I worked for Intel during the .com bust era. It was interesting to watch as we came up on quarterly deadlines where it was going to be tight. In order to make sure that we made money travel was frozen, discretionary spending was frozen, and the worst was the constant freezing and unfreezing of hiring. All to make sure we hit the quarterly targets. When the hiring doors were unlocked there was a sense that we had to get someone in fast before they closed again. You can guess how effectively that works as a hiring strategy…
CEOs these days have it tough (and have for a while) with the short termism that reigns supreme in the investing industry. Very few are able to keep a long term vision on course when it comes at the cost of short term profits (Jeff Bezos is a great example of a CEO who has been able to do this IMO).
But it isn’t just CEOs everyday product/software teams have this same problem. The short term focus for those teams is the looming product deadline, the current support crisis, or the feature that sales or marketing is clamoring for (and in some cases selling already). Those concerns can easily consume 100% of a team’s bandwidth. When that happens it is easy to put all your eggs in the here and now. That often leads to the cannibalism of the long term strategy for your product.
Software and product leaders would be wise to practice the principles of diversified investing. Even though I am a long ways from retirement my retirement funds have a blend from conversative to risky in them. Likewise as you consider the velocity/capacity of your team and where you should invest you need to make sure that you have a blend of short, medium, and long term investments. Engineering enhancements (like a new build or version control system), experimenting with technologies that you will want to be integrating into your product in the next one to two years, etc… need to have some capacity reserved for them amongst all the tactical requests coming from users and the business.