Lesson Learned: Understand that people don’t like surprises

(except the kind that result in bigger paychecks)

This blog post is part of a series of leadership lessons that I have learned from 40 years in tech.

Great leaders understand that people on their teams plan their work and lives to perform well both in their jobs and personal commitments. They recognize that habitually and carelessly changing plans, priorities, or direction for their teams has downstream effects, which can disrupt lives and erode engagement over time.

However, this doesn’t mean that great leaders are afraid or hesitant to make changes or respond to opportunities. Instead, they foster a culture that facilitates adaptation to changing circumstances. They thoughtfully manage change by understanding its ramifications and considering them before taking action. Furthermore, they communicate with their teams, informing them of upcoming changes and explaining the reasons behind them.

In one company where I worked, the CEO had a bad habit of immersing himself completely in cultivating business opportunities, neglecting to keep others informed of potential related work. He would wait until the last minute to seek help from the marketing team for presentations and other supporting materials, disrupting their other work and personal lives. It was not uncommon for such requests to come in at 5:00 PM or later, causing the team to cancel their evening plans, order dinner in, and work until midnight. The company culture celebrated these efforts as “whatever it takes” heroism.

This pattern persisted for many months, leading to the disengagement and resignation of some of the most talented individuals. However, the CEO eventually learned from this experience. He began giving the marketing team advance notice of potential work and priority changes a day or two beforehand, rather than needlessly waiting until the last minute. He also started inquiring about the team’s ongoing projects to better understand the implications of changing priorities. Above all, he simply encouraged the team to ask the question, “When do you need this?” to prevent them from assuming that they had to drop everything and complete the task by the following morning.

In retrospect, the necessary changes seemed obvious, but it took the loss of talented individuals before anyone considered changing the culture.

Ultimately, it boils down to this: people dislike surprises and great leaders work to avoid them.