What I learned from two years of Leadership Groups

In 2018, I met the love of my life. A few months into the relationship, we had one of our first real fights. As emotions started rising, my then-boyfriend (now-fiancee) pulled out a booklet from his backpack and slapped it on the table. “Can we follow this rubric?” he said in desperation, as he opened the booklet to a page that was titled “The Clearing Model.” I rolled my eyes at the idea that we needed a rubric for communication, but I entertained him. We went through the model step by step, and after we completed it, I was surprised to find that I felt a lot better and a lot more connected with him. The conflict was indeed mostly cleared.

That’s what got me intrigued with Conscious Leadership Group (CLG), a group that he had been a part of for 3 years. So I signed up to join a Forum, skeptical, but hungry for any type of leadership support. I had never joined any of these Silicon Valley “CEO groups” at that point and generally despised the exclusive nature of them all. But I was also curious about them, given how much people raved about how helpful these groups were. Being the CEO of a startup is a really lonely, stressful job, especially as a first-time founder. Sometimes all I wanted was to be able to crack a joke and be able to laugh about it with someone who empathized with the bitter realities of the job.

It took a few months, but my work with the CLG Forum quickly started to open my eyes and transform my life. I didn’t hesitate to sign up for a second year. I became so addicted to this type of self-help work that I also signed up for the Leaders in Tech (LIT) group, led by Carole Robin, who is probably most known for teaching the infamous “Touchy Feely” course at the Stanford Business School (the course constantly had a long waiting list and was booked full every quarter.)

In addition to these leadership groups, I am also a huge proponent of mental health therapy as a preventative measure to strengthen our mental muscles, similar to how we go to the gym to strengthen our physical muscles and promote our physical health. I was fortunate to have found an amazing therapist through Two Chairs. Going to therapy to get individualized attention on somewhat of a weekly basis helped me increase my awareness of how I criticized myself in my head. From that awareness came an ability to accept, understand, and move on.

None of this came cheap, and none of it was easy. In total, I spent about $40,000 over two years, in addition to countless hours of studying, practicing, introspecting, meditating, processing, and crying.

Whenever I come across something incredible, the first thing I want to do is share it with others. Unfortunately, at this price tag, I know most can’t afford to join these programs themselves. The lessons I learned through this work are so powerful and core to who we are as human beings that there’s no reason why it should be restricted to startup founders (though I understand why these programs target this demographic.) I hope to share some form of this incredible thing I found by compiling some of the lessons I’ve learned through doing this work. At the end of this article, I’ll also refer you to a few resources that might help you on your journey. And if you’d like to join one of these groups but don’t have the financial resources, they also offer a few scholarships that you can apply to.

Lesson 1. Humans are incredible storytellers

One of the first lessons I learned from CLG was to separate fact from story. While that might seem trivial, most people confuse stories and opinions as fact, and this confusion is what leads to most conflicts. A fact is something that can be recorded by a camera, things that can be observed. In reality, very few things are facts. For example, “he got frustrated with me” is not a fact, whereas “he started speaking faster” is a fact. Most of the time, we observe facts, and we then make inferences about the other person’s state, their thoughts, their emotions, and their intentions. These inferences often create conflict during a conversation. In Leaders In Tech, we coined this as “going over the net,” with the “net” serving as a metaphor for what separates two peoples’ realities. Another body of work that teaches this is Nonviolent Communication. When we go over the net and make claims about another person’s feelings or intentions, we come off as accusatory and we are often mistaken. As a result, this puts the other person in a defensive mode, where they now feel that they need to justify and correct these false claims about their intentions. This is how fights escalate.

The recognition that there are multiple stories that can be created from the same facts allows us to move to a state of curiosity.

Separating fact from story is also one of the premises of meditation. In meditation, we practice observing sensations and thoughts as they appear and separating ourselves from them. This separation allows us to observe the facts as they are: the sights, sounds, and smells. This separation then allows us to recognize the stories we create to explain these observations, which subsequently allows us to explore new stories to explain the same observations. The recognition that multiple stories can be created from the same facts allows us to move to a state of curiosity. In a curious state, conflicts are often much more easily resolved.

When I coach my team to help them navigate interpersonal conflict, I often do so by asking questions that challenge them to think about different versions of their story that they can tell about the other person’s motives and emotions. This empathetic curiosity then sets the stage for both sides to engage in conversation and learn more about one another, often building a closer, more trusting relationship as a result.

Understanding the usefulness of storytelling — while simultaneously understanding that many stories can be told from the same facts — gives us incredible power.

Stories, however, aren’t simply there to create conflict. Humans evolved the ability to tell stories through millions of years of evolution because it serves a benefit on our ability to survive. We tell stories to influence. We tell stories to learn. The stories we tell create our identity. Stories give us meaning. Understanding the usefulness of storytelling — while simultaneously understanding that many stories can be told from the same facts — gives us incredible power. It gives us the ability to write our past and our future. In psychotherapy, I explore the stories I told about my past with my therapist. In doing so, we were able to reexamine these stories from the past and ask which ones were no longer true and no longer served me.

Lesson 2. Building Trust through Disclosure

Another lesson I learned was that in the absence of information, humans make up stories to fill in the gaps. This also fits in line with our incredible talent as storytellers. The consequence of this realization is that we can build trust by disclosing our inner thoughts and inner state. This was an incredible lesson for me. As a natural introvert and a very private and independent person, I often kept a lot of my thoughts and feelings to myself because “I didn’t want to trouble the other person” or “I didn’t want to burden them with something they can’t change.” As a result, people rarely felt like they understood me and often misinterpreted my actions. Voluntary disclosure about my inner state alleviated the other person from having to guess where my actions and words were coming from, which resulted in others sharing that they felt much closer and connected with me.

In the absence of information, humans make up stories to fill in the gaps.

As CEO, I often found myself feeling overwhelmed by the expectation I placed on myself to solve all the problems in the company. During my one-on-ones with people, I often asked them how they were doing and if they were faced with any technical or personal challenges. I tried to give each person individualized attention and help mentor them and work through problems with them. However, it can be overwhelming when ten different people in the company come to me simultaneously with their challenges asking for my help, which happened often. Rarely in my one on ones did I talk about my own challenges or responsibilities, which also included fundraising, board management, and business development. In the past, when people asked me “how are you,” I often replied with an automatic “good,” even if I was far from it. Gradually, I learned to share some of this information and share my feelings of overwhelm. Doing so helped my team empathize and realize that if I wasn’t able to address their issue right away, it wasn’t because I thought their issue was unimportant. It also helped people feel more connected to me in realizing that even the CEO can feel like a fish out of water sometimes, that it was okay for them to feel that way sometimes too, and that we were a team trying to build something great together, something that was bigger than all of us.

We brought the practice into our meetings as well. Before each meeting, we’d start with an emotional check in- thumbs up or down. It was okay to be a thumbs down, and that knowledge built empathy. For example, if a coworker notices that you have been silent throughout their presentation, they’ll know that it’s because you’re dealing with the emotions you walked into the room with, not because you hated their presentation.

Lesson 3. Be ready for messiness

Most people, when they think about this type of work, expect to learn superpowers that improve every aspect of their lives and get them what they want. Often, that’s not what happens. Most people have spent their whole lives setting up relationships and situations that were not in integrity with their values and what they truly wanted to stand up for, and coming into integrity with that naturally leads to an unwinding of these relationships. Some of these aspects of your life might transition with you to your new life, and some may not. Building a more integrated life inevitably means being willing to lose some things you love. It means being willing to let go. Being willing to draw boundaries inevitably means that some people won’t accept it. In order to draw boundaries, we need to first let go of trying to control the outcome.

Being willing to draw boundaries inevitably means that some people won’t accept it.

Most people operate in a world of zero-sum, one where no one is willing to change, where egos are constantly competing. If you really dive into this type of work, then you’ll start to show up differently. For me, a lot of my work was about feeling my anger around situations rather than accepting them and wishing/hoping they were different. This meant that I showed up to voice my opinions more, to point out when something wasn’t working. Not everyone liked that. I’m sure some people thought I was smoking something. But for me, I felt more in integrity with myself than I ever had before.

It’s important to note that being ready for messiness doesn’t mean that things will spin out of control. A core concept of this work is that you always have the choice. You can’t choose how others will react to something, but you can always choose what you do or how you respond to it. You can choose whether you want to draw a boundary or not, and where you want to draw it. But a conscious choice to not draw a boundary and accept the consequences is different from an unconscious one — one where you continue to agonize over the injustices done onto you and why the other person keeps crossing your unstated boundary. Being aware of the stories in your head and feelings in your heart that are controlling your actions doesn’t mean that those stories or feelings are wrong or need to be changed — it simply gives you the power to act from a place of choice, rather than a place of reactivity.

Lesson 4. Create clearer agreements upfront

The biggest lesson I’ve learned from this work and from the last 5 years of doing a startup is that it’s always better to place the uncomfortable discussions about expectations upfront. To be clear, by “better”, I mean higher integrity, lower stress, and more trusting relationships. If you get excitement out of keeping agreements ambiguous so you can “trick” the other side and get the better end of the deal for yourself, then you obviously should not follow these practices.

Ambiguous agreements leave room for each person to interpret the agreement as they see fit, which often is the version that each side most wants to see.

Many relationship conflicts are caused by vague or incomplete agreements. Ambiguous agreements leave room for each person to interpret the agreement as they see fit, which often is the version that each side most wants to see. Since everyone holds different values and motives, this often leads to differing expectations, which results in conflict down the road. This is true for relationships between cofounders, investors, employees, and friends and family. The more uncomfortable the thought of having a discussion, the more important it is for you to have it.

The more uncomfortable the thought of having a discussion, the more important it is for you to have it.

Radical Candor is a great book that covers how having these difficult conversations can allow us to be better leaders, friends, and coworkers. A lot of marriage self-help books are also centered around this idea of having difficult conversations upfront, before entering into a marriage. Recognizing unclear agreements is one of the most useful practices in my day-to-day life. Being willing to have these upfront conversations may feel difficult at first, but everyone feels a sigh of relief once they’ve been had and each side feels like they’re walking away with a more complete understanding of what to expect.

Lesson 5. This is a life’s work

Even the coaches of this work struggle with conflict, stories, and unclear expectations. A big part of making progress on this work is accepting that we are all works in progress and choosing to commit to growth. It can be easy to get frustrated if you expect to see results too quickly, but if you commit every time, then within a year, you’ll look back and see how you’ve grown. I try to keep the following equations in mind:

0.95¹ = 0.95
0.95⁵ = 0.77
0.95²⁰ = 0.36
0.95⁵⁰ = 0.08

This is my way of reminding myself that if each time you practice something, it feels like you’re still falling short and change is occurring painstakingly slowly, persistence and dedication to the work will guarantee to lead you to extraordinary places.

Below are some books I recommend if you are interested in diving more into any of these topics

Books and Resources

• 15 Commitments of Conscious Leadership, by Diana Chapman
• Connect: Building Exceptional Relationships with Family, Friends, and Colleagues, by Carole Robin
• Daring Greatly: How the Courage to Be Vulnerable Transforms the Way We Live, Love, Parent, and Lead, by Brene Brown
• The Conscious Leadership Group Resources — videos, guided meditations, and many handouts on most of the material taught in CLG
• Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships, by Marshall Rosenberg
• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity, by Kim Scott
• Waking Up, a guided meditation app by Sam Harris. These are a set of courses that walk you through the philosophy of meditation.
• A short TED talk on the power of stories: https://ideas.ted.com/the-two-kinds-of-stories-we-tell-about-ourselves/