Thoughts on the intersection of life + work and why human connection is essential

Jennifer Smithwood-Green shares thoughts on the intersection of life + work and the broad influence of L&D.

Jennifer Smithwood-Green, L&D, People and Culture expert, recently sat down with Jason Lavender of Electives for a People Developing People interview.

During their conversation, Jenn shared thoughts on:

1. Getting people outside their comfort zones
2. Connecting people to learning content
3. Leaders leading by example
4. Learning KPIs
5. People exceeding their personal expectations
6. Helping people see meaning in their work
7. What modern managers need most
8. The broad impact of L&D

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Jason Lavender, Co-Founder + CEO of Electives: Welcome, Jenn. Please share your background and the path that got you into the People space.

Jennifer Smithwood-Green, L&D, People Ops and Culture Expert: I mark the beginning of my career in People and L&D as my time spent as a wilderness expedition instructor with Outward Bound.

I didn't realize it then, but almost a decade and a half later, I draw on that experience in everything I do. We were literally leading teams in harsh, dynamic and challenging environments. And that's what we're called on to do today, albeit within environments that are now largely virtual.

I was with Outward Bound for 10 years. I went from being an expedition instructor to overseeing staff training and recruitment. I then headed up the HR function for Outward Bound's Boston base and progressed into executive leadership roles.

While at Outward Bound, I realized how fascinated I was by the psychology of leadership and its immense influence on an organization and everything that organization influences around it.

I returned to school to get my Master’s in organizational psychology, which led me to different industries. I consulted across nonprofit, tech, and law. Then, for the past six years, I’ve held internal leadership positions for global tech companies — both in the people and the learning functions — where I've had a ton of fun working with minds that think very differently than mine. 

Jason: So cool! If you could teach one class to corporate employees related to wilderness, what would it be? 

People open up when they’re outside their comfort zones.

Jenn: I mean, if I had the opportunity, I would take every team outside – literally on a trail, in a boat, up a mountain – into any context where everyone's a little bit out of their comfort zones. It's a great opportunity to have people open up to sharing and hearing diverse perspectives and backgrounds, and it opens people up to learning and connection. You can absolutely create this, to a degree, without the excursion, though.

Jason: We’ve always said that in the future state of Electives, we would love to offer field trips. So we'll keep you in the loop if that happens one day!

The broader role of People leadership seems to have shifted quite a bit over the last five years. People sometimes say it was because of the pandemic, but it feels like changes were happening well before that — and they are still happening. What is your take on these shifts?

The future of learning is about connecting people to other people and to the content they’re learning.

Jenn: I was leading the HR function for Outward Bound, Boston in 2014. At that point, we were still spending a good majority of time defining and redefining roles and technical skill sets/competencies to train and manage to. Outward Bound was and remains at the forefront of leadership and what we historically think of as “soft-skills” development. Especially ten years ago, training was still a “check the box” activity at most organizations.

It wasn't until I came out of grad school, and genuinely understood what organizational development was, that I saw learning take a real strategic seat within organizations.

More recently, we’ve started to recognize L&D as something that directly drives performance, employee engagement and retention. 

We've experienced a huge surge in content creation, and it will only get bigger with the introduction of AI.

The revolutionary approach is to help people connect with and apply the right content instead of just consuming it… to look closely at how we match that content to experiences that create connection and help people retain and apply what they’ve learned in real-time — and not just to their jobs but to their lives. We need to understand it's meaningful.

AI will provide us with many benefits. It will save design and material development time, allowing us to shift our focus to creating intentional learning experiences that drive the learner's connection.

I was at PTC, a global tech company during the pandemic. We had offices all over the world. Suddenly, in 2020, everybody went remote, and it occurred to me that we'd always been a global organization—this shouldn’t seem so new. Globalization, exceedingly large amounts of data, asynchronous work…was trending long before the pandemic. But it took being forced apart to realize how integrated our work was.

Learning that and devising different ways to deliver training without being in-person at headquarters were just some of the huge shifts the pandemic highlighted but did not precipitate.

Jason: One of our colleagues at Electives always says, “The future of L&D is content curation, not content creation.”

To your point, AI will make content creation easier, and now it’s up to us to create experiences to connect people to the content. That's where the power is.

What do you think is the difference between companies that successfully build learning cultures and those that do not?

To build a learning culture, leaders must demonstrate their prioritization of learning.

Jenn: The first thing that comes to mind is whether or not leaders are investing in their own learning and making that visible to their teams. Are they creating spaces where learning is seen as an imperative and an asset instead of an obligation?

The number one way to see the perceived value of learning in an organization is to observe the behaviors of the leadership team.

I'm a big proponent of psychological safety (and I call it many different things to sneak it into the learning agenda) to help teams create environments that encourage curiosity and learning from one another. You see that at organizations that are successful at growing leadership internally.

Learning must be incorporated into the workflow on a structural, systemic level. Every company has some sort of performance process. Deliberately tracking L&D goals alongside business OKRs brings a sense of shared accountability to learning and growth and really fuels it across the organization.

I focus on teams learning together and being accountable for each other's learning.

Jason: One of the fun things we always ask people is, “Building a learning culture at work would be easier if…”

Learning KPIs need to be tracked alongside business OKRs.

Jenn: …if the organization is tracking learning goals alongside others.

During quarterly meetings, leadership reports on the business metrics and the learning KPIs. There are general metrics around learning hours and experiences. And you track the return on that learning …the value-add.

Like, what did that team do as a result of that new skill set? For example…

They learned of a new technology that they're now using. They learned to work together more productively. Those are the kinds of goals that promote learning.

Adaptive leadership and communication skills help us work better and be more productive.

Jason: What are you most passionate about in the L&D space today?

Seeing people exceed their personal expectations is gratifying.

Jenn: I'm so grateful whenever I witness an individual or a team exceed their expectations of what they thought they were capable of.

Those “aha” moments when folks try a new approach or way to think about something, and it gets them through something that they've been stuck on, especially when it's related to how they work together or when it solves a problem about how we work more productively together.

Teams trying to solve big, difficult problems can have fun together if they learn skills that help them draw out the best of one another. When those moments happen, it fuels my passion for the work we do.

Jason: I see some of those moments in our classes, and it’s totally a dopamine burst. When I read our post-class testimonials, someone says, “I never thought about it from that lens….” it feels so good.

The Electives mission is to help people grow and connect. We offer live learning, because we understand how powerful connections with the instructor and the other learners can be.

In addition to learning, what have you seen that boosts connection at work?

The most important thing we can do is help people see meaning in their work.

Jenn: The most important thing we can do as learning leaders is connect people to their work and help them see meaning in it.

I wrote my thesis and did my graduate research on meaningful work, and I found that connection is the common denominator that drives motivation, learning, behaviors and performance. It is where we should be focused, so that’s why I've always partnered with Electives.

Learning is the most powerful tool we have, and the best way to help people change behavior is to bring them together to work it out live.

I will always design programs where people can understand a model or a theory, reflect and then designate live learning time together to be about dialogue and connecting ideas.

I’ve moved away from the idea of training as just that I'm just going to teach you something. Now I think it's really about the facilitator bringing diverse experiences and perspectives on a topic and asking the right questions to help people have a dialogue and share ideas. That's the learning that sticks and creates the positive changes that you want to see in leadership. It changes behavior and culture across the organization.

Jason: The relationships you build in that dialogue come back in many different ways. Whether you need something two weeks from now or you're trying to brainstorm with someone a month from now, building those relationships lasts forever, and they become meaningful in so many different ways. 

What skills do modern managers need today and in the future?

We need to help managers connect with and learn from each other.

Jenn: It's going to come down to interpersonal relationships and being able to speak with other humans.

We should focus on building connections and fostering learning agility across all levels of leadership.

Creating psychologically safe spaces, or environments where people feel safe sharing ideas and trying things out, will be important because we're moving so rapidly now. Humans haven't fundamentally changed that much, and we're never going to keep up with technology. We need to be able to try things out, test our theories and learn from others more than ever.

I hope to see more time dedicated to connecting with and learning from each other. Great advances now allow us to automate some things and to get people trained on technical capabilities more quickly. That allows us the space and time to dedicate to relationships and building spaces where we can innovate together.

Jason: I saw a report the other day predicting the skills that will be most needed in 2027. AI was on the list, but the skills above it were all human and adaptive skills. We need those more than ever.

As we close, Jenn, what advice do you have for someone newer within a People leadership or L&D role?

The impact of L&D can be much broader than a job, a team or a company.

Jenn: Now is probably the most exciting time ever to be in this work, and the most important opportunity is creating a connection between business success and the potential of the people. Especially as we think about incorporating AI, that human potential becomes so much more pronounced. Now is our opportunity to figure that out.

The learning we do at work comes home, goes into our communities and affects the whole human experience. It's time for us to expand our thinking about the work we do within organizations and think about it much more broadly. Now is the time to lean into those opportunities and think about how our roles can help shape the lives of leaders, their teams and beyond.

I'm waiting for us to shed the notion of work-life balance, that there can be some clearly defined separation. It’s become more and more clear that we should be thinking about work-life integration. And when we think about learning and development, we think about how wide that intersection between work and life is. It makes the work all that more exciting because we’re not just influencing someone's ability to do their job or to grow in their career. We can actually help people improve the quality of their lives and the quality of the lives around them.

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About Jennifer Smithwood-Green

Jennifer Smithwood-Green is a forward-thinking Learning & Organizational Development professional with more than 15 years of experience enhancing human potential at global organizations. Her expertise lies in crafting strategic talent solutions, boosting leadership qualities and fostering team collaboration, all of which aim to increase productivity and spur innovation. Jenn has a notable history of leading initiatives that significantly improve organizational effectiveness and enhance culture.

Jenn’s skill set spans several key areas, including Organizational Development, Global HR, Learning Strategy Design and Transformational Leadership. In her recent role at Mosaic Group, as Director of Learning and Organizational Development, Jenn developed and executed a global strategy that drastically increased engagement and participation in development programs.

In her career, Jenn has shown a profound ability to guide transformation efforts, from enhancing performance processes to integrating psychological safety practices within the workplace. Her work in developing leadership and organizational development strategies has been recognized and applied across various sectors, including tech, manufacturing, and healthcare.

Jenn holds a Master of Arts in Organizational Psychology from William James College, where she explored meaningful work's contribution to wellbeing and purpose in the workplace. Her educational background includes a Bachelor of Fine Arts in Design from Lesley University.

Dedicated to fostering inclusive and supportive environments, Jenn volunteers her time and expertise to several causes and organizations focused on social services, economic empowerment and disaster relief. Her certifications, including in Generative AI in Learning and Development and Psychological Safety, underscore her commitment to continuous learning and applying cutting-edge insights to her work. 

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