David Hassell Of 15Five: “There will be a continued move toward organizations needing to be aware of and caring for the emotional and psychological well-being of their people”

There will be a continued move toward organizations needing to be aware of and caring for the emotional and psychological well-being of their people. On our HR Superstars podcast, we interview heads of HR at some of the world’s largest and most successful companies. We interviewed Lori McLeese, CHRO at Automattic (WordPress.com) and she agreed […]

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There will be a continued move toward organizations needing to be aware of and caring for the emotional and psychological well-being of their people. On our HR Superstars podcast, we interview heads of HR at some of the world’s largest and most successful companies. We interviewed Lori McLeese, CHRO at Automattic (WordPress.com) and she agreed that companies are starting to realize that it’s their prerogative to start caring for the mental and emotional wellbeing of their employees. At the time (late 2020) Lori was renegotiating their benefits package and she demanded higher benefits for mental health support.


There have been major disruptions in recent years that promise to change the very nature of work. From the ongoing shifts caused by the COVID19 pandemic, the impacts caused by automation, and other possible disruptions to the status quo, many wonder what the future holds in terms of employment. For example, a report by the McKinsey Global Institute that estimated automation will eliminate 73 million jobs by 2030.

To address this open question, we reached out to successful leaders in business, government, and labor, as well as thought leaders about the future of work to glean their insights and predictions on the future of work and the workplace.

As a part of this interview series called “Preparing For The Future Of Work”, we had the pleasure to interview David Hassell.

David Hassell believes that when leaders support employees in becoming their best selves, high engagement and performance and uncommon loyalty naturally result. As co-founder and CEO of 15Five, David co-developed the leading human-centered performance management platform and co-created the science-inspired Best-Self Management methodology to help leaders address the hidden factors that stimulate sustainable growth and development — things like intrinsic motivation, strengths, and psychological safety. David has been featured in CNN, Fast Company, and Wired, and was named by Forbes Magazine as “The Most Connected Man You Don’t Know in Silicon Valley”. Follow him on Twitter at @dhassell, on LinkedIn, and tune into his HR Superstars Podcast.


Thank you so much for joining us in this interview series! Our readers like to get an idea of who you are and where you came from. Can you tell us a bit about your background? Where do you come from? What are the life experiences that most shaped your current self?

I grew up in New Jersey and then graduated from college over twenty years ago with a degree in computer engineering. I was recruited by a 7,000-person public consulting firm and then quickly relegated to, “beige cubicle land.” I worked ten-to-eleven-hour days from a windowless computer lab in Roseland, NJ, doing work that I described as “soul-crushing.”

In hindsight, I now realize that it wasn’t the work itself, nor the environment that were to blame, but it was the organization’s poor culture and the lack of context that was given to me about my work. How did my work impact the company, the world, anyone?

It was that experience that propelled me into entrepreneurship earlier than I’d expected, so in the summer of 1999, I co-founded an ad-tech company in NYC and was on my way! But after the initial excitement wore off, I once again found myself struggling. I wasn’t producing the results I had hoped for, and I felt this sense of emptiness about the products and services we were building for our customers. Here I was living what I thought was my dream, and nothing seemed to be going right.

This launched me into a near decade-long inquiry and exploration where I studied everything, I could get my hands on, from productivity to psychology (and everything in between) and attended seminars ranging from personal development to business. While I may not have been consciously aware of it at the time, what I was really seeking was a sense of meaning & purpose, I was seeking to become my Best-Self.

Perhaps most impactful and serendipitous of all, I met Simon Sinek in 2007, who two years later gave his famous TED talk that’s now garnered over 56 million views. Simon shared that what sets apart the most extraordinary companies and entrepreneurs from everyone else, are those who clearly know and lead from their WHY in everything they do. This final piece seemed to be the key I’d been missing for experiencing both success and fulfillment combined.

I also learned that, more often than not, there’s a huge gap between the possibilities portrayed by thought leaders like Simon, and what we experience inside most organizations today. One of the reasons his message resonates so strongly is because it calls to that part of each one of us that has a deep desire to be and become our Best-Self.

So, when it came time to start my next company, I realized that my WHY was to support people in being and becoming their best selves. At the outset, I asked the question, “What if we built a company whose sole purpose was unlocking the potential of the people in it? What if our product was designed to help unlock the potential of each person at the organizations we served? Wouldn’t that lead to uncommonly high performance and loyalty?”

From that question, 15Five was born.

What do you expect to be the major disruptions for employers in the next 10–15 years?

We are going to continue to experience a change of the guard demographically. The majority of the Baby Boomers will have moved completely out of the workforce. Millennials and GenX will assume most top leadership, and Gen Z will be moving from early to mid-career.

This may set up some additional generational values conflicts, less so than between Boomers and Millennials but an increase of youth being brought up in a very different social context of how they communicate and work with one another. There’s also a different level of expectation around social change and political advocacy.

That’s a good thing, and at the same time companies are going to have to navigate people’s needs and desires to be more open politically in the workplace, which can lead to conflicts.

We also could see even greater labor shortages, depending on how things play out macroeconomically. As business keeps growing, finding skilled workers is a challenge in general. And with the move to remote work, great talent is already deciding to live where they desire, which increases the competition for the best talent.

How should employers pivot to adapt to these disruptions?

I’m hopeful that we will find the balance between advancing business outcomes and organizational stands for social justice. Employers will walk the fine line of being vocal and taking a stand, while not alienating populations of their employee base. So, pivoting includes educating themselves, getting outside help via DEI experts, and getting better at listening to employees.

As for the macroeconomic challenges, businesses will refine how they work with, support, and manage a geographically distributed workforce in a remote-first world. Technologies will continue to improve to support that, with budgets that were allocated towards offices will be redirected towards communication and collaboration technologies and travel budgets for teams to be together in-person as often as is reasonable.

The choice as to whether or not a young person should pursue a college degree was once a “no-brainer”. But with the existence of many high-profile millionaires (and billionaires) who did not earn degrees, as well as the fact that many graduates are saddled with crushing student loan debt and unable to find jobs it has become a much more complex question. What advice would you give to young adults considering whether or not to go to college?

You have to weigh the pros and cons between skill acquisition and credentials, as well as the opportunity cost and real cost of a degree. College is expensive! Many folks get into a situation where they are paying off debt for half of their career or more.

People need to understand the difference between education and credentialing. College isn’t necessarily the best structure to create real-world skills in creative domains, because for years students are learning in the abstract. But there are still many organizations that require a college degree. Also, degrees from certain high-profile colleges — like the Ivy League — are used as a shortcut to determine ability because of the high standards for acceptance and successfully completing the degree requirements there. This can be a proxy for excellence that can provide open doors in certain industries.

It all depends on the desired career path and each person’s unique skills, abilities, and talents. Certainly, the game has changed for certain roles. There are engineers coming up through coding bootcamps, people can mix a two-year degree with other less expensive online learning options and acquire real-world experience via internships.

I’m certainly not saying that a college degree is a waste of time or money, and a college degree can help buttress your resume for your first opportunity. But I do believe that people can get creative, especially if they are seeking a more entrepreneurial path.

Despite the doom and gloom predictions, there are, and likely still will be, jobs available. How do you see job seekers having to change their approaches to finding not only employment, but employment that fits their talents and interests?

Do you mean because of emerging technologies like AI and Machine Learning? I read a Forbes article years back that explained how AI would actually create millions of new jobs. New technology renders old ones obsolete, but also creates more net new opportunities for people. We just have to be creative and courageous enough to pivot as individuals, leaders, and really as a society. A great example of this is going from fossil fuels to more sustainable energy sources. Do people lose their jobs when a coal plant shuts down? Absolutely. But the private industry can work together with the public sector to train these workers in new careers in solar, wind, hydroelectric, or whatever energy innovation is on the horizon.

The statistics of artificial intelligence and automation eliminating millions of jobs, appears frightening to some. For example, Walmart aims to eliminate cashiers altogether and Dominos is instituting pizza delivery via driverless vehicles. How should people plan their careers such that they can hedge their bets against being replaced by automation or robots?

I’ll add that you have to keep abreast of industry trends and emerging technologies. You must continue to learn and grow and upskill. Remember the NASA mathematician, Dorothy Vaughan? When she worked for the Langley Research Center, she saw that machine computers were going to be the future, and taught herself and others programming languages like FORTRAN and other concepts to prepare them for the transition.

Technological advances and pandemic restrictions hastened the move to working from home. Do you see this trend continuing? Why or why not?

Absolutely. The biggest concerns have been technologies for remote communication, data sensitivity, maintaining a healthy culture, and trust. Leaders ask, “Are my employees actually working and being productive?”

Technology is helping with communication and data sensitivity and many organizations are elevating their people leaders and seeking strategic HR business partners to ensure healthy remote-first cultures.

As for trust, in most cases this fear is usually misguided, and all the data I’ve seen points to increased productivity since the pandemic began. Adam Grant shared about a recent Nick Bloom experiment showing that if you let call centers work from home, they’re 13% more productive. Adam said, “It’s not just because they save commute time — it’s also that they’ve been given real autonomy. They have flexibility around where they work, when they work, and how they work, and they don’t feel like they’re being micromanaged.”

Based on Self-Determination Theory, the idea is that there are four aspects that independently lead to someone feeling more intrinsically motivated, and those are Relatedness (with others), Autonomy, Mastery and Purpose, which some call the intrinsic motivation RAMP.

The formula I’ve found that works is granting trust, treating employees like adults, and then putting in place the right set of accountability and communication structures to ensure that wins, challenges, and results are being surfaced, and the right conversations are happening at the appropriate cadence. Things like weekly check-ins and 1-on-1s are critical here, and by standardizing these practices across an organization, leaders will ensure a high degree of consistency and effectiveness.

What societal changes do you foresee as necessary to support the fundamental changes to work?

The biggest two that come to mind are childcare and an increased focus on mental health.

What changes do you think will be the most difficult for employers to accept?

Really the two above. We need to have a shift in prioritizing childcare, beginning with significant time off for both parents, and continued flexibility for caring for minors in a hybrid work future. Mental health still carries a stigma in society and in the workplace, with managers often being afraid to broach this topic. We need employers to realize that things have changed and that they need to support the whole employee with mental health days, a plethora of resources, and space to be with family.

What changes do you think will be the most difficult for employees to accept?

I think some employees will genuinely miss in-person connections and may feel fatigued by continued meetings via Zoom or other video conferencing tech.

The COVID-19 pandemic helped highlight the inadequate social safety net that many workers at all pay levels have. Is this something that you think should be addressed?

Absolutely.

In your opinion how should this be addressed?

Access to healthcare, child-care, and a well thought out process that supports loss of income in the long term.

Despite all that we have said earlier, what is your greatest source of optimism about the future of work?

I believe in people. I believe that they have the ability to grow into our infinite potential. I see many businesses realizing that the (virtual) workplace is where we spend most of our waking lives and companies are beginning to understand the level of influence they have over creating the social change that their employees and customers demand, and truly supporting employees to have fulfilling, healthy lives both personally and professionally.

Historically, major disruptions to the status quo in employment, particularly disruptions that result in fewer jobs, are temporary with new jobs replacing the jobs lost. Unfortunately, there has often been a gap between the job losses and the growth of new jobs. What do you think we can do to reduce the length of this gap?

We must make training more available, access communities that are under-represented, and create more fluid avenues for entry-level employment by creating partnerships between universities and businesses.

Okay, wonderful. Here is the main question of our interview. What are your “Top 5 Trends To Watch In the Future of Work?” (Please share a story or example for each.)

In general, there are four forces you can typically look to in order to see where things are headed: 1) technological innovation, 2) economics, 3) political change, and 4) demographic shifts. You can almost guarantee that tech over the next ten years is going to reshape how work gets done and that is incredibly hard to predict. I suppose it will depend on the facets of communication and collaboration that are found to impact productivity. For example, if immersive experiences like virtual or augmented reality are found to be more connecting than just a regular two-dimensional zoom call, that could become a trend. As for the other factors, there is increasing income inequality and so that will have effects on work and incomes in general. There’s increasing political polarization and social justice issues, and employees are pressuring leaders to take political stances both inside and outside of the company. The most illustrative recent example of this was the surge of social activism following the murder of George Floyd in May of 2020. Thousands of businesses put out statements and changed policies as a result. And organizations that don’t participate in political dialogue are coming under scrutiny. This happened with BaseCamp creating policies against political discourse in the workplace (actually that was more than scrutiny, it was rage.)

There will be a continued move toward organizations needing to be aware of and caring for the emotional and psychological well-being of their people. On our HR Superstars podcast, we interview heads of HR at some of the world’s largest and most successful companies. We interviewed Lori McLeese, CHRO at Automattic (WordPress.com) and she agreed that companies are starting to realize that it’s their prerogative to start caring for the mental and emotional wellbeing of their employees. At the time (late 2020) Lori was renegotiating their benefits package and she demanded higher benefits for mental health support.

DEI will become central to attracting and retaining the best talent. We are seeing Chief Diversity Officers becoming more common. We are hiring a Director of DEI at 15Five, because this is such an important focus for us not just internally and our recruiting, hiring, retention and performance management efforts, but in how we build our product. This person will advise and advocate for ethical product feature development; balancing market needs with the psychological safety of marginalized communities and assist our R&D and Go-to-Market teams by ensuring our product and messaging is contributing to workplace equity.

There will be a continued reshaping of how work gets done — around hybrid work. This will impact the makeup of offices and the impacts to business travel and meetings. Workplaces once needed to have a fixed space for every employee, but that will continue to shift into collaboration centers. Even when I graduated from college in 1998, some companies had a hotelling concept for consultants who visited different offices. They would have a rolling filing cabinet that could be taken to a temporary desk. Another podcast interview we had was with Jennifer Christie, the CHRO of Twitter. They made headlines very early into the pandemic by announcing that a remote work option would be available to their 5,000+ full time workforce, forever. This interview took place in 2020 as Jennifer was looking forward to the return to the office and she shared that before COVID, most people were working from an office most of the time. They took a survey in April 2020 and there was a huge shift to people who wanted some type of hybrid experience. Jennifer’s plan was to use office spaces differently — rather than dedicated desks, more collaboration spaces. She foresaw people coming into the office for specific reasons, rather than it being routine.

Hybrid and remote work will also reshape the structure of communities, and cities that used to support a largely commuting workforce. Think about how much infrastructure was built up around people commuting to work, and all of the restaurants and other services provided in a downtown district. You are going to see homes and communities being designed differently to accommodate certain workers and creating demand for services closer to home. This could mean more mixed-use zoning for services like coffee shops or restaurants in lower density neighborhoods for people who aren’t commuting as regularly and living away from city centers.

Can you please give us your favorite “Life Lesson Quote”?

“The reward of our work is not what we get, but what we become.”

― Paulo Coelho

Can you share how this quote has shaped your perspective?

I have shifted to seeing work and business as a learning journey, not a game to win or lose. Everyone can work and evolve and find deeper levels of our fulfillment. It’s become a lifelong mission to support the people in my life in that experience because I know that it’s available for everybody.

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 or she might just see this if we tag them.

I’d like to have a conversation with Elon Musk about the intersection of moving rapidly toward a future of incredible technologies being ubiquitous and balancing that with human thriving. We have Artificial Intelligence, Machine Learning, Self-driving cars, space travel etc. In a way that increases human thriving. Technology can have a negative impact by being habit forming or disconnecting from deep connection with other humans and nature, and there can be positive impacts like creating greater efficiency or safety. This is a complex topic, and it would be fascinating to hear his thoughts.

Our readers often like to follow our interview subjects’ careers. How can they further follow your work online?

You can follow me on Twitter and LinkedIN, and keep up with the latest updates from our company at 15Five.com. I also release a new HR Superstars podcast with my cofounder 2–3 times a month, where we interview heads of people at some of the world’s most successful companies.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this. We wish you continued success and good health.

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