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A CEO asked me about the most common mistakes made by my clients, most of whom are also CEOs. I had to consider how my clients would answer that question, and I think the overarching theme would be: They waited too long.

  1. They waited too long to establish sufficient structure in the culture's routines. Early in a company’s life, too much structure is suffocating, but eventually a regular cadence for routinely occurring events (such as 1:1s) adds stability and reduces decision fatigue.
  2. They waited too long to get serious about self-care: sleep, exercise, meditation, and time away. These practices are essential for effective leadership, but they're never urgent, so they don’t happen until the leader realizes how important they are.
  3. They waited too long before realizing that they need blocks of open, unstructured time on their calendar to do their best thinking. This can be 30 minutes a day, or 1/2 day every other week, or 1 day a month, or 1 week a quarter, or all of the above.
  4. They waited too long when making the difficult decision to fire someone. There were good reasons for the delay--there always are--but in hindsight they generally wish they’d acted sooner, and often all parties would have benefited.
  5. They waited too long to hire an executive assistant or chief of staff. This often involves letting go of concerns that hiring personal staff will be perceived as egotistical or self-aggrandizing. As a result, conscientious leaders can go through an extended period of time when their attention is being spent on low-value activities.
  6. They waited too long to transform HR from a compliance and administration function to a a truly strategic function that accelerates the business.
  7. They waited too long to form a clearly delineated senior executive team, resulting in an ill-defined group with a shifting membership that is ultimately a less-safe environment for leaders.
  8. They waited too long to manage up with members of the board.

In closing, it's worth nothing that all of these choices and decisions (from merely blocking off time on the calendar all the way up to firing someone) involve risk and uncertainty, which stir up complex feelings that can't be controlled but must be regulated.

Updated March 2021.

Photo by Mike Babiarz.