The problem: As the CEO of a burgeoning young startup poised to raise tens-of-millions in the next fundraising round, Sam felt too stretched to put much time and effort into shaping the culture of his organization. Sam cared sincerely about thinking through and facilitating what he thought would be a healthy organizational culture, but could never get around to dedicating time to it.
Tracing the structure: A general heuristic for when clients struggle with time management is that it is typically a prioritization issue, wrapped up in conflated assumptions about sequencing, timing, urgency levels and other planning imprecision. This ended up being the case with Sam, who was of two minds about spending time thinking through culture because it was important as a matter of principle, but ultimately lost in head-to-head prioritization against taking action to pay salaries and generating revenue.
After examining his beliefs about taking management action in closer detail, we found that a key bottleneck was not trusting his managers to take on the requisite amount of autonomy and responsibility, concluding that he ultimately needed to intervene on most things.
Option 1: Work through trust issues associated with management in general
Option 2: Work on trust issues associated with specific individuals he works with
Option 3: Explore surrounding beliefs about trusting staff with important roles and tasks. Determine whether trust levels can change according to performance across certain dimensions.
Option 4: Produce work plans on a granular level that compensate for his trust issues without intervening on his beliefs about trusting staff
Option 5: Determine whether he truly believes in the importance of designing corporate culture. He could simply feel that the culture is going well enough untouched, or was simply caught up in the narrative endorsement of culture being important without underlying believing it was true.
Largely Option 3 – After exploring more about his trust issues related to delegation and project management, it came to light that, in fact, he would be able to come to trust his managers to take on increasing responsibility in order to free his time up. Sam had implicitly pegged each individual at certain capability levels, not building into his planning the potential for growth and earned autonomy. We worked through his management approach in closer detail, clarifying what standards would need to be met in which domains. We then built in incremental tests for increasing responsibility and establishing feedback indicators for assessing performance. These more granular plan steps and contingency plans ended up carving out a viable path towards being able to spend more time thinking through the culture of his organization.