What was your best boss like?

I’ve had the fortune of working for not only some very excellent bosses throughout my career but also the companies themselves.  The relatively few moments I spent in malfunctioning companies made me appreciate how building an organization that is morally rich is really hard but the benefits to its employees and customers are enormous.  You’re engaged, excited to start another day at work, and know you make a real difference.  These companies listen more than they talk, push decision-making down to the people that know best, and never push their responsibilities or blame on others.  My best bosses exemplified these attributes.  

Most of the CIOs I reported to did not have technical backgrounds but understood it well enough to make good decisions.  The CIOs that did understand Information Technology knew they weren’t the experts but recognized when the experts did not appreciate the bigger picture.  Their biggest value was knowing the right people throughout senior leadership, what was important to them, cultivating relationships, and understanding the politics.  This was critical as the 1980s and 1990s were filled with centralizing data centers, consolidating software, and combining staff to reduce costs.   Standardizing the technology enabled the organization to work together instead of being siloed.  Imagine a corporation with a dozen email systems, multiple domain names, and then trying to sync it all together.  Companies with good CIOs brought email and many other disparate technologies stacks together more quickly and they benefitted sooner.

The best bosses are easy to recognize.  They are the ones that you remain in contact with and look forward to the next time together.  Friends for life.


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