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My Fellows Retreat with Leaders in Tech

In fall of 2018 I had one of the most formative self-development experiences I’ve ever had to date — attending a Fellows retreat with Leaders in Tech (LIT). My mind was blown because it is SO different from many of the offerings out there, and I wanted to write a post to share what this organization is about and how it’s made a difference. In fact, it made such an impact that I jumped on the opportunity to get more involved and joined their Board of Directors last year.

What is Leaders in Tech? LIT is an organization that provides personal development programs for founders and leaders at tech companies. Their flagship experience is called a a T-group session, and it is based on Stanford’s well-known Interpersonal Dynamics course (aka “Touchy Feely” to GSB crowd).

The Fellows experience

Let me walk through the mechanics of the LIT experience first, before speaking to the impact. The weekend was a fully immersive experience and structured as bringing together roughly a dozen leaders at a hotel for four days. Over the course of the retreat, the facilitators regularly introduced teach pieces that introduced content/frameworks to the group. The teach pieces provided scaffolding for the conversation by giving the group concepts and vocabulary to use. However, the experience was largely experiential, unstructured, and didn’t follow a set curriculum. On some level, you can describe it as we had a schedule with large blocks of time with no agenda where we sat in a circle and talked. This is the opposite of a programmed course with lectures and topics. As the group spent time together, I got to know them better and better as people, and we built up a shocking amount of trust and disclosure.

It’s hard to describe the experience and almost easier to describe what it was NOT:

  • a curriculum to learn a structured set of skills
  • a forum to bring business-oriented challenges to a set of peers to find advice and solutions
  • a networking opportunity to meet other people

It’s actually something else. The LIT website describes it as “an experiential learning format focused on discovering when and how you are most influential, how others really think and feel about how you act, and how you lead” but I don’t feel that it captures all of what it is. In effect, it’s a shared group conversation where the group sets the content and agenda and you learn from each other. The quality of the group I suspect makes a big difference, and I was impressed by how curated and high-quality the group was.

Overall the experience was super impactful to me personally and professionally, and also hard to describe. So I’ll try to explain that more below.

The power of the T-group

As someone who works with others in a 1:1 way, I’ve been reflecting a lot about the power of the group experience. There is unique benefit from learning from others’ experiences that is hard to capture through individual work. Whenever someone else describes a problem or situation they are facing, as an observer, it can feel so clear what the solution should be. However, as they unpack the considerations and feelings that go into their situation, it’s always more complex than that. In the T-group, there’s space to describe a situation in detail and for the group to ask follow-up questions.

I got just as much if not more value from participating in someone else’s experience as I did in sharing my own. T-group is unique because it’s possible to get the reactions of everyone participating and hear how it’s landing. This opportunity to hear the other side is like a supercharge to understanding interpersonal dynamics.

What I learned from Leaders In Tech

I will be the first to admit that I came into my LIT retreat extremely skeptical about whether it was a good use of my time. Since then I’ve talked to many others who shared the same skepticism and came out as a believer. It takes a glance at the quotes people have left to see the impact of the experience.

LIT shattered some long-held stories that I had in my head about how the world works. The opportunity to get real-time feedback from someone else (their story, their reactions, their thought process) was a game-changing opportunity for me to break down these beliefs. I have an entire single spaced page of notes and feedback jotted down, and here are my top 3 takeaways.

Relationships are not a function of time or luck, they can be actively sought out and nurtured. After spending 4 days with my T-group, I came away feeling a closeness and connection to them that surpassed many of my long-standing friendships. I had been under the impression that sometimes I get lucky with someone and “click” or friendships are built on time spent together, which means it’s hard to create deep friendships in our time-starved world. However, LIT taught me that there are steps we can take to improve the quality of time spent and build relationships intentionally.

The flawless leader is not the one people love to follow. Growing up in an appearance-oriented Asian culture, I held the belief that the winning strategy is to put your best foot forward and downplay the challenges (this concept is also known as “saving face”). This makes it hard to admit mistakes or discuss problems. As I watched others share their challenges, I became aware that the feelings it evoked were not loss of respect but the exact opposite. These are the kind of people I wanted to follow! It occurred to me that maybe some of the things I’ve crammed down as shameful, boring, and unliked, are actually sources of strength and connection. This has translated into a more positive, proactive way of tackling difficult conversations and driving a result.

There’s always another side to the story. As I shared my own thoughts or listened to others, it was striking to me how often my initial impression could be way off by what was actually going on. In T-group, sometimes we’d take a pause and ask someone, how did you react to what was just said to you? and the answers were fascinating. My favorite framework from LIT is the idea of The Net which has made it far easier to constructively give and receive feedback.

LIT created an opportunity for me to get some honest feedback on the impressions others had of me good and bad. And many of the foundational challenges of being a leader lie in exactly this realm, which is how this stuff translates into the business world. How can you get really good at identifying and addressing conflicts as they arise in your team? Can you get faster at admitting problems and fixing them? While the tactical and operational work of building companies is often what gets the focus, these intangibles are just as important.

LIT is enacting change, one human at a time

I see LIT is an antidote to the cultural problem that many founders and leaders are facing in their work today. It was originally founded during the time of the #metoo movement rising and a lot of articles about toxic workplaces, with the belief that a small group of committed leaders can set the standard for what it looks like to build a successful AND culturally healthy company.

Many leaders feel an intense pressure to posture and say everything is great when it’s not. There’s an idea that we must wear “The Mask” that is our public face, when inside we may be stewing with inner turmoil. Founders already have one of the most difficult jobs out there, and struggling in isolation shouldn’t be yet another burden. This pressure at the top magnifies inside companies as well. If the fearless leader is working around the clock and admitting no difficulty, what kind of norm does that establish within the team? These are the challenges that compound to create unhealthy workplaces.

I don’t see the output of this work as encouraging leaders to be bleeding hearts that are in touch with their feelings and mentally healthy at the cost of their business execution. I see it as a win-win to unlock the possibility of a better way. There is a better way to build a resilient organization that executes faster. Or to retain and engage employees. Or to keep leaders saner and more compassionate. The more conversations we have on this, the better off we are. This is part of why I’m so excited to be on their board helping them do this great work in the community.

If this resonates with you and you’re interested in learning more about Leaders in Tech, visit their website here. Applications for Fellows are also open through May 4 and you can apply here.