Remote by Default. As employers attempt to attract candidates with more flexible policies, they will embrace remote first as an office policy. Expectations around presence, delivery and even what full time work means change permanently. Some will work two jobs, in parallel, raising questions of confidentiality and non-compete agreements.

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 Jen L’Estrange.

Jen is the Managing Director of Red Clover, a strategic human resources consulting firm that specializes in working with rapidly growing small and mid-sized businesses. Prior to founding Red Clover, Jen worked in corporate HR leadership roles where she had the opportunity to live and work in over 10 countries. That experience informed her business and talent strategy for Red Clover where she focuses on hiring consultants who have worked in cross functional leadership roles before transitioning to HR.

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.

That’s a tough question, there are so many! I guess the first would have to be becoming a parent. It changed me for all the reasons that you might think, but I was surprised at how becoming a parent helped me see work in a different perspective. All of a sudden, work ‘stuff’ didn’t affect me the same way. While I was still committed to my career, I didn’t take things quite as seriously or as personally as I did before. There’s something about keeping a tiny human being alive that changed my focus.

The second has to be becoming a business owner and employer. For me, the decision to hire employees was by far the best — and riskiest — decision that I’ve made to date. Every business owner who ran a payroll in April of 2020 knows exactly what I’m talking about here. But it’s not only about the risk. Being an employer is an opportunity to define core values and a company culture that supports our goal of being best in class in terms of the services we offer our clients and an employer of choice for our candidates. We are intentional in our talent goals and purposeful in our definition of core values, competencies and performance evaluation. The result has been the establishment of a highly performing team that I am proud to lead, and serve, every day.

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?

I think knowledge work will be done largely remotely, with an increased focus on decentralized global delivery — even for small businesses. Virtual assistants will be accessible to everyone and eventually shift to automation and machine-based support for much of our administrative functions.

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

If you build a workforce of lifelong learners who are aligned with your company values and culture, you have nothing to worry about. The workforce will adapt as it needs to and the values-based approach will allow you to make the tough calls when you need to.

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?

Employees are really looking for flexibility and an opportunity to genuinely contribute and, unfortunately, some employers think that they can close that gap with more money. If employees learned anything at all during the pandemic, it was how to spend money differently, and in many cases more efficiently, than they had before. While wage compression is an issue, it’s not all about the money. In the end, people want to feel that they are valued. They want to be seen. If, as employers, we’re going to be successful at that, and in turn retain our people, then we have to give them a role in discussing and deciding how to do their work effectively. An example of this includes projects that engage employees in job and organizational redesign that focuses on remote and hybrid work. Holding employees accountable for an outcome and allowing them to figure out when they need to be onsite is much more effective than prescribing a set number of days in the office.

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

The work from home experience, collectively, accelerated our readiness for change. The speed with which we all shifted to remote work showed that we could adapt quickly and make it work. Going forward, we will see both employers and employees assimilate new work practices, policies, and overall ways of working more quickly and with less disruption than we have in the past.

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?

Our tax system is woefully behind in terms of supporting business and, specifically, those businesses that want to employ a remote workforce across the United States. If we are serious about the future of work, we need to accept the fact that the employer may not be physically located in the same place as the employee and the business may not be ‘created’ in the place where the employee turns on a laptop. Otherwise, US based companies large and small will continue to look overseas for knowledge based workers.

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

I am continually impressed by our collective resilience in the face of adversity. I am confident that our people, and especially the new graduates coming into the workforce now after navigating so much change in their educational experience, will be able to handle whatever comes their way.

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?

Candidly, I don’t see much happening that’s really innovative yet. There is a stigma with mental health that is based in fear — of what we don’t understand and often cannot control. There is little support in terms of healthcare coverage, and policies are generally lacking for all but the very large employers. I don’t think we’ll see real workplace innovation until we normalize the conversation around mental health and genuinely begin treating it the same way we treat any illness.

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?

I think the overall message is about managing change. As leaders, the headlines give us an idea of climate, but more importantly, they inform our conversations internally. These articles can be used to start conversations on what needs to change and how the organization should work together going forward. Culture evolves through changes in the behaviors that are reinforced and rewarded. Five years ago, a leader who opted to work from home one day a week risked being overlooked for promotion and thought of as someone who didn’t take their career seriously. Today, we hire people into leadership positions that we have never met in person.

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

  1. Remote by Default. As employers attempt to attract candidates with more flexible policies, they will embrace remote first as an office policy. Expectations around presence, delivery and even what full time work means change permanently. Some will work two jobs, in parallel, raising questions of confidentiality and non-compete agreements.
  2. Robots and Automation. As companies search for more permanent solutions to the talent shortage, look for more and more automation and robotics in multiple sectors, starting with manufacturing, hospitality, and retail.
  3. High Employee Turnover. Employees continue to job hop, struggling to replace the sense of community that they lost when they went remote. They try to trade it for money, it doesn’t work, and they keep moving and looking for connection.
  4. Everybody’s Going Global. Even the smallest businesses will look for opportunities to hire employees overseas or in lower cost areas of the country in order to capitalize on labor arbitrage and tax savings. Over time, those savings erode, but the real long-term impact is on leadership succession planning.
  5. HR has its Day in the Sun. With employment costs continuing to be the largest expense on the P&L for many companies, finding and retaining the right people to support business growth reaches a new level of criticality. Truly effective Human Resources support is the new hot commodity with organizations springing up to support businesses as an outsourced partner.

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?

“The behavior you get is the behavior you tolerate”. I’m not sure who said it, but there’s a version of the same quote in Extreme Ownership by Jocko Willink and Leif Babin. As a leader, I not only have a responsibility to communicate my expectations, but I also have to be ready to give candid feedback and correct issues when I see them. I don’t shy away from giving critical feedback to team members, but I do make sure that I do it with kindness and from the perspective of wanting to see them at their best.

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.

I’d have to say lunch with Mike Rowe. He’s one of the few individuals out there who recognizes the issue with US education and who pushes for more comprehensive training and development for tradespeople.

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?

The best way to connect with us is through our website and our LinkedIn page (

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