Armor vs. Authenticity

Part of leading a startup is raising money from investors, often professional investors (VCs) and high-net-worth individuals (angels). I learned over time that people who have or manage large amounts of investable capital develop “armor” to keep their distance from eager entrepreneurs. Similarly, self-taught learning to be a startup executive is often accomplished by hearing the stories of those who have gone before and been there/done that. Unfortunately, successful CEOs frequently have that same polished armor, making it hard to see what they did.

Recently, I had the opportunity to watch a fireside chat with a former Fortune 100 CEO who happened to be a highly accomplished woman. She was polished and articulate as she responded to her interviewer’s questions, I was struck by the sense that she was wearing invisible armor.

What did I wish for? I wanted to hear some deidentified war stories, some examples of decisions that were hard to grapple with and how she had tackled them, and some of those you-cannot-really-believe-this-is-happening moments. I wanted to hear about the authentic struggles that would help those of us who had not stood in those rarified places. I wanted to know how I could relate to them and pluck out insights into how executive leaders like me and others in the audience could handle similar situations we might face in the future. 

My friend who was with me and I talked about it later. We noted that while this supremely experienced leader had said absolutely nothing wrong, we longed to hear about her authentic experience. What she had learned from making hard decisions. How she had guided her organization through the ups and downs of business. Instead, we felt like she was someone who had perfected her ability to be ever-poised and professional, with nary a crack to show that she might be human (like us). She had developed a suit of invisible armor with a set of defensive shields that ensured that, in the end, it felt like we heard from someone who was beyond human.

The contrast was tremendous because others I have listened to that day and over the years have captured their moments of struggle and lessons learned in a way that felt authentic, real, and relatable. Those stories were inspiring and helped me and others to feel inspired and empowered to tackle the problems we were trying to solve as executive leaders. Engaging with the polished armor rather than the authentic struggles limited the learning opportunity from the inside-the-trenches view, which is the #1 way one learns to excel as an executive leader.

So, after having alerted you to the contrast between armored and authentic, what are the actionable implications? Here are some of my takeaways:

• Seek opportunities to engage one-on-one with other executive leaders and friendly investors so that it is safer to share what they have experienced and keep their confidence. The insights of fellow CEOs have been some of my best learning opportunities. Sharing the trauma of dealing with unexpected setbacks helps assuage the loneliness at the top. Seeking the perspective of friendly investors who do not have a stake in my business can provide a broader perspective of what is “normal” without the entanglements of conflicting roles.
  
  
• Seek out groups and venues that value authenticity and are supportive. For me, Women Business Leaders in Healthcare and Michigan Founders Fund both have supportive, authentic cultures that I deeply appreciate. I am sure there are other places you can find “your people.” Your support network will likely not be amongst your team because it sometimes gets muddled when reporting relationships are mixing with vulnerability.
  
  
• Keep in mind that not all groups or people are safe. Some are profoundly competitive and even vicious, so be alert when you first arrive to assess culture and character. Observe, test, and evaluate. For example, I don’t typically find pitch competitions, hyper-competitive CEOs, and some investors to be supportive, and that is when I keep my own armor in place. If everyone is armored up, take that as a cautionary sign.
  
  
• Offer your own authentic experiences to others as that invites reciprocation. Executive leadership is often peer-to-peer, so if you want someone else to risk letting their guard down, you might want to offer some of that yourself to test the waters. That is how some of my most potent mutually supportive relationships have developed. However, sometimes I have found that others are unwilling to open up their armor, so I approach this step-by-step to see whether there is mutual interest. Thank you to all of you out there who have shared your hearts, passion, and struggles with me! I value you deeply.
  
  
• Finally, check out content such as my written www.StartupCEOBlog.com blog posts and when I am a podcast guest (links are here) as I do try to reveal some of the difficulties, challenging moments, and struggles I and others have experienced. This is a guiding principle for me when I create content since it is what helped me learn and grow during my entrepreneurial journey and one way that I can try to give back to the community, where it can be hard to get behind the facades.

Learning to excel as a leader is challenging because much is self-taught, so when you discover mentoring gems, engage!