Holding an Annual Strategic Planning Retreat

Since we here at OnStrategy just held our annual strategic planning retreat, I figured this would be a great chance to post about holding these retreats at your organization(s). We spend a lot of time helping businesses build and maintain their plans, but getting ready for our own (and my own first facilitation) gave me a chance to review what we teach ourselves. Here’s a quick rundown of what an annual retreat should focus on:

So You’ve Had a Strategic Plan in Place for at Least a Year, Now What?

The meeting rhythm should begin with an annual strategic planning session of at least two days in length. Ideally, you should hold this retreat at an offsite location. Although this isn’t necessary, it does help shut out distractions.  During this session, the team reviews how well they’re executing their business strategies and achieving the targets they set. The review process goes as follows:

1. Start with a review of the mission, vision, and values.
Make sure that these statements are current and still relevant to your organization.

2. Assess the long-term business assumptions and conduct a traditional SWOT (strengths, weaknesses, opportunities, and threats) analysis.
This step provides a current understanding of the marketplace and the true capabilities of your organization. More info on SWOT can be found in our archives.

3. Identify the long-term strategic objectives.
Quite often these stay the same for several years, with just a few modifications.  Your strategic objectives are the big mileposts on the way to your vision.

4. Set short-term goals and action items if possible.
Normally the team does not spend time in the details; instead, assign a goal to a team member who can then flesh out how it will get accomplished.

5. As the manager of the strategic plan, collect all of the work completed in this session and compile it into a final document.
Distribute copies of the compiled document, so everyone knows what they’re responsible for achieving.

I’ll post a recap of the facilitation here on the blog, but if you have any questions about the process please let us know!



What is 2 + 5 ?
Please leave these two fields as-is:
All fields are required.

Free Guides & Resources

OKRs that work
Setting OKRs that Work

A FREE downloadable guide and canvas to build Objectives and Key Results.

SWOT Assessment Guide

A FREE downloadable guide and canvas to complete a SWOT analysis, synthesize it into Competitive Advantages, and then use your SWOT to create SMART goals.

Guide to Create KPIs with 100 Example Metrics

A FREE downloadable guide to learn the basics of Key Performance Indicators with 100 example metric sources for ever department of your organization.

Free Guide for Writing Better SMART Goals

Download the FREE guide to learn how to create goals that have impact in your organization.

Growth Strategy
Free Guide to Build a Growth Strategy

A FREE downloadable guide and canvas to create a growth strategy that clearly defines where you play and how you’ll win.

Goals and OKR Cycle
Goals/OKR Cycle Guide

A FREE downloadable guide and canvas to establish a quarterly rhythm for OKRs and Goals.

OKR Essentials
OKR Essentials Cheat Sheet

Download the free cheat sheet to guide you through building and refreshing OKRs.

Join 50,000 Other Leaders Engaged in Transforming Their Organizations

Subscrbe to get the latest agile strategy best practices, free guides, case studies, and videos in your inbox every other week.

We Believe in Empowering Teams to do Amazing
Work, Consistently and Passionately

Success isn’t a list of flashy logos. It’s about helping anyone who wants to lead a great organization.
If that’s you, join our list of clients – you’re in good company:

Armen EZR Multnomah RHA SEO Monitor
Chobani Cisco Armen KIA Patagonia
Concordia College Davenport Fairbanks St. John's Washoe County School District
Boys and Girls Club BSA Cancer Society Maryland Food Bank Make A Wish
CMPD Long Beach San Francisco City of Sparks Washoe County