CEO Self-Reflection

Originally posted on June 11, 2022

Self-reflection is an important skill. In startups, CEO self-reflection can be very hard to do. Sometimes it seems nearly impossible for early-stage companies. The startup is always on - building, selling, pivoting, hiring, fundraising - all with limited resources!

The startup CEO is the probably involved in everything - small and big stuff. Taking a day off from the day-to-day operations of the business is hard. But this is exactly the reason that CEO self-reflection away from the daily cadence is important because it helps the CEO stay focused on the most strategic items, prioritize key actions, and mature as a leader.

If you are a startup CEO, plan taking a day or two or three off. Tell your board of directors that you are not available for a few days unless it's emergency and tell your executives or able staff to take things over. Do something that takes you mind off from running the business. Do something other than running the company :) At the end of that break, spend one hour to write down the answers to the following questions before you go back to the daily grind.

CEO self-reflection questions:

  • What major milestones did we achieve in a quarter, a month, a year (pick a time horizon)
  • What small wins has turned out to become big wins? Why?
  • What were major misses? Why?
  • What did I do well?
  • Looking back, where could I have allocated more time and reduced time in another area? Why?
  • Am I spending enough time talking to customers, prospective customers?
  • How was the last few board meetings? Is your board reactive or giving unified strategic and tactical advice?
  • How do I feel about my team?

If you are a startup CEO, take a break. Summer is a good time.

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