Sarah Sheehan On How We Need To Adjust To The Future Of Work

Learning and Development as major players in retention. L&D isn’t usually thought of as a top driver of retention, but we know that the vast majority of people will stay longer at a company that invests in their development. (LinkedIn Workforce research has it at 94% of people.) L&D leaders have a huge opportunity to […]

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Learning and Development as major players in retention. L&D isn’t usually thought of as a top driver of retention, but we know that the vast majority of people will stay longer at a company that invests in their development. (LinkedIn Workforce research has it at 94% of people.) L&D leaders have a huge opportunity to reframe their work around retention. That looks like self-directed, unstructured opportunities to learn and grow in the moments that it’s most relevant and applicable.


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 Sarah Sheehan.

Sarah Sheehan is the Co-Founder and President of Bravely. Her diverse background in HR and as a sales leader made her passionate about helping companies build healthy cultures. Prior to Bravely, Sarah was an executive at Gilt City, serving as the Head of Sales and leading a 65-person sales team, after spending over a decade working in various HR roles at SiriusXM, Coach, and Gilt Groupe.


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.

Thanks for chatting with me! First, growing up as the daughter of a lawyer definitely shaped who I am today. My father spent a larger portion of his career representing women and POC who had faced discrimination, especially within the workplace. Being exposed to this at a young age gave me an early understanding of how the scales were often tipped.

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?

What’s not changing anytime soon are the fundamental needs people have for their lives at work. The need to grow, to be recognized and appreciated, and to feel connected to a purpose are all deeply human. Once the baseline need for financial stability is met, these become the main drivers shaping people’s professional lives.

What I predict will be different — there are people working today who will go their whole careers without spending more than a few years at a single company. Most companies are still structured with longer tenures in mind. I think this’ll change in the next 10–15 years, and companies will have adjusted to the fact that most of their workforce is temporary. That shift affects how we have to think about onboarding, career pathing, and learning and development.

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

My biggest piece of advice would be to place emphasis on individualized support. Everyone’s experience is different, so the resources, benefits, and development opportunities that you’re offering need to account for that. What may benefit one employee will not have the same level of impact for another. Having that diversity of support options is only the first step: you also need to ensure that people across the organization know what’s available to them and feel empowered to get the resources they need.

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?

For the first time, employees are in the driver’s seat, setting their go-forward requirements and expectations. There’s still so much that we don’t know about how this will play out. What I’d say to employers who are worried about being able to keep up with the demands and expectations is that individualized support is a conversation, not a transaction. Ultimately, both an employee and their employer want the employee to be able to meaningfully contribute to the organization, so supporting employee well-being is in everyone’s best interest. We can close the gaps by framing the conversation around that desired outcome, rather than a yes-or-no binary of whether employee expectations can be met.

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 is the present and future of work; we’ll never go back to the way we once worked. Because we’ve learned how to adapt to this new work environment for almost two years, most people say that they don’t want to return to a fully in-person work schedule.

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 had a huge effect on the way we connect with people. Now that we’re in a virtual environment, it takes extra focus to consciously build relationships at work and continue to connect with people. Since it is likely that remote work is here to stay, people need to be intentional about the way they are cultivating these connections long term.

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

Although the adjustment to a new landscape of work wasn’t easy, there’s now an acceptance that although things will not be the same, we have the opportunity to redefine the way we work. Two years ago, most company leaders would probably have said that going fully remote was impossible. Now that’s been proven false, so we have to ask ourselves: “What else are we wrong about?” Nothing about the old status quo has to be held sacred anymore; it’s all up for conversation. That’s immensely exciting to me.

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?

There are a lot of things organizations can do to focus on mental health right now, and it should be top priority for all companies. One of the biggest problems that I’ve found is that there is a lack of “in the moment” support, leaving employees with limited options of where to turn to. Resources like Bravely provide a confidential third party to assist employees in developing coping mechanisms and strategies to navigate what they are facing at work. Resources like this, that are outside the walls of the company, but that provide immediate support to strategize on how to move forward are essential to lowering stress levels, ultimately leading to a higher sense of well being.

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?

It’s funny — at Bravely, we were calling it “The Great Reengagement” even before some of the other monikers took off. What it all comes back to is that the right societal conditions came together for us to suddenly see a huge fallout from workplace issues that have gone unaddressed for a long time. I think it’s a positive sign that so many people are trying to relabel “The Great Resignation” as a call-to-action, whether it’s “Reevaluation,” “Reshuffle,” or any of the others. The main takeaway for companies should be that your people are your most valuable asset, so if you’re doing what’s right for them, you’re doing what’s best for the company as a whole.

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. Investment in the whole population. The M.O. for decades has been to invest professional development resources in managers and “emerging leaders,” which only exacerbates inequities and gives more support to the people who were already set up for greater success. There are good intentions behind this: managers make or break the employee experience. Still, the benefits clearly haven’t trickled down. People at all levels of their organizations are leaving in droves, often because they feel invisible at their companies. I recently heard a story about someone who’s been asking prospective employers whether they offer Bravely, because the coaching she had with us at her last job was such an important part of her experience there. She wants to know that wherever she works next, she’s still being personally invested in.
  2. Belonging and connection as KPIs. Building and maintaining connections at work is harder than ever, but when you don’t have a sense of connection and belonging on your team, the organization suffers in so many ways. The new mandate on leaders is to be facilitators of connection. That’s just part of the job now. Of course, you can’t call something a priority if you aren’t measuring progress over time. We recently ran a (not-at-all scientific) poll on our LinkedIn and saw that 88% of respondents thought connection should be treated as a KPI. I think we’ll see more companies making a conscious effort to quantify, track, and improve these elements of engagement in the near future.
  3. Greater transparency around values. We all remember the period after the murder of George Floyd when every company was releasing statements of solidarity with Black Lives Matter. It was almost routine to publicly speak up after events with that level of impact, but that time felt different. People were seeing their companies’ statements and saying, “Wait a minute — that doesn’t match my experience here.” They felt empowered to speak up and tell their companies to start living their values, and to actually demonstrate their commitment to inclusion and equity. I think that was just the beginning of companies being held accountable to their values from within.
  4. Flexibility becoming truly flexible. We’ve heard so much about “flexibility” that it’s almost a buzzword at this point. It’s been talked about as if it’s this panacea for The Great Resignation: “give people flexibility, and they’ll stay.” But I don’t think we’re all operating from the same definition of flexibility. It isn’t just telling people they can work from home when they want or unlimited PTO.I think we’ll start to see employers saying to themselves, “We’re offering all this flexibility and time off, but people are still burning out. Why?” The answer is that those things can be great, but it’s all lip service unless it’s backed up by a culture built on trust. When I think back to my maternity leave (pre-COVID), I’m grateful for the support that allowed me to fully take the time off without fear of negative repercussions on my career. If I needed that as a co-founder of the company, it’s even more necessary for others.
  5. Learning and Development as major players in retention. L&D isn’t usually thought of as a top driver of retention, but we know that the vast majority of people will stay longer at a company that invests in their development. (LinkedIn Workforce research has it at 94% of people.) L&D leaders have a huge opportunity to reframe their work around retention. That looks like self-directed, unstructured opportunities to learn and grow in the moments that it’s most relevant and applicable.

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?

Since I was a teenager I have loved the quote from Joseph Campbell: “The privilege of a lifetime is being who you are.” I have personally struggled throughout my career to find my voice or gain the confidence needed to continue to reach for and achieve my goals. What would my career have looked like if I had felt like I could bring all of me to work? And what about all the underrepresented people who are also struggling because they feel like they do not belong or do not have the confidence to express their ideas or ask for what they need? These questions played a big part in my co-founder and deciding to build Bravely. We want everyone to be able to be exactly who they are at work.

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.

Brené Brown — She was years ahead of the rest of us in talking about vulnerability. In 2020, vulnerability became a major theme at Bravely, particularly around how managers could adjust their leadership style for the “new normal.” The past 2 years which included the pandemic, continued social injustice, and burnout was a call for leaders to demonstrate a new level of empathy and compassion. Brene’s approach is very much in line with how I have intentionally chosen to lead throughout my career and I believe will be a new requirement going forward.

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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