The fastest quarter of the year has begun. The slower, longer days of summer have given way to workweeks shortened with frequent holidays and evenings interrupted with activities, engagements and annual events. In a minute, it will be the new year.

That is exactly why we should start writing our leadership letters now.


A leadership letter can be many things: an inspiring speech at a year-end event; a note sent to each employee; or a detailed account written as an act of reflection. Regardless of the audience, annual letters are a valuable tool for leaders.

The best letters honestly capture the team or organization’s feelings from the end of last year through the peaks and valleys of the current year.

They include a factual review and, ideally, illustrative anecdotes. And finally, they serve to reconcile the positive intents at the start with the reality of the path so that a course can be set again for the coming year.

On the flip side, leadership letters should not gloss over challenges, spin stories or in any way not genuinely convey the intent or feelings of staff or leadership. The main point of the letter should be to acknowledge where we are and set the stage for where we can realistically be based on the experiences and knowledge gained over the past year.


While letters to the staff are most often from the Board or the corner office, leadership letters really can come from any level.

From managers to executives, every leader should carve out the time to reflect on the year and make some decisions about the one to come. Ideally, those reflections and ideas are shared with the team to improve understanding, garner buy-in and reinforce the mission and purpose of the organization.

In some cases, however, sharing a letter with the team may not be practical or desired. In those situations, a letter should still be written, if only for us to have our own chronicle of events for perspective and inspiration.


This is the best time to start drafting the letter for three reasons. First, there is still time to make it thoughtful. A letter thrown together with haste will sound like a letter thrown together with haste and thus undermine its importance.

Second, it gives us a chance to make it known we are doing it and inspire others to participate or do the same with their teams. This both holds us accountable and motivates others.

Finally, it may just give us that one last chance to adjust, change course or really understand something that did not go as planned.

Next steps

When shared with an audience, a leadership letter can be a year-end letter, capturing the highlights of the year, thanking employees and giving everyone permission to take a break. However, to ensure it is a valuable tool that conveys authenticity, the letter should also acknowledge challenges and give appropriate weight to successes.

As such, the best approach can be to start by writing an unabridged and unabashedly honest version to ourselves first, then decide what and how to convey the essential points to the team.

Either way, the bottom line is, to be one of those inspiring leaders that has seemingly superhero control over time, we should take the time now to start writing a leadership letter.