A Day in the Life of a Senior Leader

Chapter 5. The Seven Milestones and Meetings That Matter Every Year

As a senior leader, you live your life by your calendar. There is the omnipresent question of what you are going to do next, but frequently you need to step back and look at the month…or the year. You are looking for the presence (or absence) of seven important events:

Strategic planning

An off-site meeting (or series of meetings) with peers and leadership wherein you decide what the team is actually going to do next year. The rest of this list flows from here.

Headcount planning

With a strategy in place, this is budget planning for next year, where you explain how many humans you’ll need to build the thing.

Annual goals

Here you set well-defined and measurable goals that have been agreed upon between you and your manager.

All-hands

Wherein you sit down with the entire team, break bread, and take time to understand the health of people, projects, and processes. Frequently.

Talent planning

A cross-functional meeting where you explain the performance of your team members to peers and leadership. (Read the next chapter.)

Your review

A spoken and written discussion between you and your manager wherein you discuss how you measured against your prior goals and define the next set of annual goals. A low-stakes midyear check-in is ideal.

Compensation review

Invariably associated with the review, but this is a separate conversation because money corrupts the review. In this meeting, you will discuss base ...