Lesson Learned: Make and execute high-level, strategic decisions that make it easier for everyone else in your organization to win.

Alan Gilbert
2 min readMay 22, 2023

This blog post is part of a series of leadership lessons that I have learned from 40 years in tech. This one will be short and sweet.

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When leaders make the right strategic decisions, they have a dramatic and positive impact on employees’ productivity and engagement. One of a leader’s most crucial roles is to establish strategy, prioritize, and make difficult decisions that position their company on a playing field where employees can more easily win. For every opportunity, it is essential to carefully define winning, and only pursue those where your team or company possesses a unique strength or unfair advantage. Conversely, it is vital to pass on opportunities where such advantages are lacking. This approach is key to achieving sustainable, long-term success.

Companies that lack focus and make undisciplined decisions create unnecessary difficulties for themselves. They typically end up relying on employees to compensate through sustained long hours and brute force, which ultimately results in them becoming disengaged and leaving. Remember, you cannot do everything, so it is crucial to stay on playing fields where winning comes more naturally and to step away from those where it does not.