is one project you are particularly proud to have accomplished?
When we embarked on this work, we had a very business-minded perspective — we wanted to bring data to the ambiguity of work and use it to create smarter processes. What we discovered really surprised us — not only was flexibility better for productivity, it was better for a sense of belonging — in particular for people of color, caregivers and women.
It was particularly fascinating because for so long we had been having this conversation about diversity in tech. But, for the first time, we saw this moment as the opportunity to shift the conversation to also talk about the impact of inclusion and how to leverage flexibility to do that.
It’s actually quite personal to my professional journey. Despite what I do for my job now, I’m actually very introverted. In the old way of working — the brainstorming meeting was a format that wasn’t a place for me to shine. Even when I was the expert in the room, I still remember it was so hard to get my voice in at meetings. Fast forward to today, we now break up these meetings and do brain-writing over brainstorming. We take time to write our ideas down and give people ample time to think deeply and contribute ideas before jumping into a small and often shorter live discussion of our ideas.
Throughout my career, I’ve experienced feeling left out. It took this transformational moment to acknowledge that we can make work different for so many people by questioning those old assumptions and redesigning the way that we work to actually bring more people and voices to the table in a truly inclusive way. As I try to balance my life as a mom and not being able to make it to every single meeting, I think about the value this creates for families and caregivers. With all of its flaws, video conferencing has leveled the playing field. Now, how do we keep that sentiment as we design the next phase of work?
How has your experience in product shaped your approach to thinking about the future of work?
There are two core skills of a product leader that have shaped how I think about our work and research. First, great product leaders focus on the customer — building empathy, listening to experiences, finding out the pain points and building a deep understanding of use. Now, your people are your product.
Woven throughout all of our research is this common theme of moving from top-down mandates made by a few leaders to developing deeper empathy for your full employee base — listening to their preferences, finding out how they work best and getting better at connecting with your people.
Second, product people focus on redesigning an experience. For the way we work, we want to move from retrofitting to redesigning. At the beginning of the pandemic, we just lifted and shifted what we did in the office directly into virtual practices. But for product people, it’s the uncanny ability to think about the problem to solve and design something new that meets that need in a better way. This way of thinking helps us break from old assumptions to do something better, drive toward true change and flip the model on its head.
For example, it means reevaluating if we need a meeting to get work done. Ask yourself, “Are we using this meeting to discuss, debate, decide or develop an employee?” If it doesn’t fit in one of those categories, then you probably don’t need the meeting. Ultimately, what most people find is that many meetings aren’t that productive and it’s a much better use of time to send a quick update. A product mindset helps you ask questions about how something works without just assuming that this is the way something is done.
How do you keep learning about your field?
For my team, I create a culture of experimentation. If something isn’t working, I ask my team — what new strategy should we try? We continue to iterate our team norms to get better at flexible work.
I also find it very helpful to talk to people in different industries and at different levels. These conversations spark new ideas and help me find new ways of implementing flexibility that I may or may not have tried. One really impactful story that I share in the book is about the power of team-level agreements. I talk a lot about them as a tool to help set expectations for team norms — it’s important to be intentional and explicit about them.
I always had this core assumption that this works if your team is primarily office based because some of these norms are around collaboration hours. When I was in a conversation with a leader at a Fortune 500 retail company with frontline and desk-less workers in retail stores and manufacturing plants, I referenced team-level agreements. I shared this might only be useful for her headquarters people. This leader replied with a surprising answer — she acknowledged why I would say that but, she shared that her frontline managers would value this tool even more!
Because frontline workers don’t have a lot of freedom, these employees care a lot about having more trust and flexibility such as managing their shift schedules. This gives their managers a tool to start a conversation, engage with their teams and build stronger relationships while having an open discussion about how they talk about schedule flexibility in a new and different way. It provides an easy way to codify and share across managers so they can learn from each other.
I wish I had thought of it this way — it was so helpful to hear this leader share their perspective and it opened my eyes to the possibility of what we can do with team-level agreements, especially for those who are in the field trying to make this work.
Fast forward, what does the future of communications at work look like?
My thesis is that it’s going to be flexible, inclusive and connected. The same themes will be pulled through and what that translates to and what I’m most excited about is that it will be a lot more human and a lot more inclusive. My hope is that it is also going to be more fun!
People don’t give enough credit to the fun. The best teams you’ve worked on are when they enjoy themselves and are connected to purpose. Ultimately, they end up doing much better work and are more fun to be around.
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