Pull vs. Push as a strategy to return to work. Rather than mandating return to work, organizations can provide flexibility to allow workers to choose when the right days are for them to be in the office. Work spaces should be redefined and redesigned as “hubs”, where employees can gather for business events and social collaboration to enhance company culture.


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 Deb Tenenbaum.

Deb joined AppDirect 2+ years ago to lead the global HR and Facilities functions. She was part of the company for just 3 weeks before the pandemic notoriously changed the course for how employers and employees navigate a digital first ecosystem. Deb was previously Chief People Officer at Yapstone where she led efforts to drive hyper-growth through aggressive hiring, redefining processes, cultural transformation, employment branding, and more. She has also led either People, Communications and Learning functions at Epicor Software, Charles Schwab, Rearden Commerce, Loudcloud/Opsware, and Netscape. In 2019, she was named one of the year’s Most Influential Women in Payments by PaymentSource. She holds a Bachelor’s from UC Santa Barbara and a Master’s from the University of San Francisco.


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.

The moment I became a mom, my world changed forever. I am a single parent who raised three kids on my own. My journey with my children has been one of self awareness, gratitude and extreme blessings along with a deep appreciation for the ability to persevere and be resilient. Many of my parenting experiences can be applied to my corporate experiences: authentic leadership, the importance of being value-centric and leading by example, humility, resilience and the importance of excellent communication.

In addition to my parenting experiences impacting my life, I was fortunate enough to participate in a program called Semester at Sea, 30 years ago. This was a program where college students lived on a ship that went completely around the world in 100 days. 50 days on ship were devoted to college courses and 50 days on land were focused on the experiences of traveling and exploring other cultures. As a college student, this experience opened my mind to diversity and inclusion in ways I could never have imagined had I not experienced these cultures. I learned so much about myself; stepping out of society and onto a ship where I knew no one and setting sail on a voyage around the world, disconnected from friends and family (no internet then!) and opening myself up to connect with new cultures.

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?

Employees want more out of their employment than just a paycheck, they want a purpose and to make an impact. I don’t believe this will change in the next 10–15 years, but it will become more of a driving force for employees. The need to be connected to something bigger than themselves and the ability to make an impact on the greater good while expanding their own skill sets, knowledge and experiences will be incredibly important to a worker.

The pandemic amplified the technology age, propelling us into an era of talent anywhere. A worker now doesn’t have to consider moving their family for new employment. Instead, they can apply to work at companies anywhere in the world, opening a whole new world of potential employment that ignites their passions. Employers need to step into the talent anywhere concept as a permanent component of work and provide employees with flexibility and agility. It has become a conversation around trust — trusting that an employee can get business results by working within their timeframes and in a space that is conducive to their needs — an employee-centric model. I believe workers will still want connections to the workplace, but less around functional collaboration but more emphasis on social collaboration. Employers will need to create different “pulls” to return to the office through amazing collaboration space, social gatherings and business events rather than “push” employees to be in the office for mandatory set days. Employees will want connections, but in different ways than the traditional workspace and management practices provided pre-pandemic.

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

Embrace that we have now entered an era of being digital-first with human connections. Our default should be a more employee-centric work environment where an employee can choose whether they want to be in the office, and if not, have the technology to support them remotely. With that being said, employers need to look for ways to connect digitally with a variety of communication channels, while also connecting socially by facilitating in-person experiences. Our role as employers should be to create an environment — in person or virtual — where an employee can do their best work.

To future proof an organization, make sure the foundation is strong with organizational values that are operationalized as verbs not nouns. Values in action are seen in our behaviors and as we lead into the future, there will be more emphasis on authentic leadership and leading by example. Employees will still want relationships with managers and to see them as resources to foster their professional growth, even if they are not sitting right next to them. Therefore, the foundation for the future needs to have excellent, transparent and timely communication that connects employees to the business purpose that is inspiring them to be committed to the organization.

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?

Most companies are trying to approach hybrid work by keeping the traditional assumptions of work and putting a few changes in place. For instance, employees need to be (mentally) present at work and at their desk with a set schedule. Today, employers are applying traditional models and methodologies to the workplace rather than leveraging the power of talent anywhere to expand their resource pool. My recommendation to organizations is to see talent anywhere as a competitive advantage, both on an employee satisfaction level and as a cost optimization strategy. As a result, there will be less real estate cost along with opportunities to hire talent in regions with lower cost structures than the U.S. Allowing the employee to choose whether they want to work on site provides an enhanced employee experience. However, there are still opportunities for in-person interactions, as management can coordinate on-site team work, meetings, new hire onboardings and more.

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

The pandemic fundamentally changed the psychological relationship between employer and employee. Gone are the days of the traditional worker — we have entered an era of what I call the “knowledge nomad.” Employees are transient, seeking employment in regions they thought were never accessible to them thanks to the digital economy. It provides employers a new challenge of managing commitment vs. retention.

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?

The pandemic has been an interesting sociological case study in a variety of ways. I truly believe that the rhythm of work life balance has changed dramatically. There used to be a separation between work and home, and now it is blended together. As a result, we need to find ways to separate the two and know when to make prioritization trade-offs between the two.

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

We are incredibly fortunate to be working in an era where technology opens so many new opportunities for how we work. In an era of innovation, I’m optimistic that we have an opportunity to redefine the psychological employer/employee contract. Gone are the days of the “traditional” office worker who commutes to work from 9–5pm and retires from the same company after 25 years. The digital transformation era is not just about where we work, but it allows us the opportunity to re-evaluate how we lead and manage within organizations. Do we need to have annual reviews? Does a person really need to be in a role for 2–3 years before being eligible for a promotion? Does a worker need to be on site to be successful in their role? I think this is both a fascinating and challenging time for us as leaders because we can no longer rely on traditional management practices, and instead need to re-invent our management practices based upon this new employee-centric, flexible and agile mindset.

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?

At AppDirect, we believe that to create an environment where you can do your best work, you first need to be able to be your best self. This is the foundation of our philosophy around employee Peak Performance — which places a focus on mind, body, spirit and habits. We have partnered with third parties to provide content on each component of Peak Performance, which has contributed to the de-stigmatization of mental wellness. We have over 87% global adoption with the content for peak performance. Organizations of the future have an opportunity to invest in the personal wellness of each employee, not solely with stellar medical benefits, but by embracing new ways to enhance an employee’s peak performance through concepts such as biometric performance and seeking the balance of mind and body.

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?

A lesson I learned from living and working during a pandemic has been to always expect the unexpected and in doing so, resilience along with perseverance are critical success factors. All three of these headlines have a common denominator –change. Leaders are being challenged more than ever to not only react to change, but to drive change and employees are demanding it. They have been confined by “shelter in place” mandates with the sense of no control for their lives for over two years. Now, the worker is emerging from their cocoon to take more risks, pursue new passions and move to new areas. Leaders need to be flexible to these changes, but also anticipate them and change their management style accordingly. Perhaps managers are entering their own “Great Reformation”.

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

  1. Talent without Boundaries: There is less emphasis on companies being in “cities” as physical concentration of talent becomes less needed and from the employee perspective, less desirable.
  2. How we manage needs to iterate in today’s digital economy. There has been a lot of discussion around generational workers and how each generation has different expectations for their relationship with the workplace. I actually believe it is less about generational expectations but more around how technology has been part of each generation’s day to day life experiences. Younger generations have always had the internet and have a different level of reliance on technology, while older generations have less dependence on technology and more on face-to-face communication. Yet, our management practices were established over 50 years ago with principles such as: 1) needing to be present and seen to make sure you are doing your work, 2) needing to put a certain amount of years into a role before being promoted, and 3) only increasing salaries annually. Additionally, younger generations grew up with video games that promote problem solving and quick advancement to new levels of the game. Our 50 year old management practices are no longer impactful to today’s digitally advanced workplace and need to change to embrace how technology has influenced our expectations of the workplace.
  3. Digital-First with Human Connections — Technology helped to keep a pandemic-dominated world both informed and connected for two years. Within organizations, we see how technology can both establish and maintain meaningful connections and touch points through a screen and keyboard. Yet, we can’t lose sight of the importance of face-to-face interaction as we are social creatures by nature that seek connection. Therefore, in organizations we need to focus on the importance of evolving the “human skill set” — communication effectiveness, expectation setting, quality feedback. There will be a danger zone for leaders to over emphasize digital connectivity because of the ease and cost of leveraging technology vs. harnessing the power of face-to-face interaction at the right time. However, there is an opportunity for both to live in harmony.
  4. Pull vs. Push as a strategy to return to work. Rather than mandating return to work, organizations can provide flexibility to allow workers to choose when the right days are for them to be in the office. Work spaces should be redefined and redesigned as “hubs”, where employees can gather for business events and social collaboration to enhance company culture.
  5. An increased awareness and measurement on the “whole self” including mental health, total wellness and biometric-based performance. Organizations need to embrace the importance of supporting and encouraging the entire well being of an employee (mind, body, spirit and habits) so they can do their best work. At AppDirect, we do this through the variety of Peak Performance initiatives that I previously shared.

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?

There are really two quotes that I try to integrate into my personal and professional lives. The first is, “be the change you want to see in the world.” For me, it really is about taking ownership of wanting your personal and professional life to improve rather than focusing on how others need to change. Earlier, I mentioned the importance of authentic leadership which for me is about leading by example. If I want something to change, how can I drive that change?

The second quote that inspires me is that “no act of kindness is too small to have a big impact.” As we navigate the new normal of a post-pandemic world, understanding how our actions and our acts of kindness can have a significant impact is really important. It can be as simple as showing compassion and empathy for a parent trying to present on a Zoom call with their toddler crying and the manager letting them know that we can reschedule the call and acknowledging that it is more important for them to focus on their child. That act of kindness probably has a greater impact than we can imagine on the parent/employee.

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.

Elon Musk — Elon believes in innovation and constant iteration on ideas to create a sustainable future for our planet. The digital age is requiring our traditional management methodologies to iterate so we can foster the innovation of people to meet the challenges facing our society. Elon recently made a bold decision to mandate all Tesla employees to return full time to the office or risk being fired. As this is contrary to my views on the future of work and the need for flexibility, I’d value the opportunity to explore Elon’s perspectives and whether he would see this philosophy working at SpaceX or other technology organizations and why? In addition, I’d be curious to learn from his leadership experiences at PayPal, Tesla and SpaceX and discuss how organizations need to change the way we define the employee experience to foster innovation in our digital economy, not deter it.

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?

[email protected] or linkedin.com/in/deb-tenenbaum-a063b8

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