If one is doing a good job at growing a company the amount of issues, challenges and successes will grow over time. With that the days and nights become full and the concern arises in the CEO's mind as to the prioritization of the things. And yes, most CEO's can readily assess and order priorities. They also worry more than your average bear because situational analysis skills are critical to success. Worry enables many start up leaders to anticipate what will go wrong and contemplate possible reactions. Yet, the time spent worrying isn't time spent defining responses and decreasing time to react.
Nonetheless because of worry, they don't always react as quickly and as well to things as they would, upon further reflection, wish they had. I argue that time spent worrying is a waste for start up leaders. Why, well, one can't always anticipate what will go wrong. So, my thought is produce action plans, think about responses, reduce reaction time while limiting scenario creation effort. Just make up possible problems and spend time contemplating responses. Short response times with effective plans is the order of the day.
Woulda, Coulda, Shoulda can haunt anyone in any position. This is particularly true for someone who makes many critical decisions. In talking and working with those folks, I find there is more regret about arriving at the right conclusion sooner than the occasional mis-step.
To counter that, I typically ask CEO's to tell me what would be the content of two headlines in tomorrow's paper -- one of which is the best news possible from the company's perspective and the other the worst news possible. You would be surprised how many times the imagined headlines actually make into reality and the paper. In any case, the act of imagining these headlines prompts the CEO to do some critical things. First, the CEO can assess possible steps to progress the best headline and mitigate the effects of the worst headline. Second, the CEO can prepare an action plan in response to the arrival of either headline into the company's future.
The process of preparing for these 2 events shortens the response time while enhancing the quality of the company's response in the moment.
The CEOs I have done this with will often muse about how unlikely they thought either headline was at the time of its creation.