Great Leaders are Deeply Introspective
Good leaders never stop learning. That they are tirelessly curious about their products and world should be of no surprise. That they are just as driven to understand themselves should not be either. Of all the things one can study, the self is most transcendental and fundamental. A great deal hangs on it.
Understanding our needs, the origin of our motivations, our strengths and weaknesses, is not a ‘nice to have’. It is (literally) essential. Self-awareness is knowing what we are good at and how we can help. It inspires security and trust. Think of it as the oxygen mask you must put on before assisting those beside you.
Introspection allows us to see those bits of ourselves that need a little polish. In the ideal, it affords us the humility to ask for outside help when needed. We are all imperfect. If we understand the limits and limitlessness of personality, we can finely balance the mix of people in our teams for harmony and success.
This is a process. The goal looms rather large. Small changes in habit require very little daily effort but compound wonderfully over time. As with a language, the more we work at this, the larger our vocabularies. The more words for snow, so to speak, the more precise our insight.
The writer Alain de Botton asks us to be so encyclopedic about our shortcomings that we could fill a book with them, title it My Insanity, and be secure enough to give it to friends, family, and any prospective partner. This won’t work for everyone. But heed the underlying call: if we ever hope to lead well, we need to be open to self-discovery outside the workplace.
Bearing that even the longest journey starts with small steps, here is a list of guides that might help on the founder’s path to self-knowledge. By all means skip sections to what you respond to most strongly.
- Professional Coaching
- Peer Forums
- Personality Tests
One of a VC’s most rewarding duties is walking with entrepreneurs on their way to success. Part of having gone somewhere before (at NXTP, we’ve helped some 200+ companies) is pointing out pitfalls, trying to ask questions that lead to insight, sharing in joy, and reframing problems to make the path smoother for those who follow.
Many times, mentoring refers to startup specific questions: when is it best to raise capital, which metrics remain most meaningful, what tactics work for proportional growth, etc. As a business grows, so does trust among the participants. We find that a relationship born in professional mentoring often blooms into personal mentoring — happily so.
Having one-to-one meetings with investors and other entrepreneurs is another avenue. This is especially true if there is some chemistry. One of the strengths of accelerator programs ( YC, Techstars, 500, GAN) is the formalization of networks and bonds that far exceed the spaces where they began. Endeavor forges similarly strong connections. In all the above, the relationships can last for decades.
It is not necessary to formalize this mentoring relationship, but it is important to dedicate regular space to developing them.
This type of mentoring is not rented, but if it does add value, it is decent to reward that sweat equity in a way that aligns with the long-term interests of the mentor (if she is not already an investor).
As anyone who has struggled on a dance floor knows, some things that we take to be innate are anything but. Beyond the depth that an investor, veteran entrepreneur, or VC can provide, there are professional coaches entirely dedicated to understanding and advising on individual and group dynamics.
One cannot be good at everything. Believing that is a flaw in itself. What a coach is good at is picking up on strengths and weaknesses from a uniquely independent vantage point that. This is especially helpful in understanding where you might fit in a team and how to structure one where each teammate compliments the other.
The possibilities here run into the hundreds. Fit is vital. It is best to act on the recommendation of someone you trust.
One of the wisest investments of time and money is in the study of the self and its vast unknowns.
Is it not exciting to see the truths in the stories we tell ourselves, the fictions too, and the root cause of so many of our actions? Recognizing the gap between the person we wish to be and who we are at present illuminates (even if it is briefly dispiriting). Psychotherapy does not promise any answers to these questions, just a method for remaining curious about the dimension of our personality and who we really are.
Therapy takes place in the same room, one-on-one, consistently — consistently above all else. It is a process of understanding yourself in the presence of another. What are your blind spots? How can you navigate this world more smoothly? How is your present being spoiled by relitigating the past? What are your clichés? To what degree are you aware of these things?
Of all the recommendations here, if you prioritize one, prioritize this and stick with it for at least a couple of months. As with all relationships, a good fit is critical.
Meditation is the resource I find most useful for calming the thoughts that keep me from acting clearly. Surface thoughts pass and I can connect with a more enduring self. I can be more present in the moment. Some describe this as a centering, and it can feel that way.
The challenge is to create the habit of being able to meditate daily and sustain this practice over time. Whether through a basic course or an app, you will need some minimum of training to start meditating.
If you wish to go the latter route, there are many options ( Headspace, Calm, Take A Break, …). I recommend Sam Harris’ Waking Up because it offers both practical guidance and a lot of interesting theory that you can digest at your own pace.
As leaders of our own organization, we often find work and even personal obstacles that are difficult to share with other people for a (fortunate) lack of similar experience.
Having a group of leading peers from non-competing organizations is very valuable. Sharing war stories, triumphs, and giving genuine and interested advice is rewarding for all participants.
That is exactly what organizations like YPO, REF, EO, VISTAGE, and HBS Forums do.
I recommend you comb your connections to see who might belong to any of these organizations or similar. Over time, you will likely develop relationships of great trust and, speaking from experience, close friends.
Many people in business find personality tests useful both as a tool of self-inquiry and one especially suited to assembling well-balanced work teams. Some even become evangelical after using them intensively. (I am not, but your mileage may exceed mine. They take hardly any time and, even if in disagreement, ask good starting questions.)
The most popular of the tests is the Myers-Briggs indicator or typological inventory. The MBTI is a self-reported questionnaire that assesses how people perceive their environment and make decisions within it.
The indicator differs from other standardized tests and quantifiers, such as IQ, in that it does not return a score on a single characteristic, rather a matrix classifying the types of a person’s preferences. According to Myers and Briggs’ theory, while types and parameters are innate, parameters can be improved just as we improve our abilities, while types, if the individual is in a healthy environment, will define themselves naturally over time.
The MBTI orders psychological differences into four sets of opposing pairs or ‘dichotomies’ (extrovert/introvert, sensory/intuitive, rational/emotional, qualifying/perceptual) whose combinations give rise to sixteen distinct psychological types. No type is better or worse; however, Briggs and Myers thought that individuals would naturally have a preference for a specific combination of differences. Similar to how a right-handed person finds writing with his left tiring, individuals find it difficult to use psychological preferences that are the opposite of their own.
There is a shorthand for each of the sixteen types that corresponds to their underlying four preferences. E.g.:
- ENTJ — Extroversion, Intuition, Thinking, Qualifier (Judging)
- INTJ — Introversion, Intuition, Thinking, Qualifier (Judging)
- ISFP — Introversion, Sensory, Emotional (Feeling), Perceptive
- INTP — Introversion, Intuition, Thinking, Perceptual
I am INTJ.
Tatiane Guedes, the personal coach of one of our portfolio founders, recommends trying the enneagram of personality. This is a classification system not too distinct from the MBTI and, while its method is under something of a cloud, the sketch of self-knowledge or personal development it draws can spark some good thought.
The enneagram describes nine personality archetypes with unique strategies for dealing with their affairs. As these personalities become agitated they can blur into one other. That is, one can behave quite distinctly under stress (and knowing how one acts when stressed is crucial in a startup).
If you want to take the test you can download the app here. My main type is 3 and the second is 7.
Lastly, Instagram co-founder Kevin Systrom and Ray Dalio both recommend the Golden Personality Type. Something of an MBTI on pep pills, the test blends that test’s types with the enneagram’s focus on how we respond to stressors.
Whether you consider any or all of the above, never stop reading. There is no greater red flag when sitting across from a founder than discovering they haven’t cracked a book since grad school.
Choose books that resonate with our world and time. Here are some personal recommendations.
The Trillion Dollar Coach
Since only a lucky few got to sit opposite legendary coach (sport and business) and Valley exec Bill Campbell, consider The Trillion Dollar Coach the next best thing. That lucky few? Steve Jobs, Larry Page, Eric Schmidt, and many more lights in tech. (The title is a guess at the total market value of the companies he’s had a hand in.)
What was his great insight? Pure and simple, to be a great manager you have to be a great coach. The higher you climb, the more your success will depend on making other people succeed, which is, by definition, what coaches do.
Bill Campbell’s approach to being a great coach was to inspire five distinct factors in every team:
Pick the right players and then let them shine. Choosing the right players is the foundation of any team, but it is how you lead them that makes all the difference. The order in that last sentence matters.
Only coach the coachable was another of Bill Campbell’s rules. Warren Buffet has a reputation for investing in companies where management is flexible and willing to listen. He believed that marrying someone intent upon changing them is one of the biggest reasons leading to divorce. Similarly, investing in companies with the intention of changing rigid management will ultimately lead to failure.
A great coach is “someone who tells you what you don’t want to hear, who has you see what you don’t want to see, so you can be who you have always known you could be.” You must communicate to your players that you believe in them more than they believe in themselves — all while pushing them to be more courageous. The top players have “smarts and hearts”: the ability to learn fast, a willingness to work hard, integrity, grit, empathy, and a team-first attitude.
Jerry Colonna was a VC who became an executive coach to some of the most effective CEOs in the entrepreneurial ecosystem. His was an unusual blend of Buddhism, Jungian therapy, and businessman-like directness aimed at helping leaders overcome psychological traumas.
is a journey of radical self-inquiry. It could help reset your life by sorting through emotional baggage that holds you back professionally, and, more importantly since we only have one life, in your relationships.
If you respond to his way of seeing, Colonna’s consultancy runs a blog that extends the ideas in Reboot to address even more of those problems that sit unpredictably on the Venn diagram of Work and Life. He is very good about answering reader’s questions — yours perhaps.
Tribe of Mentors
Another standout is Tim Ferris’ Tribe of Mentors. There is a common belief that the answers we seek will come at the end of a long and esoteric search. Ferris’ would have none of that. More often than not, if we do some mix of the above, the advice we seek appears in front of us when it is needed most.
Ferris’ book is a repository of good advice overlooked — wisdom that lives right out in front of us if we only know how to see it. A large and diverse group of people who have achieved something give the advice they wish they had received back when they were people who hadn’t.
If the book clicks with you, a next step might be to read its spiritual sequel, Tools of Titans. More practical advice with even more economy of phrase.
I do hope these tips help you enjoy looking inward, help you become a better leader, and help you become who you want to be. As always, feel free to reach out at aa [at] nxtp.vc. We’ll try to respond in person or on the blog.
Originally published at https://nxtp.vc on April 19, 2021.