Managed IT Services Blog - Seattle, WA | Dynamic Computing

The Seasons of Planning | Dynamic Computing

Written by Kevin Gemeroy | Jan 21, 2026 1:15:45 AM

Every January, shortly after we kick off the new year, we embark on one of my favorite exercises:  Annual Planning.  As I wrote about last quarter, this all started back in 2018, and after a series of failures, we’ve managed to get it down to a science…kind of.

At its core, our process is pretty simple.  We start by putting each team in a conference room together and asking them to perform a SWOT analysis on their team.  That leads to a lot of interesting (and sometimes uncomfortable) conversations.  

We ask (and frankly push) everyone on the team to participate, and the process is facilitated by one of the members of our Leadership Team who does NOT manage that department.  We ask that the team’s manager be the note taker and to listen more than they talk.  We encourage the team to speak frankly and freely, making the process a very much bottom-up approach.

We also ask the teams to answer a series of questions, which may differ from year to year.  Usually, they’re geared toward supporting growth goals, but we review and update the question list annually.  This helps us get input directly from the team on what’s needed to support our plans and goals for the upcoming year.

Each team follows the same process and is asked to identify and figure out how to solve their own biggest challenges.  The process yields new information and new ideas every year.  It also gives every member of the team a chance to participate and to feel heard.

In February, our Leadership Team will head down to Scottsdale, Arizona, to get some sun, play some mini-golf, and spend the better part of 3 days in a conference room stitching 5 different and disparate team plans together into a single, cohesive annual plan.  While we can’t promise that each team will get exactly what they wanted, we can ensure that we’ll all be moving forward in the same direction, with a document to guide us for the year.

Does your team have any sort of annual planning ritual?  Drop me a line at kevin@dynamiccomputing.com and let me know what works well for your company!