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.
- The alternative: Recognize the value of sufficient structure and routine: "The fluidity and ambiguity that foster creative problem-solving in an early stage startup will feel like chaotic dysfunction at a later point in the company’s development."
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.
- The alternative: Realize that self-care on a leader's part is an investment in the business, "a necessary practice to insure that they are able to fulfill their responsibilities as a senior leader as effectively as possible," not an indulgence or a sign of inadequacy.
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 year, or all of the above.
- The alternative: Be aware that what's urgent isn't necessarily important, and what's important isn't necessarily urgent, and we're often pressured to steal time and attention from important tasks to feed urgent needs.
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.
- The alternative: Consider Peter Drucker's sage advice: "I have never seen anyone in a job for which he was inadequate who was not slowly being destroyed by the pressure and the strains, and who did not secretly pray for deliverance."
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.
- The alternative: View the process of obtaining executive support as a necessary organizational dynamic that occurs in three stages, going from no assistance to dedicated assistance to professional assistance.
6. They waited too long to transform HR from a compliance and administration function to a truly strategic function that accelerates the business.
- The alternative: Hire a truly strategic people leader.
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.
- The alternative: Recognize the need to establish such a body, even--and especially--when it lequires levelling early leaders who are still valued contributors but whose growth hasn't kept pace with the organization.
8. They waited too long to manage up with members of the board.
- The alternative: Be deliberate about by investing in those relationships and holding consistent one-on-one conversations prior to every board meeting.
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.
