Sam Underwood On How We Need To Adjust To The Future Of Work

Employees being more firm with availability. Right now, many employees are still coping with being always-on. Bosses now IM at night, and clients know if they send an email at 8pm, they might just get a response by 10pm. Employees will start to more specifically list their available hours on resumes and email signatures, and […]

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Employees being more firm with availability. Right now, many employees are still coping with being always-on. Bosses now IM at night, and clients know if they send an email at 8pm, they might just get a response by 10pm. Employees will start to more specifically list their available hours on resumes and email signatures, and get more confident in setting remote-work boundaries.


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 Sam Underwood.

Sam Underwood is VP of Strategy for Futurety, a Columbus, OH based data analytics firm. He manages client strategy and relationships, in addition to coordinating a team of 14 fulltime employees working on data analytics and digital marketing projects. He also supports special projects for Futurety Real Estate, a sister company that manages several commercial and residential properties across two states.


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.

I graduated from college in the depths of the Great Recession, and applied to nearly 200 jobs with no offers. I ultimately began my career working as a day laborer for a landscaping company, working 20 hour shifts shoveling snow and picking up trash at the mall, just to make ends meet. I finally landed a “career job” 9 months later, in which I suddenly found myself as the digital marketing decisionmaker for many of the same companies where I had been the trash guy just a month before!

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?

Right now, we’re definitely in the midst of a gigantic shift in the workforce, in a much more employee-friendly way. Out of necessity, employers have adjusted their expectations to the “how” of getting work done, with the realization that the results can be the same regardless of when or where that work is being completed.

With this in mind, I don’t believe the shift is going to continue to happen as quickly as it has over the last 2 years — we won’t be in a state of constant change forever. 10 years from now, working from home will be normal (rather than a perk); working on off-schedules for childcare or other reasons will be routine; and we’ll all still have a boss to answer to, even though it may be via IM more often than in a boardroom.

However, one thing that I believe will radically change is the expectations of employers for education and/or previous experience required for certain jobs. A few years ago, I was able to travel to Cambodia for a mission trip to work with local entrepreneurs in digital media. The first thing that struck me was that they were all self-taught, often via YouTube; and the second thing, was that their work was absolutely outstanding. What they may have “lacked” in experience (in current standards), they more than made up for in passion and attention to detail. With this in mind, I anticipate that future employers will likewise start to see the trend that a skilled employee is not always better than a passionate employee, and start prioritizing passion and genuine interest over past skills and experience. Both are important, but in a world where you can teach yourself a new skill in a few hours on YouTube, regardless of where in the world you live, there will eventually be some real-world implications, in a great way.

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

Be open-minded to what type of person is the best fit for your organization. The only thing that isn’t changing today, is that everything is always changing — hire people that embrace that reality. Very few people who feel like they’ve “made it” are going to be jumping on board a new technology, or tool, or technique, and it’s the hungry ones who are going to be the most successful in the future, and who will make your organization successful by extension.

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?

We’re in the midst of a huge reorganization of how educational systems work. College enrollment is down dramatically, and even the ways in which elementary schoolers learn has been permanently changed. Employers of the future will need to be flexible in what demands they expect from their employees, especially as it relates to formal education. No college degree? No problem, as long as you know how to learn from Wikipedia, Google, and YouTube.

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

Future employers will begin to prioritize how well someone works in ambiguous situations; namely, can you be productive when your boss is offline and a deadline looms? The flexibility afforded by WFH is incredible, both for employees and their families, but the flip side is that as this becomes normal, employees will need to embrace being successful in situations where expectations are higher but direction and/or feedback is lacking.

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?

Statistically, the pandemic had the greatest negative influence on those who were already vulnerable in a sense. For us to move forward as a society, we need to accept that life is still difficult, stressful, and uncertain for a large share of our community. Profits are up, the economy is booming, but only for some. We need to find a way to welcome back in some of the people who are not currently participating in the economy, whether for personal/family reasons (childcare, healthcare) or for skills reasons (digital shifts). We need to take it more seriously that many people are very willing and ready to have a greater role in the workforce, but may need just a little help or guidance to take a big step towards a future that will benefit all of us.

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

By many measures, productivity is up along with wages and employment. The shift to WFH isn’t just benefitting employees, who now have more flexibility and autonomy; it’s great for employers too. I’m optimistic that we can keep moving forward towards a future where there’s less mistrust between employees and employers, to share in the rewards of good work, together.

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?

Honestly, there’s no magic formula or innovative “hack” to help employees feel supported. In our organization, we buy everyone lunch once a week, and offer flexible scheduling for childcare, and wellness benefits, and so on. But all of this means nothing if we’re not treating employees as real people from the start. That’s the most innovative strategy you can take when it comes to people management — stop viewing your employees as “resources” and start engaging with them as full people, with hopes, fears, families, and everything that comes with our shared humanity. That’s what really shines through and makes a workplace, worth working at.

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?

In my experience, what’s happening in the workplace right now is really a matter of employees finally having the ability to reevaluate what workplace fits them the best, and having the opportunity to go find that. Every employee that has departed my team over the last 2 years has had a really good reason for doing so — an opportunity at radical career growth, flexible scheduling to support a startup dream, or a shift to a role they’ve always wanted.

What a leader can take from this is, make sure you’re a step ahead of where your employees want to be. If an employee leaves, and it’s a surprise, to whom is it really a surprise? Employees are looking for the best place to support who they want to become in 1, 5, or 10 years — how can your workplace become that for them without them having to interview elsewhere?

Let’s get more specific. What are your “Top 5 Trends To Track In the Future of Work?” (Please share a story or example for each.)

  1. Greater acceptance of alternative educational backgrounds. It’s way, way too easy now to learn many different skills online, without a formal college degree. If you’re motivated, you can learn the basics of HTML, digital marketing, graphic design, or UX with some dedicated time on Udemy or Coursera, and supplement as-needed with YouTube — and be an outstanding employee.
  2. Employer emphasis on results, rather than methods. The overarching narrative of the WFH revolution is the shift from “Did you get your hours in this week?” to “Did you get your work done this week?” Employers who want an all-star team will learn to measure prospective new hires based on results, rather than specific methods (within reason). We’ll start seeing employers ask for more quantifiable results as part of job applications, and show less interest in experience/educational requirements.
  3. Employees being more firm with availability. Right now, many employees are still coping with being always-on. Bosses now IM at night, and clients know if they send an email at 8pm, they might just get a response by 10pm. Employees will start to more specifically list their available hours on resumes and email signatures, and get more confident in setting remote-work boundaries.
  4. Increased awareness of employees’ and coworkers’ humanity. Over the last 2 years of Zoom calls, we’ve all met our coworkers’ cats, dogs, and significant others, probably with some regularity. This has ushered in a reality where we all suddenly realize that we’re all just people who sign off and get on with the rest of their lives, in much the same way, every night. In turn, I’m hopeful that this gives rise to a future workplace reality where we can all jump on board to help when a coworker needs a little extra help or understanding.
  5. Increased employee tenure. This one is a little bit of a wild card, so stay with me: With all the turnover the last few years, there may be an increased desire amongst many employees to find a place they love, and stay there. Even in the best of times, the job search process is tedious, frustrating and painful, and no one wants to jump into that world again until it’s really necessary. So many employees have switched jobs in the last 2 years, that we may see many of these same employees more willing to stick it out as they settle into routines at their new organizations.

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?

I love this quote by the great basketball coach John Wooden: “Failure isn’t fatal, but failure to change might be.” No matter how talented, skilled, expert, or even lucky you are, not being able to adapt to a new environment or reality can be a fatal error in your life or career. This is even more true over the last 2 years.

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.

Right now, I’m reading “Quiet Strength” by great NFL coach Tony Dungy, and I’m really inspired by his example of leading a team in a positive direction, while being in many ways a better listener than speaker.

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?

I’m active on LinkedIn and regularly write for our company blog at futurety.com.

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

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