Lifelong Learning. The pace of skill change is accelerating. Glassdoor Research has shown increasing turnover in skills, with 50 percent of the words used in job descriptions five years ago no longer appearing in today’s job descriptions. The number of students studying fossil fuels, for example, is rapidly decreasing, as those skills and jobs face a terminal decline.


When it comes to designing the future of work, one size fits none. Discovering success isn’t about a hybrid model or offering remote work options. Individuals and organizations are looking for more freedom. The freedom to choose the work model that makes the most sense. The freedom to choose their own values. And the freedom to pursue what matters most. We reached out to successful leaders and thought leaders across all industries to glean their insights and predictions about how to create a future that works.

As a part of our interview series called “How Employers and Employees are Reworking Work Together,” we had the pleasure to interview Andrea Small.

Andrea Small is design leader, strategist, and educator. As a former Stanford d.school teaching fellow, she and her cohort created award-winning education experiences. Currently, she teaches at the Stanford d.school and leads storytelling and design strategy for Samsung Research America’s R&D Innovation team. Andrea has worked with some of the world’s most iconic brands, including Nike, Nivea, Facebook, iRobot, Starbucks, and Herman Miller.


Thank you for making time to visit with us about the topic of our time. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today.

When I was in my first real tech job, I had the opportunity to travel to China (Dongguan and Shenzhen) and tour a number of mobile phone accessory factories, places making things like gelskins, packaging, and car chargers.

We went to a dozen factories of various sizes, specialties, and conditions. We watched pitches from the factories, touting their equitable conditions. We saw workers on the line, stress testing car chargers until they caught fire, or gluing leather, or soldering electronics. We saw where they lived and ate their meals. We saw the waste manufacturing produced.

I wish that every designer had the opportunity to see with their own eyes how design comes into the world. Like many designers, I’m a visual and experiential learner. This first, early-career trip to see manufacturing forever changed my perspective about why and how we make things. It’s hard to understand something so abstract or large in scale. But we must consider all the levels of design, from the materials of the objects themselves to the workers and their communities.

Let’s zoom out. What do you predict will be the same about work, the workforce and the workplace 10–15 years from now? What do you predict will be different?

In 10–15 years, I think much will be the same and that we will still be trying to define the future of work. It’s a puzzle with no end, an ouroboros. We will still be trying to increase collaboration, creativity, and productivity and seeking tools that support collaboration, communication, and community, in and out of the physical office.

What will be different in 10–15 years? Hopefully a lot.

It will no longer work to explain away the old ways of doing things with lines like, “that’s just how things are done here” or “it’s like that everywhere,” which is only unfortunate for the people who have benefited from these skewed and dysfunctional systems. Representation in leadership will look radically different, and, as a result, we will start to see deeper changes and culture shifts taking place.

In 10–15 years, AI, machine learning, and automation will free us from repetitive and redundant tasks, allowing us to focus on creative, ambiguous challenges. New tools will help us leave behind the binary strategy of offices vs. remote workers. Advancements in healthcare systems will affect how we work. With our experience, we will have a more informed reaction to future pandemics.

What advice would you offer to employers who want to future-proof their organizations?

I don’t believe in “future proofing.” The future is real and there is nothing you can do to stop it. “Future-proofing” emphasizes the protection of current systems and the prevention of future disruption.

Instead, think about “future-readying” your organization. Learn to welcome the future. Build systems that flex and adapt to whatever comes next. Help everyone manage and understand uncertainty. Embrace that what works today might not work tomorrow. Or, what works for one person might not work for the next. Change, as we know, is the only constant. You can’t prevent it, but you can shift your attitude to accept what it brings (good, bad or otherwise).

What do you predict will be the biggest gaps between what employers are willing to offer and what employees expect as we move forward? And what strategies would you offer about how to reconcile those gaps?

Covid-19 made us prioritize our lives and jobs, starting with the essentials. For many, the math just didn’t work out. Leaving the office meant leaving long commutes, excessive travel, and toxic/ableist/discriminatory work culture. With distance to evaluate, people came to the conclusion that it’s just not worth it to go back, and no amount of free lunches will make it worth it. We can work anywhere with technology, so why would we be tethered to one place?

But some workers want to come to the office. They may have loud roommates and slow WiFi at home. If the office has a gym, crazy fast internet, and a kegerator, why work at home?

Others may want to come to an office because they face too many distractions and conflicting responsibilities while working from home. Parents with young children, for example, are made to balance the impossible: high productivity with continuous childcare and remote learning.

One strategy for reconciling that gap is to assume a culture of prototyping. Instead of trying to eliminate the gap by figuring out who to displease, experiment with ways for both realities to exist. It’s going to take time before we change the deep layers of culture that promote certain behaviors (like showing up in person) over others (efficiently working with autonomy). A good way to navigate the ambiguity of conflicting realities is to try different things out in lower risk ways.

We simultaneously joined a global experiment together last year called “Working From Home.” How will this experience influence the future of work?

When I was the director of product and portfolio strategy at Herman Miller, I worked on a project to understand the future of systems. We went around to a dozen cities and toured some of the most beautiful offices in North America.

Everywhere we went, the offices were barely occupied. Office managers told us time and time again that people were just… elsewhere. Traveling for work, in meeting rooms, at home. This was in 2017, so the way we work was already changing. It has made sense to work flexibly for a long time.

The global experiment proved that if we have to work together remotely, we can. If we have to work asynchronously, we can. If we have to let our teammates rest or focus on something other than work, we can.

We have created technology to work anywhere. Computers went from the size of a room to the size of a fingernail for a reason. Constraining work to one spot is like forcing a race car driver to stay in the slow lane.

So, the future of work all comes down to trust. Do employers trust their employees to effectively do their jobs and communicate with teammates? Do workers trust their workplaces to make ethical decisions and put community before profit? In the future, there will be little excuse for excluding someone who couldn’t be there in person for an emergency reason. I sincerely hope I never hear anyone say, “I have to drive through this deadly snow storm to make it to my weekly 20-minute standup tomorrow” — ever again.

We’ve all read the headlines about how the pandemic reshaped the workforce. What societal changes do you foresee as necessary to support a future of work that works for everyone?

Big societal changes must happen to create a future of work that suits everyone. Whether unintentionally and intentionally, we’ve created institutions rooted in racism, sexism, and ableism, which reward only a slim demographic of people.

Social movements in civil rights, women’s rights, and LBGTQ rights, like the Black Lives Matter movement, can support a future of work that works for everyone. I would like to think that we have made recent progress concerning race and equity, but there is still an astronomical amount of work to do. In STEM, for example, there’s endless work to do along the “leaky pipe” — a system filled with invisible barriers that lead to the rejection of people of color, particularly Black women, transgender people, and disabled people.

What is your greatest source of optimism about the future of work?

The US Patent Office opened in 1790. As legend goes, in 1899 the head of the Patent Office resigned and said they should close the Patent Office because “everything that could be invented has been invented.” I’m filled with hope when I’m reminded of this. There is so much more to discover.

Creativity across humankind is what’s going to get us out of all our jams, so it is creativity that gives me hope about the future of work. It’s not always possible to reshape broken, outdated systems. To get radically better solutions we must be able to imagine a world that is totally different, outside of the confines of what we know today.

Today, I’m really optimistic about Mixed Reality (AR/VR). We’ve made incredible strides in how we interact with technology. We’ve also made great advances in gesture and voice inputs. These advancements often started by prioritizing the experience of people with disabilities. Creating technology that works for more people, not just a slim set of specific users, ultimately creates better products.

Our collective mental health and wellbeing are now considered collateral as we consider the future of work. What innovative strategies do you see employers offering to help improve and optimize their employee’s mental health and wellbeing?

Roughly 75 percent of all US employees are affected by mental illness. Long misunderstood and taboo, mental illness is slowly but surely being destigmatized.

Companies must go beyond superficial offerings. This is not to discount activities like webinars or mandatory training, but the most effective strategies present a range of approaches and recognize that nothing is one-size-fits-all when it comes to mental health and wellbeing. Approaches must also go deeper into the culture and structure of the company and examine how people are incentivized, rewarded, excluded, and included.

By focusing on mental health and wellness, organizations can also overcome some of the challenges of remote work. Strategies that center education help workers learn more about themselves and ultimately create more tenable working conditions. Workers that feel seen and supported by their place of employment are happier and more motivated.

It seems like there’s a new headline every day. ‘The Great Resignation’. ‘The Great Reconfiguration’. And now the ‘Great Reevaluation’. What are the most important messages leaders need to hear from these headlines? How do company cultures need to evolve?

Journalist and writer Kara Swisher calls it the “Great Re-evaluation,” and this is the characterization I most align with. Re-evaluation isn’t just about workers re-evaluating their jobs and careers. This is also an opportunity for organizations to re-evaluate their systems, partners, practices, and strategies.

Culturally, we need to shift away from tying physical presence to performance. Right now, data suggests that managers are biased against people who don’t come in. They see people in the office as being “higher performance” than people who work elsewhere. At the same time, more women than men want to work from home for a huge variety of reasons, from toxic workplace culture to untenable hours combined with other home pressures. The bias for in-office workers results in more men getting promoted, worsening the gender pay gap. Work culture needs to evolve in a way that prioritizes the psychological and physical safety of all.

Let’s get more specific. What are your “Top 5 Trends To Track In the Future of Work?”

Navigating Ambiguity

Of course, this is my #1! Hybrid work and autonomy open businesses to more variables, and with that more uncertainty. New technologies will introduce new challenges. (Will people want to work all day in VR? Is it even healthy?)

There is still a massive amount of uncertainty regarding the pandemic, and lots of mixed emotions. Some businesses still believe that we’re going to go back to a “way it was.” This creates certainty where there is none, but it’s artificial certainty. It is uncomfortable to admit we don’t know what’s next. We won’t know what the ripple effect will be. We still take off our shoes at airports 21 years after 9/11. It’s really hard to say what the long-term effects will be because we’re in it right now. We don’t have the distance to observe new patterns.

Imagining the future means stepping into that ambiguity and allowing multiple possible paths to exist. As complexity increases (and it will) the skill of navigating ambiguity will only become more important.

Inclusive Hybrid Work

After the dust settles, hybrid work will be sticking around. One of the many positive aspects of hybrid work is that it can create more equitable and diverse work environments. In some ways, it can better support people with varying physical, cognitive, and sensory capacities than the physical office experience once did. Even if an office building is designed to be accessible, navigating a large campus on crutches, for example, might be more taxing than joining remotely.

In their Inclusive Design Toolkit, Microsoft defines inclusive design as “designing a diversity of ways for everyone to participate in an experience with a sense of belonging,” not “making one thing for all people.”

Recently at Stanford’s Womxn in Design “Designing for Inclusion” Conference, we did an exercise to redesign a student event while considering different requirements. My team was tasked with redesigning the event through the eyes of someone with chronic fatigue syndrome. When we considered solutions for these participants, we came up with better ideas for everyone to get involved in the event.

We are far from total inclusivity and equity, but going remote meant better access for some people who require accommodations. We were forced to think about how our activities can go from in-person (which limits the audience to a certain set), to going remote, which gives people more ways to be included.

Disentangling Identity and Work

For a certain set of businesses, Covid-19 put new power in the hands of the workers. People had the chance (or were forced to, depending on your context) reevaluate their values in relation to their work. Do we like our employer/co-workers? Is the workload sustainable? Are the conditions humane? Do we agree with work policies? How do our jobs align with our personal values?

The pandemic showed many people that work matters less than world events, physical wellness, and mental wellness. We are moving from a culture where your work is your identity to a phase where work is transactional, and “it’s just a job.” Your life is not necessarily your career.

We know now that the office is not the culture, perks don’t erase toxicity, and collaboration and creativity can happen anywhere. It’s about the people, not the place.

Lifelong Learning

The pace of skill change is accelerating. Glassdoor Research has shown increasing turnover in skills, with 50 percent of the words used in job descriptions five years ago no longer appearing in today’s job descriptions. The number of students studying fossil fuels, for example, is rapidly decreasing, as those skills and jobs face a terminal decline.

As technology changes and skills rapidly become obsolete, workers will need to reskill or upskill to maintain their work. There will be more fluidity between working and learning. People who can adapt and learn new tools will be prioritized over people with a deep skill set that might soon become irrelevant.

Interaction Wanderlust

Imagine you’re on the MTA commuting to Manhattan from Brooklyn. You see ads, you see how people dress, you listen to music, or read a book, or look at your phone. You leave the station and go up the street, walking past an infinite amount of inputs.

All of these little interactions shape us. For example, we don’t learn how to dress only from an Instagram ad. We make decisions from a combination of inputs: ads, interactions, and unplanned observations.

Serendipity shapes us. It’s dull and exhausting to see the same things day in and day out. Sameness can be fatiguing. While we’ve proven that we do not have to fly to Paris for a one-day workshop, that it’s irresponsible and wasteful, we’ve lacked serendipity (for better or worse). For the people who thrive this way, it’s going to feel great to travel again, to fill the tank back up.

As we experiment with how, where, and when we work, Wanderlust will play a significant role, not just in our mental health but in helping us to bring more creativity into our work. A friend’s coworker just attended their weekly meeting from a pool in Hawaii. They said they were going to be offline for a bit at the beach, and the reaction from the team was, “That is awesome.” If we can, why don’t we?

I keep quotes on my desk and on scraps of paper to stay inspired. What’s your favorite “Life Lesson Quote”? And how has this quote shaped your perspective?

“You can’t put the toothpaste back in the tube.”

I love all forms of this idiom. It implies that some outcomes cannot be reversed. It’s how I feel about the future of work in the context of the pandemic. We will not be going back to how things were. And honestly, why would we want to?

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He, she, or they might just see this if we tag them.

Yes. Dan Levy. I’ve seen every episode of Schitt’s Creek five times. Dan, I love your eyeglass collection, and your interior style is drool worthy. Your style is impeccable, and I think you should be designing furniture. I would love to discuss this in more detail with you. Coffee?

For the VC funders out there:

Like everyone else in Silicon Valley, I have an idea for an app and platform. The app is in the social justice space, and centers on tools for trauma survivors (in and out of the workplace), designed with trauma victims at the center. Who is working on this topic? I believe the right partner is out there to develop this tricky and ambiguous but impactful idea.

Our readers often like to continue the conversation with our featured interviewees. How can they best connect with you and stay current on what you’re discovering

My book, Navigating Ambiguity: Creating Opportunity in a World of Unknowns, released on April 19, is available here.

I’m on Twitter, Instagram, and LinkedIn. You can find all the ways to contact me and check out my other published work (like the Intersectional Design Card Deck, a tool to help teams build radically inclusive solutions) by heading on over to my Linktree here.

Thank you for sharing your insights and predictions. We appreciate the gift of your time and wish you continued success and good health.