However beautiful the strategy, you should occasionally look at the results. -Sir Winston Churchill
Everyone has a boss. It doesn’t matter if you’re the person taking orders at a drive through or a CEO of a multinational company. Everyone reports to somebody in someway.
The CEO has to go before the board and answer questions. Someone once described such a meeting as a group of “scary men with pencils”.
As I’ve matured into my role as Director of Technology, I not only deal with the people who work under me everyday, but I also concern myself with my own chain of command. Regularly, I am questioned about a deliverable or project.
When you underpromise on a task, and you overdeliver results, you’re a star. Your team looks great, you look great and most importantly, you demonstrate that you can be trusted and relied upon.
While I don’t want to get into politics, the example of President George W. Bush comes to mind. He may be the CEO of the country, the board is Congress and shareholders are American citizens. When he presented the Iraq war, he overpromised results (America would be greeted as liberators, Iraq would be a bastion of democracy in the Middle East, etc, Weapons of Mass Destructio in huge stockpiles, etc), and four years later sits with an abysmal approval rating after underdelivering on results.
Politics aside, my tendency is to provide a worst case scenario as a way of managing expectations. This provides buffer and it makes us look like stars when we beat expectations!