Inner Foundations of Entrepreneurial Leadership

Venture capitalist John Lilly gets pitched for funding by 400 entrepreneurs a year.  Here he is explaining how he evaluate the candidates:

You start to expand the scope of the questions to try to see two things. One is the quality of their thought process. And the other is how they interact with you. Do they become defensive? Do they become aggressive? Are they listening?  You’re trying to get a sense of whether, in a complicated situation with a lot of things going on, can they be honest and candid and still get to a productive place. Sometimes you get honest and candid, and sometimes you get antagonistic or defensive.

The qualities he describes here — clarity of thought, emotional balance, non-reactiveness — are hallmarks of what I call grounding.

Grounding is the capacity to remain centered amid complexity and challenge; to think with clarity and flexibility in the midst of flux and uncertainty; to avoid over-confidence and rigidity while remaining detached and impersonal, even when the stakes are high.

Entrepreneurship involves treading uncharted terrain and tackling challenges that haven’t been tackled before.

I have never seen an entrepreneurial path without unexpected setbacks and unforeseen obstacles.

The entrepreneurs that succeed are those manage to remain centered, balanced, thoughtful and reflective as they navigate these uncharted waters.

Grounding is what makes that possible.

So how do you develop or improve your grounding Most believe it’s an inborn trait or the product of long experience.  The truth, I think, is simpler and somewhat counter-intuitive.

Grounding arises from a good understanding of how our mind works: when our mind is clear and when it is cluttered; when to trust our thinking and when to be cautious; how to respond when we lack clarity or when insecurity or strong emotions overtake us.

Just a few key pieces of wisdom about the human mind can be transformational in deepening our grounding.  For example:

  • Understanding that we have rising and falling moods enables us to ride the emotional rollercoaster with grace and constancy and with far less exhaustion and fallout
  • Understanding our perceptions shift along with our moods (i.e., people and circumstances will look very different over time) introduces an enormously helpful degree of patience and curiosity
  • Understanding our mind continually produces new ideas and fresh insights on a continual basis frees us from obsessing or ruminating and allows for a more consistent engagement with the tasks at hand.

Leaders with grounding have an uncanny ability to keep calm and carry on, to remain relatively unswayed by the slings and arrows of circumstance, to seek and respond to feedback and take difficult conversations in stride.

They steer clear of counter-productive (inner and outer) drama. And they value the clear mind and reflectiveness that are the sine qua non of good leadership.

From a grounded place, things tend to go more smoothly. Work gets simplified. Performance hums along. Solutions arise.  And it all feels natural and ordinary: responsive, drama-free productivity.

In other words: Every investor’s dream.