Coaching

"Non-Traditional" is my term to describe leaders who are navigating social contexts that don’t quite comprehend their struggles — e.g. moms in VC, minority founders raising money from mostly white investors, and sensitive souls with big ideas who want to succeed without abandoning their hearts. In addition to the normal stressors of leadership, many non-traditional leaders must privately navigate difficult social dynamics involving gender/race/identity:

• “Will my colleagues still respect me if I take full maternity leave?”
• “Should I speak up to my colleagues about their racist comments?”
• “My friends see me differently now that I’m a founder. How do I be this version of me in relationships that don’t understand who I’m becoming?”
• "My colleagues expect me to be cutthroat and ruthless to succeed, but that's not who I am. How do I stay true to myself and succeed in this environment?"
• “I want to be a good/authentic leader… but I’m stressed as hell. How can I be strong for my team when I’m barely keeping it together myself?”
• “Should I stay in my current misogynistic job and change the system from within… or quit and start my own thing?”

I love helping leaders navigate difficult and under-emphasized questions like these.

Many leaders are high achievers who’ve been "go go go"-ing their entire lives. This lifestyle produces a certain kind of success, but many leaders wake up one day wondering, “Is this really me? Am I really happy? Is this the life I want to live?”

These questions can be really scary and feel like existential crisis or the "b-word"... burnout. It can be very helpful to have someone walk with you during this moment to help you honor who you've been up til now and explore who you are becoming. 

I know these questions intimately myself, and I'm honored to create spaces for you to take a step back, do some important self-reflection, and discover what wants to come through you now. 

Founders

Many founders get guidance on building their business, but few get guidance on leading their people.

That's unfortunate. The truth is: as a founder, the way you lead has bigger impact on your employees than your product has on your customers. Not to mention, as a leader, your job is to accomplish goals through others' work. Meaning, people are your most important "resource."

How do you...

• Develop reports into the leaders they can (and need to) be?
• Stop "supervising" others and let them lead?
• Delegate in a way that actually reduces your IC work?
• Onboard new hires so  that they hit the ground running with institutional knowledge, rather than "just start" and create chaos?
• Inspire people to genuinely care about your vision?
• Assess a candidate's "culture fit" without bias?
• Know when to fire someone? And how to do it?
• Help people feel both psychologically safe and meaningfully challenged?
• Build a culture of both high performance and belonging?

I love helping founders work through these often ignored questions to become the best leader of people they can be. 

Co-Founders

Co-Founder relationships fail  too often. They start with excitement and end with resentment and grief about what could have been. But it doesn’t have to go that way.

I help co-founders work through tension and develop tools to have healthy, productive relationships. 

Venture capital is extremely competitive and full of uncertainty. Not only do you have to create deal flow and assess opportunities quickly, you also have to bet on human beings — the biggest wild card of all. As a VC friend of mine says, “The average VC-Founder relationship lasts longer than the average American marriage. But we have to choose to get hitched in under 3 weeks.”

In order to earn a founder’s trust, assess their potential, and make sound investment decisions at that pace, VCs must be mentally sharp, emotionally self-aware, and crystal clear about their values and decision making paradigm. When I coach VCs, we focus on creating a lifestyle that supports the highest possible mental and emotional functioning. This includes calendar management, delegation, EA best practices, and mind/body routines that help you access an inner state of calm focus and alertness. Then, I help you learn how to wow founders with the quality (not quantity) of your attention and to assess founders themselves, not just their business.

I also help with discovering your unique value add as a VC, marrying thesis and mission, and navigating team dynamics within your firm.

So many teams struggle to go from polite & political (“we’re fine”) to honest and high performing (”We love each other and we’re crushing it.”) Leaders often blame “communication,” but in every case, it’s deeper than that. I love helping teams work through subterranean tensions so they can finally get to “We’re crushing it.”

My favorite tool for teams is the Enneagram. You can read about my approach with team building and the Enneagram here.

The Enneagram is more than a personality framework. It’s an incisive self-awareness tool that helps you see the patterned ways you get “stuck” and stay disconnected from your true nature. You may have heard of it before, but I’m willing to bet you haven’t really learned it. 

There are a lot of personality frameworks out there. Disc. The Big 5. Myers Briggs (MBTI). Jungian Archetypes. Etc. All of them promise to help you understand yourself and others better, and to varying degrees, they deliver. But I believe that the Enneagram is by far the richest, deepest, and most facilitative of vertical development. It is as interested in your “strengths and weaknesses” as it is in your core wounds, defensive patterns, and who you are underneath all of that. It also shows a spectrum of “health” within each personality type and provides a map for how to become a healthy version of your type. In this way, the Enneagram is itself a model of personal growth. Most deeply, the Enneagram’s point of view is that you are actually NOT your personality. You are the Essential Self underneath it, and your personality is what shows up when you forget your true nature.

The Enneagram must be studied to reap its benefits. It points to aspects of your experience that you are not aware of yet, and it takes time to assimilate them. In this way, the Enneagram is different from the other tools in this PDF in that it is less a tool you use and more a framework you study. Or rather, a framework that helps you study yourself. The very process of learning the Enneagram in certain contexts has been shown in early studies to facilitate vertical development.

The Enneagram is fundamentally about how you use your body, heart, and mind. If you grew up in the West, you likely don’t know what “the intelligence of the body” really means. You may even be skeptical of the phrase. This is not a criticism of you, but it is one of our culture. We are a mental society that doesn’t pay much attention to the heart and body. But they are very real, very vivid dimensions of experience that shape every moment of your life, whether you are aware of it or not. The Enneagram helps you tune into to these dimensions of your experience.

So, the Enneagram is useful for vivifying your own inner world. But it also helps you understand others’ inner worlds, and in so doing, it helps you grow one of the most important later stage capacities — the ability to take others’ perspectives and see their validity. There is no better tool for this than the Enneagram. 

Two words of caution: 

1. You may have already taken your test and think you know your type. But tests aren’t very good, and when I work with clients, I correct more tests than I confirm. More importantly, consider learning your type the beginning of your Enneagram journey. Learning you're a 3 is the easy part. Learning that you’re NOT a 3 is the lifelong journey of the Enneagram.

1. The Enneagram reveals your psyche with clarity and precision, and this may be uncomfortable. Be kind to yourself. It may help to learn with others or a facilitator. 

I’m delighted to bring you this extraordinary tool that has impacted my life more than any other. 

The Work of Byron Katie is a simple and powerful tool for inquiring within. I credit it for the most important healing moment of my life. Here’s how it works.

You begin by thinking of a situation that bothers you, for example, “My wife doesn’t listen to me.” Then you fill out a Judge Your Neighbor Worksheet, which guides you in putting all of your judgmental thoughts on paper. Then, for each statement you write, you ask 4 questions: 

1. Is it true?
2. Can you absolutely know that it’s true?
3. What happens when you believe the thought?
4. Who would you be without the thought? 

Finally, you are invited to consider alternatives to your original statement, such as:

1. My wife does listen to me.
2. I don’t listen to me.
3. I don’t listen to my wife.

The Work is the most consistently ego-dissolving tool I have ever come across. It’s for this reason that people often resist doing it, myself included. We humans cling to our suffering and our stories about the world, and The Work calls them directly into question.  

Byron Katie herself is a beacon of clarity, love, and wisdom, and the way she works with people is extraordinary. It’s worth checking out her books, podcast, and YouTube channel.

If you’ve never done The Work, please try it first with a facilitator, since some aspects are not intuitive.

We all avoid hard conversations. Unfortunately, the conversations we avoid are the ones we most need to have. So the question is… how do you go about it? How do you actually start one? What words do you even use?

Nonviolent Communication (NVC) is a structured way of speaking and listening that enables meaningful, authentic connection. It helps you identify your feelings and needs, express them cleanly, and hear those of others’. Sounds simple, but the results are radical. 

In case you haven’t noticed, conversation shapes our world. It’s amazing to me that this isn’t talked about more. Every brainstorm session, every board meeting, every family dinner is shaped by conversation. We build relationships, explore possibilities, and coordinate action through conversation, and what we say or don’t say makes conversation smooth or bumpy. NVC provides conversational “training wheels” in the form of vocabulary, sentence structures, and mental models for navigating the conversations that matter most.

In my coaching with teams and executives, no topic surfaces more frequently than breakdowns in conversation, usually in the form of people not saying something that needs to be said or saying something too abrasively. NVC can help.

A final note: many vertical development practices are done alone or with a partner. NVC is one of the only tools that can be applied in the fray of normal living. The other person doesn’t even have to know what NVC is. It still works.

In the 80s, therapist Richard Schwartz kept noticing that clients were saying things like, “Well, part of me really loves him, and part of me wants to strangle him, and another part of me…” After a while, he asked himself, “What’s the deal with all of these parts?” He invented Internal Family System as a way to work with those parts. 

The basic insight isn’t new. We are not a single, unified consciousness. Instead, we are comprised of “many I’s” that contradict each other (To use Gurdjieff’s term for the same phenomenon). Schwartz’s brilliant innovation was to have you interact with your parts as though they are whole, intelligent entities.

This may not seem revolutionary, but it is. For example, a part of you may feel afraid to say “no” to social invitations, so you end up saying yes and getting overwhelmed with obligations. In IFS, you ask the part questions like, “What are you afraid will happen?” and it answers you back. In the process, you uncover your “Self” — the calm, clear “you” that is now speaking to this “part.” Major healing can happen from here, enabling your whole inner system to relax. 

IFS facilitate vertical developmental by releasing trauma energy that stifles inner progress. It also helps you experience (not just “see”) that you are bigger than your parts. This is a key developmental step, and one that we do again and again as we “climb the ladder” of development. 

It’s worth noting that IFS is a non-pathologizing form of therapy and is itself a product of post-conventional stages of development. While earlier-stage therapies conceive of treating pathology, IFS takes the view that there are “no bad parts.” They are all here for a reason and are best met with compassion and respect — not just because they protect your deepest vulnerabilities, but because that’s what actually gets lasting therapeutic results.

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Note: It is fascinating to look at the evolution of any field from a developmental perspective. All human disciplines develop along the same trajectory as individuals do, since the ideas that define a discipline come from humans at a particular stage of development themselves. Psychology was inherited its pathology model from medicine, which gave rise to the Diagnostics and Statistics Manual — the great tome of all possible psycho-pathologies that therapists use to diagnose their patients and bill insurance companies for “treatments.” The field of psychotherapy has evolved through ideas like Behaviorism, Cognitive-Behavioral Therapy, Humanism (or client-centered therapy), transpersonal psychology, and the now emerging Integral psychology, of which IFS, with its treatment of individuals as holons made of parts, could be said to be a part. The path follows a clear trajectory of vertical development.

20th century American philosopher Eugene Gendlin was fascinated by the idea that meaning exists before we give it words. It’s somewhere — but where? Gendlin later coined the term felt sense to describe one’s non-verbal, bodily sense of a whole situation.

Through research with Carl Rogers,⁷ Gendlin discovered that a clients’ ability to improve from therapy depended not just on the therapist’s skill, but on the clients ability to access his felt sense. One of Gendlin’s students, Ann Weiser Cornell, explains:

Clients who pause in the midst of talking and allow a fresh “felt sense” to form about the life situation they are wrestling with, and then continue to pay attention to it, tend to do better in psychotherapy than clients who don’t. This finding has been replicated in more than 50 studies (Hendricks, 2001).⁸

Gendlin realized that the ability to access one’s felt sense could be taught, and he called the process Focusing. It’s kind of like meditation, but you do it with a parter who helps you “stay with” your felt sense.

Why would you do that? Because, as Gendlin discovered, felt senses “imply a way forward.” When you put your finger on a hot stove, the pain “implies” that you should remove your finger. Similarly, a murky pit in your stomach also implies something, but it’s usually not clear right away. 

Of the tools on this page, this one may seem the most "abstract." But in my experience, it’s one of the most grounded tools on the list. Focusing is a close cousin of IFS in that what you encounter as a felt sense is often a “part.” Focusing helps you meet your parts “from the body up,” as opposed to “from the mind down.”

Breathwork is an umbrella term for various breathing techniques that help you reduce stress, get “in the zone,” and more. 

The breath is the only part of the autonomic nervous system that you can control, and it turns out that by breathing in certain ways, you can access non-ordinary states of consciousness that help you process deeply held trauma, experience transpersonal states, and even contact mystical truths and spiritual ecstasy. (Transpersonal just means “beyond yourself.” For example, in a transpersonal experience, you might feel at one with humankind, nature, or the universe.) Sounds cool, and it is. Also maybe sounds scary, and it can be, but breathwork is totally safe when facilitated by an experienced practitioner who can scan for contra-indications and support during intense moments. 

It must be said that many people explore non-ordinary states of consciousness as recreation, and I have no quarrel with this. But many people who experience temporary transpersonal states make the mistake of thinking that they have stabilized at a higher stage of development, and this is a false conclusion. Ken Wilber has made clear that we can glimpse reality from later stages during peak experiences, but we interpret those experiences from our current center of gravity. Breathwork and psychedelics are promising vertical development accelerators, but they do not catapult us into advanced stages permanently. We must still “do the work.”

Surprised to see this here? Psychedelics are incredibly exciting vertical development tools, since they can induce stable states of non-ordinary consciousness for long enough to really “get somewhere” on an inner journey.

I understand that psychedelics can terrify people, and with reason. They can take you to intense inner places that, without proper preparation or oversight, can overwhelm you. 

But the history of psychedelics in human history is by and large positive. Indigenous cultures around the world have used them ceremonially for millennia to connect to Nature, God, and each other. Many Western people report that their first experience with psychedelics is one of the most beautiful and important moments of their lives, after which they felt more connected to their hearts, to themselves, and to humanity. 

From a brain point of view, entering a non-ordinary state of consciousness simply means going beyond your “Default Mode Network” — the set of neural nets that comprise your “normal” state and therefore shape your perception of reality. Research has shown that psychedelics create new neural connections and open you to fresh ways of seeing the world. They can also temporarily decrease feelings of fear and defensiveness, allowing you to confront old memories and process trauma that would otherwise be too painful.

On the whole, Western media has painted too dark a portrait of psychedelics. I believe that with proper facilitation, the benefits outweigh the risks. If you are skeptical, please check out the Multidisciplinary Association for Psychedelic Studies (MAPS), whose research on MDMA is currently in stage 3 clinical trials for treating PTSD and is showing extraordinary results. Johns Hopkins is studying psilocybin as a treatment for depression, with similar results. Clearly, there is tremendous healing power in psychedelics, and I believe that making facilitated psychedelic experiences available at scale can pave the way for a mentally healthy and vertically developed society more than just about any other single stroke. 

However, a warning belongs here. Psychedelics can facilitate vertical development, but they are not silver bullets. You still must “do the work.” And, as much potential as psychedelics have to help you heal trauma and connect to your higher self, they also have a dark side and must be treated with caution and respect. The book’s How to Change Your Mind by Michael Pollen and Consciousness Medicine by Francoise Bourzat are good places to start learning.

Psychedelics are, of course, also illegal in most states, and I do not condone or encourage breaking the law, so all of this is offered as information only.