In this edition, CULTURED had the pleasure to talk with Lindsey Caplan, Senior Director of Learning & Organizational Development at Flexport. Lindsey shares her journey into the field and her approach to bringing people and companies together around a common goal. You can read more of her writing at

CULTURED: Tell me about a typical day for you and what you do as part of leading the Learning and Organizational Development function?

LC: Every day is different—which is part of the fun. On a typical day I wear about 7 or 8 hats:  from coach, at an individual level or team level, to instructional designer; to a facilitator; maybe a bit of a consultant; sometimes a strategist; a cultural anthropologist, and so on. And then there’s a manager hat as well which involves leading the team and making sure they are successful, engaged, and on track. Being able to go back and forth between telling and asking (inquiry) is an important part of the balance I try to achieve.

CULTURED: What were the pivotal moments in your career that brought you to that function? What made you eventually land in learning development?

LC: The central theme in my work over the past 15 years has been gathering and bringing people together. I started my career as a sitcom writer in Hollywood. Being a writer meant I was focused on entertaining and observing people, and thinking about how to get each character from A to B. You have to think empathically about the situation that each character is in to help them get to B.

While this line of work was very fascinating and fun, I knew I wanted to have a more direct impact on people; it was kind of a lonely experience. Through a series of fortunate events, I found myself in the Learning and Development department at Dreamworks Animation.

There, I learned how to bring people together and move people from A to B from an educational context. I was lucky to have an amazing boss and mentor who clearly saw that L&D was what I was meant to do and helped set me on a path I hadn’t realized for myself. This is one of the reasons why I’m so passionate about learning at work – I experienced the care and development that comes from someone believing in you.

Through my experience at DreamWorks I became very well-versed in creating and delivering learning experiences, but knew I wanted to add more to my toolkit. I wanted to learn how else people move and change, so I went and got my Masters Degree in organizational psychology. I rely on all these different hats and tools in different ways.

CULTURED: What are the parts of your job that really excite you? Why do you love doing them? What are the parts that were the most challenging?

LC: There is a lot that excites me. For one, there is a lot of creativity in creating and designing experiences that help people get from A, to B. One of my core values is creativity and I’m glad to be able to rely on that strength in much of my work.

And then there’s the freedom to not just put programs in place, but to understand (where we can) the root cause of a specific challenge and how to improve it. But, what I enjoy most is the reward of helping others – that can’t be matched.

As far as challenges go, part of the fun and the challenge is that humans are complex and change is as well. As rewarding as this work can be, we don’t always get to see our work through or to know if or how helpful our work was. Growth isn’t instant; it’s a process.

There are so many factors involved in this work, so part of my role is not just being here to program, but also to figure out the ways in which our program or solution might be affected; what gets in the way; how to ensure it’s transferred; how to build these environments and the system to ensure that it sticks. A common mistake I see people make is spending so much time on content that we forget the context in which it will be received, and what could get in the way of it sticking.

CULTURED: How did you address this challenge? Maybe you could give us an example with a specific part of a program where it was actually important for you that it got picked up?

LC: One of the programs we created was an internal company university. It was very successful—maybe a little too successful. We had a full slate of classes that people took and were excited for; everyone was signing up and the waiting lists were huge, and that university became, in people’s minds, the sole place to go learn and develop. “I’m going to wait for this class,” or, “This person is having X, Y, and Z issues,” and so on, “what classes should they take?”.

While this university is a place where people could come to learn and grow, it was meant to be the kickstart to more conversations and more development; not the cornerstone of learning. It became such a large part of the culture that, in some ways, was viewed incorrectly as the only place for learning in the company, which was a challenge that I didn’t foresee.

We tried a bunch of things to tackle this issue. One was putting all our formal and informal umbrella programs underneath so that employees viewed our internal university as more than just classes; it was mentorships, and speakers, and all the things that we envisioned.

We also tried to create a platform and resources for people to pull down and create their own classes and formal learning opportunities. Our thinking was, you don’t need to wait for us to create a class, this is something people can do on their own. But the reality is, considering the time and energy investment it took to create these classes, people became a bit too reliant on us as opposed to having ownership and sharing classes across the organization.

This reframing or re-educating of learning as part of our everyday is a challenge for many organizations. One of the things that we thought about was, “what’s getting in the way?”. We looked for what was, and ultimately re-framed our own work to be about increasing an employees’ sense of clarity, progress, and confidence…not simply improving the university. 

We wanted to reframe our work around the outcomes instead of only communicating one solution. 


CULTURED: What role do you think data play in your experience?

LC: Data is very important. Everything is data. Some people want certain kinds of data: numbers are data, but emotions are also data. What data serves to do is make an experience or a subset of experiences more real, more personal, and less abstract.

Data helps to take something that might be abstract and fluffy—especially in our world—and make it more “comfy.” Presented the right way, it can help to make sense of a subjective experience in a more objective way in language that others can connect to or will reveal something to them.

CULTURED: Regarding the field of people analytics and using quantitative data within a company to solve people issues, what excites and what worries you?

LC:  An exciting part is the immediacy that these tools provide, especially if I can view real-time or immediate feedback loops. A good example of this is an employee engagement survey, which is often a very long feedback loops: usually one year at most large organizations. While this tooling is impressive, every good thing can also be used for evil or used improperly.

There still needs to be someone to educate on the meaning of this data and how to act on it. Also, it’s important to learn how to not get paralyzed by too much data; to just stare at it without acting upon said data.

I’m very used to running employee engagement surveys or feedback loops where people go straight to the red, or come up with quick strategies as the best courses of action, as opposed to analyzing and learning to actually use the data as a starting point for a conversation or more inquiry.

I’m a fan of tools that make life easier and take manual processes and automate them. However, I also believe that a tool is only as good as the people who use them, which is something not many individuals understand properly.


CULTURED: Why do you think we, as humans, jump to solutions so quickly before actually understanding the problem?

LC: That’s the million-dollar question. It often starts implicitly, with the ways we’ve traditionally been rewarded or praised for “checking the box” or simply “doing the thing”.

Similarly, it’s very common in the learning & development field for people to look for a training class or course as if that is the all-time, singular solution. Sure, we want these classes to be helpful and one of the ways we can support that is if they are done as a part of a larger solution that is continually reinforced.

Let’s align on outcome first – the tool or solution comes later.


CULTURED: What unpopular opinions do you hold about the HR and people space?

LC: There is immense potential and possibility when a group comes together – especially in organizations.  But when we gather in a room, we don’t always maximize this. We pull people together to only have our efforts fall on deaf ears. We invest money and then wonder why the initiative didn’t stick.

Subsequently, very few of these gatherings create real change or commitment, whether its a training class, offsite, town hall, etc. I am writing a book on gatherings as the unit for change in organizations and what we can learn from entertainment, education, and business on how to improve our investment and our efforts.

CULTURED: Thanks a lot for the interview and see you soon! 

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