Self-Awareness as a First-Time CEO

I got my creative thang on a few weeks ago and decided to make my first infographic. Stay tuned – I will finish it this week and it will be distributed through the normal channels (this blog, my twitter – @chrisheivly, TSF twitter – @TSF_VC, etc.).

The exercise of gathering relevant and interesting facts about what we do was something slightly awkward for me. You see I spend so much time charging ahead (like most of us) that I had not taken any time to look back. At least in broad summary, data-driven terms. As we have matured as a seed investment fund, we have seen very real patterns emerge. At the end of every TSF session, Dave and I review what is working and what is not and adjustments are made for the next cohort. These are mainly tactical decisions. About 1-2 times per year we also take a day or two and go offsite to discuss future thoughts. All of that is standard playbook for most companies.

But I am talking about something different here. I am thinking more data-driven insights. So, I wondered whether some of you operate like I have and whether we all should take a few hours every so often to do an in-depth look back. The largest benefit would be some level of learning about our companies and ourselves.

The one pattern I am obsessed with the last few weeks is self-awareness. Really good entrepreneurs are very self-aware of who they are and as importantly what they are not. We work predominantly with first-time entrepreneurs. By definition you have some major blind-spots, gaps and serious issues. I like to think we act more like Andreessen Horowitz where CEO’s evolve and our job is to help them grow.

But to grow, one has to be brutally self-aware. What do self-aware CEO’s do and don’t do?

  • They are transparent with their investors and staff as part of their culture.
  • They openly discuss what they are comfortable with and what they are uncomfortable with.
  • They don’t tell themselves those little lies about their lack of skills.
  • They don’t bullshit anyone.
  • They ask the tough questions and create an environment where everyone can ask those same questions.
  • They don’t hide their doubts.
  • They love feedback and can’t wait to get more. They listen and process that feedback honestly.
  • They reach out to others for help. But do so in a checked-ego manner.
  • They are true to themselves. No posser attitudes.

They are happy about who they are and what they could be when doing all of the above well.

Too often I see first-time entrepreneurs playing the role of CEO instead of being an honest operator in a ever-changing, multi-person team.
Just build a great business without all the ego. You will be amazed at the freedom that comes from releasing the burden of posing as a CEO.

Speaker, investor, mentor, startup founder. One of 3 or 4 Co-Founders of MapQuest (sold to AOL for $1.2B). Managing Director of $25M Venture Fund in late 90's. CEO, COO or President of various companies ranging from $200k to $20M in size. One of two Managing Directors of The Startup Factory (35 investments across 7 cohorts), founder and MC of the Big Top Reverse Job Fair and national writer and speaker waxing poetic around startups and startup communities. Currently EIR @ Techstars with Brad Feld ~ Startup Communities, to help community leaders around the world grow their startup community.

1 comments On Self-Awareness as a First-Time CEO

  • Great thoughts here Chris. It’s really easy for young CEO’s to get too excited about being a Chief Executive Officer. But the title barely applies in the first years… the better title is probably startup founder. I think that comes with better connotations and more effective default behavior.

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Speaker, investor, mentor, startup founder, national writer waxing poetic about founders, startups and startup communities. Currently EIR @ Techstars with Brad Feld ~ Startup Communities, to help community leaders around the world grow their startup community.


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