Weekend Words: Grayscale Moments

High impact and require a combination of resources to navigate

Leadership is a loaded term and being a good leader has no real definition. The judgement we pass on one being a good/bad leader is one of the more subjective and relative accolades in our world. Who I might consider a good leader or dub to be a strong founding team could differ greatly from another individual. That’s also what makes investing and business, in general so dynamic and fun-- there’s rarely a clear right answer.

When it comes down to it, the quantitative measures such as revenue growth or profitability are just a few readings that reflect the output of a strong leader or founding team. They don’t necessarily reflect the deeper hardships of decision making and team management. These are what I call the grayscale moments. Grayscale moments are high impact and require a combo of EQ and IQ to see through.

These moments could potentially make or break a company. When we say quality of founding team, it’s these moments we want to optimize for as much as possible. Decisions might include:

  • Setting culture, core principles, and operating cadence
  • Evaluating broader company strategy
  • Discontinuing popular but non-core products
  • Balancing transparency vs need to know in terms of information among team members
  • Talent acquisition and management

It’s no easy feat to “color” one’s way through these and there’s no perfect person or leading indicator to find that rockstar manager. It’s an iterative and dynamic process full of ups and downs. All we can do as business people is to actively to develop ourselves on multiple vectors for such moments. I myself continue to wade through a variety of grayscale moments and combined with observing other leaders, it appears that hard work, preparation, complementary talents, conviction, and character help folks navigate through.

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